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, makingthem 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 carbocationsite.Primary alkyl halides as a reactant violates one of the three standard limitations to Friedel-Crafts alkylation reactions. Productis the major product ofthe reduction shown.Na, CH 3OHNH3ВD

In presence of Na and NH3 , it undergos Birch reduction.

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Product v is the major product of the reduction shown. Na, CH 3OH NH3 B D

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.52P: Alcohols are important for organic synthesis, especially in situations involving alkenes. The...

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Concept explainers

Reactions of Ethers

Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.

Epoxides

Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.

Williamson Ether Synthesis

An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.

Question

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.

Product
is the major product of
the reduction shown.
Na, CH 3OH
NH3
В
D

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