Question

Propose a plausible synthesis of the following transformations.

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Answer 1

Answer:

b.

hv, Br2 Br NaOEt 1. 0; 2. MeS سه " H

In this reaction, the cyclopentane compound undergoes radical bromination at the tertiary position because the tertiary radicsals are more stable. after that it undergoes E2 elimination in presence of the base NaOEt to give the cyclopentene compound. In presence of Ozone, it undergoes cleavage of the double bond and then gives us the product.

c.

PCC 1. ВНЗ 2. H;0), NaOH ОН H 1.CH3MgBr, 2. H2O ОН

The butene with BH3 in presence of alkaline H2O2 undergoes hydroboration oxidation reaction to give alcohol 1-butanol. The alcohol is oxidised in presence of PCC reagent to the butyraldehyde. This aldehyde can be reacted with Grignard reagent to give us the 2-pentanol.

d.

1.СH MgBr, 2. Н40 ОН H,Cro, о

The cyclohexanecarbaldehyde is reacted with Grignard reagent to give the alcohol 1-cyclohexylethanol. The alcohol on oxidation with chromic acid gives us the required product.