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Chapter 18: Q13P (page 581)

How would you prepare the following diols?

Short Answer

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Answer

a)

b)

Step by step solution

01

Step-by-Step SolutionStep 1: Diols

Diols are compounds containing two hydroxyl groups (-OH). Trans-diols are formed by the opening of epoxides on reaction with aqueous acid. The C-OH and O-H bonds are formed, and the C-O bond is broken.

02

The preparation of (a) compound

a. In the first step, the compound is reacted with OsO4 , and pyridine. Both oxygens of OsO4 approach from the same side of the alkene. In the second step, the reaction with OsNaHSO3 , and H2O , the break down of cyclic Os compound happens, and forms diols along with osmium salt are formed.


The formation of Diol

03

The preparation of (b) compound

b. In the first step, 1-methylcyclohexene is reacted with peroxy acid and forms an epoxide ring. On further reaction with H3O+, trans-1,2-diols are formed.


The formation of Diol

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Safrole, a substance isolated from the oil of sassafras, is used as a perfumery agent. Propose a synthesis of safrole from catechol (1,2-benzenediol).

Predict the major product of each of the following reactions:

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  1. Methyl propyl ether
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Give IUPAC names for the following compounds (reddish brown 5 Br; yellow 5 S):
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