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Which of the following compounds undergoes elimination via an E2 mechanism?

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Question: Which of the following compounds undergoes elimination via an E2 mechanism?

Options:

  1. 2-bromopentane
  2. 2-bromo-2-methylpropane
  3. 1-bromobutane
  4. 3-bromopropanol

Correct Answer: 2-bromopentane

Solution:

2-bromopentane can undergo E2 elimination because it has a beta-hydrogen available for elimination, while the others either do not or favor different mechanisms.

Which of the following compounds undergoes elimination via an E2 mechanism?

Practice Questions

Q1
Which of the following compounds undergoes elimination via an E2 mechanism?
  1. 2-bromopentane
  2. 2-bromo-2-methylpropane
  3. 1-bromobutane
  4. 3-bromopropanol

Questions & Step-by-Step Solutions

Which of the following compounds undergoes elimination via an E2 mechanism?
  • Step 1: Understand what E2 elimination means. E2 is a type of reaction where a base removes a hydrogen atom (beta-hydrogen) from a carbon adjacent to a carbon with a leaving group (like bromine).
  • Step 2: Identify the compound in the question, which is 2-bromopentane. This compound has a bromine atom (the leaving group) and adjacent carbon atoms that have hydrogen atoms (beta-hydrogens).
  • Step 3: Check if 2-bromopentane has beta-hydrogens. Look at the structure: the carbon with the bromine is connected to other carbons that have hydrogen atoms. Yes, it has beta-hydrogens.
  • Step 4: Compare with other compounds in the question. Determine if they have beta-hydrogens or if they favor different mechanisms (like E1 or substitution).
  • Step 5: Conclude that since 2-bromopentane has beta-hydrogens and a good leaving group, it can undergo E2 elimination.
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