Which mechanism is favored in the reaction of a tertiary alkyl halide with a str

Practice Questions

Q1
Which mechanism is favored in the reaction of a tertiary alkyl halide with a strong nucleophile?
  1. S_N1
  2. S_N2
  3. E1
  4. E2

Questions & Step-by-Step Solutions

Which mechanism is favored in 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, meaning they have a lot of surrounding groups that make it hard for nucleophiles to attack directly.
  • Step 4: Learn about the S_N1 mechanism. This mechanism involves two steps: first, the halide leaves, forming a carbocation (a positively charged carbon), and then the nucleophile attacks the carbocation.
  • Step 5: Realize that the S_N1 mechanism is favored for tertiary alkyl halides because the carbocation formed is stable due to the surrounding carbon groups.
  • Step 6: Conclude that because of steric hindrance and the stability of the carbocation, the S_N1 mechanism is favored in this reaction.
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