atoms were defined in Section 2.5.

Isobutane, isopentane, and neopentane (Fig. 4.2) are example

alkanes. In neopentane the central carbon atom is bonded to four car
Butane and isobutane have the same molecular formula: C4H10.
140 have their
Chapter 4 Nomenclature and Conformations atoms connected
of Alkanes in a different order and are, therefore, co
and Cycloalkanes
(Section 1.3). Pentane, isopentane, and neopentane are also constitu
Alkana dan Sikloalkana
Figure 4.1 Ball-and-stick too, have the same molecular formula (C5H12) but have different str
4.2 Shapes of Alkanes models for three simple
A. Alkana alkanes.
A general tetrahedral orientation
Propaneof groups—and thus sp3 hybridization—is
Butane the rule for the Pent
Alkana biasa disebut dengan
carbon atoms senyawa
of all alkanes andhidrokarbon
cycloalkanes. jenuh.
We canDisebut
representhidrokarbon karenaasdi
the shapes of alkanes
CH3CH2CH3 CH3CH2CH2CH3 CH3CH2CH
shown in Fig. 4.1.
dalamnya hanya terkandung
Butane and atom
pentane karbon dan hidrogen.
are examples
or of alkanes Disebut jenuh karena
that are sometimes orcalled hanya memiliki
“straight-chain” o
alkanes.
ikatan tunggal C-H danOneC-C glance
saja.at three-dimensional
Alkana memiliki models,
rumushowever,
umu shows that because
CnH2n+2 , di manaof their tetra-
n adalah
hedral carbon atoms the chains are zigzagged and not at all straight. Indeed, the structures
bilangan asli yang
that menyatakan
we have depicted jumlah
in Fig. atom
4.1 arekarbon. Alkana
the straightest jugaarrangements
possible sering disebut of the sebagai
chains
because rotations about the carbon–carbon single bonds produce arrangements that are even
senyawa alifatikless
(Yunani
straight.=Aaleiphas yang berarti
better description lemak).This
is unbranched. Halmeans
ini dikarenakan
that each carbonlemak-lemak
atom within
the chain is bonded to no more than two other carbon atoms and that unbranched alkanes
hewani mengandung
containkarbon rantaiand
only primary panjang yang
secondary mirip
carbon dengan
atoms. alkane.
Primary, secondary, and tertiary carbon
atoms were defined in Section 2.5.
Alkana dengan satuIsobutane,
formulaisopentane,
dapat membentuk beberapa
and neopentane (Fig. struktur molekul.ofMisalnya
4.2) are examples alkana
branched-chain
alkanes. In neopentane the central carbon atom is bonded to four carbon atoms.
dengan empat atom karbon dapat membentuk normal butana dan isobutana, keduanya sama-
Butane and isobutane have the same molecular formula: C4H10. The two compounds
have their
sama memiliki rumus C4H10 . in a different order and are, therefore, constitutional isomers
atoms connected
molekul
(Section Figure 4.2 Ball-and-stick
1.3). Pentane, Isobutane are also constitutional isomers.
isopentane, and neopentane Isopentane
They,
models for three
Figure 4.1 Ball-and-stick too, have the same molecular formula (C5H12) but have different structures.
models for three simple branched-chain alkanes. CH3CHCH3 CH3CHCH2CH3
alkanes. In each of the compounds
one carbon atom CH3 CH3
Propane Butane
is attached to more than Pentane
CH3CH2CH3 two otherCHcarbon atoms.
CH CH CH or CH3CH2CH2CH2CH3 or
3 2 2 3

or or or

Helpful Hint
butana isobutana
You should build your own
molecular models of the
Hal yang sama juga terjadi untuk
compoundsC6H in 14 , dan
Figs. 4.1 seterusnya. Suatu senyawa yang memiliki jumlah
and 4.2. View them from different
dan macam atom sama perspectives
tetapi berbeda dalam penataannya disebut dengan isomer. Isomer
and experiment
with how their shapes change
berasal dari bahasa Yunani;
whenisos + meros
you twist various yang
bonds. berarti terbuat dari bagian yang sama. Senyawa
Make drawings of your structures.

seperti butana dan isobutana hanya berbeda pada urutan atom yang terikat satu sama lainnya,
Figure 4.2 Ball-and-stick Isobutane
disebut isomer konstitusional. Isopentane Neopentane
models for three CH3
branched-chain alkanes. CH3CHCH3 CH3CHCH2CH3
Isomer konstitusional tidak terbatas hanya untuk alkana, tetapi juga padaCH3sebagian
In each of the compounds CCH3 besar
one carbon atom CH3 CH3
is attached to more than organik. Isomer konstitusional bisa berbeda pada susunan kerangkaCHatom
senyawa 3 karbon
two other carbon atoms. or or or
(seperti pada butana dan isobutana), perbedaan gugus fungsi (seperti pada etanol dan dimetil
eter), atau berbeda pada penempatan gugus fungsi (isopropilamina dan propilamina).
Meskipun memiliki formula yang sama, sifat-sifat fisika kimia dari isomer biasanya berbeda,
Helpful Hint
seperti titik didih, titik leleh dan kereaktifan kimia, seperti contoh pada senyawa heksana.
You should build your own
molecular models of the
compounds in Figs. 4.1
and 4.2. View them from different
perspectives and experiment
with how their shapes change
when you twist various bonds.
Make drawings of your structures.
 4.2 Shapes of Alkanes 14
4.2 Shapes of Alkanes 141
TABLE 4.1 Physical Constants of the Hexane Isomers
TABLE 4.1 Physical ConstantsCondensed
of the Hexane Isomers Index of
Molecular Condensed Structural Bond-Line mp bp (°C)a Index Density
of
b
Refractionc
a b c !1
Formula
Molecular Structural Formula Bond-Line Formula
mp bp (°C) (°C) Density
(1 atm) Refraction
(g mL ) (nD 20°C)
Formula Formula Formula (°C) (1 atm) (g mL!1) (nD 20°C)
C6H14 CH3CH2CH2CH2CH2CH3 !95 68.7
20 0.659420 1.3748
C6H14 CH3CH2CH2CH2CH2CH3 !95 68.7 0.6594 1.3748
20
C6H14 C6H14CH CHCHCH CHCH2CH2CH3
CH3 CH !153.7 60.3
60.3 !153.70.653220 0.6532
1.3714 1.3714
3 2 2 3

CH3 CH3

C6H14 C6H14CH3CH2CHCH CH2CHCH2CH

CH32CH !118 63.3 !118 0.664320
63.3 0.664320
1.3765 1.3765
CH3 CH3
C6H14 CH3CH9CHCH !128.8 58 0.661620 1.3750
C6H14 CH3CH9CHCH !128.8 58 0.661620 1.3750
CH3 CH3
CH3 CH3

C6H14 CH3 !98 49.7 0.649220 1.3688

C6H14CH39 C9CH2CHCH3 !98 49.7 0.649220 1.3688

CH3CH39C9CH2CH
a
Unless otherwise indicated, all boiling CH
points given in this book are at 1 atm or 760 torr.
b
The superscript indicates the temperature 3at which the density was measured.
c a of refraction is a measure of the ability of the alkane to bend (refract) light rays. The values reported are for light of the
The indexUnless otherwise indicated, all boiling points given in this book are at 1 atm or 760 torr.
D line ofbthe sodium spectrum (nD).
The superscript indicates the temperature at which the density was measured.
c
The index of refraction is a measure of the ability of the alkane to bend (refract) light rays. The values reported are for light of the
D line of the
and sodium structural(nformulas
spectrum D).
Write condensed
Umumnya semakin bond-line
bercabang struktur hidrokarbon, semakin rendah titikReview
for all of the constitutional isomers with
the molecular formula C7H16. (There is a total of nine constitutional isomers.)
Problem 4.1
didihnya dibanding
dengan struktur isomerand
Write condensed lainnya. Salah
bond-line satuformulas
structural penjelasan
for alluntuk gejala ini adalah
of the constitutional isomersbahwa
with molekul
Review Problem 4.1
Constitutional isomers, as stated earlier, have different physical properties. The differ-
the molecular formula C H . (There is a total of nine constitutional isomers.)
7 16
bercabang yang
ences may not kompak
always be large, tidak akan melilit
but constitutional isomers seperti
are alwaysrantai
found tolurusnya.
have differ- Karena itu, lebih sedikit
ent melting points, boiling points, densities, indexes of refraction, and so forth. Table 4.1
energi
gives yang ofdiperlukan
someConstitutional untuk of
the physical properties
isomers, mengubah
asthe C6H14
stated molekul-molekul
isomers.
earlier, bercabang
have different physical menjadi
properties. wujud gasnya,
The differ-
As Table
ences4.2mayshows, the number
not always of constitutional
be large, isomers that
but constitutional is possible
isomers increases
are always found to have differ-
penjelasan
dramaticallylainnya yaitu
as the number
ent melting points, adanya
of carbon
boiling rantai
atoms in the samping
points, membuat
alkane increases.
densities, indexes molekul
of refraction, and so memiliki luas
forth. Table 4.1permukaan
The large numbers in Table 4.2 are based on calculations that must be done with a
gives some of the physical properties of the C H isomers.
yang lebih Similar
computer. kecil,calculations,
akibatnyawhich memiliki
take into energi dispersi
6 14
account stereoisomersrendah.
(Chapter 5) as well
As Table
as constitutional 4.2indicate
isomers, shows,that
theannumber
alkane withof the
constitutional
formula C167Hisomers that is possible increases
336 would, in the-
dramatically as the number of carbon atoms in the alkane increases.
ory, have more possible isomers than there are particles in the observed universe!
The large numbers in Table 4.2 are based on calculations that must be done with a
Tabel berikut iniSimilar
computer. menunjukkan
Number
jumlah
calculations,
of Alkane
isomer
which take
Isomers
yang mungkin,
into account yang
stereoisomers jumlahnya
(Chapter naik seiring
5) as well
TABLE 4.2
as constitutional isomers, indicate that an alkane with the formula C
167 336 H would, in the-
dengan naiknya
ory, have jumlah atomisomers
more possible karbonthan
suatu
theresenyawa alkana.
Possible Number
are particles
of
in the observed universe!
Molecular Formula Constitutional Isomers
C4H10 2
C5H12 Number of Alkane Isomers 3
TABLE 4.2
C6H14 5
C7H16 Possible
9 Number of
C8Molecular
H18 Formula Constitutional
18 Isomers
C9H20 35
C10H22 C4H10 75 2
C15H32 C5H12 4,347 3
C20H42 C6H14 366,319 5
C30H62 C H 4,111,846,763 9
7 16
C40H82 62,481,801,147,341
C8H18 18
C9H20 35
C10H22 75
C15H32 4,347
C20H42 366,319
C30H62 4,111,846,763
C40H82 62,481,801,147,341
 4.3 IUPAC NOMENCLATURE OF ALKANES, ALKYL HALIDES,
ALCOHOLS
ANDAlkana
1. Penamaan
Alkana diberi nama berdasarkan jumlah atom karbonnya. Penamaan diambil dari bahasa
1. Common (trivial) names: the older names for organic compounds
Yunani, kecuali untuk satu hingga empat atom karbon, yaitu metana, etana, propana, dan
1) Acetic acid: acetum (Latin: vinegar).
butana. Akhiran ana ditambahkan pada akhir tiap nama untuk memberikan ciri bahwa senyawa
2) Formic acid: formicae (Latin: ants).
tersebut adalah alkana. Selanjutnya, pentana berarti terdiri dari lima atom karbon, heksana
terdiri2.dariIUPAC (International
enam karbon, Union
contoh yang of Pure
lainnya and Applied
tercantum Chemistry
pada table berikut : ) names: the
formal system of nomenclature for organic compounds

Tabel…. Alkana Rantai lurus

Table 4.4 The Unbranched Alkanes

Number of Formula Number of Formula

Name Name
Carbons (n) (CnH2n+2) Carbons (n) (CnH2n+2)
1 Methane CH4 17 Heptadecane C17H36
2 Ethane C2H6 18 Octadecane C18H38
3 Propane C3H8 19 Nonadecane C19H40
4 Butane C4H10 20 Eicosane C20H42
5 Pentane C5H12 21 Henicosane C21H44
6 Hexane C6H14 22 Docosane C22H46
7 Heptane C7H16 23 Tricosane C23H48
8 Octane C8H18 30 Triacontane C30H62
9 Nonane C9H20 31 Hentriacontane C30H62
10 Decane C10H22 40 Tetracontane C40H82
11 Undecane C11H24 50 Pentacontane C50H102
12 Dodecane C12H26 60 Hexacontane C60H122
13 Tridecane C13H28 70 Heptacontane C70H142
14 Tetradecane C14H30 80 Octacontane C80H162
15 Pentadecane C15H32 90 Nonacontane C90H182
16 Hexadecane C16H34 100 Hectane C100H202

2. Gugus Alkil

Jika satu atom hidrogen dibebaskan dari sutau alkana maka diperoleh struktur yang disebut
~6~
alkil. Gugus alkil tidak stabil jika berdiri sendiri, alkil merupakan bagian dari molekul yang
besar. Gugus alkil diberi nama sesuai dengan rantai alkananya dengan mengganti akhiran –ana
menjadi –il. Contohnya alkil dari metana adalah metil, sedangkan etana yang kehilangan satu
hidrogen disebut etil. Simbol R digunakan untuk menyatakan gugus alkil. Oleh karena itu
 The functional group of an alkyne is its carbon–carbon triple bond. Alkanes do not have
a functional group. Their molecules have carbon–carbon single bonds and carbon–hydrogen
bonds, but these bonds are present in molecules of almost all organic compounds, and
C 9 C and C 9 H bonds are, in general, much less reactive than common functional groups.
We shall introduce other common functional groups and their properties in Sections 2.5–2.11.
Table 2.3 (Section 2.12) summarizes the most important functional groups. First, however,
let us introduce some common alkyl groups, which are specific groups of carbon and hydro-
gen atoms that are not part of functional groups.
rumus umum untuk alkana
solom_c04_137-185hr.qxd R-H .Kombinasi
24-09-2009 11:22 Pageantara
143 alkil dengan gugus fungsi yang lain akan
menghasilkan ribuan and
2.4A Alkyl Groups senyawa. Contohnya:
the Symbol R Ketika alkana tidak bercabang, dan atom hidrogen
Alkyl groups
yang are the groups
dihilangkan that atom
adalah we identify for purposes
hidrogen of naming
terminal, compounds.
namanya They are:
menjadi
groups that would be obtained by removing a hydrogen atom from an alkane:

ALKANE ALKYL GROUP ABBREVIATION BOND-LINE MODEL

CH3 9 H
solom_c04_137-185hr.qxd CH3 11:22
24-09-2009 9 Page 143 Me-
4.3 IUPAC Nomenclature of Alkanes, Alkyl Halides, and Alcohols
Methane Methyl

CH3!H CH CH !H CH3CH2CH2!H CH3CH2CH2CH2!H

CH3 CH2 9 H CH3 CH2 39 2 Et-
Methane Ethane Propane Butane
Ethane Ethyl
CH3! CH3CH2! CH3CH2CH2! CH3CH2CH2CH2!

Methyl Ethyl Propyl Butyl

CH3 CH2 CH2 9 H CH 3 CHIUPAC
4.3 2 CH2 9Nomenclature
Pr-of Alkanes, Alkyl Halides, and Alcohols 14
Propane Me- Propyl Et- Pr- Bu-

CH3!H CH3CH2!H CH3CH2CH2!H CH3CH2CH2CH2!H

Methane Ethane Propane Butane
CH3 CH2 CH2 CH
CH H
2 9! CH3 CH
CH2 CH
CH2 CH
!2 9 CH3Bu-
CH2CH2! CH3CH2CH2CH2!
3 3 2
Butane Butyl
Methyl Ethyl Propyl Butyl

WhileKimia Organik
only one Me-
alkyl I can be derived
group Et-from methane or ethane Pr-(the methyl and ethyl Bu- 71
groups, respectively), two groups can be derived from propane. Removal of a hydrogen from
one of the end carbon atoms gives a group that is called the propyl group; removal of a
3. Tata from
hydrogen nama the Alkana
middle Bercabang
carbon atom gives a group that is called the isopropyl group.
4.3B Nomenclature of Branched-Chain Alkanes
Ada beberapa Ada
The names and structures
tahap beberapa
of these
now.dalam
learnBranched-chain
groupstahap
are
penamaan
used dalam
so penamaan
frequently
alkane
in
bercang
organic alkana:
chemistry
: offollowing
that
you should them alkanes
See Section 4.3Carefor
named
namesaccording
and to the
structures rules:
branched alkyl
groups derived from butane and other hydrocarbons.
Tahap 1 . Temukan
We can simplify1. Locate
much
rantai
of ourthe
utama
longest
future
hidrokarbon
continuous
discussion chain
if, at this point,ofwecarbon atoms;
introduce this chain determines the
a symbol
Tahap
that is widely
satu:
used in
Temukan
parent name
designating
rantai
for structures
general
utama
the alkane. of organic
hidrokarbon
We designate
molecules: thethe
following
symbol compound, for example,
R.
a. Rantai utamaa hexane adalahbecause
rantai the
hidrokarbon terpanjang yang ada dalam molekul.
R is used as a generalassymbol to represent any longest
alkyl continuous
group. For example,chainRcontains
might besix
a carbon atoms:
methyl group, an ethyl group, a propyl group, or an isopropyl group:
a. Rantai utama CH3CH2CH adalah
2CH2CHCH rantai
3 or hidrokarbon terpanjang
4.3B Nomenclature of Branched-Chain Alkanes
––

CH3 Methyl These and

LongestEthyl
chain CH3
CH CH
3
Branched-chain yang
2
alkanes adaare dalam molekul.
named according
others
can to
be the following rules:
CH3 CH2 CH 2 Propyl
CHThe CHCH Isopropyl designated by R.
1. Locate3 longest
the 3longestcontinuous
continuous chain mayofnot
chain alwaysatoms;
carbon be obvious from determines
this chain the way the formula
the
is written. Notice, for example, that the following CH
alkane is designated
parent name for the alkane. We designate the following compound, for example,
3 as a heptane
as a because
hexane becausethe longest chain contains
the longest
Thus, the general formula for an alkane is R 9 H.
sevenchain
continuous carbon atoms:six carbon atoms:
contains
CH2
CH2CH
CH33CH2CH2CH2CHCH3 or
––

Longest chain CH3 H3C CHCH CH2CH3

CH3CH2CH2CH CH3
2. Number the longest chain beginning with the end of the chain nearer the
The longest continuous chain may not always be obvious fromCH the2CH
way the formula
2CH3we illustrated
substituent. Applying this rule, we number the two alkanes that
is written.
Dinamai sebagai Notice,
heksana fortersubstitusi
example, that the following alkane is designated as a heptane
previously in the following way: Dinamai sebagai heptana tersubstitusi
because the longest chain contains seven carbon atoms:
Substituent
Gambar
5 3.6.
3 Contoh
1 penamaan
6 4 suatu alkana
6 4 2 7 5 3

2
Substituent 1
2. Number the longest chain beginning with the end of the chain nearer the
substituent. Gambar
3. Use the numbers
2.1. Contoh
Applying obtained
this rule, penamaan
number theofsuatu
weapplication
by two alkanathat we the
rulealkanes
2 to designate illustrated
location of
b.the Jika
previously in ada
the dua
following rantai
way: yang sama panjang, pilih salah
substituent group. The parent name is placed last, and the substituent satu
group,
b. Jika ada dua rantaibyyang
preceded sama designating
the number panjang, pilih salahonsatu
its location yang ismemiliki
theSubstituent
chain, substituen
placed first. Numbers lebih
are yang 5 memiliki
separated from 1 substituen
3 words by a hyphen.
6 lebih
Our banyakare 2-methylhexane and
4 two examples
banyak. 3-methylheptane,
6 4 2
respectively:
7 5 3

CH3 5 3 1
2
6 4
Substituent 6 4 2 1 7 5 3
dinamai sebagai heksana 2 dengan
H3.3CUse theCnumbers
CHCH
Substituent 2CHby
obtained 2CHapplication
3 of rule 2 to designate the
Longest location of
dua substituen, bukan sebagai
1
H Locant
the substituent group. The parent namechain
is placed last, and the substituent group,
2-Methylhexane heksana
preceded by the number designating its location dengan satu first.
3-Methylheptane
on the chain, is placed substituen
Numbers
CH2CH3
 2,3-Dimethylbutane 2,3,4-Trimethylpentane 2,2,4,4-Tetramethylpentane

Application of these six rules allows us to name most of the alkanes that we shall
encounter. Two other rules, however, may be required occasionally:
4.3B Nomenclature of Branched-Chain Alkanes
7. When two chains of equal length compete for selection as the parent chain,
144 Branched-chain alkanes are named according to of
theAlkanes
following rules:
choose the
Chapter chain with theand
4 Nomenclature greater number of substituents:
Conformations and Cycloalkanes
1. Locate the longest continuous chain of carbon atoms; this chain determines the
parenttwo
4. When name
or for
morethesubstituents
alkane.
7 5We designate
are 1 the following
3 present, give each compound,
substituentfor
a example,
number
6 4 2
as a hexane because the longest continuous chain contains six carbon atoms:
corresponding to its location on the longest chain. For example, we designate the
following compound as 4-ethyl-2-methylhexane:
CH3CH2CH2CH2CHCH3 or

––
Longest chain CH3
2,3,5-Trimethyl-4-propylheptane (four substituents)
2,3,5-Trimethyl-4-propylheptane
(four substituents)
The longest continuous chain may not always be obvious from the way the formula
4-Ethyl-2-methylhexane
is
8. When branching Gambar
written. Notice, 2.1. Pemilihan
for example,
first occurs at an equal rantai
that the terpanjang
following
distance alkane
from eitheris end
designated as a heptane
of the longest
The substituent
because the groups
longest should
chain be listed
contains alphabetically
seven carbon (i.e., ethyl before methyl).* In
atoms:
chain, choose the name that gives the lower number at the first point of difference:
deciding on alphabetical order, disregard multiplying prefixes such as “di” and “tri.”
Tahap dua: Nomori atom-atom dalam rantai utama
5. When two substituents are 6 present
4 on the 2 same carbon atom, use that number twice:
5 3 1
a. Mulailah dari ujung rantai yang paling dekat dengan rantai samping untuk
2. Number
memberi the longest
nonor urut chain
pada rantai beginning with the end of the chain nearer the
utama.
3-Ethyl-3-methylhexane
2,3,5-Trimethylhexane
substituent. Applying (not this
2,4,5-trimethylhexane)
rule, we number the two alkanes that we illustrated
6. When two or
previously in more substituents
the following way: are identical, indicate this by the use of the pre-
fixes di-, tri-, tetra-, and so on. Then make certain that each and every substituent
Solved Problem 4.1 has a number. Commas are used to separate numbers fromSubstituenteach other:
5 3 1 6 4
Provide an IUPAC name for the following alkane.6 4 2 7 5 3

2
72 St. Layli Prasojo, S.Farm., Apt.
Substituent 1

2,3-Dimethylbutane 2,3,4-Trimethylpentane 2,2,4,4-Tetramethylpentane

3. Use the numbers obtained by application of rule 2 to designate the location of
1 CH3 7 CH3
the substituent
Application group.
ofgroups
theseinsix The
rules parent
allowsname
us to isname
placed last, and
most the the substituent
that wegroup,
*Some handbooks also list the order of increasing size or complexity (i.e.,ofmethyl alkanes
before ethyl). shall
preceded
encounter.
An alphabetical by the number
Two other
listing,2 however, designating
rules,
is now by however,
far the its
may
most widely location on
besystem.
used the chain, is
required occasionally:
6 CH2 placed first. Numbers
are separated CH2 from words by a hyphen. Our two examples are 2-methylhexane and
BUKAN
7. When two
3 chains of equal length compete for selection
4 respectively: 5 4 the parent chain,
as
3-methylheptane, H3C C CHCH2CH2CH3
choose
H3C the C chainCHCH with2CH
the2CHgreater
3 number of substituents:
H 5 3 1 6H 4
6 4 2 7 5 CH32CH2CH3
CH2CH2CH37 5 3
5 6 7 6 4 2 1 3 2 1
2
Substituent Longest
1
Gambar 3.8. Penomoran
chain rantai utama
Locant 2-Methylhexane 3-Methylheptane

b. JikaGambar 2.3. samping

ada rantai Penomoran rantaiurutan
dengan utama yang sama dari
2,3,5-Trimethyl-4-propylheptane
kedua ujung, pilih salah
(four satu ujung yang memiliki rantai
substituents)
b. Jika ada rantai samping dengan urutan yang sama dari kedua ujung, pilih salah
8. When sampingfirst
branching kedua yang
occurs at lebih dekat.
an equal distance from either end of the longest
satu ujung yang memiliki rantai samping kedua yang lebih dekat.
chain, choose the name that gives the lower number at the first point of difference:
9 CH3 1 CH3
6 4 2
8 CH2 CH3 5 3 1 2 CH2 CH3
3 2 1 7 8 9
7
H3C C CH2CH2CH CHCH2CH3 BUKAN H3C 3 C CH2CH2CH CHCH2CH3
H 6 5 4 H 4 5 6
2,3,5-Trimethylhexane
2,3,5-Trimethylhexane
CH 2CH
(not (not 2,4,5-trimethylhexane)
2,4,5-trimethylhexane)
3 CH2CH3
Gambar 3.9.
Solved Problem 4.1
Tahap tiga: Identifikasi
Tahap tiga: Identifikasi tiap substituen
tiap substituen
Provide an IUPAC name for the following alkane.
a. Beri nama rantai samping berdasarkan
a. Beri nama nomor urut
rantai samping dalam rantai
berdasarkan utama
nomor urut dalam
rantai utama

9 CH3
*Some handbooks also list the groups in order of increasing size or complexity (i.e., methyl before ethyl).
An alphabetical listing, however, is now by far the most widely used system.
8 CH CH3
2

7 3 2 1
H 3C C CH2CH2CH CHCH2CH3
H 5 4
6
CH2CH3
3-Etil-4,7-dimetil-
 3. Use 9the
CHnumbers
3 obtained by application of rule 21 CH to 3designate the location of
the substituent group. The parent name is placed last, and the substituent group,
8 CH2 CH3
preceded by the number designating its location on the2 chain,
CH2 is placed CHfirst.
3 Numbers
3 2 1
are
H3C separated
7
C from words by
CH2CH2CH CHCH2CH3 a hyphen. Our
BUKAN two examples
3 are 2-methylhexane
7 8 9and
H3C C CH2CH2CH CHCH2CH3
3-methylheptane,
H 6 5 respectively:
4 H 4 5 6
37-185hr.qxd 24-09-2009 11:22 Page 144 CH2CH3 CH2CH3
5 3 1 6 4
6 4 2Gambar 3.9. 7 5 3

2
Substituent
Tahap tiga: Longest
Identifikasi tiap substituen 1
chain
Locant 2-Methylhexane 3-Methylheptane
a. Beri nama rantai samping berdasarkan nomor urut dalam
rantai utama
44 Chapter 4 Nomenclature and Conformations of Alkanes and Cycloalkanes
solom_c04_137-185hr.qxd 9 CH311:22
24-09-2009 Page 144
4. When two or more substituents are present, give each substituent a number
corresponding to its location on the longest
8 CHchain. For example, we designate the
CH3
following compound as 4-ethyl-2-methylhexane:2
7 3 2 1
H 3C C CH2CH2CH CHCH2CH3
H 5 4
6
144 4-Ethyl-2-methylhexane
Chapter 4 Nomenclature
CH2CH3and Conformations of Alkanes and Cycloalkanes
3-Etil-4,7-dimetil-
The substituent groups should be listed alphabetically (i.e., ethyl before methyl).* In
deciding on alphabetical order, disregard multiplying4.prefixes
Whensuch two or more
as “di” substituents are present, give each substituent a
and “tri.”
Gambar2.4.
Gambar 3.10.Penamaan
Penamaan rantai
correspondingrantai samping
samping
to its location on the longest chain. For example, we des
5. When two substituents are present on the same carbon atom, use that number twice:
following compound as 4-ethyl-2-methylhexane:

b. Jika dua atau lebih substituen identik, tandai ini dengan menggunakan prefix di-, tri-,
3-Ethyl-3-methylhexane

tetra-,
6. Whendan seterusnya.
two or Kemudian
more substituents pastikan
are identical, setiap
indicate this by thesubstituen
use of the pre-memiliki nomor.
4-Ethyl-2-methylhexane
fixes di-, tri-, tetra-, and so on. Then make certain that each and every substituent
has a number. Commas are used to separate numbers from Theeach
substituent
other: groups should be listed alphabetically (i.e., ethyl before m
deciding on alphabetical order, disregard multiplying prefixes such as “di”
37-185hr.qxd 24-09-2009 11:22 Page 144
5. When two substituents are present on the same carbon atom, use that num

Kimia Organik I 73

2,3-Dimethylbutane 2,3,4-Trimethylpentane 2,2,4,4-Tetramethylpentane 3-Ethyl-3-methylhexane

2,3-Dimethyl- 2,3,4-Trimethy- 2,2,4,4-Tetramethyl- 3-Ethyl-3-m3thyl-
Application of these six rules allows us to name most of the alkanes
6. When two orthat we shall
more substituents are identical, indicate this by the use o
44 encounter.
Chapter Two other rules,
4 Nomenclature andhowever, may be required
Conformations occasionally:
of Alkanes
fixesanddi-,Cycloalkanes
tri-, tetra-, and so on. Then make certain that each and every s
b. Jika ada dua substituen has a number.terikat
Commas pada satu karbon,
7. When two chains of equal length compete for selection as the parent chain, are used to separate numbers from each other:
4. When two or more substituents keduanyaare present, give each substituent a number
choose the chain with the greater numberdiberi nomor yang sama.
of substituents:
corresponding to its location on the longest chain. For example, we designate the
following compound as 4-ethyl-2-methylhexane: CH3
7 5 3
CH2CH3
6 4 2 1

2,3-Dimethylbutane 2,3,4-Trimethylpentane 2,2,4,4-Tetramethyl

H3C C CHCH2CH2CH3
4-Ethyl-2-methylhexane
Application of these six rules allows us to name most of the alkanes tha
The substituent groups should be listed alphabeticallyencounter.
(i.e., ethylTwo other
before rules,Inhowever, may be required occasionally:
methyl).*
2,3,5-Trimethyl-4-propylheptane
deciding on alphabetical
CH
order, disregard multiplying 3prefixes such as “di” and “tri.”
substituents) 7. When
(foursolom_c04_137-185hr.qxd two chains
24-09-2009 of144
11:22 Page equal length compete for selection as the pare
5. When two substituents are present on the same carbon atom, use that number twice:
choose the chain with the greater number of substituents:
3-etil-2,2-dimetil-
3-etil-2,2-dimetil-
8. When branching first occurs at an equal distance from either end of the longest
Gambar
chain, choose the name that gives the lower2.6. Penamaan
number rantai
at the first point samping 7
of difference: 5 3
Gambar 3.11. Penamaan rantai samping
3-Ethyl-3-methylhexane 6 4 2 1

6. When two or more substituents 6 4are identical,

2 indicate this by Chapter
the use4ofNomenclature
the pre- and Conformations of Alkanes and Cycloalkanes
5 3 1441
fixes di-, tri-, tetra-, and so on. Then make certain that each and every substituent
Tahap empat: Tulis nama sebagai kata tunggal
has a number. Commas are used to separate numbers from each other: 4. When two or more substituents are present, give each substituent a number
Tahap empat: Tulis nama sebagai kata tunggalcorresponding to its location on the longest chain. For example, we designate the
2,3,5-Trimethylhexane following 2,3,5-Trimethyl-4-propylheptane
compound as 4-ethyl-2-methylhexane:
(not 2,4,5-trimethylhexane)
CH 3 (four substituents)
CH3
Solved Problem 4.1 2,3-Dimethylbutane 8. When branching first occurs
2,2,4,4-Tetramethylpentane at an
CH equal
2CH3 distance from either end of t
CH2 2,3,4-Trimethylpentane
CH3 4-Ethyl-2-methylhexane
chain, choose the name that gives the lower number at the first point of d
Application The substituent groups should be listed alphabetically (i.e., ethyl before methyl).* In
Provide an IUPAC name for the following alkane.of these six rules allows us to name most of the alkanes that we shall
Hdeciding
C on alphabetical
C order,
CHCH disregard
CH CH multiplying prefixes such as “di” and “tri.”
encounter.
H3Two
C other
C rules,CH
however,
2CH2CH
may beCHCH
required
2CH3
occasionally: 3
6 are present
2 2 3
4 on the 2same carbon atom, use that number twice:
5. When two substituents
H 5 3 1
7. When two chains of equal length compete for selection as the parent chain,
choose the chain with the greater number CH
of substituents:
CH 2 3 CH3 3-Ethyl-3-methylhexane

6.
2,3,5-Trimethylhexane
When two or more substituents are identical, indicate this by the use of the pre-
7 5 3
3-Etil-4,7-dimetilnonana
6 4 2 1 fixes 3-Etil-2,2-dimetilheksana
di-, tri-,(not
tetra-,2,4,5-trimethylhexane)
and so on. Then make certain that each and every substituent
*Some handbooks also list the groups in order of increasing size or complexity (i.e., methyl before ethyl).
 solom_c04_137-185hr.qxd 24-09-2009 11:22 3-etil-2,2-dimetil-
Page 145
4-Ethyl-2-methylhexane
Gambar
The substituent groups should3.11. Penamaan
be listed rantai samping
alphabetically (i.e., ethyl before methyl).* In
deciding on alphabetical order, disregard multiplying prefixes such as “di” and “tri.”
5. When two substituents are present on the same carbon atom, use that number twice:

Tahap empat: Tulis nama sebagai kata tunggal

CH3 4.3 IUPAC3-Ethyl-3-methylhexane

Nomenclature of Alkanes, Alkyl Halides, and Alcohols
4.3 IUPAC Nomenclature of Alkanes, Alkyl Halides, and Alcohols 1
6. When two or more substituents are identical, indicate this byCH the use of the pre-
3
di-,2 tri-, tetra-,CHand so on. Then make certain that each and every CH
fixes CH 2CH3
substituent
3
has a number. Commas are used to separate numbers from each other:
STRATEGY AND SOLUTION We find the longest chain (shown in
STRATEGY
blue)
HC3 CAND SOLUTION
to be seven2 carbons;
CH CH CH
2
WeCHCH
find CH
therefore
2
the longest chain
the
3
H3C (shownCin
parent name is heptane.
CHCH2CH2CH3
5 7
blue) to be
There areseven
H carbons;substituents
two methyl therefore the parent
(shown nameWe
in red). is heptane.
number the 45 7
Two 4
There are two methyl substituents (shown in red). We number the Two 6 Longes
chain so as to give the firstCHmethyl group the lower number. methyl Longest
2CH3 CH3 3 6 chain
chain so as to give the first methyl group the lower number. methyl
groups
2,3-Dimethylbutane
The correct name, therefore, is 3,4-dimethylheptane. 2,2,4,4-Tetramethylpentane
2,3,4-Trimethylpentane Numbering the groups 3 1 chain
The correct name, therefore, is
3-Etil-4,7-dimetilnonana 3,4-dimethylheptane. Numbering the
3-Etil-2,2-dimetilheksana 21
chain 3-Etil-4,7-dimetilnonana
from theofother
Application these end
six to give
rules allows 3-Etil-2,2-dimetilheksana
4,5-dimethylheptane
us to name most ofwould
thehavehave that we shall
alkanes 2
chain from the other
Gambar endPenamaan
3.12. to give 4,5-dimethylheptane
alkana lengkap dengan would
substituennya
been incorrect.
encounter.
Gambar
been 2.7.Two
incorrect. other rules,alkana
Penamaan however,lengkap
may be required
dengan occasionally:
substituennya
7. When two chains of equal length compete for selection as the parent chain,
choose the chain with the greater number of substituents:

4. Latihan. 7 5 3
6 4 2 1
Which structure
1. Which
Struktur manakah does not represent
yang 2-methylpentane?
bukan2-methylpentane?
2-methylpentane? Review Problem
structure does not represent Review Problem 4.
(a) (b) (c) (d)
(a) (b) (c) (d)
2,3,5-Trimethyl-4-propylheptane
(four substituents)

Write8.the
When branching
structure first occurs
and give at an name
the IUPAC equal distance from either
for an alkane end of the
with formula C longest
H that has
6 14 Review Problem
2. Write
Tulis the structure
C6and give the hanya
IUPAC name for an alkane
atwith formula H14 Cthat
C6difference:has danReview Problem 4.
onlystruktur
chain, and
primary Hsecondary
choose yang
14the name mempunyai
that gives
carbon the lower
atoms. struktur
number dengan
the first point atom
of primer
only primary and secondary carbon atoms.
sekunder dan beri
Draw bond-line namafor
formulas menurut
all of 6the5IUPAC
4
isomers 2
3 of C 8H18 that have (a) methyl substituents, Review Problem
Draw bond-line formulas for all of the isomers of C8H118 that have (a) methyl substituents, Review Problem 4.
and (b) ethyl substituents.
3. Gambarkan
and isomer C8H18 model bond-line yang mempunyei (a) substituent metil
(b) ethyl substituents.
2,3,5-Trimethylhexane
dan (b) substituent etil. (not 2,4,5-trimethylhexane)

4. Beri nama struktur berikut ini

4.3C Nomenclature of Branched Alkyl Groups
Solved Problem 4.1
4.3C Nomenclature of Branched Alkyl Groups
Provide an IUPAC name In the
for Section 4.3Aalkane.
following you learned the names for the unbranched alkyl groups such as methyl,
In Section 4.3A you learned the names for the unbranched alkyl groups such as methyl,
ethyl, propyl, and butyl, groups derived by removing a terminal hydrogen from an alkane.
ethyl, propyl, and butyl, groups derived by removing a terminal hydrogen from an alkane.
For alkanes with more than two carbon atoms, more than one derived group is possible.
For alkanes with more than two carbon atoms, more than one derived group is possible.
Two groups can be derived from propane, for example; the propyl group is derived by
Two groups can be derived from propane, for example; the propyl group is derived by
removal of a terminal hydrogen, and the 1-methylethyl or isopropyl group is derived
removal of a terminal hydrogen, and the 1-methylethyl or isopropyl group is derived
by*Some
removal of a also
handbooks hydrogen from
list the groups the central
in order carbon:
of increasing size or complexity (i.e., methyl before ethyl).
by removal of a hydrogen from the central carbon:
5. TataAnnaman untuk gugus Alkil bercabang
alphabetical listing, however, is now by far the most widely used system.
Three-Carbon Groups
Three-Carbon Groups
CH CH CH
CH3CH32 CH2 3 3
Propane
Propane
CH CH CH –– CH3CHCH3
CH3CH32 CH2 2 ––2 CH3CHCH 3
––
––

Propyl Isopropyl
Propyl Isopropyl
Pr- i-Pr-
Pr- i-Pr-

1-Methylethyl
1-Methylethyl is the
is the systematic
systematic namename
for for
thisthis group;
group; isopropyl
isopropyl is aiscommon
a common name.name.
Systematic nomenclature for alkyl groups is similar to that for branched-chain alkanes, withwith
Systematic nomenclature for alkyl groups is similar to that for branched-chain alkanes,
the the provision
provision thatthat numbering
numbering always
always begins
begins at the
at the point
point where
where the the
groupgroup is attached
is attached to the
to the
main chain. There are four C 4
main chain. There are four C4 groups.groups.
_137-185hr.qxd 24-09-2009 11:22 Page 146
146
146 146 Chapter
Chapter 4 4Nomenclature
Nomenclature and
Chapter 4and Conformations
Nomenclature andof
Conformations of Alkanes
andand
Conformations
Alkanes of Cycloalkanes
Alkanes and Cycloalkanes
Cycloalkanes

Four-Carbon Four-Carbon Groups

Groups
Four-Carbon Groups
CH3 CH2 CH2 CH3
CHCH 3 CH
3 CH 2 CH
2 CH 2 CH
2 CH 3 3
Butane Butane
Butane
CH
CHCH
3
146 3 3

––
Chapter 4 Nomenclature and Conformations of Alkanes and Cycloalkanes

––
––
CH CH CH CH –– –– (CH3 )3 C––
CH CH CH CH ––3 2 2 2
CH CHCH –– CH3 CHCH2 CH3 CH2 CHCHCH3 CH2 CHCH3
(CH 3 C––
CH CH CH CH
3 2 2 ––
2 CH CHCH
3 ––
2 CH CH CHCH 3 (CH ) 3C)––

––
3 2 2 2 3 2 3 2 3 3 3

––
––
Four-Carbon
Butyl Groups Isobutyl sec-Butyl tert-Butyl (or t-Bu)
Butyl
Butyl Isobutyl
Isobutyl sec-Butyl
sec-Butyl tert-Butyl
tert-Butyl (or(or t-Bu)
t-Bu)
CH3 CH2 CH2 CH3
Butane
CH3
––
CH3 CH2 CH2 CH2 –– CH3 CHCH2 –– CH3 CH2 CHCH3 (CH3 )3 C––

––
Butyl Isobutyl sec-Butyl tert-Butyl (or t-Bu)

The following examples show how the names of these groups are employed:
Contoh-contoh berikut
The following menunjukkan
examples show how thebagaimana nama-nama
names of these groups are kelompok
employed: ini digunakan
The following examples show how the names of these groups are employed:

4-(1-Methylethyl)heptane or 4-isopropylheptane

4-(1-Methylethyl)heptane or 4-isopropylheptane
4-isopropylheptane
4-(1-Methylethyl)heptane or 4-isopropylheptane
The following examples show how the names of these groups are employed:

4-(1,1-Dimethylethyl)octane or 4-tert-butyloctane

common names isopropyl, isobutyl,

The 4-(1,1-Dimethylethyl)octane sec-butyl, and tert-butyl are approved by the
or 4-tert-butyloctane
4-(1,1-Dimethylethyl)octane
IUPAC for the unsubstituted or
groups,4-tert-butyloctane
and
4-(1-Methylethyl)heptane or 4-isopropylheptane they are still very frequently used. You should
The common names isopropyl,
learn these so4-tert-butyloctane
groupsisobutyl, sec-butyl,
well that and tert-butyl
you can recognize are approved
them any by the
way that they are written. In
TheIUPAC
common for names isopropyl,
deciding
the unsubstituted isobutyl,
on alphabetical
groups, andsec-butyl,
order
theyfor and
arethese tert-butyl
still groups you are approved
should
very frequently by should
disregard
used. You the
structure-defining
IUPAC
learn for thegroups
these unsubstituted
prefixes thatgroups,
so well youand
are written
that inthey
can areand
italics
recognize still veryany
separated
them frequently
from
waythe used.
theybyYou
thatname shouldThus
a hyphen.
are written. In tert-butyl
learn
nama-nama these groups
decidingumum so well
isopropyl, that
precedes ethyl,
on alphabetical you can
isobutyl,
order but recognize
forethyl
these sec-butyl,
precedes them
youdan
groupsisobutyl.*any way that
tert-butyl
should they are
disregarddisetujuiwritten.
olehIn IUPAC
structure-defining
deciding
prefixesonthat
alphabetical
There
are written order onefor
inisitalics theseseparated
five-carbon
and groups
groupyou
withshould
from an IUPAC
the namedisregard
approved
by structure-defining
a hyphen.common
Thus name that you should
tert-butyl
untuk kelompok
prefixes that are yang
also
written tidak
know:
in the
italics tersubstitusi.
2,2-dimethylpropyl
and separated
precedes ethyl, but 4-(1,1-Dimethylethyl)octane fromDalam
group,
the
ethyl precedes isobutyl.* or 4-tert-butyloctanenamemenentukan
commonly
by a called
hyphen. urutan
the
Thus abjad
neopentyl
tert-butyl untuk
group:
precedes ethyl, but ethyl precedes isobutyl.*
There is one five-carbon group with an IUPAC approved common name that you should
kelompok
The ini
common
There dengan
is one namesmengabaikan
isopropyl,
five-carbon group with prefiks.
isobutyl,
an IUPAC Jadi
sec-butyl, tert-butil
approved mendahului
tert-butyl
andcommon are that
name youetil,
approved bytetapi
the etil
should
also know: the 2,2-dimethylpropyl group, commonly called the neopentyl group:
IUPAC CH3and they are still very frequently used. You should
also know:for
mendahului thethe2,2-dimethylpropyl
isobutyl.unsubstituted groups,
Ada satu group, commonly
kelompok limacalled the neopentyl
karbon dengan group:
nama umum yang
learn these groups so well that CH3 you can recognize
9 C9CH 2 9 them any way that they are written. In
deciding
disetujui on alphabetical
IUPAC yangCHjuga
3
order for these
harus Anda groups you should
ketahui: disregard
kelompok structure-defining yang
2,2-dimetilpropil,
CH3
CH3 in italics and separated
prefixes that are written from the name by a hyphen. Thus tert-butyl
CH3 9 C 9neopentyl:
biasa precedes
disebut ethyl,
kelompokbut ethylCH 29
precedes isobutyl.*
CH3 9 C9CH2 9
There is one five-carbon
CH3 group with an2,2-Dimethylpropyl
IUPAC approved common name
or neopentyl that you should
group
also know: the 2,2-dimethylpropyl
CH3 group, commonly called the neopentyl group:
Review Problem 4.5 (a) In addition to the 2,2-dimethylpropyl (or neopentyl) group just given, there are seven
2,2-Dimethylpropyl
other five-carbon groups. Drawor neopentyl
bond-line groupfor their structures and give each struc-
formulas
CHits 2,2-Dimethylpropyl or neopentyl group
ture 3 systematic name. (b) Draw bond-line formulas and provide IUPAC names for all
Review Problem 4.5 (a) In addition toofthe
the 2,2-dimethylpropyl
isomers of C7 H16 . (or neopentyl) group just given, there are seven
CH3 9 C 9 CH2 9
Review Problem 4.5 (a)other five-carbon
In addition to thegroups. Draw bond-line
2,2-dimethylpropyl (orformulas
neopentyl)forgroup
their structures
just given,and giveare
there each struc-
seven
turefive-carbon
other its systematicCHname.
groups.
*The Draw(b) Draw
bond-line
abbreviations
3 i, s, bond-line
and t formulas
are formulas
for
sometimes their
used for and provide
structures
iso-, sec-, and IUPAC
and
tert-, give names
each
respectively. for
struc- all
tureofits
thesystematic
isomers ofname. . Draw bond-line formulas and provide IUPAC names for all
C7 H16(b)
of the isomers of C7 H16 .
2,2-Dimethylpropyl
2,2-Dimethylpropyl or neopentyl
or neopentyl group
group
*The abbreviations i, s, and t are sometimes used for iso-, sec-, and tert-, respectively.
*The abbreviations i, s, and t are sometimes used for iso-, sec-, and tert-, respectively.
Review Problem 4.5 (a) In addition to the 2,2-dimethylpropyl (or neopentyl) group just given, there are seven
other five-carbon groups. Draw bond-line formulas for their structures and give each struc-
ture its systematic name. (b) Draw bond-line formulas and provide IUPAC names for all
of the isomers of C7 H16 .

*The abbreviations i, s, and t are sometimes used for iso-, sec-, and tert-, respectively.
solom_c04_137-185hr.qxd 24-09-2009 11:22 Page 147

B. Klasifikasi Atom4.3
Hidrogen
IUPAC Nomenclature of Alkanes, Alkyl Halides, and Alcohols
Atom-atom hidrogen dari suatu alkana diklasifikasikan berdasarkan atom karbon
4.3D Classification of hidrogen
Hydrogen
yang melekat padanya.
4.3Atom
IUPAC yangAtoms
Nomenclature terikat
of pada
Alkanes, atom
Alkyl karbon
Halides, primer
and adalah
Alcohols
The hydrogen atoms of an alkane are classified on the basis of the carbon atom to which
atom
they hidrogen
are attached.primer (1°),atom
A hydrogen danattached
seterusnya. Senyawa
to a primary berikut,
carbon atom 2-metilbutane,
is a primary (1°)
4.3D Classification of Hydrogen Atoms
hydrogen atom, and so forth. The following compound, 2-methylbutane, has primary,
memiliki atom hidrogen primer, sekunder (2°), dan tersier (3°).
The hydrogen atoms of an alkane are classified on the basis of the carbon atom to which
secondary (2°), and tertiary (3°) hydrogen atoms:
they are attached. A hydrogen atom attached to a primary carbon atom is a primary (1°)
1 ! Hydrogen atoms
hydrogen atom, and so forth. The following compound, 2-methylbutane, has primary,
secondary (2°), and tertiary (3°) hydrogen atoms:
CH3
1 ! Hydrogen atoms
CH3 CH CH2 CH3
CH3
3! Hydrogen atom 2! Hydrogen atoms
CH3 CH CH2 CH3
On the other hand, 2,2-dimethylpropane, a compound that is often called neopentane, has
only primary hydrogen atoms:
3! Hydrogen atom 2! Hydrogen atoms
Pada 2,2-dimethylpropane, senyawa yang sering disebut neopentane, hanya
On the other hand, 2,2-dimethylpropane, a compound that is often called neopentane, has
memiliki atomhydrogen
only primary hidrogen primer:
atoms:
CH 3

H3C C CH3
CH3
CH3
H3C C CH3
2,2-Dimethylpropane
CH (neopentane)
3

2,2-Dimethylpropane
2,2-Dimethylpropane (neopentane)
4.3E Nomenclature of Alkyl(neopentane)
Halides
Alkanes bearing halogen substituents are named in the IUPAC substitutive system as
4.3E Nomenclature
haloalkanes:
C. Sifat-sifat Alkana of Alkyl Halides
CH 3CH2halogen
Cl CH3CH CH2F in the IUPAC
CHsubstitutive
3CHBrCH3 system as
AlkanaAlkanes bearing
memiliki substituents
afinitas yang rendahare terhadap
2named
senyawa lain, dan relatif inert.
Chloroethane
haloalkanes: 1-Fluoropropane 2-Bromopropane
Meskipun
! demikian,
When
CHtheCH alkana
Cl chaindapat
parent bereaksi
has both a halo
CH dengan
CHand
CHanFalkylsenyawa lain
substituentCH dalam
attached
CHBrCHto it,kondisi
number yang
3 2 3 2 2 3 3
the chain
sesuai. Alkana from the
Chloroethane
bereaksi end nearer
dengan the first substituent,
1-Fluoropropane
oksigen selama prosesregardless of whether it is halo oradalah
2-Bromopropane
pembakaran, produknya
alkyl. If two substituents are at equal distance from the end of the chain, then num-
! When the parent chain has both a halo and an alkyl substituent attached to it, number
karbondioksida
ber thedan
chainair
fromserta membebaskan
the end sejumlah
nearer the substituent that hasenergi dalam
alphabetical bentuk panas.
precedence:
the chain from the end nearer the first substituent, regardless of whether it is halo or
alkyl. If two
Contohnya metana substituents
(gas are at equal
alam) bereaksi distance
dengan from themenurut
oksigen end of thereaksi:
chain, then num-
ber the chain from the end nearer the substituent that has alphabetical precedence:
CH4 + 2O2 CO2 + 2H2O +890 kJ/mol
Cl Cl
Gambar 2.8. Reaksi
2-Chloro-3-methylpentane pembakaran metana
2-Chloro-4-methylpentane
Common names for many Cl simple haloalkanes are still widely
Cl used, however. In this com-
system, called functional class
mon nomenclature2-Chloro-3-methylpentane nomenclature, haloalkanes are named
2-Chloro-4-methylpentane
Alkanaas juga dapat bereaksi
alkyl halides. dengan
(The following Clare
names 2 ketika campuran
also accepted by thekeduanya
IUPAC.) diradiasi dengan
Common names for many simple haloalkanes are still widely used, however. In this com-
sinar ultraviolet. Tergantung
mon nomenclature padafunctional
system, called jumlah class
kedua nomenclature,
reaktan Cldan lama reaksi,
haloalkanes
Br produk
are named
as alkyl Cl
halides. (The following names are also accepted by the IUPAC.)
substitusi hidrogen alkanaBr Brmenghasilkan campuran produk klorinasi.
oleh atom klorida
EthylCl Isopropyl Cl Br
Contohnya, metana bereaksi
chloride Br
bromide
dengan tert-Butyl
Cl
bromideBr
Isobutyl
2 menghasilkan
chloride
Neopentyl
campuran produk yang terdiri
bromide
dari CH3Cl, CH Cl , CHCl
Ethyl 2 2 3 , dan CCltert-Butyl
Isopropyl 4 menurut reaksi:
Isobutyl Neopentyl
Draw bond-line formulas and give IUPAC substitutive names for all of thebromide
chloride bromide bromide chloride isomers of Review Problem
(a) C4H9Cl and (b) C5H11Br.
Draw bond-line formulas and give IUPAC substitutive names for all of the isomers of Review Problem
(a) C4H9Cl and (b) C5H11Br.
Kimia Organik I 75

CH4 Cl2 CH3Cl + HCl

Cl2
CH2Cl + HCL

Cl2
CHCl3 + HCl

Cl2
CCl4 + HCl

Gambar
Gambar 3.14.2.9. Reaksi
Reaksi metana
metana dengan
dengan Cl2 Cl2

Alkana memperlihatkan peningkatan titik didih dan titik lebur

Alkana memperlihatkan peningkatan titik didih dan titik lebur sesuai dengan
sesuai dengan peningkatan bobot molekulnya. Hal tersebut terjadi
peningkatan bobot molekulnya. Hal tersebut terjadi karena adanya energi dispersi yang
karena adanya energi dispersi yang lemah antar molekul. Energi
lemah antar molekul. Energi dispersi meningkat sesuai dengan peningkatan ukuran
dispersi meningkat sesuai dengan peningkatan ukuran molekul.
molekul. Akibatnya titik didih dan titik lebur meningkat dengan semakin panjangnya
Akibatnya titik didih dan titik lebur meningkat dengan semakin
rantai alkana.
panjangnya rantai alkana.

Faktor lain yang mempengaruhi titik didih alkana adalah

adanya rantai samping (cabang). Misalnya pentana, tanpa cabang
D. Sikloalkana: Isomer Cis-Trans dalam Sikloalkana
memiliki titik didih 36.10C, titik didih isopentana (2-metil butana)
Selain alkana dengan rantai terbuka, di alam juga terdapat alkana dalam bentuk cincin.
27.850C, sedangkan untuk neopentana (2,2-dimetilpropana) memiliki
Senyawa tersebut dinamakan sikloalkana atau senyawa alisiklik (alifatik siklik).
titik didih 9.50C. Adanya rantai samping membuat molekul memiliki
Apabila
78
cincin sikloalkana adalah –CH2 - maka senyawa tersebut memiliki rumus
St. Layli Prasojo, S.Farm., Apt.
luas permukaan yang lebih kecil, akibatnya memiliki energi dispersi
umum (CH2) n atau CnH2n .
rendah.

3. Gugus Alkil

Jika satu atom hidrogen dibebaskan dari sutau alkana maka

diperoleh struktur yang disebut alkil. Perlu dicatat bahwa gugus alkitl
siklopropana siklobutan siklopentana sikloheksana
tidak stabil jika berdiri
Gambar sendiri, alkil merupakan
3.17. Beberapa bagian dari molekul
contoh sikloalkana
78 St. Layli Prasojo, S.Farm., Apt.
Gambar 2.10. Beberapa contoh sikloalkana

Senyawa-senyawa
Senyawa-senyawa alosiklik
alosikliksiklopropana dengan
dengansiklobutan
cincin cincin
berbedaberbeda
siklopentana terdapatterdapat
sikloheksana berlebihan di alam.
Gambar 3.17. Beberapa contoh sikloalkana

berlebihanprostaglandin,
Contohnya, di alam. Contohnya, prostaglandin,
hormon yang hormonluasyang
mengatur secara bermacam fungsi
Senyawa-senyawa alosiklik dengan cincin berbeda terdapat
mengaturmanusia
fisiologis secara luas bermacam
termasuk fungsi
berlebihan diagregasi
alam. fisiologis
Contohnya, prostaglandin, manusia
platelet darah,
hormon yang termasuk
dilatasi bronkus, dan
mengatur secara luas bermacam fungsi fisiologis manusia termasuk
agregasi platelet
penghambatan darah,
sekresi dilatasi
agregasi plateletbronkus,
gastrin, memiliki cincin dandan
darah, dilatasi bronkus, penghambatan
karbon lima anggota
penghambatan sekresi sekresi
(siklopenatana).
gastrin, memiliki cincin karbon lima anggota (siklopenatana).
gastrin, memiliki cincin karbon lima anggota (siklopenatana).
O
O

OH O
O
H
H
H
OH OH

Gambar 3.18. Struktur prostaglandin E1 OH

Gambar 3.18.
Steroid, Struktur
seperti kortison, prostaglandin
mengandung cincin-cincin yang terikat E1
satu sama lain, tiga cincin dengan enam anggota (sikloheksana) dan
satu cincin lima anggota (siklopentana).

H
H
OH OH
Steroid, seperti kortison, mengandung cincin-cincin yang terikat satu sama lain, tiga
cincin dengan Kimia
enam anggota
Organik I (sikloheksana) dan satu cincin 79
lima anggota
79
(siklopentana). Kimia Organik I

HOH2C
HOH2C
O
O
CH3
CH3

O
O
OH
OH
CH3 H
CH3 H

H H

O H H

Gambar 3.19. Struktur kortison

Gambar
O 3.19. Struktur kortison
1. Penamaan sikloalkana Gambar 3.19. Struktur kortison
1. Penamaan sikloalkana

a. Temukan rantai utama a. Temukan rantai utama

Hitung jumlah atom karbon penyusun cincin dan jumlah karbon

Sikloalkana dengan hanya
1. Penamaan satu cincin
sikloalkana
dalam substituennya.
dinamai dengan menambahkan awalan siklo
Jika jumlah karbon dalam cincin sama dengan

ke nama-nama alkana yang memiliki

rantai utamajumlah atom karbon yang sama. Hitung
jumlah karbon dalam substrituen, maka senyawa tersebut diberi nama
a. Temukan
sebagai sikloalkana tersubstitusi alkil. Akan tetapi jika jumlah karbon
jumlah atom karbon penyusun
dalam
Hitung jumlah cincin
substituen atom
lebih banyakdan
karbon jumlah
dari penyusun
pada karbon
karbon dalam
cincin dandalam
cincin jumlahsubstituennya.
maka karbon Jika
senyawa tersebut diberi nama sebagai alkana tersubstitusi sikloalkil.
jumlah karbon dalam
dalam cincin sama
substituennya. dengankarbon
Jika jumlah jumlah karbon
dalam cincindalam substrituen, maka
sama dengan
jumlah karbon dalam CH
senyawa tersebut diberi nama substrituen, maka senyawa
sebagai sikloalkana
3
CH CHtersebut
CH CH diberi nama
tersubstitusi alkil. Akan tetapi
2 2 2 3

sebagai sikloalkana tersubstitusi alkil. Akan tetapi jika jumlah karbon

jika jumlah karbon dalam substituen lebih banyak
Metilsiklopentana dari pada karbon dalam cincin
1-siklopropilbutana
dalam substituen lebih banyak dari pada karbon dalam cincin maka
maka senyawa tersebut diberi nama sebagai alkana tersubstitusi sikloalkil.
Gambar 3.20. Contoh penamaan suatu sikloalkana
senyawa tersebut diberi nama sebagai alkana tersubstitusi sikloalkil.

CH3 CH2CH2CH2CH3

Metilsiklopentana
Gambar 3.20. 1-siklopropilbutana
Contoh penamaan suatu sikloalkana
Gambar 3.20. Contoh penamaan suatu sikloalkana

b. Jumlah substituen dan beri nama

Sikloalkana tersubstitusi alkil atau halogen, mulailah penomoran dari atom karbon
yang mengikat substituen tersebut. Untuk substituen kedua dan seterusnya diberi
nomor sekecil mungkin.
 b. Jumlah substituen dan beri nama

Sikloalkana tersubstitusi alkil atau halogen, mulailah penomoran

dari atom karbon yang mengikat substituen tersebut. Untuk substituen
kedua dan seterusnya diberi nomor sekecil mungkin.

CH3 Br
CH3
1 1
6 2 2 6
2 CH2CH3
3
1 5
3
5 H3C 3 CH3
4 CH3 4 5 C 4
H2

1,3-dimetilsikloheksana 1-etil-2-metilsiklopentana 1-bromo-3-etil-5-metilsikloheksana

Cl

1 CH3
CH3 2
5
2
1
4 3
Br
CH2CH3
1-kloro-3-etil-2-metilsiklopentana 1-bromo-2-metilsiklobutana

Gambar 3.21. Contoh penamaan beberapa sikloalkana tersubstitusi

Gambar 3.21. Contoh penamaan beberapa sikloalkana tersubstitusi

2. Isomer cis-trans dalam sikloalkana

2. Sifat fisik sikloalkana
Dalam beberapa hal, sifat kimia sikloalkana mirip dengan
Sikloalkana alkana
juga memiliki titikterbuka).
asikloik (rantai lebur yang jauhsama-sama
Keduanya lebih tinggi daripada
non polar dan alkana rantai
c04_137-185hr.qxd terbuka.
24-09-2009 11:22Rapatan
Page dalam
156
cenderung inert.satu
Akangolongan, alkana
tetapi terdapat dan mendasar.
perbedaan sikloalkana adalah
Pertama, yang paling
sikloalkana
padat dari semua kurang fleksibel
kelompok senyawadibandingkan
organik.dengan
Semuaalkana rantaidan sikloalkana
alkana
memiliki kerapatan yang kurang dari 1,00 g mL 1 (kerapatan air pada suhu 4 ° C).
Akibatnya, minyak bumi (campuran hidrokarbon yang kaya akan alkana) terapung

156 diatas air. 4

Chapter Nomenclature and Conformations of Alkanes and Cycloalkanes

abnormally high melting points. The compound 2,2,3,3-tetramethylbutane, for example,

Kelarutan
melts atAlkana
100.7°C.dan sikloalkana
Its boiling point is hampir sepenuhnya
only six degrees higher,tidak larut dalam air karena
106.3°C:
polaritasnya yang sangat rendah
CH3 CHdan
3 ketidak mampuan alkane untuk membentuk
CH3 cair
ikatan hidrogen. Alkana 9C9 dan sikloalkana
9C9CH 3 larut dalam satu sama lain, dan alkane
CH3 dalam
dan sikloalkana umumnya larut CH3 pelarut dengan polaritas rendah. Pelarut yang
2,2,3,3-Tetramethylbutane
baik untuk alkane dan sikloalkana adalah benzena, karbon tetraklorida, kloroform,
Cycloalkanes also have much higher melting points than their open-chain counterparts
dan (Table
hidrokarbon
4.4).
lainnya. Berikut beberapa sifat fisik sikloalkana

TABLE 4.4 Physical Constants of Cycloalkanes

Number Refractive
of Carbon bp (°C) mp Density, Index
Atoms Name (1 atm) (°C) d20(g mL-1) 20
(nD )
3 Cyclopropane !33 !126.6 — —
4 Cyclobutane 13 !90 — 1.4260
5 Cyclopentane 49 !94 0.751 1.4064
6 Cyclohexane 81 6.5 0.779 1.4266
7 Cycloheptane 118.5 !12 0.811 1.4449
8 Cyclooctane 149 13.5 0.834 —

Density As a class, the alkanes and cycloalkanes are the least dense of all groups
of organic compounds. All alkanes and cycloalkanes have densities considerably less than
1.00 g mL!1 (the density of water at 4°C). As a result, petroleum (a mixture of hydrocar-
bons rich in alkanes) floats on water.

Solubility Alkanes and cycloalkanes are almost totally insoluble in water because of
their very low polarity and their inability to form hydrogen bonds. Liquid alkanes and
cycloalkanes are soluble in one another, and they generally dissolve in solvents of low
polarity. Good solvents for them are benzene, carbon tetrachloride, chloroform, and other
 Two groups bonded by only a single bond can undergo rotation about that bond with respect
to each other.
! The temporary molecular shapes that result from such a rotation are called con-
formations of the molecule.
! Each possible structure is called a conformer.
E. Konformasi senyawa
! An analysis rantai
of the energy terbuka
changes that occur as a molecule undergoes rotations
about single bonds is called a conformational analysis.
Dalam senyawa rantai terbuka gugus-gugus yang terkait oleh ikatan sigma berotasi
ikatan itu. Oleh karena itu atom-atom dalam suatu molekul rantai terbuka dapat
memiliki tak terhingga
4.8A Newman banyak posisi
Projections anddidalam
How ruang relative
to Draw satu terhadap yang
Them
Helpful Hi
lain.When
Memang etana sebuahanalysis,
we do conformational molekulwekecil,
will findtetapi etanatypes
that certain dapat
of memiliki penataan
structural formu-
Learn to draw Newman
las are especially convenient to use. One of these types is called a Newman projection and sawhorse formul
dalam ruangand
formula secara berlain
another type islainan, penataan
a sawhorse manaSawhorse
formula. disebut formulas
konformasi.
are much like handheld molecular m
dash–wedge three-dimensional formulas we have used so far. In conformational analyses, compare them with you

we will make substantial use of Newman projections.

Newman projection Sawhorse formula

formula

To write a Newman projection formula:

Untuk menemukan konformasi akan digunakan tiga jenis rumus yaitu : Rumus
! We imagine ourselves taking a view from one atom (usually a carbon) directly
dimensional,
along a rumus bolaaxisdan
selected bond to thepasak dan
next atom (alsoproyeksi Newman
usually a carbon atom). (disarankan
untukmenggunakan model
! The front carbon and itsmolekul dalam
other bonds memperbandingkan
are represented as . konformasi yang
berlainan).
! TheSuatu rumusandbola
back carbon dan pasak
its bonds dan rumus
are represented as dimensional
. adalah refresentasi
tiga dimensi dari model molekul suatu senyawa. Suatu proyeksi Newman adalah
pandangan ujung ke ujung dari dua atom karbon saja dalam molekul itu. Ikatan
solom_c04_137-185hr.qxd 24-09-2009 11:22 Page 158

yang menghubungkan kedua atom ini tersembunyi. Ketga ikatan dari karbon depan
Nampak menunju ke pusat proyeksi, dan ketiga ikatan dari karbon belakang hanya
Nampak
158 sebagian. Chapter 4 Nomenclature and Conformations of Alkanes and Cycloalkanes

The dihedral
angle (!) between
these hydrogens
is 180 ".
! = 60 °
H
H H H!
! H H
H H
H H H
H

(a) (b) (c)

Figure 4.4 (a) The staggered conformation of ethane. (b) The Newman projection formula for the

Gambar 4.4 (a) Konformasi etana . (B) Rumus proyeksi Newman untuk konformasi
staggered conformation. (c) The dihedral angle between these hydrogen atoms is 60°.

staggered (c) Sudut dihedral antara atom-atom hidrogen ini adalah 60 °.

In Figs. 4.4a,b we show ball-and-stick models and a Newman projection formula for the
staggered conformation of ethane. The staggered conformation of a molecule is that con-
formation where the dihedral angle between the bonds at each of the carbon–carbon bonds
is 180° and where atoms or groups bonded to carbons at each end of a carbon–carbon bond
Karena adnya rotasi mengelilingi ikatan sigma, maka suatu molekul dapat memiliki
are as far apart as possible. The 180° dihedral angle in the staggered conformation of ethane
is indicated in Fig. 4.4b.
konformasi berapa saja. Tetapi konformasi- konformasi tertentu lebih stabil
The eclipsed conformation of ethane is shown in Fig. 4.5 using ball-and-stick models
and a Newman projection. In an eclipsed conformation the atoms bonded to carbons at
each end of a carbon–carbon bond are directly opposed to one another. The dihedral angle
daripada yang lain. Konformasi yang disukai disebut conformer . conformer
between them is 0°.
The dihedral

bukanlah isomer karena dapat saling dipertukarkan,angle

conformer-
these
(!) between
hydrogens conformer adalah
is 0 ". !

sekedar orientasi ruang yang berbeda-beda dari molekul yang

H H itu-itu juga.

Figure 4.5 (a) The eclipsed H H

conformation of ethane. H H
(b) The Newman projection
formula for the eclipsed
conformation. (a) (b)

4.8B How to Do a Conformational Analysis

Now let us consider a conformational analysis of ethane. Clearly, infinitesimally small
changes in the dihedral angle between C 9 H bonds at each end of ethane could lead to an
infinite number of conformations, including, of course, the staggered and eclipsed confor-
mations. These different conformations are not all of equal stability, however, and it is
known that the staggered conformation of ethane is the most stable conformation (i.e., it
is the conformation of lowest potential energy). The fundamental reason for this has recently
 H H H
H

(a) (b) (c)

Figure 4.4 (a) The staggered conformation of ethane. (b) The Newman projection formula for the
staggered conformation. (c) The dihedral angle between these hydrogen atoms is 60°.

Dalam rumus etana dan 3-kloro-1-propanol, telah diperagakan konfomer goyang,

dalamana
In Figs.atom-atom hydrogen
4.4a,b we show atau gugus-gugus
ball-and-stick terpisahprojection
models and a Newman sejauh mungkin satu
formula for thedari
solom_c04_137-185hr.qxd staggered conformation
24-09-2009 11:22 Page of ethane.
159 The staggered conformation of a molecule is that con-
yangformation
lain karena
whereikatan C-C angle
the dihedral dapatbetween
berotasi,
the maka
bonds atatom-atom hydrogen dapat
each of the carbon–carbon bondsjuga
is 180° and where atoms or groups bonded to carbons at each end of a carbon–carbon bond
saling menutup (eclipsed), atau sedapat mungkin berdekatan satu dibelakang yang
are as far apart as possible. The 180° dihedral angle in the staggered conformation of ethane
lain is(konformasi
indicated in Fig. 4.4b. Agar lebih jelas digambarkan berikut ini dalam keadaan
eclipsed).
The eclipsed conformation of ethane is shown in Fig. 4.5 using ball-and-stick models
bukanandeclipsed
a Newman benar-benar.
projection. In an eclipsed conformation the atoms bonded to carbons at
each end of a carbon–carbon bond are directly opposed to one another. The dihedral angle
between them is 0°.
4.8 Sigma Bonds and Bond Rotation 159

later chapters that it is a general stabilizing effect). Figure 4.6 a shows the The dihedral over-
favorable
angle (!) between
lap of s and s* in ethane by color coding of the orbital phases. these hydrogens
If we now consider the eclipsed conformation of ethane (Fig. 4.6 b), where is 0 "the
. C! 9H
bonds at each carbon are directly opposed to each other, we see that the bonding s C 9 H
orbital at one carbon does not overlap to as great an extent with the adjacent antibonding H H
orbital as in the staggered conformation. The possibility for hyperconjugation is diminished,
and therefore the potential energy of this conformation is higher.
Figure 4.5 (a) The eclipsed H H
conformation of ethane.The s– s* interactions in ethane are present in more complicated moleculesH as well.H (a)
(b) The Newman projection
However, where atoms and groups larger than hydrogen are involved in a conformational
formula for the eclipsed
conformation.
analysis, such as our example in Section (a)4.9, it is likely that repulsion of the(b)
electron clouds
involved in the bonding of those groups increases in importance as the cause of the stag-
gered conformation being most stable.
Rotasi mengelilingi ikatan sigma sering kali disebut rotasi bebas, tetapi sebenarnya
The energy difference between the conformations of ethane can be represented graphi-
4.8B
potential
cally in a rotasi Howdiagram,
inienergy
tidaklah tobenar-benar
DoasashownConformational
in Figure
bebas. Analysis
4.7. In ethane
konformasi the energy
eclipsed differ-
(dari) etana kira-kira 12
ence between the staggered and eclipsed conformations is about 12 kJ mol!1. This small
Now-1let us consider a conformational analysis of ethane. Clearly, infinitesimally small
barrier to KJ mol
rotation kurang
is called stabil (lebih
the torsional barrier tinggi
of theenerginya) dibandingkan
single bond. Because dengan konfomer
of this bar-
changes in the dihedral angle between C 9 H bonds at each end of ethane could lead to an
rier, some molecules will wag back and forth with their atoms in staggered or nearly stag-
infinitekarena
goyang, numberadanya
of conformations,
tolak-menolakincluding,antara
of course, the staggered and ikatan
electron-elektron eclipseddan confor-atom- (b)
gered conformations, while others with slightly more energy will rotate through an eclipsed
mations. These different conformations are not all of equal stability, however, and it is
conformationatomto another
hydrogen. staggered conformation. At anykonformasi
given moment, unless the ketemper- Figure eclipsed
4.6 The bonding C 9 H
known that the Untuk
staggeredberotasi
conformationdari of ethane is thegoyang
most stable konformasi
conformation (i.e., it
ature is extremely low (!250°C), most ethane molecules will have enough energy to orbital is the orbital where one
is the conformation of lowest potential energy). The -1 fundamental reason for this has recently
lobe of a single phase
undergo bond1mol, molekul
rotation
come to light.etana memerlukan 12 KJ mol .
from one conformation to another.
(represented by one color)
Quantum mechanical calculations by L. Goodman and V. T. Pophristic (Rutgers
envelops the C 9 H atoms. The
University) have shown that the greater stability of the staggered conformation adjacent unfilled antibonding
in ethane
H H orbital is the orbital where the
over the eclipsed conformation is mainly due to favorable overlap between sigma (s) bond-
phase changes between the
ing orbitals from the C 9 H bonds at one carbon and unfilled antibonding sigma (s*) carbon orbitals
and its hydrogen atom.
H H
at the adjacent carbon. In ethane’s staggered H conformation,
H electrons from a given bond- conformation
The staggered
ing C 9 H orbital on one carbon can be shared with an unfilled s* orbital at the
Eclipsed adjacent
of ethane (a) has greater overlap
carbon. This phenomenon of electron delocalization (via orbital overlap) from a between filled bond-the bonding C 9 H
ing orbital to an adjacent unfilled orbital is called hyperconjugation (and we orbital shall see and the adjacent
in
antibonding orbital than in the
Potential energy

eclipsed conformation (b).

12 kJ mol–1 The orbital overlap shown in (a)
leads to the lower potential
energy of the staggered
conformation of ethane.
H H
H H H H

H H H H
Figure 4.7 Potential energy H H
changes that accompany Staggered Staggered
rotation of groups about the
Rotation
carbon–carbon bond of ethane.

What does all this mean about ethane? We can answer this question in two different ways. The idea that certain
If we consider a single molecule of ethane, we can say, for example, that it will spend most conformations of
molecules are favored originates
of its time in the lowest energy, staggered conformation, or in a conformation very close
from the work of J.H. van’t Hoff.
to being staggered. Many times every second, however, it will acquire enough energy He was also winner of the first
through collisions with other molecules to surmount the torsional barrier and it will rotate Nobel Prize in Chemistry (1901)
through an eclipsed conformation. If we speak in terms of a large number of ethane mol- for his work in chemical kinetics.
ecules (a more realistic situation), we can say that at any given moment most of the
molecules will be in staggered or nearly staggered conformations.
If we consider more highly substituted ethanes such as GCH2CH2G (where G is a
 H H H H
G H
Conformers like these cannot be
isolated except at extremely
low temperatures.

Butana seperti etana dapat memiliki konformasi eclipsed erbeda dan goyang. Dalam
butana terdapat 2 gugus metil yang relative besar, terikat pada dua karbon pusat.
Dipandang dari kedua karbon pusat, hadirnya gugus-gugus metil ini menyebabkan
9 Conformational Analysis of Butane
terjadinya 2 macam konformasi goyang, yang berbeda dalam hal posisi.
If we consider rotation about the C2 9 C3 bond of butane, we find that there are six impor-
: tant conformers, shown as I–VI below:
CH3 H CH3 CH3
H H CH3 H
H H
H H CH3 H H H
CH3 H
Butane
I II III
An anti An eclipsed A gauche
conformation conformation conformation
Helpful Hint
u should build a molecular H3 C CH3 CH3 H CH3
odel of butane and examine its H CH3
solom_c04_137-185hr.qxd 24-09-2009 11:22 Page 161
rious conformations as we
scuss their relative potential H H H H
ergies. H H H H H CH3
H
IV V VI
An eclipsed A gauche An eclipsed
conformation conformation conformation
4.9 Conformational Analysis of Butane
The anti conformation (I) does not have torsional strain from steric hindrance because
the groups are staggered and the methyl groups are far apart. The anti conformation is the
most stable. The methyl groups in the gauche H3C CH3conformations III and V are close enough
to each other that the dispersion forces between them are repulsive; the electron clouds of
H CH
the two groups are soH CH close
3 that they repelH each other.
H This repulsion causes
3 the gauche con-
H !1 H
formations to have approximately 3.8 kJ Eclipsed mol IV more energy than the anti conformation.
H H H H
The eclipsedH3conformations
C H (II, IV, and VI) represent energy H maximaCH3 in the potential
energy diagram (Fig. 4.8). Eclipsed conformations II and VI Eclipsed
Eclipsed II
have VIrepulsive dispersion
Potential energy

forces arising from the eclipsed methyl groups–1and hydrogen atoms. Eclipsed conforma-
19 kJ mol
tion IV has the greatest energy –1
of all because of the added large repulsive dispersion forces
16 kJ mol 16 kJ mol–1
between the eclipsed methyl groups as compared to II and VI.
–1 –1
Although the barriers to rotation3.8 kJ molin 3.8 kJ mol
a butane molecule are larger than those of an ethane
molecule CH
(Section
3 4.8), they are still CH3 far too small to permitCH3 isolation of the gaucheCH3 and anti

conformations
H H
at normal Htemperatures.
3C H
Only at extremely
H
low temperatures
CH3 H
would
H
the
molecules
H have
H insufficient energies
H Hto surmount these
H barriers.
H H H
CH3 H H CH3
Anti I Ga uche III Ga uche V Anti I
Figure 4.8 Energy ch
0° 60° 120° 180° 240° 300° 360° that arise from rotation
Rotation the C2 9 C3 bond of bu

Gugus-gugus metal
We saw earlier ini satu
(Section terhadap
2.16C) yang lain.
that dispersion konformasi
forces goyang
can be attractive. dalam
Here, how- mana
ever, we find that they can also be repulsive, leading to steric hindrance. Whether
gugus metil terpisah
dispersion sejauh
interactions lead tomungkin
attraction disebut konfomer
or to repulsion anti.
depends on konformasi
the distance goyang
that separates the two groups. As two nonpolar groups are brought closer and
dimana gugus -gugus berdekatan , disebut konfomer gauche.
closer together, the first effect is one in which a momentarily unsymmetrical
distribution of electrons in one group induces an opposite polarity in the other.
The opposite charges induced in those portions of the two groups that are in closest
proximity lead to attraction between them. This attraction increases to a maximum
as the internuclear distance of the two groups decreases. The internuclear distance
at which the attractive force is at a maximum is equal to the sum of what are called
the van der Waals radii of the two groups. The van der Waals radius of a group is,
in effect, a measure of its size. If the two groups are brought still closer—closer
than the sum of their van der Waals radii—the interaction between them becomes
Makin besar gugus-gugus yang terikat pada 2 atom karbon, akan makin besar.
Selisih energi antara konformasi- konformasi molekul itu diperlukan lebih baniyak.
Energi untuk mendorong 2 gugus besar agar berdekatan daripada gugus kecil. Etana
hanya membutuhkan 12 KJ mol- utk berotasi dari konformasi goyang ke eclipsed
sedangkan butana memerlukan 16 - 19 KJ mol- untuk konformasi anti ke
konformasi dimana gugus-gugus metil eclipsed. Hubungan untuk rotasi penuh
mengelilingi ikatan karbon 2-karbon 3 butana.

F. Isomer cis-trans dalam sikloalkana

Beberapa sifat kimia sikloalkana mirip dengan alkana rantai terbuka. Keduanya
sama-sama non Kimia
polar dan cenderung inert. Akan tetapi terdapat
Organik I 81
perbedaan
mendasar. Pertama, sikloalkana kurang fleksibel dibandingkan dengan alkana
terbuka. Ikatan tunggal (ikatan sigma) pada alkana asliklik dapat
rantai terbuka. Ikatan tunggal (ikatan sigma) pada alkana asliklik dapat berputar.
berputar.
Kimia Organik I 81
H H

C Ikatan tunggal (ikatan sigma) pada alkana asliklik dapat

terbuka.
C
H H H
Hberputar. H H

HH
C H
C
H
C C H
H H H
H H H H

H
Gambar C Perputaran ikatan tunggal karbon-karbon
3.22. C dalam
Gambar 3.22. Perputaran ikatan tunggal
etana
karbon-karbon
H
H dalam etana
H
Pada sikloalkana, ikatan yang terbentuk kurang bebas untuk berputar.
Gambar 3.22. Perputaran ikatan tunggal karbon-karbon dalam
Misalnya siklopentana, bentuknya
etana adalah segitiga rigid dan planar.
Pada sikloalkana, ikatan yang terbentuk kurang bebas untuk berputar. Misalnya
Putaran pada ikatan
Pada sikloalkana, ikatankarbon-karbon tidak bebas
yang terbentuk kurang mungkin terjadi tanpa
untuk berputar.
siklopentana, bentuknya
merusak adalah
siklopentana,segitiga
cincin.
Misalnya rigid
bentuknya adalah dan
segitiga rigid planar.
dan planar. Putaran pada ikatan

karbon-karbon tidakPutaran
mungkinpada ikatan karbon-karbon tidak mungkin terjadi tanpa
terjadi
H tanpa merusak cincin.
merusak cincin.

H C H

H H
H C C
HC H
C
H
C
H H

H
Gambar 3.23. Struktur siklopropana.
Gambar
Tidak mungkin 3.23. Struktur
terjadi siklopropana.
perputaran tanpa memecah cincin
Gambar 3.23.
Tidak mungkin terjadiStruktur siklopropana.
perputaran tanpa memecah cincin

Tidak mungkin terjadi perputaran tanpa memecah cincin. Oleh karena strukturnya
yang siklik, sikloalkana memiliki dua sisi yaitu sisi atas dan bawah. Hal ini
memungkinkan sikloheksana memiliki kemungkinan isomerisme berdasarkan letak
substituennya. Contohnya, ada dua bentuk isomer dari 1,2-dimetilsiklopropana.
 82 St. Layli Prasojo, S.Farm., Apt.

Oleh karena strukturnya yang siklik, sikloalkana memiliki dua

sisi yaitu sisi atas dan bawah. Hal ini memungkinakn sikloheksana
memiliki kemungkinan isomerisme berdasarkan letak substituennya.
Pertama dengan dua Contohnya,
gugus metil
ada duapada
bentuk sisi
isomeryang sama, kedua dengan gugus metil
dari 1,2-dimetilsiklopropana.
Pertama dengan dua gugus metil pada sisi yang sama, kedua dengan
pada posisi yang berlawanan. Kedua bentuk isomer merupakan molekul yang stabil,
gugus metil pada posisi yang berlawanan. Kedua bentuk isomer
dan dapat dikonfersi merupakan
dari bentuk
molekulsatu ke bentuk
yang stabil, lainnya
dan dapat dikonfersi dari tanpa memecah cincin atau
bentuk satu
ke bentuk lainnya tanpa memecah cincin atau tanpa membentuk
tanpa membentuk ikatan baru.
ikatan baru.

H3C H
H3C CH3

H CH3
H H

Gambar 3.24. Isomer 1,2-dimetilsiklopropana

Gambar 3.24. Isomer 1,2-dimetilsiklopropana
Tidak seperti isomer konstitusional seperti pada butana dan

Tidak seperti isomerisobutana

konstitusional
dimana terdapat seperti
perbedaan pada butana atom-
urutan penempatan dan isobutana dimana
atomnya. Kedua isomer 1,2-dimetilsiklopropana memiliki tempat
terdapat perbedaan ikatan
urutan penempatan
yang sama, atomatomnya.
tetapi berbeda pada Kedua isomer 1,2-
posisi atom-atomnya.
Semuawa senyawa yang memiliki posisi ikatan atom yang sama tetapi
dimetilsiklopropana memiliki tempat ikatan yang sama, tetapi berbeda pada posisi
berbeda pada orientasi tiga dimensinya disebut stereoisomer.

atom-atomnya. Semuawa senyawa yang memiliki posisi ikatan atom yang sama
tetapi berbeda pada orientasi tiga dimensinya disebut stereoisomer.
Kimia Organik I 83
Kimia Organik I 83

Isomer konstitusional CH3

Isomer konstitusional
Isomer konstitusional CH3
berbeda pada ikatan H H H
berbeda pada ikatan
berbeda pada ikatan
atom-atomnya H3CH C CC CH dan HC H2 2 H2 2 H2 2
C C C C C CH CH3
atom-atomnya CH3 dan 3
H3C C
atom-atomnya 3 HH 3 3

StetreoisomerStetreoisomer
posisi
Stetreoisomer H3H
C3C CH
CH33
H3C
H3C H H
posisi
ikatan sama tapi posisi
ikatanikatan
berbeda samasama
tapi berbeda
tapi berbeda padapada
pada posisi posisitigatiga dimensinya H
H CH3
CH3
posisi tiga dimensinya H
H H
H
dimensinya
Gambar 3.25. Isomer konstitusional dan stereoisomer
Gambar
Gambar 3.25.3.25. Isomerkonstitusional
Isomer konstitusional dandan
stereoisomer
stereoisomer
1,2-dimetilsiklopropana merupakan salah satu contoh stereoisomer
1,2-dimetilsiklopropana merupakan salah satu contoh stereoisomer
yang disebut isomer cis-trans. Awalan cis- berarti terletak pada sisi
yang yang
disebut isomer cis-trans. Awalan cis- berarti terletak pada sisi
1,2-dimetilsiklopropana merupakan salah satu contoh stereoisomer yang disebut
sama, sedangkan trans- untuk menyatakan posisi yang
yang sama, sedangkan trans- untuk menyatakan posisi yang
isomer cis-trans.berlawanan.
Awalan cis- berarti terletak pada sisi yang sama, sedangkan trans-
berlawanan.
untuk menyatakan posisi yang berlawanan.

G. Sintesis Alkana dan Sikloalkana

Alkena dan alkuna bereaksi dengan hidrogen dengan adanya katalis logam seperti
nikel, paladium, dan platinum untuk menghasilkan alkana. Reaksi umum adalah
reaksi di mana atom-atom molekul hidrogen ditambahkan ke setiap atom karbon-
karbon, ikatan rangkap dua atau rangkap tiga dari alkena atau alkuna. Ini akan
mengubah alkena atau alkuna menjadi alkana:
 of the hydrogen molecule add to each atom of the carbon–carbon double or triple bond of
178 Chapter 4 Nomenclature and Conformations of Alkanes and Cycloalkanes
the alkene or alkyne. This converts the alkene or alkyne to an alkane:
General Reaction
of the hydrogen molecule add to each atom of the carbon–carbon double or triple bond of
the alkene or alkyne. This converts the alkene or alkyne to an alkane:
H Pt,: Pd, or Ni
ReaksiC Umum C H C Pt H C H
!
General Reaction ! 2 H2
solvent, solvent,
C H pressure C H C pressure H C H
C H Pt, Pd, or Ni C H C Pt H C H
Alkene ! Alkane Alkyne ! 2 H2 Alkane
solvent, solvent,
C H pressure C H C pressure H C H
The reaction is usually carried out by dissolving the alkene or alkyne in a solvent such
as ethyl alcohol (C
Alkene 2 5
H OH ), adding the metal
Alkane
catalyst, and
Alkyne
then exposing the mixture
Alkane
to
hydrogen gas under pressure in a special apparatus. One molar equivalent of hydrogen is
Thetoreaction
required reduce anis alkene
usuallytocarried out by
an alkane. dissolving
Two the alkeneare
molar equivalents or required
alkyne intoa reduce
solventansuch
as ethyl
alkyne. (Wealcohol (C2H5the
shall discuss ), adding theofmetal
OHmechanism catalyst,inand
this reaction then 7.)
Chapter exposing the mixture to
hydrogen: gas under pressure in a special apparatus. One molar equivalent of hydrogen is
Contoh
Specific
required to Examples
reduce an alkene to an alkane. Two molar equivalents are required to reduce an
alkyne. (We shall discuss the mechanism of this reaction in Chapter 7.)
CH3 CH3
Specific Examples Ni
CH3 9C"CH2 ! H2 CH3 9C9CH2
EtOH
CH3 (25°C, 50 atm) H CH
H3
2-Methylpropene Ni Isobutane
CH3 9C"CH2 ! H2 CH 9C9CH
3 2
EtOH
(25°C, 50 atm) H H
Pd
! H2
2-Methylpropene Isobutane
EtOH
(25°C, 1 atm)
Cyclohexene Pd Cyclohexane
! H2
EtOH
O (25°C, 1 atm)
Pd O
! 2 H2
Cyclohexene Cyclohexane
ethyl acetate

Cyclononyn-6-one Pd Cyclononanone
O
O ! 2 H2
ethyl acetate

Cyclononyn-6-one Cyclononanone
Review Problem 4.19 Show the reactions involved for hydrogenation of all the alkenes and alkynes that would
Referensi
yield :
2-methylbutane.

Review Problem 4.19 1.Show

Solomons, T.W.G
the reactions and.
involved forFryhle, C.B.,2011,
hydrogenation Organic
of all the alkenes Chemistry, Tenth
and alkynes that Edition,
would
yield 2-methylbutane.
John Wiley & Sons, Inc., United States of America.
17 How to Gain Structural Information from Molecular Formulas and the
2. Prasojo, S.L., Kimia Organik I, Tinggi Ilmu Farmasi “Yayasan Pharmasi”
dex of Hydrogen Deficiency
Semarang.
4.17 How to Gain Structural Information from Molecular Formulas and the
A chemist working with an unknown compound can obtain considerable information
Index of Hydrogenabout
Deficiency
3. its
Wilbraham, A.C
structure from and Matta,molecular
the compound’s M.S, (terjemahan
formula and itsSuminar Achmadi), 1992,
index of hydrogen
deficiency (IHD).
Pengantar
A chemist Kimia
working with Organik
an unknowndan Hayati,
compound Penerbit
can obtain IYB, Bandung.information
considerable
Theits
about
! index of hydrogen
structure from thedeficiency
compound’s (IHD)* is defined
molecular as theand
formula difference
its index in of
thehydrogen
num-
4. ber
Fessenden,
of pairs
R.J. dan Fessenden, J.S., 1986, Organic Chemistry,
of hydrogen atoms between the compound under study and an acyclic
3rd edition
deficiency (IHD).
alkane having the same number of carbons.
! The index of hydrogen deficiency (IHD)* is defined as the difference in the num-
Saturated
ber acyclic
of pairshydrocarbons
of hydrogen haveatomsthe generalthe
between molecular
compound formula
under Cnstudy
H2n !2and. Each dou-
an acyclic
ble bond alkane
or ringhaving
reducesthethesamenumber
number of of
hydrogen
carbons.atoms by two as compared with the
formula for a saturated compound. Thus each ring or double bond provides one unit of
Saturated acyclic hydrocarbons have the general molecular formula CnH2n !2. Each dou-
ble bond chemists
*Some organic or ringrefer
reduces the number
to the index ofdeficiency
of hydrogen hydrogen atoms
as the byoftwo
“degree as compared
unsaturation” or “the with the
formula for a saturated compound.
number of double-bond equivalencies.” Thus each ring or double bond provides one unit of

*Some organic chemists refer to the index of hydrogen deficiency as the “degree of unsaturation” or “the
number of double-bond equivalencies.”