JEE Main · 2021 · 01 Sep 2021 · Shift 2 · Alcohols Phenols and Ethers

In the following sequence of reactions a compound

A

, (molecular formula

C_{6} H_{12} O_{2}

) with a straight chain structure gives a C4 carboxylic acid. A is

A LiAlH_{4} H_{3} O^{+} B Oxidation C_{4}

- carboxylic acid

(A) $CH_{3} - CH_{2} - CH_{2} - O - CH = CH - CH_{2} - OH$
(B)(see structure)
(C) $CH_{3} - CH_{2} - CH_{2} - COO - CH_{2} - CH_{3}$ ✓ Correct
(D) $CH_{3} - CH_{2} - COO - CH_{2} - CH_{2} - CH_{3}$

Answer: (C)

Solution

Reduction by

LiAl H_{4}

and acid work-up converts an ester into two alcohols, and the subsequent oxidation must give a four-carbon acid, so one of those alcohols is butan-1-ol. The straight-chain

C_{6} H_{12} O_{2}

ester that yields butan-1-ol is ethyl butanoate,

C H_{3} C H_{2} C H_{2} COOC H_{2} C H_{3}

. Its reduction gives butan-1-ol and ethanol, and oxidation of butan-1-ol gives butanoic acid, a

C_{4}

carboxylic acid.

A

is ethyl butanoate.

JEE Main · 2021 · 01 Sep 2021 · Shift 2 · Single correct option

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JEE Main · 2021 · 01 Sep 2021 · Shift 2 · Alcohols Phenols and Ethers

Solution

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