Question 1
Identify which of the following molecules would undergo the fastest S
N1 reaction.

◦ I
◦ II
◦ III
◦ IV
◦ V
Question 2
Identify which of the following compounds would undergo the fastest S
N1 reaction along with the best supporting explanation.

◦ (I) would undergo the fastest S
N1 reaction because it has the greatest amount of angle strain.
◦ (II) would undergo the fastest S
N1 reaction because it has less angle strain than the cyclopropene.
◦ (I) would undergo the fastest S
N1 reaction because it would form a stable aromatic carbocation intermediate.
◦ (III) would undergo the fastest S
N1 reaction because it has the no angle strain since it is acyclic.
◦ (III) would undergo the fastest S
N1 reaction because it forms a resonance stabilized carbocation intermediate.