Chapter 22, Problem 22.66AP

Interpretation Introduction

(a)

Interpretation:

The structures of three monobromo derivatives obtained from reaction of $2-\text{methylcyclohexanone}$ with ${\text{Br}}_{\text{2}}$ in presence of $\text{HBr}$ are to be predicted.

Concept introduction:

In organic chemistry, the carbonyl compound is a class of functional group which contains a $\text{C}=\text{O}$ group. They are of two types. aldehyde $-\text{CHO}$ and ketone $\text{RC}=\text{OR}$. They are the oxidized product of alcohol. Halogenation reaction of carbonyl compounds takes place in the presence of ${\text{Cl}}_{\text{2}}$, ${\text{Br}}_{\text{2}}$, ${\text{SO}}_{\text{2}}{\text{Cl}}_{\text{2}}$ and so on. It may result in the formation of enol and enolate ion in case of saturated compounds.

Interpretation Introduction

(b)

Interpretation:

The isomer in part (a) which is obtained from the most stable enol is to be stated.

Concept introduction:

Tautomers are isomers which differ only in the position of the protons and electrons of the double bond of the electronegative atom in the compound. There is no change in the carbon skeleton of the compound. This phenomenon which involves simple proton transfer in an intramolecular fashion is known as tautomerism. The very common example of tautomerism is Keto-enol tautomerism. It is possible in either way acid or base-catalyzed.