Chapter 22.9, Problem 23PTS

(a)

Interpretation Introduction

Interpretation: The major products are to be found when the given compounds are treated with excess methyl iodide followed by aqueous silver oxide and heat.

Concept Introduction:

The reagents such as methyl iodide and silver oxide are used as the reaction conditions which are called Hofmann elimination. The amines undergo exhaustive alkylation in the presence of excess methyl iodide producing quaternaryammonium salt which is excellent leaving group. After treatment with strong base, aqueous silver oxide and heat, the quaternary ammonium salt provides alkenes. Alkene formation involves in $\text{E2}$ elimination.  Through $\text{E2}$ elimination, the major product is less substituted alkene with trace amount of more substituted alkene.

To find: The major product of cyclohexyl amine in Hofmann elimination

Draw and analyze the structure of cyclohexyl amine

(b)

Interpretation Introduction

Interpretation: The major products are to be found when the given compounds are treated with excess methyl iodide followed by aqueous silver oxide and heat.

Concept Introduction:

The reagents such as methyl iodide and silver oxide are used as the reaction conditions which are called Hofmann elimination. The amines undergo exhaustive alkylation in the presence of excess methyl iodide producing quaternaryammonium salt which is excellent leaving group. After treatment with strong base, aqueous silver oxide and heat, the quaternary ammonium salt provides alkenes. Alkene formation involves in $\text{E2}$ elimination.  Through $\text{E2}$ elimination, the major product is less substituted alkene with trace amount of more substituted alkene.

To find: The major product of (R)-3-methyl-2-butanamine in Hofmann elimination

Draw and analyze the structure of (R)-3-methyl-2-butanamine

(c)

Interpretation Introduction

Interpretation: The major products are to be found when the given compounds are treated with excess methyl iodide followed by aqueous silver oxide and heat.

Concept Introduction:

The reagents such as methyl iodide and silver oxide are used as the reaction conditions which are called Hofmann elimination. The amines undergo exhaustive alkylation in the presence of excess methyl iodide producing quaternaryammonium salt which is excellent leaving group. After treatment with strong base, aqueous silver oxide and heat, the quaternary ammonium salt provides alkenes. Alkene formation involves in $\text{E2}$ elimination.  Through $\text{E2}$ elimination, the major product is less substituted alkene with trace amount of more substituted alkene.

To find: The major product of N,N-dimethyl-1-phenylpropan-2-amine in Hofmann elimination

Draw and analyze the structure of N,N-dimethyl-1-phenylpropan-2-amine.