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Chapter 18: Q13P (page 581)

How would you prepare the following diols?

Short Answer

Expert verified

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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Most popular questions from this chapter

How would you prepare the following ethers using a Williamson synthesis?

  1. Methyl propyl ether
  2. Anisole (methyl phenyl ether)
  3. Benzyl isopropyl ether
  4. Ethyl 2,2-dimethylpropyl ether

Show the product, including stereochemistry, that would result from reaction of the following epoxide with HBr

The red fox (Vulpesvulpes) uses a chemical communication system based on scent marks in urine. One component of fox urine is a sulfide whose mass spectrum has M+=116. IR spectroscopy shows an intense band at 890 cm−1and 1HNMR spectroscopy reveals the following peaks:

1.74 δ(3H, singlet); 2.11 δ(3H, singlet); 2.27 δ(2H, triplet, J=4.2 Hz); 2.57 δ(2H, tripletJ=4.2 Hz, ); 4.73 δ(2H, broad). Propose a structure consistent with these data. [Note:(CH3)2S absorbs at 2.1 δ].

Name the following ethers:

b)

We saw in section 17-4 that ketones react withNaBH4 to yield alcohols. We’ll also see in section 22-3 that ketones react withBr2 to yield α-bromo ketones. Perhaps surprisingly, treatment withNaBH4 of theα -bromo ketone from acetophenone yields an epoxide rather than a bromo alcohol. Show the structure of the epoxide, and explain its formation.

Acetophenone An α-bromo ketone
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