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Chapter 23: Q34. (page 924)

Question: What hydrogen atoms in each compound have a pka鈮� 25?

Short Answer

Expert verified

Answer

The hydrogen atoms in each compound have a pKa 鈮� 25, as shown below:

Step by step solution

01

Criteria for acidity

A compound is considered to be highly acidic when the intermediate structure formed after the proton abstraction is stabilized by resonance or -I effect of the adjacent group (generally an electronegative element).

02

 Step 2: Stability of the negative charge

The negative charge formed after the proton abstraction undergoes extensive resonance along with the exertion of -I effect of the adjacent group. More the stability of the conjugate base formed, more will be its acidity.

Representation of the resonating structures

The -I effect is shown by the carbonyl group.

Representation of the resonating structures

The -I effect is shown by the carbonyl group.

Representation of the resonating structures

The -I effect is shown by the phenyl group.

Based on the explanations, the hydrogen atoms in each compound have a pKa 鈮� 25, as shown below:

The acidic hydrogen a.

The acidic hydrogen b.

The acidic hydrogen c.

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