Carbons 1 and 4 of 1,3-cyclohexadiene are equivalent (they form the same carbocation upon protonation.) Likewise, carbons 2 and 3 are also equivalent... Draw the bond-line formula (or skeletal structure) of the carbocation formed by protonation of C-2 or C-3 to verify that it is not allylic and therefore not a stable as the one formed by protonation of C-1 or C-4.

Carbons 1 and 4 of 1,3-cyclohexadiene are equivalent (they form the same carbocation upon protonation.) Likewise, carbons 2 and 3 are also equivalent... Draw the bond-line formula (or skeletal structure) of the carbocation formed by protonation of C-2 or C-3 to verify that it is not allylic and therefore not a stable as the one formed by protonation of C-1 or C-4.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter5: Stereochemistry At Tetrahedral Centers

Section5.SE: Something Extra

Problem 70AP

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