6 P - Organic Chemistry (Mcmurry)

Question

Question: Predict the products of the following reactions:

(a) 

(b) 

(c) 

Step-by-Step Solution

Answer

(a) 

(b) 

(c) 

Step-by-Step Solution Step 1: Preparation of alcohols

 

Alcohols can be prepared from many other compounds like alkene, aldehydes, ketones, alkyl halides and esters. The methods used for preparing alcohols from alkenes are hydration, oxymercuration-demercuration and hydroxylation of alkene.

 

Step 2: The product of the reaction in (a)

(a) In the given reaction, hydroboration of alkene takes place. The oxidation of alkene occurs, which yields syn, and the hydration product formed is non-Markovnikov. This means the hydroxyl group is bonded to that carbon which is less substituted.

Preparation of alcohol

Step 3: The product of the reaction in (b)

(b) In the given reaction, oxymercuration-demercuration of alkene takes place. The given alkene is treated with , and then the product is treated with . The hydration product is formed by the Markovnikov rule, which means the hydroxyl group is bonded to that carbon of alkene, which is more substituted.

 

Preparation of alcohol

Step 4: The product of the reaction in (c)

(c) In the given reaction, hydroxylation of alkene takes place. The given alkene is treated with and followed by reduction with . A meso-5,6-Decanediol (cis diol) is formed, which has syn stereochemistry.

 

Preparation of alcohol