Chapter 8.SE, Problem 24VC

Interpretation Introduction

Interpretation:

The alkene from which the alcohol shown can be prepared is to be stated. Among the two, epoxide hydrolysis and OsO₄, the method which can be used to prepare the diol also is to be stated.

Concept introduction:

During epoxidation an oxygen atom is transferred to the double bond in alkene with syn stereochemistry. Both C-O bonds are formed o the same face of the double bond. The epoxides undergo a acid catalyzed hydrolysis during which the ring is opened to give a trans-1,2-diol.

The hydroxylation with OsO₄ also occurs with syn stereochemistry. The addition of OsO₄ to the alkene gives a cyclic osmate which is cleaved by using aqueous NaHSO₃ to yield a cis-1,2-diol.

To state:

The alkene from which the alcohol shown can be prepared. Further to state, among epoxide hydrolysis and OsO₄, the method which can be used to prepare the diol.