Which is the correct mechanistic sequence in the Birch reduction? Na, CH3OH NH3

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
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Which is the correct mechanistic
sequence in the Birch reduction?
Na, CH3OH
NH3
Protonation, single electron
transfer, protonation, single
electron transfer
Two single electron transfers
followed by two protonations
of the anionic carbons
Single electron transfer,
protonation, single electron
transfer, protonation
Protonation, two single
electron transfers, protonation
Transcribed Image Text:Which is the correct mechanistic sequence in the Birch reduction? Na, CH3OH NH3 Protonation, single electron transfer, protonation, single electron transfer Two single electron transfers followed by two protonations of the anionic carbons Single electron transfer, protonation, single electron transfer, protonation Protonation, two single electron transfers, protonation
Why won't most primary alkyl halides react in Friedel-Crafts alkylation reactions?
O Primary alkyl halides undergo methyl shifts under the standard conditions of Friedel-Crafts alkylation reactions, making
them unreactive.
Primary alkyl halides create primary carbocations which are too high in energy and too readily undergo rearrangement.
Primary alkyl halides do not form a sigma complex after a nucleophilic attack since they connect at the primary carbocation
site.
Primary alkyl halides as a reactant violates one of the three standard limitations to Friedel-Crafts alkylation reactions.
Transcribed Image Text:Why won't most primary alkyl halides react in Friedel-Crafts alkylation reactions? O Primary alkyl halides undergo methyl shifts under the standard conditions of Friedel-Crafts alkylation reactions, making them unreactive. Primary alkyl halides create primary carbocations which are too high in energy and too readily undergo rearrangement. Primary alkyl halides do not form a sigma complex after a nucleophilic attack since they connect at the primary carbocation site. Primary alkyl halides as a reactant violates one of the three standard limitations to Friedel-Crafts alkylation reactions.
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