Question

Design a synthesis of (s)-3-azido-2-methylpentane from (s)-2-methyl-3-pentanol?

Answer 1

To synthesize (S)-3-azido-2-methylpentane from (S)-2-methyl-3-pentanol, the hydroxyl group is first converted to a tosylate, followed by an SN2 substitution with sodium azide, keeping the (S) stereochemistry.

Step-by-step explanation:

To synthesize (S)-3-azido-2-methylpentane from (S)-2-methyl-3-pentanol, a sequence of reactions that maintain the (S) stereochemistry is needed:

1. Convert the alcohol group of (S)-2-methyl-3-pentanol to a good leaving group, such as a tosylate, by treating it with p-toluenesulfonyl chloride (TsCl) in the presence of a base.
2. Substitute the tosylate with an azide group using sodium azide (NaN3) to form (S)-3-azido-2-methylpentane via nucleophilic substitution (SN2 mechanism), maintaining the stereochemistry.

This reaction sequence relies on an initial functional group transformation followed by a stereospecific substitution to achieve the target compound.