Chapter 12, Problem 39P

(a)

Interpretation Introduction

Interpretation: Using cyclohexanone as the starting material, the given compound has to be synthesized.

Concept Introduction:

Hydride reduction using $NaB{H}_4$:

 $NaB{H}_4$ - Sodium borohydride is a reducing agent.

 It reduces aldehydes, ketones and carboxylic acids into alcohols.

 General scheme:

(b)

Interpretation Introduction

Interpretation: Using cyclohexanone as the starting material, the given compound has to be synthesized.

Concept Introduction:

Hydride reduction using $NaB{H}_4$:

 $NaB{H}_4$ - Sodium borohydride is a reducing agent.

 It reduces aldehydes, ketones and carboxylic acids into alcohols.

 General scheme:

  

 Dehydration of alcohol using concentrated acid:

 Alcohols get converted into alkene by the treatment of concentrated acid such as sulfuric acid. In this reaction, the alcohol gets eliminated as water molecule and forms the alkene double bond.

 General scheme:

 

(c)

Interpretation Introduction

Interpretation: Using cyclohexanone as the starting material, the given compound has to be synthesized.

Concept Introduction:

Hydride reduction using $NaB{H}_4$:

 $NaB{H}_4$ - Sodium borohydride is a reducing agent.

 It reduces aldehydes, ketones and carboxylic acids into alcohols.

 General scheme:

  

Conversion of alcohol into alkyl halide:

In this conversion, the alcohol gets converted into alkyl halide using hydrogen halide and with the elimination of a water molecule.

(d)

Interpretation Introduction

Interpretation: Using cyclohexanone as the starting material, the given compound has to be synthesized.

Concept Introduction:

Imine formation:

Aldehyde or ketone reacts with a primary amine and forms imine in mildly acidic conditions.

Example for the formation of imine is shown here:

  

• Imines contain $C=N$ .
• Imines are also called as Schiff bases, named after Hugo Schiff who described their formation.

Reduction of imine:

Imine when undergoes hydrogenation reaction, it gets converted into amine.

Example

  

(e)

Interpretation Introduction

Interpretation: Using cyclohexanone as the starting material, the given compound has to be synthesized.

Concept Introduction:

Wittig reaction:

It is the conversion of a ketone or an aldehyde into alkene using the ylide of phosphorus.

General Scheme

  

Reduction of alkene:

Alkene when undergoes hydrogenation reaction, it gets converted into alkane.

Example