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The order of acidic strength of the hydr...

The order of acidic strength of the hydrogen atom `(H_(alpha), H_(beta), H_(gamma))` in the given molecule is :
`CH_(3)-underset(H_(beta))underset(|)(CH)-overset(O)overset(||)(C )-underset(H_(gamma))underset(|)(CH)-overset(O)overset(||)(C )-underset(H_(alpha))underset(|)(CH_(2))`

A

`H_(gamma)gt H_(alpha) gt H_(beta)`

B

`H_(gamma)gt H_(beta) gt H_(alpha)`

C

`H_(alpha)gt H_(beta) gt H_(gamma)`

D

`H_(beta)gt H_(alpha) gt H_(gamma)`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the order of acidic strength of the hydrogen atoms \( H_{\alpha}, H_{\beta}, H_{\gamma} \) in the given molecule, we will analyze the stability of the resulting anions formed when each hydrogen is removed. ### Step-by-Step Solution: 1. **Identify the Structure**: The molecule can be represented as: \[ CH_3 - CH - C(=O) - CH - C(=O) - CH_2 \] Here, \( H_{\alpha} \) is attached to the carbon adjacent to the carbonyl group, \( H_{\beta} \) is attached to the carbon between the two carbonyl groups, and \( H_{\gamma} \) is attached to the carbon adjacent to the second carbonyl group. 2. **Remove Each Hydrogen**: - **Removing \( H_{\alpha} \)**: When \( H_{\alpha} \) is removed, we form a carbanion: \[ CH_3 - C^{-} - C(=O) - CH - C(=O) - CH_2 \] The negative charge is on a carbon adjacent to one carbonyl group (C=O), which is an electron-withdrawing group. This increases the stability of the carbanion. - **Removing \( H_{\beta} \)**: When \( H_{\beta} \) is removed, we form: \[ CH_3 - CH - C(=O) - C^{-} - C(=O) - CH_2 \] Here, the negative charge is on a carbon between two carbonyl groups. The presence of two electron-withdrawing groups (C=O) stabilizes the carbanion even more than in the case of \( H_{\alpha} \). - **Removing \( H_{\gamma} \)**: When \( H_{\gamma} \) is removed, we form: \[ CH_3 - CH - C(=O) - CH - C^{-} - CH_2 \] The negative charge is on a carbon adjacent to one carbonyl group, similar to \( H_{\alpha} \), but here the carbon is also adjacent to a carbon that has a positive inductive effect due to the carbonyl group. This makes the carbanion less stable compared to the one formed by removing \( H_{\beta} \). 3. **Compare the Stability of Carbanions**: - The carbanion formed by removing \( H_{\beta} \) is the most stable due to the presence of two electron-withdrawing carbonyl groups. - The carbanion formed by removing \( H_{\alpha} \) is less stable than that of \( H_{\beta} \) but more stable than that of \( H_{\gamma} \). - The carbanion formed by removing \( H_{\gamma} \) is the least stable due to the presence of only one electron-withdrawing group. 4. **Order of Acidity**: Based on the stability of the resulting carbanions, the order of acidic strength is: \[ H_{\beta} > H_{\alpha} > H_{\gamma} \] ### Final Answer: The order of acidic strength of the hydrogen atoms is: \[ H_{\beta} > H_{\alpha} > H_{\gamma} \]
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