Which base works best to maximize the E2 product in the reaction?(CH3)2CHCH2CH2CH2Br+base-->(CH3)2CHCH2CH=CH2

Question

1. KOCH2CH3 2. NaOCH2CH3 3. NaOC(CH3)3 4. NaOH

Answer 1

3.) NaOC(CH3)3 (t-butoxide) is by far the best base for a E2 reaction.

Why? Because it is very sterically hindered so it cannot act as a nucleophile. Also those 3 methyl groups are electron donating to an area where there is already a negative charge. It wants a proton!

NaOH is nowhere near as sterically hindered, so it can do a nucleophilic substitution which is not what you want.

Answer 2

3