Chapter 9.SE, Problem 40AP

Interpretation Introduction

a)

Interpretation:

How to carry out the conversion shown is to be stated.

Concept introduction:

Terminal alkenes can be converted in to aldehydes with same number of carbon atoms by hydroboration-oxidation reaction. The addition of water occurs with syn stereochemistry following anti-Markovnikov stereochemistry to yield an alcohol. The alcohol upon oxidation yields an aldehyde.

To state:

How to carry out the conversion shown.

Interpretation Introduction

b)

Interpretation:

How to carry out the conversion shown is to be stated.

Concept introduction:

The alkene is converted in to a dibromo derivative by treating with Br₂ in the presence of CH₂Cl₂. The dibromo derivative is then treated with two equivalents of KOH when dehydrohalogenation takes place yield a terminal alkyne. The terminal alkyne is then converted in to its sodium salt. The sodium alkynide when treated with CH₃Br yields the next higher alkyne which when reduced by Li in liq.NH₃ produces the trans alkene.

To state:

How to carry out the conversion shown.