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The ease of hydrolysis in the compounds ...

The ease of hydrolysis in the compounds `underset((I))(CH_3COCl),CH_3CO-underset((II))O-COCH_3,CH_3underset((III))(COOC_2H_5)and CH_3underset((IV))(CONH_2)` is of the order

A

`I gt II gt III gt IV`

B

`IV gt III gt II gt I`

C

`I gt II gt IV gt III`

D

`II gt I gt IV gt III`

Text Solution

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The correct Answer is:
To determine the order of ease of hydrolysis for the given compounds, we need to analyze the structure of each compound and the influence of the substituents attached to the carbonyl carbon. The compounds are: 1. **(I) CH₃COCl** (Acetyl chloride) 2. **(II) CH₃COO-COCH₃** (Acetic anhydride) 3. **(III) CH₃COOC₂H₅** (Ethyl acetate) 4. **(IV) CH₃CONH₂** (Acetamide) ### Step 1: Identify the nature of the substituents - **(I) CH₃COCl**: Chlorine is a strong electron-withdrawing group. - **(II) CH₃COO-COCH₃**: The presence of the acyl group (O-COCH₃) can also withdraw electrons, but not as strongly as chlorine. - **(III) CH₃COOC₂H₅**: The ethyl group (C₂H₅) is an electron-donating group, which makes the carbonyl less electrophilic. - **(IV) CH₃CONH₂**: The amine group (NH₂) is also an electron-donating group, making the carbonyl even less electrophilic compared to the ethyl group. ### Step 2: Analyze the electrophilicity of the carbonyl carbon The ease of hydrolysis is directly related to the electrophilicity of the carbonyl carbon. The more electrophilic the carbonyl carbon, the easier it is for water to attack and hydrolyze the compound. - **(I) CH₃COCl**: The carbonyl carbon is highly electrophilic due to the strong electron-withdrawing effect of chlorine. - **(II) CH₃COO-COCH₃**: The carbonyl carbon is less electrophilic than in (I) but more than in (III) and (IV). - **(III) CH₃COOC₂H₅**: The carbonyl carbon is less electrophilic due to the electron-donating ethyl group. - **(IV) CH₃CONH₂**: The carbonyl carbon is the least electrophilic due to the electron-donating amine group. ### Step 3: Establish the order of hydrolysis Based on the analysis above, we can establish the order of ease of hydrolysis as follows: 1. **(I) CH₃COCl** (most easily hydrolyzed) 2. **(II) CH₃COO-COCH₃** 3. **(III) CH₃COOC₂H₅** 4. **(IV) CH₃CONH₂** (least easily hydrolyzed) ### Final Order Thus, the order of ease of hydrolysis is: **CH₃COCl > CH₃COO-COCH₃ > CH₃COOC₂H₅ > CH₃CONH₂**
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