Grade XII / unit-12/HIMANSHU SIR

Aldehydes, Ketones and Carboxylic Acids

Aldehydes, ketones and carboxylic acids are widespread in plants and animal kingdom. They play an important role in
biochemical processes of life. They add fragrance and flavour to nature, for example, vanillin (from vanilla beans),
salicylaldehyde (from meadow sweet) and cinnamaldehyde (from cinnamon) have very pleasant fragrances. Some of these
families are manufactured for use as solvents (i.e., acetone) and for preparing materials like adhesives, paints, resins,
perfumes, plastics, fabrics, etc.

Nomenclature
Grade XII / unit-12/HIMANSHU SIR
Grade XII / unit-12/HIMANSHU SIR
Grade XII / unit-12/HIMANSHU SIR
Grade XII / unit-12/HIMANSHU SIR
Grade XII / unit-12/HIMANSHU SIR
12.1 Write the structures of the following compounds. Grade XII / unit-12/HIMANSHU SIR
(i) α-Methoxypropionaldehyde (ii) 3-Hydroxybutanal

(iii) 2-Hydroxycyclopentane carbaldehyde (iv) 4-Oxopentanal

(v) Di-sec. butyl ketone (vi) 4-Fluoroacetophenone

Structure of the Carbonyl Group The carbon-oxygen double bond is polarised

due to higher electronegativity of oxygen
relative to carbon. Hence, the carbonyl
carbon is an electrophilic (Lewis acid), and
carbonyl oxygen, a nucleophilic (Lewis base)
centre. Carbonyl compounds have substantial
dipole moments and are polar than ethers.
 Grade XII / unit-12/HIMANSHU SIR
Preparation of Aldehydes and Ketones
1. By oxidation of alcohols

2. By dehydrogenation of alcohols

3. . From hydrocarbons
(i) By ozonolysis of alkenes:
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(ii) By hydration of alkynes:

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Preparation of Aldehydes

1. From acyl chloride (acid chloride) ,Rosenmund reduction. - Acyl chloride (acid chloride) is
hydrogenated over catalyst, palladium on barium sulphate to form aldehydes. This reaction is called
Rosenmund reduction.
2. From nitriles and esters Grade XII / unit-12/HIMANSHU SIR

Stephen reaction - Nitriles are reduced to corresponding imine with stannous chloride in the presence of hydrochloric
acid, which on hydrolysis give corresponding aldehyde. This reaction is called Stephen reaction.

Alternatively, nitriles ( and esters) are selectively reduced by diisobutylaluminium hydride, (DIBAL-H) to imines
followed by hydrolysis to aldehydes:
 Grade XII / unit-12/HIMANSHU SIR
3. From hydrocarbons
(i) By oxidation of methylbenzene Strong oxidising agents oxidise toluene and its derivatives to benzoic acids.
However, it is possible to stop the oxidation at the aldehyde stage with
suitable reagents that convert the methyl group to an intermediate that is
difficult to oxidise further. The following methods are used for this purpose.
(a) Etard reaction- Use of chromyl chloride (CrO2Cl2): Chromyl chloride oxidises methyl group to a chromium
complex, which on hydrolysis gives corresponding benzaldehyde. This reaction is called Etard reaction.

(i) By using CrO3 n acitic anhydride

 Grade XII / unit-12/HIMANSHU SIR
(ii) By side chain chlorination followed by hydrolysis
This is a commercial method of manufacture of benzaldehyde.

(iii) By Gatterman – Koch reaction When benzene or its

derivative is treated with carbon monoxide and hydrogen
chloride in the presence of anhydrous aluminium chloride or
cuprous chloride, it gives benzaldehyde or substituted
benzaldehyde.

Convert
i. Phenol to benzaldehyde
 Grade XII / unit-12/HIMANSHU SIR
ii. Ethanol to propanol

iii. ethyl chloride to propanal

iv. But-2-ennitrile to butanol

Preparation of Ketones

1. From acyl chlorides

Treatment of acyl chlorides with
dialkylcadmium, prepared by the
reaction of cadmium chloride with
Grignard reagent, gives ketones
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2. From nitriles -Treating a nitrile with Grignard reagent followed by hydrolysis yields a ketone.
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3. By Friedel-Crafts acylation reaction

 Grade XII / unit-12/HIMANSHU SIR
Example 12.1- Give names of the reagents to bring about the following transformations:
(i) Hexan-1-ol to hexanal

(ii) Cyclohexanol to cyclohexanone

(iii) p-Fluorotoluene to p-fluorobenzaldehyde

(iv) Ethanenitrile to ethanal

(v) Allyl alcohol to propenal

(vi) But-2-ene to ethanal

 Grade XII / unit-12/HIMANSHU SIR
Intext Question 12.2- Write the structures of products of the following reactions;

Physical Properties of aldehydes and ketones

➢ Methanal is a gas at room temperature. Ethanal is a volatile liquid.
Other aldehydes and ketones are liquid or solid at room temperature
➢ Type of attractive forces - dipole-dipole interactions.
➢ The boiling points of aldehydes and ketones are higher than
hydrocarbons and ethers of comparable molecular masses. It is due to
weak molecular association in aldehydes and ketones arising out of the
dipole-dipole interactions.
➢ boiling points are lower than those of alcohols of similar molecular
masses due to absence of intermolecular hydrogen bonding.
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➢ The lower members of aldehydes and ketones such as methanal, ethanal and propanone are miscible
with water in all proportions, because they form hydrogen bond with water. However, the solubility of
aldehydes and ketones decreases rapidly on increasing the length of alkyl chain
➢ The lower aldehydes have sharp pungent odours. As the size of the molecule increases, the odour becomes
less pungent and more fragrant. In fact, many naturally occurring aldehydes and ketones are used in the
blending of perfumes and flavouring agents.

Boiling point order

Q- Arrange the following compounds in the increasing order of their boiling points:
CH3CH2CH2CHO, CH3CH2CH2CH2OH, H5C2-O-C2H5, CH3CH2CH2CH2CH3

Intext -12.3 Arrange the following compounds in increasing order of their boiling points. CH3CHO, CH3CH2OH,
CH3OCH3, CH3CH2CH3
 Grade XII / unit-12/HIMANSHU SIR
Chemical Reactions
1. Nucleophilic addition reactions The aldehydes and ketones undergo nucleophilic addition reactions
Q – Write the Mechanism of nucleophilic addition reactions of Ethanal and HCN
A nucleophile attacks the electrophilic carbon atom of the polar carbonyl group changes its hybridisation from
sp2 to sp3 in this process, and a tetrahedral alkoxide intermediate is produced. This intermediate captures a
proton from the reaction medium to give the electrically neutral product. The net result is addition of Nu– and
H+ across the carbon oxygen double bond
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Q- Compare reactivity of Methanal , Ethanal and Propanone
Aldehydes are generally more reactive than ketones in nucleophilic addition reactions due to steric and electronic reasons
1. Due to positive inductive effect – Electron density on carbonyl carbon is satisfied more in ketone due to presence of two
electron releasing groups. It has more plus I effect than aldehyde which reduces the positive charge of carbonyl carbon
discourage the attack of nucleophile ,hence ketones are less reactive than aldehyde . Formaldehyde with no alkyl group
attached to carbonyl carbon is mostly active due to absence of +I effect .

2. Steric effect - As the size of alkyl group attached to carbonyl carbon increases , the steric hindrance Increases , which
discourage the attack of nucleophile therefore reactivity of aldehyde and ketones decreases with increase in number of
carbon atoms. lack of hindrance in nucleophilic attack is another reason for the greater reactivity of formaldehyde .
 Grade XII / unit-12/HIMANSHU SIR
Example 12.3 - Would you expect benzaldehyde to be more reactive or less reactive in nucleophilic addition
reactions than propanal? Explain your answer.
The carbon atom of the carbonyl group of
benzaldehyde is less electrophilic than carbon
atom of the carbonyl group present in propanal.
The polarity of the carbonyl group is reduced in
benzaldehyde due to resonance as shown below
and hence it is less reactive than propanal.

Some important examples of nucleophilic addition and nucleophilic addition-elimination reactions:

(a) Addition of hydrogen cyanide (HCN):

Aldehydes and ketones react with hydrogen cyanide (HCN) to yield cyanohydrins. This reaction occurs very slowly with pure
HCN. Therefore, it is catalysed by a base and the generated cyanide ion (CN- ) being a stronger nucleophile readily adds to
carbonyl compounds to yield corresponding cyanohydrin. Cyanohydrins are useful synthetic intermediates.
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(b) Addition of sodium hydrogensulphite: Sodium hydrogensulphite adds to aldehydes and ketones to form the addition
products The position of the equilibrium lies largely to the right hand side for most aldehydes and to the left for most
ketones due to steric reasons.

Q- How will you separate an aldehyde from a non carbonyl compound ?

Ans- With sodium bisulphite, aldehyde forms a crystalline substance which is water soluble and can be converted back to
the original carbonyl compound by treating it with dilute mineral acid or alkali. Therefore, Reaction with sodium hydrogen
sulphite is useful for separation and purification of aldehydes.
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(c) Addition of Grignard reagents:
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(d) Addition of alcohols:
Addition of alcohols: Aldehydes react with one equivalent of monohydric alcohol in the presence of dry
hydrogen chloride to yield alkoxyalcohol intermediate, known as hemiacetals, which further react with one
more molecule of alcohol to give a gem-dialkoxy compound known as acetal as shown in the reaction. Ketones
react with ethylene glycol under similar conditions to form cyclic products known as ethylene glycol ketals.

Question – discuss the role of HCl In the reaction of aldehyde or

ketones with alcohols
Ans- Dry hydrogen chloride protonates the oxygen of the carbonyl
compounds and therefore, increases the electrophilicity of the
carbonyl carbon facilitating the nucleophilic attack of ethylene glycol.
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(e) Addition of ammonia and its derivatives:
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12.18 Give explanation for each of the following: Grade XII / unit-12/HIMANSHU SIR
(i) Cyclohexanone forms cyanohydrin in good yield but 2,2,6-trimethylcyclohexanone does not.

Electron density on carbonyl carbon in 2,2,6-

trimethylcyclohexanone is satisfied more due to presence of
three electron releasing groups. It has more + I effect than
Cyclohexanon which reduces the positive charge of carbonyl
carbon and discourage the attack of nucleophile. Due to + I effect
carbonyl carbon atom of 2,2,6-trimethylcyclohexanone is less
electrophilic hence 2,2,6-trimethylcyclohexanone is less reactive
towards nucleophilic addition reactions.
2,2,6-trimethylcyclohexanon discourage the attack of nucleophile
Due to more steric effect therefore its reactivity is less

(ii) There are two –NH2 groups in semicarbazide. However, only one is involved in the formation of semicarbazones.
Ans- The other – NH2 group off semicarbazide is attached to electron withdrawing CO group, which withdraws the
electron from NH2 and the electron density on nitrogen Atom decreases therefore it cannot act as nucleophile
 Grade XII / unit-12/HIMANSHU SIR
2. Reduction
(i) Reduction to alcohols: Aldehydes and
ketones are reduced to primary and
secondary alcohols respectively by sodium
borohydride (NaBH4) or lithium aluminium
hydride (LiAlH4) as well as by catalytic
hydrogenation

(ii) Reduction to hydrocarbons:

Clemmensen reduction - The carbonyl group of
aldehydes and ketones is reduced to CH2 group on
treatment with zinc amalgam and concentrated HCl
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Wolff-Kishner reduction- The carbonyl group of aldehydes and ketones is reduced to CH2 group on
treatment with hydrazine followed by heating with sodium or potassium hydroxide in high boiling solvent
such as ethylene glycol
 Grade XII / unit-12/HIMANSHU SIR
3. Oxidation

Aldehydes are easily oxidised to carboxylic acids on treatment with common oxidising agents like nitric acid,
potassium permanganate, potassium dichromate, etc. Even mild oxidising agents, mainly Tollens’ reagent
and Fehlings’ reagent also oxidise aldehydes

Ketones are generally oxidised under vigorous conditions, i.e., strong oxidising agents and at elevated
temperatures. Their oxidation involves carbon-carbon bond cleavage to afford a mixture of carboxylic acids
having lesser number of carbon atoms than the parent ketone
 Grade XII / unit-12/HIMANSHU SIR
The mild oxidising agents given below are used to distinguish aldehydes from ketones:
(i) Tollens’ test: On warming an aldehyde with freshly prepared ammoniacal silver nitrate solution
(Tollens’ reagent), a bright silver mirror is produced due to the formation of silver metal. The aldehydes are
oxidised to corresponding carboxylate anion. The reaction occurs in alkaline medium

(ii) Fehling’s test: Fehling reagent comprises of two solutions, Fehling solution A and Fehling solution B. Fehling
solution A is aqueous copper sulphate and Fehling solution B is alkaline sodium potassium tartarate (Rochelle salt).
These two solutions are mixed in equal amounts before test. On heating an aldehyde with Fehling’s reagent, a reddish
brown precipitate is obtained. Aldehydes are oxidised to corresponding carboxylate anion. Aromatic aldehydes do not
respond to this test
 Grade XII / unit-12/HIMANSHU SIR

(iii) Oxidation of methyl ketones by haloform reaction ( IODOFORM TEST):

Aldehydes and ketones having at least one methyl group linked to the carbonyl carbon atom (methyl ketones) are
oxidised by sodium hypohalite to sodium salts of corresponding carboxylic acids having one carbon atom less than that
of carbonyl compound. The methyl group is converted to haloform. This oxidation does not affect a carbon-carbon
double bond, if present in the molecule
Iodoform reaction with sodium hypoiodite is also used for detection of CH3CO group or CH3CH(OH) group which
produces CH3CO group on oxidation.
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12.13 Give simple chemical tests to distinguish between the following pairs of compounds.
(i) Propanal and Propanone

(ii) Acetophenone and Benzophenone

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(v) Pentan-2-one and Pentan-3-one

(vi) Benzaldehyde and Propanal

(vii) Ethanal and Propanal

 Grade XII / unit-12/HIMANSHU SIR
Example 12.4 An organic compound (A) with molecular formula C8H8O forms an orange-red precipitate with 2,4-DNP reagent
and gives yellow precipitate on heating with iodine in the presence of sodium hydroxide. It neither reduces Tollens’ or
Fehlings’ reagent, nor does it decolourise bromine water or Baeyer’s reagent. On drastic oxidation with chromic acid, it gives a
carboxylic acid (B) having molecular formula C7H6O2. Identify the compounds (A) and (B) and explain the reactions involved.
 Grade XII / unit-12/HIMANSHU SIR

4. Reactions due to a-hydrogen

Acidity of α-hydrogens of aldehydes and ketones:
The aldehydes and ketones undergo a number of
reactions due to the acidic nature of α-hydrogen.
The acidity of α-hydrogen atoms of carbonyl
compounds is due to the strong electron
withdrawing effect of the carbonyl group and
resonance stabilisation of the conjugate base
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(i) Aldol condensation: Aldehydes and ketones having at least one α-hydrogen undergo a reaction in
the presence of dilute alkali as catalyst to form β-hydroxy aldehydes (aldol) or β-hydroxy ketones (ketol),
respectively. This is known as Aldol reaction
 Grade XII / unit-12/HIMANSHU SIR
(ii) Cross aldol condensation: When aldol condensation is carried out between two different aldehydes and / or ketones, it
is called cross aldol condensation. If both of them contain α-hydrogen atoms, it gives a mixture of four products
Grade XII / unit-12/HIMANSHU SIR
 Grade XII / unit-12/HIMANSHU SIR
12.9 Write structural formulas and names of four possible aldol condensation products from propanal
and butanal. In each case, indicate which aldehyde acts as nucleophile and which as electrophile.
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Cannizzaro reaction: Aldehydes which do not have an α-hydrogen atom, undergo self oxidation and reduction
(disproportionation) reaction on treatment with concentrated alkali. In this reaction, one molecule of the aldehyde is
reduced to alcohol while another is oxidised to carboxylic acid salt.
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(ii) Electrophilic substitution reaction
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(vi) The methyl hemiacetal of formaldehyde

12.5 Draw structures of the following derivatives.

(i) The 2,4-dinitrophenylhydrazone of benzaldehyde

(ii) Cyclopropanone oxime

(iii) Acetaldehydedimethylacetal

(iv) The semicarbazone of cyclobutanone

(v) The ethylene ketal of hexan-3-one

 Grade XII / unit-12/HIMANSHU SIR
12.6 Predict the products formed when cyclohexanecarbaldehyde reacts with following reagents.
(i) PhMgBr and then H3O+ (ii) Tollens’ reagent (iii) Semicarbazide and weak acid (iv) Excess ethanol and acid (v) Zinc
amalgam and dilute hydrochloric acid
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12.7 Which of the following compounds would undergo aldol condensation, which the Cannizzaro reaction and which
neither? Write the structures of the expected products of aldol condensation and Cannizzaro reaction.
(i) Methanal (ii) 2-Methylpentanal (iii) Benzaldehyde (iv) Benzophenone (v) Acetophenone (vi) Cyclohexanone
(vii) 1-Phenylpropan-1-one (viii) Phenylacetaldehyde (ix) Butan-1-ol (x) 2,2-Dimethylbutanal
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Grade XII / unit-12/HIMANSHU SIR
Grade XII / unit-12/HIMANSHU SIR
 Carboxylic acid
Structure of Carboxyl Group
Carbonyl carbon of carboxylic acid is less electrophilic than carbonyl carbon of aldehyde and ketone. Therefore
carboxylic acid does not give characteristic reactions with ammonia derivative, like aldehyde and ketone gives. The
carboxylic carbon is less electrophilic because of the possible resonance structure

Methods of Preparation Preparation of Carboxylic

1. From primary alcohols and aldehydes
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2. From alkylbenzenes
Aromatic carboxylic acids can be prepared by vigorous oxidation of alkyl benzenes with chromic acid or acidic
or alkaline potassium permanganate. The entire side chain is oxidised to the carboxyl group irrespective of
length of the side chain. Primary and secondary alkyl groups are oxidised in this manner while tertiary group is
not affected. Suitably substituted alkenes are also oxidised to carboxylic acids with these oxidising reagents
 Grade XII / unit-12/HIMANSHU SIR
3. From nitriles and amides Nitriles are hydrolysed to amides and then to acids in the presence of H+ or OH − as
catalyst. Mild reaction conditions are used to stop the reaction at the amide stage.
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4. From Grignard reagents
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5. From acyl halides and anhydrides

6. From esters
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Example 12.5 - Write chemical reactions to affect the following transformations: (i) Butan-1-ol to butanoic acid
(ii) Benzyl alcohol to phenylethanoic acid (iii) 3-Nitrobromobenzene to 3-nitrobenzoic acid (iv) 4-
Methylacetophenone to benzene-1,4-dicarboxylic acid (v) Cyclohexene to hexane-1,6-dioic acid (vi) Butanal to
butanoic acid.
 Grade XII / unit-12/HIMANSHU SIR
Intext Question 12.7 Show how each of the following compounds can be converted to benzoic acid.
(i) Ethylbenzene (ii) Acetophenone (iii) Bromobenzene (iv) Phenylethene (Styrene)
 Grade XII / unit-12/HIMANSHU SIR
Physical Properties
➢ Carboxylic acids are higher boiling liquids than aldehydes, ketones and even alcohols of comparable
molecular masses. This is due to more extensive association of carboxylic acid molecules through
intermolecular hydrogen bonding.

➢ The hydrogen bonds are not broken completely even in the vapour phase. In fact, most carboxylic acids
exist as dimer in the vapour phase or in the aprotic solvents.

➢ Simple aliphatic carboxylic acids having upto four carbon atoms are miscible in water due to the formation
of hydrogen bonds with water. The solubility decreases with increasing number of carbon atoms. Higher
carboxylic acids are practically insoluble in water due to the increased hydrophobic interaction of
hydrocarbon part. Benzoic acid, the simplest aromatic carboxylic acid is nearly insoluble in cold water.

➢ Carboxylic acids are also soluble in less polar organic solvents like benzene, ether, alcohol, chloroform, etc.
 Chemical Reactions Grade XII / unit-12/HIMANSHU SIR

Reactions Involving Cleavage of O–H Bond

i. Acidity The carboxylic acids like alcohols evolve hydrogen with electropositive metals and form
salts with alkalies similar to phenols. However, unlike phenols they react with weaker bases
such as carbonates and hydrogencarbonates to evolve carbon dioxide. This reaction is used
to detect the presence of carboxyl group in an organic compound.

The pKa of hydrochloric acid is –7.0,

where as pKa of trifluoroacetic acid
(the strongest organic acid),
benzoic acid and acetic acid are
0.23, 4.19 and 4.76, respectively.
 Grade XII / unit-12/HIMANSHU SIR
Smaller the pKa, the stronger the acid ( the better it is as a proton donor). Strong acids have pKa values < 1, the
acids with pKa values between 1 and 5 are considered to be moderately strong acids, weak acids have pKa
values between 5 and 15, and extremely weak acids have pKa values >15.

Question – Carboxylic acids add more acidic than phenol. give reason
Ans - The conjugate base of carboxylic acid, a carboxylate ion, is stabilised by two equivalent resonance
structures in which the negative charge is at the more electronegative oxygen atom. The conjugate base of
phenol, a phenoxide ion, has non-equivalent resonance structures in which the negative charge is at the less
electronegative carbon atom. Therefore, resonance in phenoxide ion is not as important as it is in carboxylate
ion. Further, the negative charge is delocalised over two electronegative oxygen atoms in carboxylate ion
whereas it is less effectively delocalised over one oxygen atom and less electronegative carbon atoms in
phenoxide ion . Thus, the carboxylate ion is more stabilised than phenoxide ion, so carboxylic acids are more
acidic than phenols
Grade XII / unit-12/HIMANSHU SIR
 Grade XII / unit-12/HIMANSHU SIR
Q- Discuss the effect of substituents on the acidity of carboxylic acids Or
Electron withdrawing group increases the acidic strength of carboxylic acid and electron releasing group
decreases the acidic strength of carboxylic acid. give reason
Ans- Electron withdrawing groups increase the acidity of carboxylic acids by stabilising the conjugate base
through delocalisation of the negative charge by inductive and/or resonance effects. Conversely, electron
donating groups decrease the acidity by destabilising the conjugate base.

Direct attachment of groups such as phenyl or

vinyl to the carboxylic acid, increases the acidity
of corresponding carboxylic acid, contrary to
the decrease expected due to resonance effect
This is because of greater electronegativity of
sp2 hybridised carbon to which carboxyl carbon
is attached.
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The presence of electron withdrawing group on the phenyl of aromatic carboxylic acid increases their acidity
while electron donating groups decrease their acidity
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Reactions Involving Cleavage of C–OH Bond
1. Formation of anhydride

2. Esterification
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Q- Write Mechanism of esterification of carboxylic
acids:
The esterification of carboxylic acids with alcohols is
a kind of nucleophilic acyl substitution. Protonation
of the carbonyl oxygen activates the carbonyl group
towards nucleophilic addition of the alcohol. Proton
transfer in the tetrahedral intermediate converts the
hydroxyl group into –+ OH2 group, which, being a
better leaving group, is eliminated as neutral water
molecule. The protonated ester so formed finally
loses a proton to give the ester.

3. Reactions with PCl5, PCl3 and SOCl2

Thionyl chloride (SOCl2) is preferred because the other two products are gaseous and escape the reaction mixture making
the purification of the products easier
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4. Reaction with ammonia Carboxylic acids react with ammonia to give ammonium salt which on
further heating at high temperature give amides.
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Reactions Involving –COOH Group
1. Reduction Carboxylic acids are reduced to primary alcohols by lithium aluminium hydride or better
with diborane. Diborane does not easily reduce functional groups such as ester, nitro, halo, etc. Sodium
borohydride does not reduce the carboxyl group.

2. Decarboxylation : sodium salt of carboxylic acid on reaction with soda lime ( NaOH + CaO) gives alkane
containing 1 less carbon atom. This reaction is used to remove - COOH group from benzene ring.
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Kolbe electrolysis Alkali metal salts of carboxylic acids also undergo decarboxylation on electrolysis of
their aqueous solutions and form hydrocarbons having twice the number of carbon
atoms present in the alkyl group of the acid. The reaction is known as Kolbe
electrolysis
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Substitution Reactions in the Hydrocarbon Part
1. Halogenation Carboxylic acids having an α-hydrogen are halogenated at the α-position on treatment
with chlorine or bromine in the presence of small amount of red phosphorus to give α-
halocarboxylic acids. The reaction is known as Hell-Volhard-Zelinsky reaction.

2. Ring substitution Aromatic carboxylic acids undergo electrophilic substitution reactions in which the carboxyl
group acts as a deactivating and meta-directing group. They however, do not undergo Friedel-Crafts reaction
(because the carboxyl group is deactivating and the catalyst aluminium chloride (Lewis acid) gets bonded to the
carboxyl group).
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12.8 How will you convert ethanal into the following compounds? (i) Butane-1,3-diol (ii) But-2-enal (iii) But-
2-enoic acid