General reaction TSOH HSO,CI Он Он R* = a carbocation new carbocation a-cyclogeraniol Он a-terpineol nerol

Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
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Like other electrophiles, carbocations add to alkenes to form new carbocations, which can then undergo substitution or elimination reactions depending on the reaction conditions. With this in mind, consider the following reactions of nerol, a natural product isolated from lemon grass and other plant sources. Treatment of nerol with TsOH forms α-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, HSO3Cl, forms a constitutional isomer, α-cyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile—a carbocation—to a double bond.

General reaction
TSOH
HSO,CI
Он
Он
R* = a carbocation
new carbocation
a-cyclogeraniol
Он
a-terpineol
nerol
Transcribed Image Text:General reaction TSOH HSO,CI Он Он R* = a carbocation new carbocation a-cyclogeraniol Он a-terpineol nerol
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