Paaras Thakur

Carboxylic Acid
& derivatives
Lecture 5
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 Reactions Involving COOH group

(i) Reduction:
The most common reagent for the reduction of a carboxylic acid to a primary alcohol
is the very powerful reducing agent LiAlH4 or B2H6.
Example The major product ‘X’ formed in the following reaction is

JEE Main 2019

 Reactions Involving COOH group

(ii) Decarboxylation
The reaction whereby a carboxylic acid loses CO2 and forms hydrocarbon is called a
decarboxylation.

This reaction is carried out by heating sodium salts of carboxylic acids with soda-
lime (NaOH: CaO = 3:1) and is also known as Kolbe reaction.
 Reactions Involving COOH group

Decarboxylation of 𝛽-keto carboxylic acids:

𝛽-keto acids decarboxylate readily when they are heated to 100–150ºC.
 Reactions Involving COOH group

Hunsdiecker reaction: The silver (I) salts of carboxylic acids react with halogens to give
unstable intermediates which readily decarboxylate thermally to yield alkyl halides.
 Heating Effects

(a) Heating effect on monocarboxylic acid :

(a) Heating effect on dicarboxylic acid :

 Heating Effects

(c) Heating effects on Hydroxy acids :

(a) Heating effect on dicarboxylic acid :

 Hell Volhard Zelinsky (HVZ) Reaction

In the presence of a small amount of phosphorus, aliphatic carboxylic acids react

smoothly with chlorine or bromine to yield a compound in which -hydrogen has been
replaced by halogen.
 Hell Volhard Zelinsky (HVZ) Reaction

Mechanism:
Example
 Ring Substitution

Aromatic carboxylic acids undergo electrophilic substitution reactions in which the

carboxyl group is meta-directing and deactivating.

Aromatic carboxylic acids do not show Friedel–Crafts reaction as aluminium chloride

(used as catalyst) binds with the carboxyl group.
 Arndt Eistert Reaction

Used to prepare the next higher homologue of an acid. This reaction sequence is
considered to be the best method for the extension of a carbon chain by one carbon
atom in cases where a carboxylic acid is available.
 Arndt Eistert Reaction

Mechanism:
Example
Example
Example
Example
Example
Example
Example
Example
Example How will you carry out the following conversions?
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