Which of the following compounds undergoes elimination via an E2 mechanism?
Practice Questions
1 question
Q1
Which of the following compounds undergoes elimination via an E2 mechanism?
2-bromopentane
2-bromo-2-methylpropane
1-bromobutane
3-bromopropanol
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.
Questions & Step-by-step Solutions
1 item
Q
Q: Which of the following compounds undergoes elimination via an E2 mechanism?
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.
Steps: 5
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.
