Chapter 17, Problem 17.52AP

Interpretation Introduction

(a)

Interpretation:

The structure of compound $A$ that is formed by the reaction of nicotine with $\text{CyP450}$ is to be stated.

Concept introduction:

The enzyme $\text{CyP450}$ stands for Cytochrome $\text{P450}$. The enzyme, $\text{CyP450}$ converts the allylic or benzylic hydrogen atoms are oxidized to hydroxyl group, $\text{OH}$. This hydroxylation takes place by radical mechanism. The enzyme $\text{CyP450}$ binds to the substrate to itself and the reaction occurs with enzyme-substrate complex.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the conversion of $A$ into $B$ in the presence of ${\text{H}}_{\text{3}}{\text{O}}^{\text{+}}$ and ${\text{H}}_{\text{2}}\text{O}$ is to be stated.

Concept introduction:

The five-membered ring is unstable due to ring strain and presence of bulky substituents present on it, which rearranges and the ring opens into an aliphatic chain. This rearrangement is done by acidic hydrolysis.