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Question

Question: \[Figure]\...

[Figure]\

Answer

The product B shown in the reaction is correctly formed.

Explanation

Solution

The given reaction involves the reduction of a bicyclic compound containing two functional groups: a ketone and a carboxylic acid. The reducing agent used is Lithium Aluminium Hydride (LiAlH₄).

Understanding the Reactant:

The starting material is a bicyclo[2.2.1]heptane derivative.

  1. It has a ketone group (C=O) at the bridge (C7 position).
  2. It has a carboxylic acid group (-COOH) attached to one of the bridgehead carbons (C1 position).

The reactant can be named as 1-carboxy-bicyclo[2.2.1]heptan-7-one.

Reactivity of LiAlH₄:

Lithium Aluminium Hydride (LiAlH₄) is a powerful reducing agent that can reduce various functional groups:

  1. Ketones: LiAlH₄ reduces ketones (R₂C=O) to secondary alcohols (R₂CH-OH).
  2. Carboxylic Acids: LiAlH₄ reduces carboxylic acids (R-COOH) to primary alcohols (R-CH₂OH).

Applying the Reaction to the Reactant:

Based on the reactivity of LiAlH₄:

  1. The ketone group (C=O) at the C7 position will be reduced to a secondary alcohol (-CH-OH). The oxygen atom of the ketone will gain a hydrogen and the carbon atom will gain a hydrogen.
  2. The carboxylic acid group (-COOH) at the C1 position will be reduced to a primary alcohol (-CH₂OH). The carbonyl carbon of the carboxylic acid will be fully reduced to a methylene group, and the hydroxyl group will remain as part of the primary alcohol.

Analyzing Product B:

The product B shown in the image is:

  1. The ketone bridge (C=O) has been converted to a hydroxyl group (-OH) attached to the bridge carbon, indicating the formation of a secondary alcohol.
  2. The carboxylic acid group (-COOH) attached to the bridgehead carbon has been converted to a primary alcohol group (-CH₂OH).

Both transformations observed in product B are consistent with the known reducing capabilities of LiAlH₄. Therefore, the product B depicted is correctly formed from the given reactant under the specified reaction conditions.

The product B is 1-(hydroxymethyl)-bicyclo[2.2.1]heptan-7-ol.

Explanation of the solution:

Lithium Aluminium Hydride (LiAlH₄) is a strong reducing agent. It reduces the ketone group (C=O) in the bicyclic system to a secondary alcohol (-CH-OH) and the carboxylic acid group (-COOH) to a primary alcohol (-CH₂OH). The product B shown in the reaction scheme correctly depicts these transformations.