Chapter 18, Problem 18.14P

Interpretation Introduction

(a)

Interpretation:

The complete mechanism and the major product of the given reaction is to be drawn.

Concept introduction:

Secondary amines react with ketones and aldehydes under mildly acidic conditions to form an enamine. Secondary amine has only one hydrogen on nitrogen and thus it forms an enamine in which an amino group is attached to an alkene carbon. The first step of the mechanism is the nucleophilic addition of nitrogen to the electrophilic carbonyl carbon of a ketone or an aldehyde. The next three reactions are proton tranfer reactions in which the hydroxyl group is converted into a good leaving group and it leaves as a water molecule. This forms a carbocation intermediate. The next step is an elimination step in which an alpha proton is lost to form an alkene.

Interpretation Introduction

(b)

Interpretation:

The complete mechanism and the major product of the given reaction is to be drawn.

Concept introduction:

Secondary amines react with ketones and aldehydes under mildly acidic conditions to form an enamine. Secondary amine has only one hydrogen on nitrogen and thus it forms an enamine in which an amino group is attached to an alkene carbon. The first step of the mechanism is the nucleophilic addition of nitrogen to the electrophilic carbonyl carbon of a ketone or an aldehyde. The next three reactions are proton tranfer reactions in which the hydroxyl group is converted into a good leaving group and it leaves as a water molecule. This forms a carbocation intermediate. The next step is an elimination step in which an alpha proton is lost to form an alkene.

Interpretation Introduction

(c)

Interpretation:

The complete mechanism and the major product of the given reaction is to be drawn.

Concept introduction:

Secondary amines react with ketones and aldehydes under mildly acidic conditions to form an enamine. Secondary amine has only one hydrogen on nitrogen and thus it forms an enamine in which an amino group is attached to an alkene carbon. The first step of the mechanism is the nucleophilic addition of nitrogen to the electrophilic carbonyl carbon of a ketone or an aldehyde. The next three reactions are proton tranfer reactions in which the hydroxyl group is converted into a good leaving group and it leaves as a water molecule. This forms a carbocation intermediate. The next step is an elimination step in which an alpha proton is lost to form an alkene.