Chapter 18, Problem 18.61P

Interpretation Introduction

(a)

Interpretation:

Hydroxylamine, ${\text{H}}_{\text{2}}\text{NOH}$, has both an OH functional group and an ${\text{NH}}_{\text{2}}$ functional group, so it can feasibly undergo reaction with a ketone or an aldehyde to produce either an acetal or an imine-like compound called an oxime. The mechanism for the reaction of hydroxylamine with acetone is to be drawn.

Concept introduction:

Under mild acidic conditions, ammonia and amines add reversibly to carbonyl groups. At very low pH, the N atom from ammonia or amine gets protonated. A protonated N has no lone pair of electrons, and hence, it would not act as a nucleophile.

Interpretation Introduction

(b)

Interpretation:

Hydroxylamine, ${\text{H}}_{\text{2}}\text{NOH}$, has both an OH functional group and an ${\text{NH}}_{\text{2}}$ functional group, so it can feasibly undergo reaction with a ketone or an aldehyde to produce either an acetal or an imine-like compound called an oxime. The major organic product for the given reaction is to be drawn.

Concept introduction:

Under mild acidic conditions, ammonia and amines add reversibly to carbonyl groups. At very low pH, the N atom from ammonia or amine gets protonated. A protonated N has no lone pair of electrons, and hence, it would not act as a nucleophile. At mild pH, the N is more nucleophilic than O.