The alkene from which the alcohol shown can be prepared is to be stated. Among the two, epoxide hydrolysis and OsO 4 , 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 OsO 4 also occurs with syn stereochemistry. The addition of OsO 4 to the alkene gives a cyclic osmate which is cleaved by using aqueous NaHSO 3 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 OsO 4 , the method which can be used to prepare the diol.

Question

Show how the following starting materials are converted to the given product by a series of two pericyclic reactions. Account for the observed stereochemistry.

Answer 1

Question

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.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Show how the following starting materials are converted to the given product by a series of two pericyclic reactions. Account for the observed stereochemistry.

Show how the following starting material is converted to the given product by a series of two pericyclic reactions. Account for the observed stereochemistry.

When 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsevproduct predominates.(a) Draw the reaction, showing the major and minor products.(b) When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results.For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl groups cis.Use your models to draw a Newman projection of the transition state to show why this stereospecificity is observed.(c) Use a Newman projection of the transition state to predict the major product of elimination of (2S,3R)-2-bromo-3-phenylbutane