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A set of reactions yielded a product (D)...

A set of reactions yielded a product (D):
`CH_(3)COOHoverset(SOCl_(2))to(A)underset(anhyd.AlCl_(3))overset("Benzene")to(B)overset(HCN)to(C )overset(HOH)to(D)`
The structure of (D) would be:

A

B

C

D

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem step by step, we will analyze each reaction and determine the structure of the final product (D). ### Step 1: Reaction of Acetic Acid with SOCl2 - **Starting Compound**: Acetic Acid (CH₃COOH) - **Reaction**: Acetic acid reacts with thionyl chloride (SOCl₂). - **Product**: The hydroxyl group (-OH) in acetic acid is replaced by a chlorine atom (-Cl), forming acetyl chloride (CH₃C(=O)Cl). **Structure**: - CH₃C(=O)Cl (Acetyl chloride) ### Step 2: Friedel-Crafts Acylation with Benzene - **Starting Compound**: Acetyl Chloride (CH₃C(=O)Cl) - **Reagent**: Benzene (C₆H₆) and anhydrous aluminum chloride (AlCl₃). - **Reaction**: This is a Friedel-Crafts acylation reaction where the acetyl group is introduced to the benzene ring. - **Product**: The product formed is acetophenone (C₆H₅C(=O)CH₃). **Structure**: - C₆H₅C(=O)CH₃ (Acetophenone) ### Step 3: Reaction of Acetophenone with HCN - **Starting Compound**: Acetophenone (C₆H₅C(=O)CH₃) - **Reagent**: Hydrogen cyanide (HCN). - **Reaction**: The carbonyl group (C=O) in acetophenone reacts with HCN, resulting in the addition of a cyanohydrin. - **Product**: The product will have a hydroxyl group (-OH) and a cyano group (-CN) attached to the same carbon. **Structure**: - C₆H₅C(OH)(CN)CH₃ ### Step 4: Hydrolysis of the Cyanohydrin - **Starting Compound**: The cyanohydrin formed in the previous step. - **Reagent**: Water (H₂O). - **Reaction**: The cyano group (-CN) is hydrolyzed to a carboxylic acid (-COOH). - **Product**: The final product will have two carboxylic acid groups, one from the hydrolysis of the cyano group and one from the original acetophenone structure. **Final Structure (D)**: - C₆H₅C(OH)(COOH)CH₃ ### Final Answer The structure of product (D) is: - **C₆H₅C(OH)(COOH)CH₃**
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