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CH3-undersetunderset(O)(||)C-CH3+PhMgBrt...

`CH_3-undersetunderset(O)(||)C-CH_3+PhMgBrtoAoverset(H_3O^+)toBunderset(Delta)overset(H_3PO_4)toC`
C is :

A

`Ph-undersetunderset(O)(||)C-CH_3`

B

`Ph-undersetunderset(OH)(|)oversetoverset(CH_3)(|)C-CH_3`

C

`Ph-undersetunderset(CH_3)(|)C=CH_2`

D

`Ph-undersetunderset(CH_3)(|)CH-CH_3`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem step by step, we will analyze the reaction of acetone (CH₃COCH₃) with phenylmagnesium bromide (PhMgBr) and the subsequent steps leading to the final product C. ### Step 1: Reaction of Acetone with PhMgBr - **Starting Material**: Acetone (CH₃COCH₃) - **Reagent**: PhMgBr (Phenylmagnesium bromide) In this step, the nucleophile (Ph⁻ from PhMgBr) attacks the electrophilic carbon of the carbonyl group in acetone. The oxygen in the carbonyl group becomes negatively charged. **Intermediate A**: \[ \text{CH}_3C(-O^-)CH_3 + \text{Ph}^- \rightarrow \text{CH}_3C(-O^-)CH_3\text{Ph} \] ### Step 2: Protonation of the Intermediate - **Reagent**: H₃O⁺ (Hydronium ion) The negatively charged oxygen in the intermediate A is protonated by H₃O⁺, forming a tertiary alcohol. **Intermediate B**: \[ \text{CH}_3C(OH)CH_3\text{Ph} \] ### Step 3: Dehydration of the Alcohol - **Reagent**: H₃PO₄ (Phosphoric acid) and heating In this step, the hydroxyl group (OH) of the alcohol is protonated, making it a better leaving group (water). The dehydration occurs, resulting in the formation of a double bond. **Final Product C**: \[ \text{CH}_3C=CH_2\text{Ph} \] ### Conclusion The final product C is an alkene with the structure: \[ \text{Ph}-\text{C}(\text{CH}_3)=\text{CH}_2 \] ### Answer C is: **Ph-CH=CH₂**
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Knowledge Check

  • CH_(3)-underset(Br)underset(|)(CH)-CH_(2)-overset(O)overset(||)(C)-CH_(3)underset(Delta)overset(N_(2)H_O(4),overset(ϴ)(O)H)(to) Product:

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    `CH_3-underset(H)underset(|)overset(CH_3)overset(|)C-CH_2OCH_3`
    B
    `CH_3-underset(OCH_3)underset(|)(CH)-CH_2CH_3`
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    `CH_3-underset(OCH_3)underset(|)overset(CH_3)overset(|)C-CH_3`
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