Chapter 8.SE, Problem 53AP

Interpretation Introduction

a)

Interpretation:

The reaction given has a serious drawback. The potential problem in it is to be explained.

Concept introduction:

The addition of hydrogen halides to unsymmetrical alkenes occur following Markovnikov regiochemistry. The halogen adds to the more highly substituted carbon in the double bond while H adds to the less highly substituted carbon atom.

To explain:

The potential problem in the reaction given.

Interpretation Introduction

b)

Interpretation:

The reaction given has a serious drawback. The potential problem in it is to be explained.

Concept introduction:

Alkenes undergo hydroxylation when treated first with O_sO₄ and then with NaHSO₃. The reaction occurs with syn stereochemistry. Both –OH groups add to the double bond from the same face to give a cis-1,2-diol as the product.

To explain:

The potential problem in the reaction given.

Interpretation Introduction

c)

Interpretation:

The reaction given has a serious drawback. The potential problem in it is to be explained.

Concept introduction:

During ozonolysis ozone adds to the double bond in an alkene to give an ozonide. The ozonide on treatment with Zn in the presence of acid gets cleaved to yield carbonyl compounds as products. During the reaction each carbon in the double bond gets an oxygen atom.

To explain:

The potential problem in the reaction given.

Interpretation Introduction

d)

Interpretation:

The reaction given has a serious drawback. The potential problem in it is to be explained.

Concept introduction:

Alkenes can be hydrated using hydroboration-oxidation reaction. The reaction occurs with syn stereochemistry following anti markovnokov regiochemistry. The addition of both H and OH takes place from the same face of the double bond. The boron and hence the –OH group gets attached to less highly substituted carbon.

To explain:

The potential problem in the reaction given.