Chapter 5, Problem 5.29AP

Interpretation Introduction

(a)

Interpretation:

Whether the peroxide is present or not, the structure of a six-carbon alkene that would give same product from reaction with hydrogen bromide is to be drawn.

Concept introduction:

The addition of one or more than one halogen atom in an aromatic compound is known as halogenation reaction. The pathway of the halogenation reaction depends on the structure of the substrate. These reactions proceed via free-radical chain reaction.

Interpretation Introduction

(b)

Interpretation:

The structure of four compounds of formula ${\text{C}}_{\text{10}}{\text{H}}_{\text{16}}$ that would undergo catalytic hydrogenation to give decalin is to be drawn.

Concept introduction:

The addition of ${\text{H}}_{\text{2}}$ in presence of catalyst is known as catalytic hydrogenation reaction. This is a syn addition. Alkene is reduced to alkane. In this reaction weak pi bond of alkene and sigma bond between ${\text{H}}_{\text{2}}$ is broken and two $\text{C}-\text{H}$ bonds are formed.

Interpretation Introduction

(c)

Interpretation:

The structure of two alkenes that give $1-\text{methylcyclohexanol}$ when treated with $\text{Hg}{\left(\text{OAc}\right)}_{\text{2}}$ in water, and then ${\text{NaBH}}_{\text{4}}/\text{NaOH}$ is to be drawn.

Concept introduction:

The oxymercuration reaction is an electrophilic addition reaction that converts an alkene into an alcohol and an alkyne into a ketone. The reagents required for this reaction are $\left[1\right]\text{Hg}{\left(\text{OAc}\right)}_2;\left[2\right]{\text{H}}_{\text{2}}\text{O,}{\text{Et}}_2\text{O}\text{or}\text{THF}$.

Interpretation Introduction

(d)

Interpretation:

The structure of an alkene with one double bond that would give only one product after ozonolysis followed by hydrogen peroxide is to be stated.

Concept introduction:

In oxidative cleavage both the sigma and pi bond of the alkene is broken and two carbonyl compounds are formed. When ozone is added to the alkene, unstable intermediate molozonide is formed which rearranges to ozonide.

Interpretation Introduction

(e)

Interpretation:

The structure of two stereoisomeric alkenes that would give $\text{3-hexanol}$ as the major product of hydroboration followed by treatment with alkaline hydrogen peroxide is to be drawn.

Concept introduction:

Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-Markovnikov rule.

Anti markovinkov rule states that the positive part of acid attached to that carbon atom in $\text{C=C}$ bond which carries minimum number of hydrogen atoms and the negative part of acid will attach to that carbon atom in $\text{C=C}$ bond which has maximum number of hydrogen atoms.

Interpretation Introduction

(f)

Interpretation:

The structure of an alkene with five carbons that would give the same product as a result of either oxymercuration-reduction or hydroboration-oxidation is to be drawn.

Concept introduction:

Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-Markovnikov rule.

Anti markovinkov rule states that the positive part of acid attached to that carbon atom in $\text{C=C}$ bond which carries minimum number of hydrogen atoms and the negative part of acid will attach to that carbon atom in $\text{C=C}$ bond which has maximum number of hydrogen atoms.