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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

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

B

(b)0`H_(gamma)gt H_(beta) gt H_(alpha)`

C

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

D

(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 \( H_{\alpha} \), \( H_{\beta} \), and \( H_{\gamma} \) in the given molecule, we will analyze the stability of the corresponding conjugate bases formed after the removal of each hydrogen atom. ### 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 terminal \( CH_2 \), \( H_{\beta} \) is attached to the \( CH \) adjacent to the first carbonyl group, and \( H_{\gamma} \) is attached to the \( CH \) adjacent to the second carbonyl group. 2. **Remove Each Hydrogen Atom**: - **For \( H_{\alpha} \)**: Removing \( H_{\alpha} \) forms a negative charge on the \( CH_2 \) group: \[ CH_3 - CH - C(=O) - CH - C(=O) - CH_2^{-} \] The negative charge is stabilized by the adjacent carbonyl groups, which are electron-withdrawing. - **For \( H_{\beta} \)**: Removing \( H_{\beta} \) forms a negative charge on the \( CH \) group: \[ CH_3 - CH^{-} - C(=O) - CH - C(=O) - CH_2 \] This conjugate base has one carbonyl group that stabilizes the negative charge through resonance. - **For \( H_{\gamma} \)**: Removing \( H_{\gamma} \) forms a negative charge on the \( CH \) group: \[ CH_3 - CH - C(=O) - CH^{-} - C(=O) - CH_2 \] Similar to \( H_{\beta} \), this conjugate base has two carbonyl groups that stabilize the negative charge through resonance. 3. **Evaluate Stability of Conjugate Bases**: - The stability of the conjugate base is crucial in determining acidity. The more stable the conjugate base, the stronger the acid. - **Conjugate Base from \( H_{\gamma} \)**: Most stable due to resonance stabilization from two carbonyl groups. - **Conjugate Base from \( H_{\alpha} \)**: Less stable than \( H_{\gamma} \) but more stable than \( H_{\beta} \) due to one carbonyl group. - **Conjugate Base from \( H_{\beta} \)**: Least stable due to the presence of the methyl group which donates electrons, counteracting the electron-withdrawing effect of the carbonyl group. 4. **Order of Acidity**: Based on the stability of the conjugate bases: \[ H_{\gamma} > H_{\alpha} > H_{\beta} \] Therefore, the order of acidic strength is: \[ H_{\gamma} > H_{\alpha} > H_{\beta} \] ### Final Answer: The order of acidic strength of the hydrogen atoms is: \[ H_{\gamma} > H_{\alpha} > H_{\beta} \]
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