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Finals Module 4 Unit 2

This document provides an introduction to organic chemistry, specifically focusing on organic compounds, their classification, properties, and examples. It discusses the molecular structure and nomenclature of organic compounds like hydrocarbons, alcohols, ethers, aldehydes, ketones, carboxylic acids, and amines. Hydrocarbons such as alkanes, alkenes, and alkynes are presented in detail, including their physical and chemical properties. The relationship between molecular structure and bulk properties is emphasized. Classification of organic compounds is based on functional groups, and this introduction covers the basic concepts related to common functional groups.
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0% found this document useful (0 votes)
87 views7 pages

Finals Module 4 Unit 2

This document provides an introduction to organic chemistry, specifically focusing on organic compounds, their classification, properties, and examples. It discusses the molecular structure and nomenclature of organic compounds like hydrocarbons, alcohols, ethers, aldehydes, ketones, carboxylic acids, and amines. Hydrocarbons such as alkanes, alkenes, and alkynes are presented in detail, including their physical and chemical properties. The relationship between molecular structure and bulk properties is emphasized. Classification of organic compounds is based on functional groups, and this introduction covers the basic concepts related to common functional groups.
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
You are on page 1/ 7

ORGANIC AND INORGANIC CHEMISTRY FOR MEDICAL LABORATORY SCIENCES

MODULE 04: INTRODUCTION TO ORGANIC CHEMISTRY

Unit 2: Introduction to Organic Compounds For these organic compounds, we will be discussing three
This unit will focus on the various organic compounds, their distinct sections. Section 1 will focus on molecular structure
classification, properties and some examples. An introduction of representative examples, with a molecular characterization
about common or trivial names, and IUPAC names will also be of the functional group. The second section will focus on
discussed using basic examples only. Refer to your learning nomenclature. Lastly, third property will be the discussion on
materials and selected videos to learn the concepts. Some the relationship between the molecular structure and bulk
exercises are provided to check what you have learned during property of the substance it is comprising.
your reading and learning sessions.
While the classification of organic compounds is shown in the
Studying organic compounds require a lot of attention to preliminary pages in your main reference, the organic
details, and a greater focus on the relationship between compounds can be classified using the scheme shown in the
molecular structure, molecular interactions and how the next page.
molecules result to the properties of the substances they
comprise. This is called the “structure-property” relationship Now, try to classify organic compounds based on your own
theme of studying organic chemistry. proposed scheme.

Unit Objectives: This is officially the start of getting to know the different
At the end of this unit, you should be able to: classes of organic compounds. To guide you, please bear in
1. Classify organic molecules based on functional groups; mind that we will discuss both the molecular context and
2. Give the trivial and IUPAC name of selected simple organic macroscopic context of the concepts. You will also study how
molecules; molecular structure influences the property of the molecule,
3. Summarize the key properties of the molecules; and, and how the property of the molecules, in turn, influence the
4. Relate the molecular properties of molecules to their bulk emergence of the physical property and chemical property of
properties. organic compounds. You need to develop an open mindset
that chemistry is NOT a collection of information. There is a
What organic compounds do you know so far? You may have distinct way of thinking in order to understand the underlying
heard of ethyl alcohol or acetic acid, right? You may have concept of the structure-property relationship theme in
talked about acetone too. But did you know that these chemistry.
organic compounds are just a tiny part of the vast list of
organic compounds known and used by humans? Hydrocarbons
As the name implies, hydrocarbons are organic compounds
Classification of Organic Compounds which are composed of carbon and hydrogen only.
The next topic is all about the classification of organic Hydrocarbons include alkanes, alkenes and alkynes, which are
compounds. You may have covered some basic group of presented in this unit. Furthermore, these groups may be
organic compounds during high school, so the discussions in subclassified as aliphatic (straight chains or branched chains),
this module are simple recall of concepts. or cyclic (closed or ring-like structures).

Organic compounds are usually classified based on the most ALKANE


dominant functional groups in their molecular structure. Probably, alkanes are the staple or representative organic
Functional groups refer to a specific arrangement of atoms in compound that you always see in organic chemistry
an organic molecule which has a distinct chemical reactivity. textbooks. A lot of concepts such as intermolecular forces of
But aside from this concept, the chemical reactivity will be attraction and its relationship to physical properties are all
influenced by it’s a) location, b) proximity to other functional related as to how alkanes exhibit them. We suggest that you
groups, and c) chemical environment where the molecule is master how the structure of alkanes contribute or influence
found in. For now, we will focus on the basic concepts related the physical properties of the pure substance they are
to each functional group to characterize the classes of organic comprising as this way of thinking can guide you later on, as
compounds. functional groups appear in the molecular structure.

The basic classification of organic compounds based on Major Concepts


functional groups is shown below. Your main reference, Alkanes have a general chemical formula of CnH2n+2, except
McMurry’s Fundamentals of Organic Chemistry, 7th edition, for cyclic alkanes. The tetrahedral hybrid orbitals of carbon
has a wider scope of discussion for several organic are involved in bond formation. The C – H is sp3 – s type and
compounds. In this module, we will only focus on the C – C bonds are sp3 – sp3 types Alkanes are sometimes
following relevant topics which will be revisited again when referred to as paraffins (L. parun affinis, meaning not enough
you take more advanced chemistry subjects. affinity) because alkanes have limited reactivity. The most
 Hydrocarbons important property of alkanes is their almost lack of polarity.
 Aromatic compounds The electronegativity difference between Carbon and
 Alcohol Hydrogen is 0.4 (2.5 – 2.1) on the Pauling scale. The only
 Ether interactions between their molecules are the very weak
 Aldehyde London dispersion forces.
 Ketone
 Carboxylic acids Physical Properties
 Amino compounds Boiling and Melting Points
 Sulfur Analogs The boiling point of alkanes is lower than most of any type of
compound with the same molecular weight. In general, both

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ORGANIC AND INORGANIC CHEMISTRY FOR MEDICAL LABORATORY SCIENCES

MODULE 04: INTRODUCTION TO ORGANIC CHEMISTRY

boiling point and melting points of alkanes increase with If an alkane has a terminal methyl branch (-CH3), the
increasing molecular weight. common name has a prefix iso

Physical Properties of Some Unbranched Alkanes

As branching in an alkane increases, the alkane molecule


becomes more compact, and its surface area decreases. As
surface area decreases, London Dispersion forces act over a
smaller surface area. Hence, attraction between molecules If an alkane has a terminal dimethyl branch, it is identified
decreases, and boiling point decreases. Thus, the least with the prefix neo
branched isomer has the highest boiling point and the most
branched isomer has the lowest boiling point.
Note: Isomers refer to compound which have similar chemical
formula but different structural formula.

Solubility If hydrogen is removed from an alkane, the partial structure


Alkanes are non-polar; thus, they are not soluble in water. that remains is called and alkyl group.
Alkanes do not dissolve in water because they do not form
hydrogen bonds with water. Alkanes, however, are soluble in
each other and in nonpolar organic compounds such as
toluene and diethyl ether.

Density
All liquid and solid alkanes are less dense than water, thus,
they float in water. The prefixes sec-(secondary), and tert-(tertiary) are used to
refer to other Carbon atoms attached to the branching
Chemical Properties carbon atom. There are four possibilities:
Combustion
Oxidation of hydrocarbons, including alkanes and
cycloalkanes, is the basis for their use as energy sources for
heat and fuel. The heat liberated when an alkane is oxidized
to carbon dioxide and water is called it heat of combustion.
Note: The symbol R is used to represent a generalized alkyl
group.

Halogenation
In this process, a substitution reaction happens when
Chlorine or Bromine is made to react with Methane (an
alkane) in a temperature of 100oC or higher, or expose it to
light.

IUPAC Names
In the early times, new compounds are named from the
If halomethane is allowed to react with more halogens, whims of the discoverers. A need for systematic naming was
further halogenations happen. thus required. The system of naming (nomenclature) used is
devised by IUPAC means International Union of Pure and
Applied Chemistry.

A chemical name typically has four parts in the IUPAC system


Nomenclature of nomenclature:
a. Prefix – answers where and what the substituents are
b. Parent – answers how many carbons are present
Common or Trivial Names
c. Locant – answers where the primary functional group is
Straight – chain alkanes carbons are connected in a row) are
d. Suffix – answers what the primary functional groups is
also called as normal alkanes, and are commonly indicated
with letter n. For example, we have n-butane, n-pentane.
For now, we use the IUPAC system to name branched-chain
Straight – chain alkanes are named according to the number
alkanes. Here are the steps.
of carbon atoms they contain. With the exception of
methane, ethane, propane and butane, the alkanes are
Find the parent hydrocarbon. The parent
named based on GREEK numbers. The suffix –ane is added to
hydrocarbon is the longest hydrocarbon chain in the
each name to identify the molecule as an alkane.
structure. The longest chain may not always be
obvious. If two chains of equal length are present,
Examples of straight – branched alkanes
choose the one with the larger number of branch
points as the parent.

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ORGANIC AND INORGANIC CHEMISTRY FOR MEDICAL LABORATORY SCIENCES

MODULE 04: INTRODUCTION TO ORGANIC CHEMISTRY

Just by looking at the two molecules, try to infer which of


Number the atoms in the main chain. Begin assigning these has higher boiling point and solubility in chloroform.
numbers at the end nearer the branch points. What is the basis of your answer?

Identify and number the substituents. Assign a We hope that you always recall what you have learned in
number called a locant to each substituent to specify alkanes as this will be relevant later on when you learn other
its point of attachment to the parent chain. If there classes of organic compounds such as alcohols, ethers,
are two substituents on the same number, assign aldehydes, ketones, carboxylic acids and many more! But
them both the same number. before that, you need to learn that hydrocarbons also include
those which contain pi bonds. These group of organic
Rule for substituent names: compounds are called alkenes.
Write the name as a single word. Use hyphens to separate ALKENE
the numbers. If two or more different side chains are present, It is important for you to recall that p-orbitals of sp2 -
cite them in alphabetical order. If two or more identical side hybridized carbon atoms are involved in the formation of pi
chains are present, use the appropriate multiplier prefixes (di- bonds. These pi bonds contribute to the inability of a pi bond
, tri-, tetra- and so forth). Don’t use prefixes for alphabetizing, to exhibit bond rotation, so the region where the pi bond is
though. Note that these are the basic rules. We will only located, is actually rigid. Also, remember that the pi bond is a
focus on the basics as the focus should be on relating site for chemical reactions, and qualitative tests were usually
molecular structure to the properties of the substances they done when you were in high school to detect, based on
are comprising. inference of course, the presence of a pi bond.

Conformation versus Configuration Major Concepts


A conformation refers to the different arrangements of atoms Alkenes have a general chemical formula of CnH2n, but of
that result from bond rotation, while a configuration is a course, it will not include cyclic alkenes. Their trigonal hybrid
three-dimensional arrangement of atoms or groups in a orbitals of carbon are involved in bond formation. The
molecule. There are different kinds of conformations. A unhybridized orbital overlap forms the pi bond. The C – H is
Sawhorse representation views the C – C bonds from an sp3 – s type and C – C bonds are sp2 – sp2 types Alkanes are
oblique angle. On the other hand, a Newman Projection views sometimes referred to as olefins. The most important
the C –C bond directly end-on and represent the two carbon property of alkenes is the presence of a carbon-carbon
atoms by a circle. double bond.

Bonds attached to the front carbon are represented in lines


Physical Properties
to a dot in the center of a circle and bonds attached to the
As a class, they essentially have the same physical properties
rear carbon are represented by lines to the edge of the circle.
as those of alkanes. They are insoluble in water, but quite
At any given instant, alkanes have staggered conformation. It
soluble in non-polar solvents like benzene, ether, chloroform
is more favored over eclipsed conformation.
or ligroin. They generally less dense than water. Boiling point
rises with increasing alkyl chain. Branching lowers the boiling
How to Illustrate Skeletal Structures
point. Certain alkenes are weakly polar.
Drawing every atom and bond is tedious so chemists have
devised a way to simplify matters. Thus, skeletal structure is
Chemical Properties
devised.
Hydrohalogenation
Hydrogen halides HCl, HBr, and HI add to alkenes to give
Rules:
1. Carbon atoms are not usually shown. haloalkanes (aka alkyl halides).
2. Hydrogen atoms bonded to carbon are not shown.
3. All atoms other than carbon and hydrogen are shown

Examples:

According to Markovnikov’s rule, in the addition of HX (where


X is a halogen) or H2O to an alkene, hydrogen adds to the
carbon of the double bond having the greater number of
hydrogen atoms. You need to learn this because the
molecular property depends on the orientation of atoms in a
molecule.
Cis-Trans Isomerism
Cis-trans isomers or stereoisomers are compounds which Acid-catalyzed hydration
have atoms connected in the same order but different in Hydration is the process involving the addition of water. Most
spatial orientation (cis = L. “on the same side”; trans = L. industrial ethanol is made by the acidcatalyzed hydration of
“across”). This topic is related to Chapter 2.8 when you read ethylene.
pages 60 to 61 on Fundamentals of Organic Chemistry, 7th
edition.

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ORGANIC AND INORGANIC CHEMISTRY FOR MEDICAL LABORATORY SCIENCES

MODULE 04: INTRODUCTION TO ORGANIC CHEMISTRY

Halogenation Between the two isomers of but-2-ene, which has a higher


Chlorine and bromine react with alkenes at room boiling point? Which has a higher melting point? Why?
temperature by addition of halogen atoms to the Carbon
atoms of the double bond. This reaction is generally carried The cis-trans isomerism is actually related to the E/Z
out either by using the pure reagents or mixing them in an designation as discussed in page 86 to 88 of Fundamentals of
inert solvent such as dichloromethane (CH2Cl2). Organic Chemistry, 7th edition.

ALKYNE
Alkynes share the same characteristic as alkenes because
The addition of Bromine is a useful qualitative test for the they also possess pi bonds. But this time, the main feature of
presence of an alkene. If we dissolve bromine in carbon alkynes is their triple bond. So, you may assume that the
tetrachloride, the solution will become red. Dibromoalkanes properties of alkenes are similar to alkynes. But, due to the
are colorless because they reacted with bromine atoms. rigidity of the triple bond, the physical properties differ when
compared to alkanes and alkenes of the same carbon
Catalytic Hydrogenation (Reduction) numbers. Note that the bond angle in a triple bond also
Alkenes react with molecular Hydrogen (H2) in the presence makes the molecules assume a different molecular geometry.
of transition metal catalyst to give alkanes. Commonly used
transition metal catalysts include Platinum, Palladium, Major Concepts
Ruthenium and Nickel.
Alkynes contain one or more triple bonds in carbon chain.
Triple bonds consist of one sigma bond and two pi bonds; less
stable that single or double bonds. The general formula:
CnHn, except of course, for cyclic alkynes. Like the C=C bond,
the carbon-carbon triple bond is also an electron-dense area.
Nomenclature
Physical Properties
Alkenes are named using a series of rules similar to those of
Again, the physical properties of alkynes will depend on a lot
alkanes with the suffix –ene used in place of –ane to identify
the family. of factors. In order for you to be guided, refer to how
molecules interact via intermolecular forces of attraction.
Note if the surface area of the molecule allows formation of
Let us learn how to give the IUPAC name first. The steps in
giving the IUPAC name of alkenes are similar to the steps in IFAs, or promote repulsion. Note if there are atoms which
makes the molecular more polar and less polar, and you can
giving the IUPAC name of alkanes.
evaluate the physical properties relatively easier
1. Name the parent hydrocarbon.
2. Number the carbons in the chain. Begin numbering at the Chemical Properties
end of the double bond. If the double bond is equidistant The chemical properties of alkynes are actually similar to
from the two ends, begin the end nearer the branch point. alkenes. Think of alkynes as having more pi bonds. These pi
This rule ensures that the double bond carbons receive the bonds are the sites of chemical reactivities. The chemical
lowest possible numbers. tests below provide you an idea on how to detect the
3. Write the full name. Number the substituents in the main presence of pi bonds in the molecules comprising a particular
chain according to their position and list them alphabetically. substance or mixture.
Indicate the position of the double bond by giving the number
of the first alkene carbon and placing that number directly Tests for Unsaturation of Hydrocarbons
before the –ene suffix.
Halogenation
If more than one double bond is present, give the position of When bromine is added to a sample alkene and alkyne, there
each and use the appropriate multiplier suffix –diene, -triene, are various results. Alkanes turn redbrown, alkenes and
-tetraene and so on. The IUPAC changed its naming rules in alkynes decolorize bromine.
1993. Instead of 2,5-dimethyl-3-heptene, the new naming
system suggests 2,5-dimethylhep-3-ene.

Common and IUPAC Names of Alkenes

Cis-trans or geometric isomerism in alkenes


Double bonds are points of rigidity in a molecule. As a result,
geometric or cis-trans isomerism is possible. In trans-but-2-
ene, two methyl groups are on the opposite sides of the
double bond. In cisbut-2-ene, the methyl groups are found on
the same side. Take a look at the molecules below.

Baeyer’s Test
A second qualitative test for unsaturation, the Baeyer test,
depends on the ability of potassium permanganate to oxidize
the carbon-carbon double bond to give alkanediols or the

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ORGANIC AND INORGANIC CHEMISTRY FOR MEDICAL LABORATORY SCIENCES

MODULE 04: INTRODUCTION TO ORGANIC CHEMISTRY

carbon-carbon triple bond to give carboxylic acids. Take a electrons = 4n + 2, where n is an integer), and c) it has a
look at the chemical equations shown below. planar geometry. If any of the criteria is not met, then the
molecule is non-aromatic. If the pi electrons = 4n, then the
molecule is antiaromatic.

Aromatic compounds are UV absorbers, and generally, the


most common reaction is related to electrophilic aromatic
substitution or EAS. Since aromatic molecules are UV
absorbers, UV light is often used to detect aromatic
The permanganate is destroyed in the reaction, and a brown compounds in analytical methods. Biological molecules such
precipitate of MnO2 is produced. The disappearance of the as DNA and proteins have aromatic molecules in them, that is
characteristic color of the permanganate ion is a positive test why UV light is used during crime scene investigations.
for unsaturation. However, care must be taken, since
compounds containing certain other types of functional Aromatic compounds may be benzenoid, non-benzenoid or
groups (for example, aldehydes, containing the --CH=O group) heterocyclic based on their molecular structure. Benzenoid
also decolorize permanganate ion. aromatic compounds resemble the structure of benzene.
Non-benzenoid aromatic compounds do not resemble the
Try to answer the following items to check your knowledge benzene ring. Lastly, heterocyclic aromatic structures have
about the hydrocarbons. other atoms such as N, S or O in their structure. Note that
1. A three-carbon cyclic alkyne is not possible because the these atoms may also exhibit various types of hybridization.
bond strain is low.
2. A Newman projection is important in justifying the effects Stability of Benzene
of syn- or anti- configuration.
Benzene undergoes substitution reaction rather than addition
3. In Baeyer’s test, the oxidizing agent is potassium
reaction. The heats of hydrogenation and combustion of
permanganate.
benzene are lower than expected. All carbon-to-carbon bonds
4. The molecular formula of the brown precipitate in Baeyer’s
in benzene is equal and intermediate in length between single
Test is MgO2.
and double bonds. Unlike alkenes, the pi bonds in benzene do
5. The cis-isomer of but-2-ene has higher boiling point than
not participate in chemical reactions. Hence, the continuous
the trans-isomer.
conjugation is maintained even during chemical reactions via
6. A radical substitution reaction in alkanes means that a
substitution reactions.
halogen becomes a nucleophile.
7. Acetylene is considered to be more polar than ethylene.
In the context of Resonance theory, benzene is a resonance
8. The slow step in the halogenation of an alkane is the
hybrid of two Kekule structures. This means that benzene
initiation step.
does not correspond to either structure I or II, but rather to a
9. A water displacement method works for the collection of
structure intermediate to I and II. Benzene is a flat molecule;
acetylene gas.
every carbon and hydrogen lying in the same plane. It is also
10. In the halogenation of ethane, the pH of the solution
symmetrical, with each carbon atom lying at the angle of a
becomes more alkaline.
regular hexagon. Every bond angle is 120o , so the hydrogen
11. The reaction between water and calcium carbide is
atoms attached to the carbon atoms in the structure are
exothermic.
actually pointed away from the center, with a bond angle of
12. A cis-isomer of but-2-ene has lower melting point than
120o relative to the vertex, which is carbon, and another
the trans-isomer.
carbon. Notice that if you view benzene in a side view, it is
13. Since the pi bond has low electron density, an alkene or
actually planar in geometry.
alkyne is nucleophilic.
14. The synthesis of an alkene from an alcohol involves
electrophilic addition.

Electrophilic Aromatic Substitution


AROMATIC COMPOUNDS Look at the arrow-pushing formalism illustrated below. The
Perhaps, aromatic molecules (aromatic compounds, if you are arrow indicates the movement of electrons. This means that
referring to substances) are one of the most interesting class the head of the arrow is an electron-deficient region, while
of organic compounds, if chemical peculiarity is a basis for the tail of the arrow is an electron-rich region.
saying so. Aromatic compounds are cyclic, and is often
illustrated with double bonds. But they do not exhibit
chemical behaviors which are commonly observed in alkenes,
even the cyclic alkenes. As you go along this lesson, pay
attention to the details on how aromaticity is determined as
this will help you in understanding their molecular properties,
physical properties, and chemical behavior.

Major Concepts
Aromatic compounds include benzene and other compounds
that resemble benzene in chemical behavior. Aromaticity of
molecules can be evaluated using the following criteria: a) It
exhibits continuous conjugation, b) it obeys Huckel’s Rule (pi

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ORGANIC AND INORGANIC CHEMISTRY FOR MEDICAL LABORATORY SCIENCES

MODULE 04: INTRODUCTION TO ORGANIC CHEMISTRY

Nomenclature of Aromatic Compounds ALCOHOL (R-OH) and PHENOL (Ar-OH)


In the early days, the word “aromatic” was used to describe
compounds such as benzene, benzaldehyde and toluene. Major Concepts
Today, we use the word aromatic to compounds that contain Alcohol and phenol are organic compounds which bear
six-membered benzene-like rings with three double bonds. resemblance to water molecules. The functional group of
alcohols is the hydroxyl group (-OH), while phenols resemble
Monosubstituted benzenes are systematically named (IUPAC alcohols, but the hydroxyl group is attached to benzene. In
nomenclature) in the same manner as other hydrocarbons, this discussion, let us focus on ethyl alcohol as the main basic
with –benzene as the parent name. The name phenyl- (fen- example for alcohols. Based on the electronegativity
nil) is used when benzene is used as a substituent. In differences, the distribution of charges is illustrated using the
addition, generalized aromatic substituents are called aryl- bond dipole arrows ad partial charge notations. The ball and
groups (abbreviated as Ar). stick model below also provide the electron density of the
whole molecule. The red region is the most electron-rich
Disubstituted benzenes are named using one of the prefixes while the blue region is the least electron-rich.
ortho- (o), meta-(m) or para-(p)
What is an effect of this charge distribution to the physical
1. An ortho- disubstituted benzene has its two substituents in and chemical property of ethyl alcohol?
a 1,2 relationship. A meta has a 1,3 relationship and an ortho
has a1,4 relationship.
2. As with cycloalkanes, benzenes with more than two
substituents are named by choosing a point of attachment as
Carbon 1 and numbering the substituents on the ring so that
the second substituent has the lowest number.
3. Substituents in IUPAC nomenclature are arranged
alphabetically.
For phenol, try to observe the distribution of electron density
Common or Trivial Names below.
The common or trivial names of major aromatic compounds
will depend on what substituent is attached to X in the
illustration below.

The chemical behavior of phenol is quite different from a


typical alkyl alcohol due to the property of benzene.
If X = CH3, the compound is called toluene Furthermore, oxygen is actually an electron-donating
If X = OH, the compound is called phenol functional group. This means that the lone pair in the oxygen
If X = NH2, the compound is called aniline in the hydroxyl group is actually “donated” to the aromatic
If X = COCH3, the compound is called acetophenone ring.
If X = CHO, the compound is called benzaldehyde
If X = COOH, the compound is called benzoic acid What does this mean then? This means that oxygen in the
If X = CH=CH2, the compound is called styrene hydroxyl group becomes less partially negative, causing bond
lengthening between oxygen and hydrogen. When hydrogen
dissociates away from the whole molecule, it contributes to
H+ ions in the solution.
Starting from the topic, the diversity of organic compounds
bearing oxygen in their molecular structure makes the This is the reason why phenol is more ACIDIC than a typical
preceding molecular structures more interesting and alkyl alcohol. The phenolate ion is stabilized further by
challenging. The next topics are basically a summarized resonance or pi electron delocalization
version of Chapter 8 in your main reference, Joahn
McMurry’s Fundamentals of Organic Chemistry, 7th edition. Physical Property
We are going to focus on basic concepts about the molecular Since alcohol molecules are organic analogs of water
structures of alcohol, phenol and ether, which are all bear molecules, the hydroxyl groups can form hydrogen bonds
striking resemblance to water molecules. Aside from that, we with water molecules. This means, alcohol molecules can
will be discussing the role of the functional groups to the intermingle with water molecules, much to the similarity to
molecular properties, chemical reactivities and bulk the interaction of water molecules with each other. This
properties of the substances they are comprising. explains why alcohol is soluble in water. However, if the alkyl
chain in the alcohol molecule increases in number, the
But let me ask you a question. When you hear the words solubility in water will decrease since alkyl groups do not
alcohol, phenol and ether, what pops into your mind? How form interactions with water molecules.
did you learn about these? What were the functions of your
examples? Your experience can actually help you in getting to Because of the ability of alcohol molecules to form hydrogen
know these classes of organic compounds. bonds, the boiling point is usually lower than water, but
higher than most groups of organic compounds. Based on this
information, what do you think is the freezing point, viscosity
and melting point of alcohol compared to alkanes?

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ORGANIC AND INORGANIC CHEMISTRY FOR MEDICAL LABORATORY SCIENCES

MODULE 04: INTRODUCTION TO ORGANIC CHEMISTRY

Chemical Property Again, take a note on the distribution of electron density.


Nucleophilic Property Note that if you compare -OH from a -OCH3, there is a
Alcohols, when transformed into alkoxides, can act as difference in the polarity. Which functional group is more
nucleophiles. Because of this, they can react with polar? Why do you say so?
carbocations in other structures and become alkoxy
substituents. Physical Properties
Acidity The physical properties of ether (pure substances) are based,
In neutral form, alcohols do not exhibit acidity. But if the again, on the strength of intermolecular forces of attraction.
atoms are arranged in such a way that it decreases the Recall what you have learned about intermolecular forces of
negative charge of oxygen in the hydroxyl group, it might lead attraction. First, what type of intermolecular force of
to deprotonation and may exhibit acidity (increases H+ ions in attraction are ether molecules capable of forming?
a aqueous solutions). The basis here is: the more stable the
conjugate base is, the more readily the hydroxyl group Nomenclature
deprotonates. Common Name
Susceptibility of Oxidation The common or trivial name is based on the groups attached
When an oxidant is present in the chemical reaction, primary to the ether functional group. Arrange substituents based on
alcohols are converted into aldehydes, while secondary complexity. In some references, the substituents may be
alcohols are converted into ketones. A strong oxidant can arranged alphabetically as well. But in our case, we will be
convert primary alcohols to carboxylic acids. using complexity as the basis of the arrangement of the
substituents.
Nomenclature
The common or trivial name of alcohols is based on the alkyl IUPAC Name
group where the hydroxyl group is attached to. Give the To give the IUPAC name, first, identify the longest chain or
name of the alkyl group then add the word alcohol. For largest ring (R1 or R2 as the parent compound. Number the
example, parent carbon skeleton to give the carbon connected to the
ether Oxygen the lower possible number. Name the OR
CH3CH2OH is called ethyl alcohol. The alkyl group is an ethyl substituent group as "alkoxy" = alkyl -ky + oxy.
group.
Examples:
(CH3)2CH-OH is called isopropyl alcohol. The alkyl group is an methoxy is CH3O-
isopropyl group. For the IUPAC nomenclature system, the ethoxy is CH3CH2O-
suffix is always -ol. The nomenclature system follows a similar propoxy is CH3CH2CH2O-
pattern as to what you did with alkenes.

For example, take a look at the example below. If you are


going to notice, the alkyl group is a butyl group. Using the rule
for determining the least possible locant position for the
functional group, which is the hydroxyl group, we are going to
start counting from the left side. If you have figured out, the
IUPAC name of the structure below is butan-2-ol.

ETHER (R1–O–R2)
The last class of organic compounds in this unit is another
organic analog of water molecule. This time, imagine that the
two hydrogen atoms in the structure of water are replaced by
alkyl or aryl groups. This difference in molecular structure
leads to a drastic change in molecular property, and chemical
behavior.

Major Concepts
Ethers are a group of organic compounds which are
considered as organic analog of water molecules. If we
compare the structure of ether to water molecules, each
hydrogen atom is replaced by an alkyl group. Relatively, ether
molecules are less polar than water and alcohols. Based on
molecular structure, ether molecules may be symmetrical or
non-symmetrical.

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