Chapter 16, Problem 26P

Interpretation Introduction

Interpretation:

The product for each of the given reaction is to be predicted by showing stereochemistry where appropriate.

Concept introduction:

The alcohol on dehydration in presence of the acid catalyst eliminates the water molecule and forms double bond.

The dihydroxylation is the addition of two hydroxyl groups to the double bond of alkene to form a $\text{1,2}$

diol. Both hydroxyl groups add to the double bond from same side of the double bond.

The alkene on hydroboration-oxidation undergoes addition of water across the double bond according to anti- Markovnikov’s rule. The hydroxyl goes to less substituted double bonded carbon and hydrogen goes to more substituted double bonded carbon.

The ketone on reduction with lithium aluminum hydride $\left({\text{LiAlH}}_{\text{4}}\right)$

in diethyl ether forms secondary alcohol and carboxylic acid forms primary alcohol.

The isolated double or triple bonds cannot be reduced by lithium aluminum hydride $\left({\text{LiAlH}}_{\text{4}}\right)$.

The hydroxyl groups oxidized to carbonyl compound on oxidation with chromic acid in a acid catalyst. The secondary alcohols on oxidation forms ketone.

Ester can be synthesized by reacting alcohol with carboxylic acid, acyl halide, or acid anhydride. In ester, the alkoxy group of alcohol bonded to carbonyl group of carboxylic acid, acyl halide, or acid anhydride.