The correct reaction/reaction sequence that would produce a dicarboxylic acid as the major product is
Correct Answer :
Solution :
The correct option is C.
To determine which reaction sequence produces a dicarboxylic acid as the major product, we analyze the reaction steps for each option:
Option A:
The starting material is 3-chloropropan-1-ol:
1. Nucleophilic substitution with cyanide ion () from replaces the chloride leaving group, yielding a hydroxynitrile:
2. Hydrolysis of the nitrile group () under basic conditions () followed by acidic workup () converts the nitrile group to a carboxylic acid group ():
This product is 4-hydroxybutanoic acid, which contains only one carboxylic acid group (a monocarboxylic acid). Therefore, Option A is incorrect.
Option B:
The starting material is D-glucose:
When treated with bromine water (), which is a mild oxidizing agent, only the terminal aldehyde group () is oxidized to a carboxylic acid group (). The primary alcohol group () remains unaffected:
This reaction yields gluconic acid, which is a monocarboxylic acid. Therefore, Option B is incorrect.
Option C:
The starting material is bromocyclohexane:
1. Treatment with potassium hydroxide in ethanol () under heating promotes a dehydrohalogenation (E2 elimination) reaction, eliminating to produce cyclohexene:
2. Treating cyclohexene with hot, acidic potassium permanganate () causes oxidative cleavage of the carbon-carbon double bond (). Both alkene carbons are oxidized to carboxylic acid groups:
This opens the ring and yields adipic acid (hexanedioic acid), which contains two carboxylic acid groups (a dicarboxylic acid). Therefore, Option C is correct.
Option D:
The starting material represents a cyclic ketone. The reagents do not lead to the ring opening or oxidative functionalization required to generate a dicarboxylic acid as the major product. Therefore, Option D is incorrect.
Access expert-curated educational resources and study materials—completely free.
Create, conduct, and manage professional online assessments with Mindyard. Perfect for teachers and institutes.
Copyright © 2026 Mindyard. All Rights Reserved.