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An ester (X) with molecular formula C9 H...

An ester (X) with molecular formula `C_9 H_(10) O_2` was treated with excess of `CH_3 Mg Br` and the complex so formed, was treated with `H_2 SO_4` to give an alkene (Y) whose ozonolysis gave a ketone with molecular formula `C_8 H_8 O` which shows positive iodoform test. The structure of (X) is

A

`C_6H_5COOC_2H_5`

B

`C_6H_5COOC_6H_5`

C

`H_3C COO C_6H_5`

D

`p-H_3COC_6H_4COCH_3`

Text Solution

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The correct Answer is:
To determine the structure of the ester (X) with the molecular formula C9H10O2, we can follow these steps: ### Step 1: Identify the Ester The molecular formula of the ester is C9H10O2. Esters are derived from carboxylic acids and alcohols. The general formula for an ester is RCOOR', where R and R' are hydrocarbon chains. ### Step 2: Analyze the Reaction with Grignard Reagent When the ester is treated with excess CH3MgBr (a Grignard reagent), it forms a tertiary alcohol after hydrolysis. This indicates that the ester must have a structure that allows for the formation of a tertiary alcohol upon reaction with the Grignard reagent. ### Step 3: Consider Possible Structures We need to consider the options given: - Option A: C6H5COOC2H5 (Ethyl benzoate) - Option B: C6H5COOC6H5 (Benzyl benzoate) - Option C: CH3COOC6H5 (Acetophenone) - Option D: Paramethoxyacetophenol ### Step 4: Evaluate Each Option 1. **Option A (Ethyl benzoate)**: - Upon reaction with CH3MgBr, it would form a tertiary alcohol, which can then dehydrate to form an alkene. - The ozonolysis of the alkene would yield a ketone that can give a positive iodoform test. 2. **Option B (Benzyl benzoate)**: - This would not lead to a tertiary alcohol upon reaction with CH3MgBr, as it would not have the necessary structure. 3. **Option C (Acetophenone)**: - This is not an ester and thus cannot be the starting material. 4. **Option D (Paramethoxyacetophenol)**: - This structure does not fit the criteria for forming a tertiary alcohol from the reaction with CH3MgBr. ### Step 5: Confirm the Correct Structure From the analysis, **Option A (Ethyl benzoate)** is the only structure that fits all the criteria: - It reacts with CH3MgBr to form a tertiary alcohol. - The tertiary alcohol can dehydrate to form an alkene. - The ozonolysis of the alkene yields a ketone that shows a positive iodoform test. ### Conclusion The structure of the ester (X) is **C6H5COOC2H5 (Ethyl benzoate)**. ---

To determine the structure of the ester (X) with the molecular formula C9H10O2, we can follow these steps: ### Step 1: Identify the Ester The molecular formula of the ester is C9H10O2. Esters are derived from carboxylic acids and alcohols. The general formula for an ester is RCOOR', where R and R' are hydrocarbon chains. ### Step 2: Analyze the Reaction with Grignard Reagent When the ester is treated with excess CH3MgBr (a Grignard reagent), it forms a tertiary alcohol after hydrolysis. This indicates that the ester must have a structure that allows for the formation of a tertiary alcohol upon reaction with the Grignard reagent. ...
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Knowledge Check

  • How many alkenes are possible with molecular formula C_(4)H_(8) :

    A
    2
    B
    3
    C
    4
    D
    6
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