Q3 / 51 · JEE Advanced 2023 (Paper 2) · Chemistry

In the following reactions, P,Q,R and S are the major products.

Figure

Figure

Figure

Figure

The correct statement about P,Q,R and S is

  • A
    P is a primary alcohol with four carbons.
  • Correct answer
    B
    Q undergoes Kolbe's electrolysis to give an eight-carbon product.
  • C
    R has six carbons and it undergoes Cannizzaro reaction.
  • D
    S is a primary amine with six carbons.

Solution

The isobutyl chloride on reaction with magnesium metal in dry ether give respective Grignard reagent. Grignard reagents produce hydrocarbon on reaction with water.

Figure

Grignard reagent can react with carbon dioxide and acidic water to give respective carboxylic acid. Carboxylic acid gives carboxylate with sodium hydroxide.This salt of carboxylic acid undergo Kolbe's electrolysis to give hydrocarbon as shown below.

Figure

Kolbe electrolysis :

Figure

The two isobutyl radicals formed in the above reaction combines to give a hydrocarbon that contain eight carbons.

Figure

The Grignard reagent formed from isobutyl chloride, reacts with acetaldehyde give respective secondary alcohol, which undergo oxidation with CrO3 gives ketone as shown below.

Figure

 

The above product undergoes aldol condensation reaction but not Cannizzaro's reaction.

The isobutyl chloride gives isobutyl cyanide on reaction with ethanolic NaCN. The cyanide undergo reduction with hydrogen in nickel gives primary amine. The primary amine formed undergo carbyl amine reaction gives isocyanide. The isocyanide gives secondary amine with lithium aluminium hydride.

Figure

Hence, the correct answer is option: 'B'.

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