Q.Which of the following amines does NOT undergo acetylation?

Step 1. Acetylation (with acetyl chloride or acetic anhydride) proceeds by the amine's nitrogen lone pair attacking the acyl carbon, and the mechanism's final step requires loss of an N-H proton to complete the substitution and release HCl (or acetic acid).

Step 2. t-Butylamine (primary) and ethylamine (primary) each have two N-H; diethylamine (secondary) has one N-H -- all three can complete the acylation and lose the necessary proton.

Step 3. Triethylamine, (C2H5)3N, is TERTIARY -- all three of nitrogen's substituent positions are already alkyl groups, leaving no N-H at all. …

Check each amine for at least one N-H -- acetylation replaces an N-H with an acetyl group, so a tertiary amine (no N-H …

• Assuming a tertiary amine's strong nucleophilicity/basicity means it reacts MORE readily with an acyl chloride -- nucleophilic attack alone is not enough; the reaction needs an N-H to lose afterwar …