Organic Chemistry (Binghampton University)
Organic Chemistry (Binghampton University)
16th Edition
ISBN: 9781308795010
Author: Carey
Publisher: MCG CUSTOM
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Chapter 10, Problem 37DSP
Interpretation Introduction

Interpretation:

The truestatements about the reaction shownare to be determined.

Concept Introduction:

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Tributyltin hydride is a reducing agent. It converts an alkyl halide to an alkane through the formation of an alkyl free radical.This free radical can undergo intramolecular cyclization.

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The attack is termed exo if the radical in the resulting intermediate ends up outside the ring, and the attack is called endoif it ends up inside the newly formed ring.

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Cyclization is extremely rapid and exo selective.Hence, in many cases, exo cyclization is favored over endo cyclization.

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The more stable free radical is the one which is more substituted.

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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.
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, αcyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile— a carbocation—to a double bond.
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