Chapter 24, Problem 24.79P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. Hence there must be one reaction that alters the carbon skeleton. Target product is a chain with OH functional group at the terminal position. Retrosynthetic approach suggests that the formation of the product through Diels-Alder reaction is followed by oxidative cleavage and reduction.

Interpretation Introduction

(c)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. This suggests that one reaction to alter carbon skeleton must occur. Retrosynthesis suggests the formation of β- hydroxy aldehyde via aldol reaction. The precursor for this reaction must be 1, 6-dialdehyde.

Interpretation Introduction

(d)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This suggests that two reactions that alter carbon skeleton must occur. The retrosynthesis of the target suggests it to be a product of Diels-Alder reaction. The two precursors of Diels alder reaction must be butadiene and an aldehyde.