Consider the following two reactions. Which is more highly regioselective, and why? Reaction 1 `Cl + HCl Reaction 2 + HCl `Cl O Reaction 1, because the regioselectivity is determined by the difference in E, leading to a 1° versus a 3° carbocation, while in Reaction 2, both products are formed from a 3° carbocation. O They should have exactly the same regioselectivity, because both reactions can give 1-chloro-1- methylcyclohexane. O Reaction 1, because the regioselectivity is determined by the difference in Ea leading to a 1° versus a 3° carbocation, which is greater than the difference in E, leading to a 2° versus a 3° carbocation. O Reaction 1, because the regioselectivity is determined by the difference in Ea leading to a 1° versus a 2° carbocation, which is greater than the difference in E, leading to a 2° versus a 3° carbocation. Reaction 2, because the regioselectivity is determined by the difference in Ea leading to a 2° versus a 3° carbocation, which is greater than the difference in Ea leading to a 1° versus a 3° carbocation.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 5E
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Consider the following two reactions. Which is more highly regioselective, and why?
Reaction 1
`Cl
+ HCl
Reaction 2
+ HCl
`Cl
Reaction 1, because the regioselectivity is determined by the difference in E, leading to a 1° versus a 3°
carbocation, while in Reaction 2, both products are formed from a 3° carbocation.
O They should have exactly the same regioselectivity, because both reactions can give 1-chloro-1-
methylcyclohexane.
Reaction 1, because the regioselectivity is determined by the difference in Ea leading to a 1° versus a 3°
carbocation, which is greater than the difference in Ea leading to a 2° versus a 3° carbocation.
Reaction 1, because the regioselectivity is determined by the difference in Ea leading to a 1° versus a 2°
carbocation, which is greater than the difference in Ea leading to a 2° versus a 3° carbocation.
O Reaction 2, because the regioselectivity is determined by the difference in Ea leading to a 2° versus a 3°
carbocation, which is greater than the difference in E, leading to a 1° versus a 3° carbocation.
Transcribed Image Text:Consider the following two reactions. Which is more highly regioselective, and why? Reaction 1 `Cl + HCl Reaction 2 + HCl `Cl Reaction 1, because the regioselectivity is determined by the difference in E, leading to a 1° versus a 3° carbocation, while in Reaction 2, both products are formed from a 3° carbocation. O They should have exactly the same regioselectivity, because both reactions can give 1-chloro-1- methylcyclohexane. Reaction 1, because the regioselectivity is determined by the difference in Ea leading to a 1° versus a 3° carbocation, which is greater than the difference in Ea leading to a 2° versus a 3° carbocation. Reaction 1, because the regioselectivity is determined by the difference in Ea leading to a 1° versus a 2° carbocation, which is greater than the difference in Ea leading to a 2° versus a 3° carbocation. O Reaction 2, because the regioselectivity is determined by the difference in Ea leading to a 2° versus a 3° carbocation, which is greater than the difference in E, leading to a 1° versus a 3° carbocation.
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