Chapter 23, Problem 23.39P

(a)

Interpretation Introduction

Interpretation:

Structural formulas for compounds A and B have to be proposed using the given data.

Concept Introduction:

Hofmann Elimination: It is a type of reaction where an $\text{β-}$ elimination takes place in a quaternary ammonium halide via E2 mechanism when treated with a strong base to give a less substituted alkene as major product.

In Hofmann Elimination, a quaternary ammonium halide first treated with moist $A{g}_{2}O$ forming quaternary ammonium hydroxide which on heating gives an alkene. An anti stereoselective elimination occurs in the quaternary ammonium hydroxide to form alkene that is less substituted.

(b)

Interpretation Introduction

Interpretation:

Structure of (A) and the bicyclic amine can be whether derived by working backwards has to be given.

Concept Introduction:

Hofmann Elimination: It is a type of reaction where an $\text{β-}$ elimination takes place in a quaternary ammonium halide via E2 mechanism when treated with a strong base to give a less substituted alkene as major product.

In Hofmann Elimination, a quaternary ammonium halide first treated with moist $A{g}_{2}O$ forming quaternary ammonium hydroxide which on heating gives an alkene. An anti stereoselective elimination occurs in the quaternary ammonium hydroxide to form alkene that is less substituted.