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Among the given compounds, the most susc...

Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is

A

`MeCOCl`

B

`MeCHO`

C

`MeCOOMe`

D

`MeCOOCOMe`

Text Solution

AI Generated Solution

The correct Answer is:
To determine which compound is most susceptible to nucleophilic attack at the carbonyl group, we need to analyze the electron density around the carbonyl carbon in each of the given compounds. The more electron-deficient the carbonyl carbon is, the more susceptible it will be to nucleophilic attack. ### Step-by-Step Solution: 1. **Identify the Compounds**: The compounds given are: - (i) CH3C(=O)Cl - (ii) CH3C(=O)H - (iii) CH3C(=O)CH3 - (iv) CH3C(=O)O=C(=O)CH3 2. **Analyze Each Compound**: - **Compound (i) CH3C(=O)Cl**: The chlorine atom is highly electronegative and exerts a -I (inductive) effect, pulling electron density away from the carbonyl carbon. This makes the carbonyl carbon more electron-deficient and thus more susceptible to nucleophilic attack. - **Compound (ii) CH3C(=O)H**: This compound has a hydrogen atom attached to the carbonyl carbon. Hydrogen does not have a significant electronegative effect, so the carbonyl carbon is less electron-deficient compared to compound (i). - **Compound (iii) CH3C(=O)CH3**: Here, both substituents are methyl groups. Methyl groups have a +I effect, which increases the electron density around the carbonyl carbon, making it less susceptible to nucleophilic attack. - **Compound (iv) CH3C(=O)O=C(=O)CH3**: This compound has two carbonyl groups. The presence of the adjacent carbonyl group can donate some electron density to the carbonyl carbon, which also reduces its susceptibility to nucleophilic attack. 3. **Compare the Susceptibility**: - Compound (i) has the chlorine atom, which significantly reduces the electron density at the carbonyl carbon, making it the most susceptible to nucleophilic attack. - Compound (ii) is less susceptible than (i) due to the absence of a strong electron-withdrawing group. - Compound (iii) is even less susceptible due to the electron-donating effect of the methyl groups. - Compound (iv) has two carbonyls, which also reduces susceptibility due to electron donation. 4. **Conclusion**: Based on the analysis, the compound that is most susceptible to nucleophilic attack at the carbonyl group is **Compound (i) CH3C(=O)Cl**. ### Final Answer: **The most susceptible compound to nucleophilic attack at the carbonyl group is CH3C(=O)Cl.**
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