Question

Question: Draw the products of each S_N1 reaction and indicate the stereochemistry of any stereogenic centers.

a.

b.

Short answer

a.

b.

Step-by-step solution

Stereochemistry of SN1  reaction

The carbocation created during S_N1 reaction possesses hybridization. This molecule owns a trigonal planar geometry, creating the possibility for a nucleophilic attack from either side.

Predicting the product and stereochemistry of SN1 reaction

a. A racemic mixture is obtained as a product by treating (R)-3-bromo-2,3-dimethylpentane with water. Br^- functions as the leaving group and H₂O functions as the nucleophile in this reaction.

Product and stereochemistry of question a

The heterolytic cleavage of the C-Br bond leads to the creation of tertiary carbocation. The nucleophile strikes from both directions, leading to the formation of racemic mixtures.

Predicting the product and stereochemistry of SN1  reaction in question b

b. The reaction of the given compound with acetate ion leads to the formation of the racemic mixture as products. Cl^- functions as the leaving group, and the acetate ion functions as the nucleophile in this reaction.

Product and stereochemistry of question b

The cleavage of the C-Cl bond generates a tertiary carbocation. The attack of the nucleophile, acetate ion from either side, leads to a racemic mixture.