Cis-1-bromo-4-isopropylcyclohexane undergoes E2 elimination, with sodium hydroxide, 5000 times faster than does trans-1-bromo-4-isopropylcyclohexane. Fully explain this reactivity difference using mechanisms which clearly show the transition state. You should draw both of these isomers in the chair form.

Cis-1-bromo-4-isopropylcyclohexane undergoes E2 elimination, with sodium hydroxide, 5000 times faster than does trans-1-bromo-4-isopropylcyclohexane. Fully explain this reactivity difference using mechanisms which clearly show the transition state. You should draw both of these isomers in the chair form.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter9: Nucleophilic Substitution And Β-elimination

Section9.7: Experimental Evidence For E1 And E2 Mechanisms

Problem 9.7P

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