Which mechanism is favored for the reaction of a tertiary alkyl halide with a st
Practice Questions
Q1
Which mechanism is favored for the reaction of a tertiary alkyl halide with a strong nucleophile?
S_N1
S_N2
E1
E2
Questions & Step-by-Step Solutions
Which mechanism is favored for the reaction of a tertiary alkyl halide with a strong nucleophile?
Step 1: Identify the type of alkyl halide. In this case, it is a tertiary alkyl halide, which means it has three carbon atoms attached to the carbon that is bonded to the halide.
Step 2: Understand what a nucleophile is. A strong nucleophile is a species that donates an electron pair to form a bond.
Step 3: Recognize that tertiary alkyl halides are bulky due to the three carbon groups attached to the central carbon. This bulkiness creates steric hindrance.
Step 4: Realize that steric hindrance makes it difficult for the nucleophile to attack the carbon directly. Instead, the reaction prefers to form a carbocation first.
Step 5: The S_N1 mechanism involves two steps: first, the halide leaves, forming a carbocation; second, the nucleophile attacks the carbocation to form the final product.
Step 6: Conclude that because of the steric hindrance and the stability of the carbocation, the S_N1 mechanism is favored for the reaction of a tertiary alkyl halide with a strong nucleophile.
