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A carbonyl compound reacts with hydrogen...

A carbonyl compound reacts with hydrogen cyanide to form cyanohydrin which on hydrolysis forms a recemic mixrture of `alpha`-hydroxy acid. The carbonyl compound `D`.

A

acetaldehyde

B

acetone

C

diethyl ketone

D

formaldehyde

Text Solution

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To solve the problem of identifying the carbonyl compound \( D \) that reacts with hydrogen cyanide to form a cyanohydrin and subsequently a racemic mixture of an alpha-hydroxy acid, we can follow these steps: ### Step-by-Step Solution: 1. **Understanding the Reaction**: - A carbonyl compound (aldehyde or ketone) reacts with hydrogen cyanide (HCN) to form a cyanohydrin. The general structure of a cyanohydrin is \( R_1R_2C(OH)(CN) \), where \( R_1 \) and \( R_2 \) are alkyl or hydrogen groups. 2. **Formation of Racemic Mixture**: - The cyanohydrin undergoes hydrolysis to form an alpha-hydroxy acid. For a racemic mixture to form, the carbon atom that is bonded to the hydroxyl group (OH) must be chiral, meaning it must have four different substituents. 3. **Choosing the Carbonyl Compound**: - We need to select a carbonyl compound that can lead to the formation of a chiral center upon reaction with HCN. - The simplest carbonyl compounds to consider are aldehydes and ketones. 4. **Analyzing Possible Candidates**: - **Acetaldehyde (Ethanal)**: \( CH_3CHO \) - Reacts with HCN to form \( CH_3C(OH)(CN)H \). Upon hydrolysis, this will yield \( CH_3C(OH)COOH \) (lactic acid), which is a racemic mixture due to the presence of a chiral center. - **Acetone (Propanone)**: \( CH_3COCH_3 \) - Forms a cyanohydrin, but the resulting product does not have a chiral center since both substituents on the carbon are \( CH_3 \). - **Diethyl Ketone (Butan-2-one)**: \( CH_3C(=O)C_2H_5 \) - Similar to acetone, it does not form a chiral center upon reaction with HCN. - **Formaldehyde (Methanal)**: \( HCHO \) - Also does not yield a chiral center as it has two hydrogen atoms attached to the same carbon. 5. **Conclusion**: - The only carbonyl compound that meets the criteria of forming a racemic mixture upon hydrolysis is **Acetaldehyde (Ethanal)**. Therefore, the carbonyl compound \( D \) is acetaldehyde. ### Final Answer: The carbonyl compound \( D \) is **Acetaldehyde (Ethanal)**. ---

To solve the problem of identifying the carbonyl compound \( D \) that reacts with hydrogen cyanide to form a cyanohydrin and subsequently a racemic mixture of an alpha-hydroxy acid, we can follow these steps: ### Step-by-Step Solution: 1. **Understanding the Reaction**: - A carbonyl compound (aldehyde or ketone) reacts with hydrogen cyanide (HCN) to form a cyanohydrin. The general structure of a cyanohydrin is \( R_1R_2C(OH)(CN) \), where \( R_1 \) and \( R_2 \) are alkyl or hydrogen groups. 2. **Formation of Racemic Mixture**: ...
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