Question

Identify the major product(s) in the reaction of (R)-2-bromopentane with sodium cyanide in DMSO solvent

Answer 1

Answer:

(S)-2-pentanenitrile

Explanation:

The reaction between (R)-2-bromopentane and sodium cyanide in DMSO occurs by SN2 mechanism.

Recall that CN^- is a strong nucleophile. In the presence of aprotic solvents, SN2 mechanism predominates with a strong nucleophile.

SN2 mechanism leads to inversion of configuration. Therefore, the major product of the reaction is (S)-2-pentanenitrile

Answer 2

There are different types of chemical reaction. (S)-2-cyanopentane is known to be the major product in the reaction of (R)-2-bromopentane with sodium cyanide in DMSO solvent.

• The (2R)-2-bromopentane is known to  reacts with sodium cyanide in DMSO solvent leading to the production of (2S)-2-methylpentanenitrile as a key product.

This formation takes place because DMSO is a polar aprotic solvent and often incline to the product formation via SN2mechanism where inversion of configuration takes place.

Nucleophilic Substitution Reaction is simply known to be a type of chemical reaction where the nucleophile attacks the reactant from the rear side.  

Note that the product gotten from this kind of reaction will habe to be of inverted stereochemistry.

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