Question:

Given below are two statements:

 Statement I

 under Clemmensen reduction conditions will give

 Statement II

 under Wolff-Kishner reduction condition will give

 In the light of the above statements, choose the correct answer from the options given below:

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Clemmensen Reduction: Reduces ketones or aldehydes to alkanes under acidic conditions.
Wolff-Kishner Reduction: Reduces ketones or aldehydes to alkanes under basic conditions, but reactive substituents like halogens may undergo side reactions.

Updated On: Jan 8, 2025
  • Statement I is true but Statement II is false
  • Statement I is false but Statement II is true
  • Both Statement I and Statement II are true
  • Both Statement I and Statement II are false
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The Correct Option is A

Solution and Explanation

Statement I:
Clemmensen reduction involves the use of Zn(Hg) and HCl, which reduces ketones or aldehydes to their corresponding alkanes under acidic conditions.
In the given compound, \(\text{H}_2\text{N} - \text{CH}_2\text{CH}_2\text{COCH}_3\), the ketone group (\(\text{COCH}_3\)) is reduced, and the intermediate carboxylic acid product (\(\text{HOOC-CH}_2\text{CH}_2\)) is correct under these conditions.
Hence, Statement I is true.
Statement II:
Wolff-Kishner reduction involves hydrazine (\(\text{NH}_2\text{NH}_2\)) and a strong base such as KOH, which reduces carbonyl groups (ketones or aldehydes) to their corresponding alkanes.
However, in the compound \(\text{Cl-CH}_2\text{CH}_2\text{COCH}_3\), the chlorine atom may react with the basic medium, leading to a side reaction (dehydrohalogenation) instead of simple reduction. The final product will not necessarily be \(\text{ClCH}_2\text{CH}_2\text{CH}_3\), as suggested.
Hence, Statement II is false.

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Concepts Used:

Aldehydes, Ketones, and Carboxylic Acids

Aldehydes, Ketones, and Carboxylic Acids are carbonyl compounds that contain a carbon-oxygen double bond. These organic compounds are very important in the field of organic chemistry and also have many industrial applications.

Aldehydes:

Aldehydes are organic compounds that have the functional group -CHO.

Preparation of Aldehydes

Acid chlorides are reduced to aldehydes with hydrogen in the presence of palladium catalyst spread on barium sulfate.

Ketones:

Ketones are organic compounds that have the functional group C=O and the structure R-(C=O)-R’.

Preparation of Ketones

Acid chlorides on reaction with dialkyl cadmium produce ketones. Dialkyl cadmium themselves are prepared from Grignard reagents.

Carboxylic Acid:

Carboxylic acids are organic compounds that contain a (C=O)OH group attached to an R group (where R refers to the remaining part of the molecule).

Preparation of Carboxylic Acids

Primary alcohols are readily oxidized to carboxylic acids with common oxidizing agents such as potassium permanganate in neutral acidic or alkaline media or by potassium dichromate and chromium trioxide in acidic media.