Organic Chemistry -Reaction of
Carboxylic Acids
Test Study Guide: -Description and
Properties
Ch.8 Carboxylic Acids -And More
CONCEPT SUMMARY
Reactions of Carboxylic Acids
1. Synthesis:
Carboxylic acids can be synthesized through the oxidation of primary alcohols or aldehydes. Common
oxidizing agents include:
i. Potassium permanganate (KMnO4)
ii. Dichromate salts (e.g., Na2Cr2O7 or K2Cr2O7)
iii. Chromium trioxide (CrO)
2. Nucleophilic Acyl Substitution:
This is a prevalent reaction mechanism for carboxylic acids.
A nucleophile attacks the electrophilic carbonyl carbon, resulting in the opening of the carbonyl group and
forming a tetrahedral intermediate.
The carbonyl group then reforms, leading to the expulsion of a leaving group.
3. Product Formation Based on Nucleophile:
If the nucleophile is ammonia or an amine, an amide is produced, which carries the suffix -amide. Cyclic
amides are referred to as lactams.
If the nucleophile is an alcohol, an ester is formed, designated with the suffix -oate. Cyclic esters are
known as lactones.
If another carboxylic acid acts as the nucleophile, an anhydride is generated. Both linear and cyclic forms
are labeled with the suffix anhydride.
Reduction of Carboxylic Acids
Carboxylic acids can be converted to primary alcohols using strong reducing agents such as lithium aluminum
hydride (LiAlH4).
The reduction process involves the formation of aldehyde intermediates, which are subsequently reduced to
primary alcohols.
Reducing Agents
Sodium borohydride (NaBH4) is a commonly used reducing agent in organic chemistry but lacks the strength
necessary to reduce carboxylic acids.
Decarboxylation of Dicarboxylic Acids
B-dicarboxylic acids and certain -keto acids can undergo spontaneous decarboxylation upon heating, resulting
in the loss of carbon dioxide.
This reaction is facilitated by a six-membered cyclic intermediate.
Saponification Process
Carboxylic Acids
Test Study Guide: -Description and
Properties
Ch.8 Carboxylic Acids -And More
CONCEPT SUMMARY
Reactions of Carboxylic Acids
1. Synthesis:
Carboxylic acids can be synthesized through the oxidation of primary alcohols or aldehydes. Common
oxidizing agents include:
i. Potassium permanganate (KMnO4)
ii. Dichromate salts (e.g., Na2Cr2O7 or K2Cr2O7)
iii. Chromium trioxide (CrO)
2. Nucleophilic Acyl Substitution:
This is a prevalent reaction mechanism for carboxylic acids.
A nucleophile attacks the electrophilic carbonyl carbon, resulting in the opening of the carbonyl group and
forming a tetrahedral intermediate.
The carbonyl group then reforms, leading to the expulsion of a leaving group.
3. Product Formation Based on Nucleophile:
If the nucleophile is ammonia or an amine, an amide is produced, which carries the suffix -amide. Cyclic
amides are referred to as lactams.
If the nucleophile is an alcohol, an ester is formed, designated with the suffix -oate. Cyclic esters are
known as lactones.
If another carboxylic acid acts as the nucleophile, an anhydride is generated. Both linear and cyclic forms
are labeled with the suffix anhydride.
Reduction of Carboxylic Acids
Carboxylic acids can be converted to primary alcohols using strong reducing agents such as lithium aluminum
hydride (LiAlH4).
The reduction process involves the formation of aldehyde intermediates, which are subsequently reduced to
primary alcohols.
Reducing Agents
Sodium borohydride (NaBH4) is a commonly used reducing agent in organic chemistry but lacks the strength
necessary to reduce carboxylic acids.
Decarboxylation of Dicarboxylic Acids
B-dicarboxylic acids and certain -keto acids can undergo spontaneous decarboxylation upon heating, resulting
in the loss of carbon dioxide.
This reaction is facilitated by a six-membered cyclic intermediate.
Saponification Process
