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PhMgBr+CH(3)-CN underset(H(3)O^(o+))rarr...

`PhMgBr+CH_(3)-CN underset(H_(3)O^(o+))rarr(A)Ph-overset(O)overset(||)(C)-O-Hunderset((2)H_(3)O)overset((1) "excess" CH_(3)-Li)rarr(A)`
Same product (A) will form in both reactions. A is :

A

`Ph-underset(CH_(3))underset(|)overset(OH)overset(|)(C)-CH_(3)`

B

`Ph-CHO`

C

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

D

`Ph-CH_(2)-CO_(2)H`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem step by step, we will analyze the two reactions involving the Grignard reagent (PhMgBr) and the product formed (A) in both cases. ### Step 1: Analyze the First Reaction 1. **Reactants**: PhMgBr + CH₃CN + H₃O⁺ 2. **Mechanism**: - The Grignard reagent (PhMgBr) dissociates into Ph⁻ and MgBr⁺. - The Ph⁻ ion attacks the carbon of the nitrile (CH₃CN), which is electrophilic due to the electronegative nitrogen. - This results in the formation of a carbocation intermediate. - The Ph group attaches to the carbon of the nitrile, yielding a new intermediate: CH₃C(Ph)N. 3. **Hydrolysis**: - Upon adding H₃O⁺, the nitrile group is hydrolyzed. - The nitrogen is protonated, and the carbon-nitrogen triple bond is converted into a carbonyl group (C=O) and an alcohol (OH). - The final product after dehydration (removal of water) is: \[ \text{Ph-C(=O)-CH₃} \] ### Step 2: Analyze the Second Reaction 1. **Reactants**: CH₃C(=O)OH + excess CH₃Li 2. **Mechanism**: - CH₃Li dissociates into CH₃⁻ and Li⁺. - The CH₃⁻ ion attacks the carbonyl carbon of the carboxylic acid (CH₃C(=O)OH). - This forms a new intermediate with a negative charge on the oxygen (alkoxide). - A second CH₃Li adds to the carbonyl oxygen, forming a more complex intermediate. 3. **Protonation**: - Upon adding H₃O⁺, the alkoxide is protonated to form the alcohol. - The final product after dehydration is also: \[ \text{Ph-C(=O)-CH₃} \] ### Conclusion Both reactions yield the same product (A): \[ \text{A} = \text{Ph-C(=O)-CH₃} \] ### Final Answer The product A formed in both reactions is **Ph-C(=O)-CH₃**. ---

To solve the problem step by step, we will analyze the two reactions involving the Grignard reagent (PhMgBr) and the product formed (A) in both cases. ### Step 1: Analyze the First Reaction 1. **Reactants**: PhMgBr + CH₃CN + H₃O⁺ 2. **Mechanism**: - The Grignard reagent (PhMgBr) dissociates into Ph⁻ and MgBr⁺. - The Ph⁻ ion attacks the carbon of the nitrile (CH₃CN), which is electrophilic due to the electronegative nitrogen. - This results in the formation of a carbocation intermediate. ...
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