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

. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B 2°C. +2°C. < cleavage Bond A • CH3 + 26. t cleavage 2°C• +3°C• Bond C Cleavage CH3 ZC '2°C. 26. E Strongest 3°C. 2C. Gund Largest BDE weakest bond In that molecule a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest C bond Produces A Weakest Bond Most Strongest Bond Stable radical Strongest Gund produces least stable radicals b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. 人 8°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. methyl radical •CH3 formed in bund A Cleavage

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.

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. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B 2°C. +2°C. < cleavage Bond A • CH3 + 26. t cleavage 2°C• +3°C• Bond C Cleavage CH3 ZC '2°C. 26. E Strongest 3°C. 2C. Gund Largest BDE weakest bond In that molecule a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest C bond Produces A Weakest Bond Most Strongest Bond Stable radical Strongest Gund produces least stable radicals b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. 人 8°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. methyl radical •CH3 formed in bund A Cleavage

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