Q37E - Organic Chemistry (Mcmurry)

Question

Identify all the acidic hydrogens ($\mathit{p}{\mathit{K}}_{\mathbf{a}}\mathbf{<}\mathbf{25}$) in the following molecules:

Step-by-Step Solution

Answer

Acidic hydrogens in (a)

Acidic hydrogens in (b)

Acidic hydrogens in (c)

Acidic hydrogens in (d)

Acidic hydrogen in (e)

Acidic hydrogen in (f)

Step 1(a): Acidic hydrogen in molecule (a)

Acidic hydrogens are those which are attached to the α-carbon that has electron withdrawing group or bonded to the electronegative atom.

The electron withdrawing group and acidic α-hydrogens in the given compound are shown below,

The acidic hydrogens in the compound shown below are bold,

Acidic hydrogens in (a)

Step 2(b): Acidic hydrogen in molecule (b)

The electron withdrawing group and acidic α-hydrogens in the given compound are shown below,

The acidic hydrogen in the compound shown below are bold,

Acidic hydrogens in (b)

Step 3(c): Acidic hydrogen in molecule (c)

The electron withdrawing group and acidic α-hydrogens in the given compound are shown below,

The acidic hydrogen in the compound shown below are bold,

Acidic hydrogens in (c)

Step 4(d): Acidic hydrogen in molecule (d)

The electron withdrawing group and α-hydrogens in the given compound are shown below,

The acidic hydrogen in the compound shown below are bold,

Acidic hydrogens in (d)

Step 5(e): Acidic hydrogen in molecule (e)

The electron withdrawing group and acidic α-hydrogens in the given compound are shown below,

The acidic hydrogen in the compound shown below are bold,

Acidic hydrogen in (e)

Step 6(f): Acidic hydrogen in molecule (f)

The electron withdrawing group and acidic α-hydrogens in the given compound are shown below,

The acidic hydrogen in the compound shown below are bold,

Acidic hydrogen in (f)