When (cis)-1-bromo-2 methylcyclohexane is treated with methanol and heat, four different products are formed - two by substitution and two by elimination. Which of the following conditions would change the outcome of this reaction by promoting the production of 3-methylhexene as the major product?
A) KOH, ethanol and heat
B) water/acetone and heat
C) tert-butoxide/tert-butyl alcohol
D) tert-butyl alcohol and heat
E) methoxide/methanol

Question

When (cis)-1-bromo-2 methylcyclohexane is treated with methanol and heat, four different products are formed - two by substitution and two by elimination.  Which of the following conditions would change the outcome of this reaction by promoting the production of 3-methylhexene as the major product? 
A) KOH, ethanol and heat 
B) water/acetone and heat 
C) tert-butoxide/tert-butyl alcohol 
D) tert-butyl alcohol and heat 
E) methoxide/methanol

Quizplus · Accepted Answer

tert-butoxide/tert-butyl alcohol is a strong base that favors elimination reactions over substitution reactions, leading to the formation of the 3-methylhexene product as the major product.

When (Cis)-1-Bromo-2 Methylcyclohexane Is Treated with Methanol and Heat, Four