16. Conjugated Systems
Conjugated Hydrohalogenation (1,2 vs 1,4 addition)
5PRACTICE PROBLEM
A chemist wanted to investigate whether the faster formation of the 1,2-addition product in the reaction of 1,3-butadiene with HBr was due to the greater proximity of the nucleophile to the C-2 carbon in the transition state. Should he investigate the reaction using 1-methylcyclopenta-1,3-diene or 2-methylcyclopenta-1,3-diene?
A chemist wanted to investigate whether the faster formation of the 1,2-addition product in the reaction of 1,3-butadiene with HBr was due to the greater proximity of the nucleophile to the C-2 carbon in the transition state. Should he investigate the reaction using 1-methylcyclopenta-1,3-diene or 2-methylcyclopenta-1,3-diene?