WHat are the products of the following reactions? Also please specify whether it's E1 or E2?
A) (CH3CH2)3CBr in NaNH2, NH3 solvents
B) CH3CH2CH2CH2Cl in KOC(CH3)3, (CH3)3COH solvents
2007-04-28 12:52:14 · 3 answers · asked by flyboy87 1 in Science & Mathematics ➔ Chemistry
a) elimination product was mentioned in above answer. tertiary bromide undergoes E1 because carbocation is stable (by hyperconjugation). you will also get some substitution product.
b)again, elimination product was mentioned above. primary chloride cannot form carbocation and so cannot undergo E1.
also, potassium t-butoxide is a strong, but bulky base which encourages elimination (strong base, poor nucleophile) so less substitution product is formed in this reaction.
2007-04-28 15:02:26 · answer #1 · answered by gordonliu 2 · 0⤊ 0⤋
gordon is correct
I'd probably argue that A is going to happen by E2. NaNH2/NH3 is a strongly basic system (it can deprotonate acetylenes)
Given the strong base and tertiary alkyl halide, E2 is favored.
2007-04-28 17:42:06 · answer #2 · answered by niuchemist 6 · 0⤊ 0⤋
A) (CH3CH2CH2)2C=CHCH2CH3 E1
B) CH3CH2CH=CH2 E2
2007-04-28 13:31:28 · answer #3 · answered by steve_geo1 7 · 0⤊ 0⤋