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PhCH(2)-overset(O)overset(||)C-Cl+CH(3)C...

`PhCH_(2)-overset(O)overset(||)C-Cl+CH_(3)CH_(2)SH to X, X` is

A

`Ph-overset(O)overset(||)C-S-underset(CH_(3))underset(|)(CH)-CH_(3)`

B

`Ph-CH_(2)-overset(O)overset(||)C-S-CH_(2)-CH_(3)`

C

`CH_(3)-CH_(2)-CH_(2)-overset(O)overset(||)C-S-Ph`

D

`CH_(3)-underset(CH_(3))underset(|)(CH)-overset(O)overset(||)C-S-Ph`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the given question, we need to analyze the reaction step by step. The reactants are PhCH₂-C(=O)Cl (a phenyl group attached to a carbonyl group with a chlorine atom) and CH₃CH₂SH (ethyl mercaptan). We want to determine the product X. ### Step-by-Step Solution: 1. **Identify the Reactants**: - The first reactant is PhCH₂-C(=O)Cl, which is a phenyl group (Ph) attached to a methylene group (CH₂) and a carbonyl (C=O) with a chlorine (Cl) as a leaving group. - The second reactant is CH₃CH₂SH, which is ethyl mercaptan (a thiol). 2. **Nucleophilic Attack**: - The sulfur atom in the thiol (CH₃CH₂SH) has lone pairs and acts as a nucleophile. It will attack the carbon atom of the carbonyl group (C=O) in the first reactant. - This attack leads to the formation of a tetrahedral intermediate where the carbonyl oxygen will have a negative charge. 3. **Rearrangement of Bonds**: - The negative charge on the oxygen will push the electrons back to form a double bond between carbon and oxygen, while the chlorine atom (Cl) will act as a leaving group and depart. - This results in the formation of a new product where the sulfur atom is now bonded to the carbon that was part of the carbonyl group. 4. **Final Product Formation**: - After the chlorine leaves, we are left with a product that has the structure: Ph-CH₂-C(=O)-S-CH₂-CH₃. - This product contains a phenyl group, a methylene group, a carbonyl group, a sulfur atom, and an ethyl group. 5. **Conclusion**: - The final product X can be represented as Ph-CH₂-C(=O)-S-CH₂-CH₃, which corresponds to a thioester. ### Final Answer: The product X is Ph-CH₂-C(=O)-S-CH₂-CH₃.
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