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Multiple Choice
Which of the following alkenes is the major product according to the rule in the dehydrohalogenation of ?
A
(ethylene)
B
cis-2-butene (, cis isomer)
C
1-butene ()
D
trans-2-butene (, trans isomer)
Verified step by step guidance
1
Identify the substrate and the type of reaction: The substrate is 2-bromobutane undergoing an E2 dehydrohalogenation reaction, which involves elimination of HBr to form an alkene.
Recall the Zaitsev rule: In elimination reactions, the major product is usually the more substituted alkene, as it is more stable due to hyperconjugation and alkyl group electron-donating effects.
Determine possible alkenes formed by elimination: From 2-bromobutane, elimination can give 1-butene (less substituted), cis-2-butene, and trans-2-butene (both more substituted). Ethylene is not a product here because it does not come from 2-bromobutane.
Compare substitution patterns: 1-butene is monosubstituted at the double bond, while 2-butene (both cis and trans) is disubstituted, making 2-butene more substituted and favored by Zaitsev's rule.
Consider stereochemistry: Between cis-2-butene and trans-2-butene, the trans isomer is more stable due to less steric hindrance, so trans-2-butene is the major product according to Zaitsev's rule and E2 elimination.