Center for Higher Secondary Education _____ Department of Chemistry

TOPIC 15: ORGANIC CHEMISTRY (CHIRALITY & CARBONYL

COMPOUNDS
GRADE 12
SEMESTER 3/2023
Checklist

P
15A: Chirality - Students will be assessed on their ability to:
15.1 know that optical isomerism is a result of chirality in molecules with a single chiral centre
15.2 understand that optical isomerism results from chiral centre(s) in a molecule with asymmetric
carbon atom(s) and that optical isomers (enantiomers) are object and non-superimposable
mirror images and be able to draw 3D diagrams of these optical isomers

15.3 know that optical activity is the ability of a single optical isomer to rotate the plane of
polarisation of plane-polarised monochromatic light in molecules containing a single chiral
centre

15.4 know what is meant by the term ‘racemic mixture’

15.5 be able to use data on optical activity of reactants and products as evidence for SN1 and SN2
mechanisms and addition to carbonyl compounds

15B: Carbonyl compounds - Students will be assessed on their ability to:

15.6 understand the nomenclature of aldehydes and ketones and be able to draw their structural,
displayed and skeletal formulae

15.7 understand that aldehydes and ketones:

i do not form intermolecular hydrogen bonds and this affects their physical properties
ii can form hydrogen bonds with water and this affects their solubility

15.8 understand the reactions of carbonyl compounds with:

i. Fehling’s or Benedict’s solution, Tollens’ reagent and acidified dichromate (VI) ions in
equations, the oxidising agent can be represented as [O]. v

ii. lithium tetrahydridoaluminate (III) (lithium aluminium hydride) in dry ether

v
(ethoxyethane) In equations, the reducing agent can be represented by [H].

iii. HCN, in the presence of KCN, as a nucleophilic addition reaction, using curly arrows,
relevant lone pairs, dipoles and evidence of optical activity to show the mechanism v

iv. 2,4-dinitrophenylhydrazine (2,4-DNPH), as a qualitative test for the presence of a

v
carbonyl group and to identify a carbonyl compound given data of the melting
temperatures of derivatives the equation for this reaction is not required.
v. iodine in the presence of alkali (the iodoform test)
v
Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 1 of 23
Center for Higher Secondary Education _____ Department of Chemistry

15A 1 CHIRALITY AND ENANTIOMERS SPECIFICATION

OBJECTIVE 15.1
& 15.2.

Different types of isomerism

• Isomerism occurs when two or more compounds have the same molecular formula but have
different structural formula or different arrangement of atoms in space.
• Isomerism can be subdivided as below

Isomerism

Structural isomerism Stereoisomerism

Chain positional functional group geometrical optical

Structural isomerism
They have the same molecular formula but different structural formulae

Ø Chain isomerism: occurs due to branching in carbon chains.

CH3

H3C CH2 CH2 CH3 H3C CH CH3

Ø Functional group isomerism: occurs due to the presence of different functional groups.
H H H H
H C C OH H C O C H
H H H H

Ø Positional isomerism: occurs due to the position in which the functional group is present.
Cl
H3C CH2 CH2 CH2 Cl H3C CH CH2 CH3

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 2 of 23
Center for Higher Secondary Education _____ Department of Chemistry

Stereo isomerism
They have the same molecular formula and structural formulae but differ in the spatial orientation
of one or more atoms.

Geometric isomerism
• Occurs in alkenes due to the restricted rotation around C=C bond.

H3C H
H3C CH3
C C C C
H CH3
H H

• In order to exhibit geometric isomerism, carbons in the double bonds should have different
atom or group of atoms attached in each carbon.
• These geometric isomers are named using cis-trans system or E-Z system.
• (Read Unit 1.7 “Introductory Organic Chemistry – Alkenes” notes)

Optical isomerism
• Optical isomerism occurs in compounds with a chiral carbon (an asymmetric carbon atom
that contains four different groups which are arranged tetrahedrally around it.)
• These compounds form non-superimposable mirror images.

OH OH
O O
C C
C HO C H
H OH
CH3 H3C
(-) lactic acid (+) lactic acid
in sour milk in muscles

• They are remarkably similar in both their physical and chemical properties. Unlike structural
and geometric isomers, they cannot be told apart by differences in their physical properties
or chemical reactivities.
• Optical activity is the ability of a single optical isomer to rotate the plane of polarization of
plane-polarized monochromatic light in molecules containing a single chiral centre. This is
the technique used to distinguish optical isomers.
• When the two optical isomers (enantiomers) are equally present, it is called a racemic
mixture.
Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 3 of 23
Center for Higher Secondary Education _____ Department of Chemistry

How to identify chiral centres in structural formulae:

You only need to consider whether there is a carbon atom joined to four different atoms
or groups.

STRUCTURE COMMENT
The single carbon atom has only three different atoms
CBr2CIF attached, so there is no chiral centre.
Carbons 1,3 and 4 in the chain have two or more hydrogens
attached,
CH3CHBrCH2CH3 so are not chiral. Carbon 2 is joined to four different groups
(methyl bromine and ethyl). So, it is a chi ra l cent re.
Carbons 1, 2, 4 and 5 in the chain have two or more
hydrogens attached, so
are not chiral. Carbon 3 is joined to only three different
CH3CH2CHBrCH2CH3 groups (two ethyl, one hydrogen and one bromine), so it is
not a chiral centre.
Carbons 1, 2 and 5 in the chain have two or more
hydrogens attached, so are not chiral. Carbon 3 is joined to
four different groups (ethyl, hydrogen, bromine and
CHBrCH3), so it is a chiral centre. Carbon 4 is joined to four
CH3CH2CHBrCHBrCH3 different groups (methyl, hydrogen, bromine and
CH3CH2CHBr). so it is also a chiral centre.

CHECKPOINT
1. What is the main similarity and the main difference between optical isomers and
geometric isomers?

2. How many chiral centres are there in each of these molecules?

(a) CH3CCl2CH3
(b) CH3CH(OH)COOH
(c) CH2Cl-CHCl-CHFCH3

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 4 of 23
Center for Higher Secondary Education _____ Department of Chemistry

15A 2 OPTICAL ACTIVITY SPECIFICATION

OBJECTIVE 15.3
& 15.4

Plane polarised light

Typical light sources are non-polarised. This means that the light consists of light of all
polarisations. By passing the light through a polariser, only light of one particular polarisation is
allowed to pass through. The light which has passed through the polariser is known as plane-
polarised light.

How a polarimeter works

What we see normally is unpolarised light, which tends to vibrate randomly in all directions.
Plane-polarised light is composed of waves that vibrate in only one plane. When polarised light
passes through a polariser, the randomly vibrating light waves are filtered so that the light
passing through is vibrating in only one direction. The plane- polarised light then passes
through a sample tube containing
some of the substance in solution.
If the substance is optically active
then the plane of polarisation will
be rotated so that it is no longer
vertical.
The rotation is anticlockwise, and
the substance can therefore be
described as 'laevorotatory'. If
the rotation is clockwise, then
the substance is 'dextrorotatory'

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 5 of 23
Center for Higher Secondary Education _____ Department of Chemistry

Properties of enantiomers
They have the identical physical properties except one exception.
That is enantiomers rotate plane polarized light in equal angles but in opposite directions.
Example, if the rotation for one enantiomer +600 the other will be -600.

Two enantiomers have identical chemical properties with one exception. That is the way they react
with enantiomers of other substances. This chemical property may be different for each
enantiomer.

15A 3 OPTICAL ACTIVITY AND REACTION MECHANISM SPECIFICATION

OBJECTIVE 15.5

Nucleophilic substitution reactions:

SN2 mechanism

S = substitution N = nucleophilic 2 = bimolecular

The term bimolecular' means that there are two species involved in the rate-determining
step. Here is the mechanism for a primary halogenoalkane that is also an enantiomer.

–
CH3
HO: CH3 CH3
HO C Br
C :Br-
F
Br
F H HO
C +
H F
H
transition state

The important thing to notice is that the arrangement of the three groups that remain
attached to the central carbon atom has been inverted (turned inside out).
• If the reaction actually occurs according to the S N2 mechanism, then the optical activity
of the product is different from that of the reactant.
• If the reactant is dextrorotatory, then the product will be laevorotatory, and vice versa.
So, by measuring the optical activity of the original halogenoalkane and the alcohol
formed, we can show whether the reaction has occurred by the SN2
mechanism.

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 6 of 23
Center for Higher Secondary Education _____ Department of Chemistry

SN1 mechanism

S = substitution N = nucleophilic 1 = unimolecular

The term 'unimolecular' means that only one species is involved in the rate-determining
step. In the SN1 mechanism, the planar carbocation can be attacked from the left or from the right,
giving a pair of enantiomers.

CH3
–
CH3 HO: C
CH3 :OH F
OH
+ H
C C
Br
F
H F H
CH3
C
HO
F
H

If the reaction occurs according to the SN1 mechanism, whether the reactant is dextrorotatory or
laevorotatory, the product has no optical activity (Racemic mixture formed).

EXERCISE 1

Draw the mechanism for;

1) Alkaline hydrolysis of a secondary halogenoalkane – 2-chlorobutane ( SN2 mechanism)

Reactant and the product, both are optically active, hence the mechanism is bi-molecular
nucleophilic substitution

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 7 of 23
Center for Higher Secondary Education _____ Department of Chemistry

2) Alkaline hydrolysis of a 20 halogenoalkane – 2-chlorobutane ( SN1 mechanism)

Reactant is optically active and the product is optically inactive (Racemic mixture formed), hence
the mechanism is uni-molecular nucleophilic substitution

CHECKPOINT
1. 2-Bromopropane and cyanide ions react together by an SN1 mechanism. Explain
why there is no change in optical activity in this reaction.

15B 1 CARBONYL COMPOUNDS & THEIR PHYSICAL

SPECIFICATION
PROPERTIES OBJECTIVE 15.6,
15.7(i) & 15.7(ii)

• Carbonyl compounds are compounds that have a carbon atom double bonded to an oxygen
atom; C=O.
• Aldehydes and ketones are carbonyl compounds that have the general formula, CnH2nO.

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 8 of 23
Center for Higher Secondary Education _____ Department of Chemistry

Nomenclature :

Aldehydes
O

• Functional group: C H

• In Aldehydes, the carbonyl carbon must contain at least one hydrogen atom.
• Suffix –al, if it is the principal functional group.
• Prefix oxo -, if it’s the secondary functional group.
• Use the priority order table to identify whether it is the principal or secondary functional
group.
• The –CHO carbon contains only one spare bond. So it is always present at the end of the
carbon chain. Therefore, locants are not required while naming.
• The longest chain carbon chain should be selected including the carbonyl carbon.

EXERCISE 2

(a) Name the following compounds.

O O
H3C CH2 CH2 C H H3C CH CH
Cl

CH3 O O
H3C CH CH CH2 CH H3C CH CH2 C H
CH3 OH

(b) Draw the following compounds.

2-methylbutanal 2,2-dimethylpentanal

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 9 of 23
Center for Higher Secondary Education _____ Department of Chemistry

Oxoethanoic acid Propenal

Ketones

• Functional group:

• In ketones, the carbonyl carbon does not contain any hydrogen atom.
• Suffix – one , if it is the principal functional group.
• Prefix – oxo, if it is the secondary functional group.
• Use the priority order table to identify whether it is the principal or secondary functional
group.
• The carbonyl carbon contains two spare bonds and it can be anywhere in the middle of the
carbon chain. Therefore, locants are required.
• The longest chain carbon chain should be selected including the carbonyl carbon.

•EXERCISE 3

(a) Name the following compounds.

O O
CH3 CH2 CH2 C CH2 CH2 CH3 H3C CH C CH CH3
CH3 CH3

O O CH3
CH3 CH2 CH2 C CH CH3 H3C C CH CH3
CH3

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 10 of 23
Center for Higher Secondary Education _____ Department of Chemistry

(b) Draw the following compounds.

2-oxopropanoic acid Pentan-2-one

Cyclohexanone 4-methyl cyclohexanone

Priority group table

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 11 of 23
Center for Higher Secondary Education _____ Department of Chemistry

Isomerism
• Isomerism is possible within aldehydes, within ketones and between aldehydes and ketones.
• Example: isomers of C4H8O

O CH3 O O
CH3 CH2 CH2 C H CH3 CH C H CH3 C CH2 CH3
Butanal 2-methylpropanal butanone

Physical properties of carbonyl compounds

• Aldehydes and ketones have distinctive smells.
• Aldehydes and ketones are polar compounds because of the polar carbonyl group, C=O.
d+ d-
C O
• So, the intermolecular forces between aldehyde molecules and between ketone molecules
are permanent dipole-dipole interactions as well as London forces.

d- O
C d+
d+ C
O d-

dipole - dipole attraction

• Therefore, they have higher boiling temperatures compare to corresponding alkanes, but
not as high as their corresponding alcohols.
• This is because permanent dipole-dipole interactions in aldehydes and ketones are stronger
than weak Van der Waals forces in alkanes, but weaker than hydrogen bonding in alcohols.

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 12 of 23
Center for Higher Secondary Education _____ Department of Chemistry

Solubility
• Shorter carbonyl compounds are soluble in water, because of the formation of hydrogen
bonding with water molecules. As the length of the carbon chain increases, they become
less soluble.

d- d+
H O H O
H C C H
H H

• Methanal (formaldehyde) is a gas at room temperature and 40% aqueous solution of this
o (formalin) is used for preserving biological specimens.
• Other shorter chained carbonyl compounds are liquids with pleasant smell.

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 13 of 23
Center for Higher Secondary Education _____ Department of Chemistry
SPECIFICATION
15B 3 NUCLEOPHILIC ADDITION REACTIONS OBJECTIVE 15.8(iii),
15.8(iv) & 15.5part

Reaction with 2,4-Dinitrophenylhydrazine

Ø The structure for 2,4- DNPH is,

NO2

NH2
O 2N N
H

Reagent : Brady’s reagent / 2,4- DNPH / (2,4-dinitrophenylhydrazine)]

Condition : room temperature
Type of reaction : Condensation
Observation : orange precipitate
Product : 2,4-dinitrophenylhydrazone

Ø The equation for the reaction between ethanal and 2,4- DNPH is shown below.

H2O
NO2 NO2
H H H H
O 2N N NH2 + O C C H O 2N N N C C H + H2O
H H H H
2,4-dinitrophenylhydrazine ethanal ethanal-2,4-dinitrophenylhydrazone

EXERCISE 4
Write the equation for the reaction of 2,4- DNPH with the following compounds and write the name
of the product formed.

i) Propanal

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 14 of 23
Center for Higher Secondary Education _____ Department of Chemistry

ii) Propanone

Identification of a carbonyl compound using 2,4-dinitrophenylhydrazine

(2,4- DNPH)

• Add 2,4dinitrophenylhydrazine to the carbonyl compound (eg: ethanal).

• An orange precipitate (ethanal-2,4-dinitrophenylhydrazone) is formed.
• Filter the precipitate and recrystallize.
• Measure the melting point of the derivative (ethanal-2,4-dinitrophenylhydrazone) and compare
with the data book value.

The identity of the original carbonyl compound can be confirmed by comparing the
experimental melting temperatures of these derivatives with data booklet values.

CHECKPOINT
Compound X reacts with 2,4-d dinitrophenylhydrazine and with iodine in aqueous alkali in
separate tests. In both cases a coloured precipitate forms. Explain which of these could be
compound X:

propanal, propan-1-ol, propan-2-ol, propanone

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 15 of 23
Center for Higher Secondary Education _____ Department of Chemistry

Reaction with hydrogen cyanide

• Aldehydes and ketones undergo heterolytic nucleophilic addition reactions.
• Oxygen atom in C=O bond is more electronegative than carbon. Therefore, electrons are more attracted
towards oxygen, making the bond polar.
• This leaves the carbon atom electron deficient and attractive to nucleophiles.
• Cyanide, CN- is a nucleophile that can be added across the carbonyl bond.
• This is a useful reaction for increasing the length of the carbon chain.

Reagent: - Sodium cyanide (NaCN) or Potassium cyanide (KCN) (source of CN-)

and Hydrogen cyanide (HCN) OR
- Sodium cyanide (NaCN) or Potassium cyanide (KCN) (source of CN-)
and dil. H2SO4 or HCl (source of H+) OR
- Hydrogen cyanide (HCN) with cold NaOH
Condition: - room temperature
Type of reaction: Nucleophilic Addition
Product: Hydroxy nitriles

The nucleophilic addition mechanism

This is a two step mechanism.

Step 1 - Nucleophile, :CN- has a lone pair of electrons. Nucleophile attacks the slightly positive
carbon atom in the C=O bond.

• This displaces the two electrons in the double bond and pushes them onto the oxygen atom.
The oxygen atom now has a negative charge.

H H
d+ d- –
– C O NC C O:
N C:
H3C
CH3
intermediate

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 16 of 23
Center for Higher Secondary Education _____ Department of Chemistry

Step 2 - The negatively charged oxygen atom acts as a base and gains a proton to form the final
product.

H H
–
NC C O: H CN NC C OH + :CN-
CH3 CH3

Reaction mechanism

H H H
d+ d- –
– C O NC C O: H CN NC C OH + :CN-
N C:
H3C
CH3 CH3
intermediate

Using optical activity as evidence

• All Aldehydes except methanal, and unsymmetrical ketones will produce hydroxy nitriles that
are optically active since the carbon has four different groups attached to it (a chiral carbon).
• Despite this the products formed appears to show no optical activity.
• This is because
o the bonds around C=O are trigonal planar.
o the nucleophile (CN-) can attack equally from either side.
o so, a racemic mixture is formed.

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 17 of 23
Center for Higher Secondary Education _____ Department of Chemistry

CN- attacks from above

–
C:
N
N C N
H C
C –
C O H O
: C
d+ d- CH3 + H OH
H3C H CH3
intermediate

These two
molecules are
OR mirror images of
one another
CN- attacks from below

CH3 –
H d+ O: CH3 OH
H + H
C O C H C
d-
H3C
–
CN CN
N C: intermediate

Racemic mixture: contains equal amounts of dextrorotatory and laevorotatory

enantiomers. Which rotates plane polarized light equally on opposite directions. Thus,
making the product mixture optically inactive.

EXERCISE 5

Draw the complete mechanism for the following compounds with HCN and name the product
formed.
i) Propanone

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 18 of 23
Center for Higher Secondary Education _____ Department of Chemistry

ii) Ethanal

15B 2 REDOX REACTIONS OF CARBONYL SPECIFICATION

OBJECTIVE 15.6,
COMPOUNDS 15.7(i) & 15.7(ii)

Reduction reactions
• Both aldehydes and ketones can be reduced to alcohols
• Reducing agents are;
• Lithium aluminium hydride / Lithium tetrahydridoaluminate (LiAIH4) in dry ether (ethoxyethane)
followed by hydrolysis with an aqueous acid.
• Sodium borohydride / Sodium tetrahydridoborate (NaBH4) in ethanol or in aqueous (water)
followed by dilute acid.
o
2[H] 2[H]

Aldehydes primary alcohol Ketones secondary alcohol

Note: LiAIH4 is a very strong reducing agent which should be used in perfectly dry condition, or else

water will hydrolyze LiAlH4.

Reagent: LiAIH4 / NaBH4

Condition: in dry ether or in ethanol
Type of reaction: Reduction
Product: Alcohol

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 19 of 23
Center for Higher Secondary Education _____ Department of Chemistry

EXERCISE 6

Write balanced equations and name the organic products formed when the following compounds
undergo reduction.

i) Butanal

ii) Butanone

Oxidation reactions
• Oxidation reactions are used to differentiate aldehydes from ketones.
• Aldehydes can be oxidized easily but ketones resist oxidation.
• This is because Aldehydes have hydrogen as a part of the functional group. This hydrogen is
absent in ketones.
• Aldehydes are easily oxidized to carboxylic acids, but ketones resist oxidation (they can be
oxidized after prolonged treatment with a very strong oxidizing agent).
• Many oxidizing agents can be used to oxidize Aldehydes. Some of these Oxidizing agents used
in the laboratory are,

§ Tollen’s reagent- ammoniacal silver nitrate solution

§ Fehling’s solution
§ Acidified potassium dichromate solution.

• The table on page 17 shows the summary of these three tests that are done to distinguish
aldehydes and ketones.

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 20 of 23
Center for Higher Secondary Education _____ Department of Chemistry

Test Reagent Method Observation Equation Explanation

Tollen’s Ammoniacal silver Tollen’s reagent Ketone – no change - Ketones are not
test nitrate solution (a is heated with oxidized.
solution of silver the test Aldehyde – 2Ag+(aq) + RCHO(aq) + H2O(l) - Ag+ is reduced to Ag
nitrate and ammonia) compound in a forms a silver metal (silver mirror)
hot water bath. mirror in the - aldehyde is oxidized to
test tube 2Ag(s) + RCOOH(aq) + 2H+(aq) carboxylic acid
Fehling’s Solution of Copper (II) Fehling’s Ketone – no change/ Ketones are not
test sulfate in water and solution is blue color of solution oxidized.
tartrate (2,3- warmed with remains -
dihydroxybutanedioate) the test
ions in Sodium compound Aldehyde – forms a 2Cu2+(aq) + RCHO(aq) + OH–(aq) - Cu2+ is reduced to
hydroxide brick-red / dark red + H2O(l) Cu+1ions (Cu2O).
precipitate of copper - aldehyde is oxidized to
(I) oxide Cu2O(s) + RCOOH(aq) + 3H+(aq) carboxylic acid
Reaction Potassium dichromate Acidified Ketone – no change/ Ketones are not
with and dilute sulfuric acid potassium orange color of - oxidized.
potassium dichromate solution remains
dichromate solution is boiled Aldehyde – colour 3RCHO(aq) + Cr2O72-(aq) + - Cr6+ is reduced to Cr3+
+
with the test changes from orange 8H (aq) ions.
compound to green - aldehyde is oxidized to
carboxylic acid.
3 RCOOH(aq) + 2Cr3+(aq) +
4H2O(l)

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 21 of 23
Center for Higher Secondary Education _____ Department of Chemistry

Distinguishing between aldehyde and ketones

Oxidation reactions using Fehling’s solution and Tollen’s reagent are used to distinguish between
aldehydes and ketones.

• A positive result for Fehling’s or Tollen’s test indicates PRESENCE of an ALDEHYDE.

• A negative result for Fehling’s and Tollen’s test indicates ABSENCE of an ALDEHYDE.

Reactions with iodine – Triiodomethane reaction (iodoform reaction)

Reagent: NaOH(aq)+I2(aq)
Condition: warm
Type of reaction: Condensation
Observation: pale yellow precipitate (triiodomethane, CHI3)
Product: triiodomethane, CHI3 + sodium salt

• This reaction is specific to organic compounds that contain a methyl group next to a carbonyl
group and alcohols that can be oxidized to form these carbonyl compounds.
• The following functional groups can give positive result in this reaction.

Examples:
O
O O
CH3 C R
CH3 C H CH3 C CH2CH3
R maybe hydrogen or a
hydrocarbon chain ethanal butanone

Note: Ethanal (the only aldehyde) and all methyl

ketones give a positive result
Examples:
OH ethanol ethanal
CH3 C R H OH H O
H H C C H H C C
R maybe hydrogen or a H H H H
hydrocarbon chain
oxidised by I2 gives the positive
Note: Ethanol and all methyl secondary to give ethanal iodoform reaction
alcohols are first oxidized by iodine to
form a carbonyl compound that has a

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 22 of 23
Center for Higher Secondary Education _____ Department of Chemistry

methyl group next to the carbonyl

carbon. This product then gives the propan-2-ol propanone
positive iodoform result. H
H OH H O H
H C C C H H C C C H
H H H H H

oxidised by I2 to gives the positive

give propanone iodoform reaction

General equation;
H O
H C C + 3I2 + 4OH
-
CHI3 + RCOO
-
+ 3I- + 3H2O
H R triiodomethane

EXERCISE 7

1. Check whether the following compounds will give positive result with iodoform reaction.

Compound Structure +ve / -ve

propanal

butanone

pentan-3-one

pentan-2-ol

2. Write the balanced equation for iodoform reaction and name the main organic compounds
formed.

Equation with ethanal;

Equation with propanone:

Grade 12/ Topic 15: organic chemistry (chirality & carbonyl compounds/sem 3/2023 Page 23 of 23