Question

1-Bromobicyclo[2.2.2]octane does not undergo an E2 reaction when treated with a strong base.

a) True
b) False

Answer 1

1-Bromobicyclo[2.2.2]octane does not undergo an E2 reaction due to steric hindrance that prevents the elimination process required for this reaction.

Step-by-step explanation:

It is true that 1-bromobicyclo[2.2.2]octane does not undergo an E2 reaction when treated with a strong base. The structure of this compound is highly hindered due to its bicyclic nature, which prevents the base from abstracting a β-hydrogen necessary for the E2 mechanism to occur. As with E2 reactions, the mechanism is bimolecular, involving the departure of a leaving group (bromine, in this case) and the abstraction of a β-hydrogen to form a double bond. However, this molecule’s rigid framework inhibits the appropriate alignment of atoms for the concerted elimination process required in an E2 reaction.