Chapter 12.13, Problem 27PTS

(a)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

  

Concept introduction:

The product molecule has one more carbon atom than the starting material. For the generation of tertiary alcohol from secondary alcohol, there must be oxidation of alcohol to the carbonyl group, after which, there must be an addition of a methyl fragment, preferably using a Grignard reagent. This after hydrolysis can yield the desired tertiary alcohol.

(b)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

  

Concept introduction: The final product has one more carbon atom than the starting material. This can be facilitated by the addition of a methyl group, preferably using a Grignard reagent after conversion of alkyne to a carbonyl compound. The Grignard intermediate then can be hydrolyzed to obtain the final product.

(c)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve the following transformation is to be determined.

  

Concept introduction:

The final product contains two additional carbon atoms, so the synthesis requires a carbon-carbon bond-forming reaction. To facilitate this, the desired product should be produced by oxidizing the generated alcohol using the proper Grignard reagent.

(d)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve each of the following transformations is to be determined.

  

Concept introduction:

The target molecule contains one additional carbon atom, so the synthesis must have a carbon-carbon bond-forming reaction. This can be achieved by using a Grignard reagent followed by an elimination reaction which can yield the desired unsaturated product.

(e)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve each of the following transformations is to be determined.

  

Concept introduction:

The target molecule contains three additional carbon atoms, so the reaction needs a Carbon−Carbon bond-forming reaction. The alkyl halide can be first treated with magnesium metal to produce a Grignard reagent, followed by a reaction with the required ketone (acetone). It can then be converted to the desired product by treatment with thionyl chloride.

(f)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

  

Concept introduction:

The target molecule has two additional phenyl groups, which can be done by adding Grignard reagent containing phenyl groups two times, followed by oxidation. The starting material contains carbonyl carbon which is the reaction center for the phenyl part of the Grignard reagent.