PROBLEM 7.24 - Organic Chemistry

Question

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

a.

 

b.

Step-by-Step Solution

Answer

a.

b.

Stereochemistry of S N 1 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 S N 1 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 S N 1 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.