Chapter 7: PROBLEM 7.24 (page 272)
Question: Draw the products of each SN1 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 SN1 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.
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