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{:(" "OH),(" |"),(Ph-C-CH...

`{:(" "OH),(" |"),(Ph-C-CH_(3)),(" |"),(" "CH_(2)-CH_(3)):}`
Which of the following combinations can not be used to prepare alcohol given above ?

A

`PhMgBr + "2 -butanone" underset(NH_(4)Cl)rarr`

B

`EtMgBr + Ph - overset(O)overset(||)(C)-CH_(3) underset(NH_(4)Cl)rarr`

C

`CH_(3)MgBr + Ph - overset(O)overset(||)(C)-Et underset(NH_(4)Cl)rarr`

D

`EtMgBr + Ph - overset(O)overset(||)(C)-CH_(2)-CH_(3)underset(NH_(4)Cl)rarr`

Text Solution

AI Generated Solution

The correct Answer is:
To determine which combination cannot be used to prepare the given alcohol structure, we will analyze the reactions of Grignard reagents with various carbonyl compounds step by step. ### Given Structure: The alcohol structure can be represented as: ``` OH | Ph-C-CH3 | CH2-CH3 ``` Where: - Ph = Phenyl group (C6H5) - CH3 = Methyl group - CH2-CH3 = Ethyl group ### Step 1: Identify the Grignard Reagents and Carbonyl Compounds We will analyze the four combinations (A, B, C, D) to see which one does not yield the desired alcohol. 1. **Combination A**: Ph-MgBr with 2-butanone (CH3C(=O)CH2CH3) 2. **Combination B**: Et-MgBr with benzophenone (PhC(=O)Ph) 3. **Combination C**: Me-MgBr with ethyl phenyl ketone (PhC(=O)CH2CH3) 4. **Combination D**: Et-MgBr with acetophenone (PhC(=O)CH3) ### Step 2: Analyze Each Reaction #### Combination A: - **Grignard Reagent**: Ph-MgBr - **Carbonyl Compound**: 2-butanone (CH3C(=O)CH2CH3) - Reaction: - Ph- (C6H5) will act as a nucleophile and attack the carbonyl carbon of 2-butanone. - The product will be: ``` Ph-C(OH)(CH3)(CH2CH3) ``` - This yields the desired alcohol. #### Combination B: - **Grignard Reagent**: Et-MgBr - **Carbonyl Compound**: Benzophenone (PhC(=O)Ph) - Reaction: - Et- (C2H5) will attack the carbonyl carbon of benzophenone. - The product will be: ``` Ph-C(OH)(C2H5)(Ph) ``` - This does not yield the desired alcohol. #### Combination C: - **Grignard Reagent**: Me-MgBr - **Carbonyl Compound**: Ethyl phenyl ketone (PhC(=O)CH2CH3) - Reaction: - Me- (CH3) will attack the carbonyl carbon of ethyl phenyl ketone. - The product will be: ``` Ph-C(OH)(CH3)(CH2CH3) ``` - This yields the desired alcohol. #### Combination D: - **Grignard Reagent**: Et-MgBr - **Carbonyl Compound**: Acetophenone (PhC(=O)CH3) - Reaction: - Et- (C2H5) will attack the carbonyl carbon of acetophenone. - The product will be: ``` Ph-C(OH)(C2H5)(CH3) ``` - This does not yield the desired alcohol. ### Conclusion: The combination that cannot be used to prepare the given alcohol is **Combination B** (Et-MgBr with benzophenone) and **Combination D** (Et-MgBr with acetophenone). However, since the question asks for a single combination, we can conclude that **Combination B** is the most distinct as it does not yield the desired structure at all. ### Final Answer: **Combination B: Et-MgBr with benzophenone cannot be used to prepare the given alcohol.**

To determine which combination cannot be used to prepare the given alcohol structure, we will analyze the reactions of Grignard reagents with various carbonyl compounds step by step. ### Given Structure: The alcohol structure can be represented as: ``` OH | Ph-C-CH3 ...
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