Haloalkanes undergo substitution reactions, sometimes taking place via an mechanism, sometimes via an SN2 mechanism. In a reaction where it is not known which specific mechanism is involved, describe how a combination of kinetic and stereochemical evidence could be used to determine which mechanism is taking place. Secondary haloalkanes are capable of reacting by both mechanisms, though the one which takes place depends on the precise reaction conditions. Briefly suggest how factors such as the strength of the nucleophile and the nature of the solvent may influence whether the reaction mechanism is SN1 or SN2

Haloalkanes undergo substitution reactions, sometimes taking place via an mechanism, sometimes via an SN2 mechanism. In a reaction where it is not known which specific mechanism is involved, describe how a combination of kinetic and stereochemical evidence could be used to determine which mechanism is taking place. Secondary haloalkanes are capable of reacting by both mechanisms, though the one which takes place depends on the precise reaction conditions. Briefly suggest how factors such as the strength of the nucleophile and the nature of the solvent may influence whether the reaction mechanism is SN1 or SN2

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

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Question

Haloalkanes undergo substitution reactions, sometimes taking place via an SN1
mechanism, sometimes via an SN2 mechanism.
In a reaction where it is not known which specific mechanism is involved,
describe how a combination of kinetic and stereochemical evidence could be
used to determine which mechanism is taking place.
Secondary haloalkanes are capable of reacting by both mechanisms,
though the one which takes place depends on the precise reaction conditions.
Briefly suggest how factors such as the strength of the nucleophile and the
nature of the solvent may influence whether the reaction mechanism is SN1 or
SN2.

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Step 1: Substitution reaction

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Step 2: Nucleophilic substitution reactions through SN1

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Step 3: Stereochemistry of SN1 reaction and reactivity

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Step 4: Nucleophilic substitution reactions through SN2

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Step 5: Stereochemistry and reactivity

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Step 6: SN1 vs SN2

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