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Identify the final product (Z) in the fo...

Identify the final product (Z) in the following sequence of reactions :
`Me_2C=O+HCNrarr(X) overset(H_3O^+)rarr(Y)overset(H_2SO_4)rarr`

A

`(CH_3)_2C(OH) COOH`

B

`CH_2=C(CH_3)COOH`

C

`HOCH_2CH(CH_3)COOH`

D

`CH_3CH=CHCOOH`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem step by step, we will analyze the sequence of reactions given in the question: 1. **Identify the starting compound**: The starting compound is acetone (Me2C=O), which is CH3COCH3. 2. **Reaction with HCN**: - In the first reaction, acetone reacts with hydrogen cyanide (HCN). The nucleophilic cyanide ion (CN-) attacks the electrophilic carbon of the carbonyl group (C=O) in acetone. - The reaction leads to the formation of a cyanohydrin. The structure of the cyanohydrin (X) will be: \[ \text{CH}_3\text{C(OH)(CN)}\text{CH}_3 \] - Here, the hydroxyl group (OH) and the cyanide group (CN) are added to the same carbon atom. 3. **Hydrolysis with H3O+**: - The cyanohydrin (X) undergoes hydrolysis when treated with hydronium ion (H3O+). The CN group is converted into a carboxylic acid (COOH) group. - The product of this reaction (Y) will be: \[ \text{CH}_3\text{C(OH)(COOH)}\text{CH}_3 \] - This compound has a hydroxyl group (OH) and a carboxylic acid group (COOH) on the same carbon. 4. **Reaction with H2SO4**: - The next step involves treating the hydrolyzed product (Y) with sulfuric acid (H2SO4). This will lead to the protonation of the hydroxyl group, making it a better leaving group. - The water molecule (H2O) will leave, forming a carbocation intermediate: \[ \text{CH}_3\text{C}^+\text{(COOH)}\text{CH}_3 \] - The carbocation is then stabilized by the adjacent methyl groups. 5. **Deprotonation**: - Finally, one of the methyl groups will lose a proton (H+) to stabilize the carbocation, resulting in the formation of a double bond. - The final product (Z) will be: \[ \text{CH}_2=\text{C(CH}_3)\text{(COOH)} \] - This compound is an α,β-unsaturated carboxylic acid. 6. **Final Product Identification**: - The final product (Z) is: \[ \text{CH}_2=\text{C(CH}_3)\text{COOH} \] - This corresponds to option B in the question. ### Summary of Steps: 1. Start with acetone (Me2C=O). 2. React with HCN to form cyanohydrin (X). 3. Hydrolyze cyanohydrin with H3O+ to form carboxylic acid (Y). 4. Treat with H2SO4 to form carbocation. 5. Deprotonate to form the final product (Z).
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