Chapter 24, Problem 24.64P

Interpretation Introduction

(a)

Interpretation: The synthesis of given compound from ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}\text{Et}$, benzene, and organic alcohols is to be devised.

Concept introduction: Gattermann reaction is the organic reaction for the formylation of aromatic compounds using hydrogen cyanide in the presence of $\text{HCl}$ gas.

Aldehyde or ketone on reaction with a base and an alkyl halide results in alkylation. The alkyl group substitutes for $\text{H}$ on the $\text{α-C}$ atom.

Interpretation Introduction

(b)

Interpretation: The synthesis of given compound from ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}\text{Et}$, benzene, and organic alcohols is to be devised.

Concept introduction: Gattermann reaction is the organic reaction for the formylation of aromatic compounds using hydrogen cyanide in the presence of $\text{HCl}$ gas.

Aldehyde or ketone on reaction with a base and an alkyl halide results in alkylation. The alkyl group substitutes for $\text{H}$ on the $\text{α-C}$ atom.

Interpretation Introduction

(c)

Interpretation: The synthesis of given compound from ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}\text{Et}$, benzene, and organic alcohols is to be devised.

Concept introduction: The Friedel-Crafts acylation is a type of electrophilic substitution reaction. The Lewis acid ionizes the carbon-halogen bond of the acid chloride and forms a positively charged carbon electrophile which reacts with benzene to form ketone.

Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, the base abstracts an acidic proton from the $\text{α}$ carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of $\text{β}$-ketoester.