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In the reaction sequence C6H5CHOoverset(...

In the reaction sequence `C_6H_5CHOoverset(NaCN//HCl)rarr(X)overset(H_2"O"//H^o+)rarr` product, Product will be

A

Optically inative acid

B

Optically inactive `alpha-` hydroxy acid

C

Racemic mixture of two optically active `alpha`- hydroxy acids

D

Racemic mixture of two optically active secondary alcohols

Text Solution

AI Generated Solution

The correct Answer is:
To solve the question step by step, we will analyze the reaction sequence provided and identify the product formed. ### Step 1: Identify the starting compound The starting compound is benzaldehyde, which has the formula \( C_6H_5CHO \). ### Step 2: Reaction with NaCN When benzaldehyde reacts with sodium cyanide (NaCN), the cyanide ion (CN⁻) acts as a nucleophile. The carbonyl carbon (C=O) in benzaldehyde is electrophilic due to the electronegativity of oxygen. The reaction can be represented as follows: \[ C_6H_5CHO + NaCN \rightarrow C_6H_5CH(OH)CN \] In this step, the CN⁻ attacks the carbonyl carbon, leading to the formation of a cyanohydrin. The product at this stage is \( C_6H_5CH(OH)CN \). ### Step 3: Treatment with H₂O and H⁺ Next, the cyanohydrin undergoes hydrolysis when treated with water (H₂O) in the presence of an acid (H⁺). During hydrolysis, the CN group is converted into a carboxylic acid (COOH). The reaction can be represented as follows: \[ C_6H_5CH(OH)CN + H_2O \rightarrow C_6H_5CH(OH)COOH \] The final product is \( C_6H_5CH(OH)COOH \), which is an alpha-hydroxy acid. ### Step 4: Determine the chirality of the product The carbon atom that is bonded to the hydroxyl group (OH) and the carboxylic acid group (COOH) is a chiral center because it is attached to four different groups: a benzene ring (C₆H₅), a hydroxyl group (OH), a carboxylic acid group (COOH), and a hydrogen atom (H). Therefore, the product is optically active. ### Step 5: Identify the correct option From the analysis, the product formed is an optically active alpha-hydroxy acid, which is a secondary alcohol. Thus, the correct answer is: **Product: An optically active alpha-hydroxy acid (secondary alcohol)** ### Summary of the Steps: 1. Identify the starting compound (benzaldehyde). 2. React with NaCN to form a cyanohydrin. 3. Hydrolyze the cyanohydrin to form an alpha-hydroxy acid. 4. Determine the chirality of the product (it is optically active). 5. Identify the correct option based on the product formed.
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