Question Details

The correct reaction/reaction sequence that would produce a dicarboxylic acid as the major product is

Options

A

B

C

D

Show Answer

Correct Answer :

Option C

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:
HO-CH2-CH2-CH2-Cl
1. Nucleophilic substitution with cyanide ion (CN-) from NaCN replaces the chloride leaving group, yielding a hydroxynitrile:
HO-CH2-CH2-CH2-CN
2. Hydrolysis of the nitrile group (-CN) under basic conditions (OH-/H2O) followed by acidic workup (H3O+) converts the nitrile group to a carboxylic acid group (-COOH):
HO-CH2-CH2-CH2-COOH
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:
CHO-(CHOH)4-CH2OH
When treated with bromine water (Br2/H2O), which is a mild oxidizing agent, only the terminal aldehyde group (-CHO) is oxidized to a carboxylic acid group (-COOH). The primary alcohol group (-CH2OH) remains unaffected:
HOOC-(CHOH)4-CH2OH
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 (KOH / EtOH) under heating promotes a dehydrohalogenation (E2 elimination) reaction, eliminating HBr to produce cyclohexene:
C6H11BrKOH / EtOH, ΔC6H10 (cyclohexene)
2. Treating cyclohexene with hot, acidic potassium permanganate (KMnO4/H2SO4,Δ) causes oxidative cleavage of the carbon-carbon double bond (C=C). Both alkene carbons are oxidized to carboxylic acid groups:
C6H10KMnO4/H2SO4,ΔHOOC-(CH2)4-COOH
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.

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