To accomplish a Markovnikov addition of water to an unsymmetrical alkene, with minimal skeletal rearrangement, the best reagents would be Water and concentrated acid Hg(OAc)2, H2O and NaBH4, NaOH Water and dilute acid BH3 in THF and H2O2 in NaOH

To accomplish a Markovnikov addition of water to an unsymmetrical alkene, with minimal skeletal rearrangement, the best reagents would be Water and concentrated acid Hg(OAc)2, H2O and NaBH4, NaOH Water and dilute acid BH3 in THF and H2O2 in NaOH

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

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.44P

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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

To accomplish a Markovnikov addition of water to an unsymmetrical alkene, with minimal skeletal rearrangement, the best reagents would be

Water and concentrated acid

Hg(OAc)2, H2O and NaBH4, NaOH

Water and dilute acid

BH3 in THF and H2O2 in NaOH

Definition Definition Organic compounds that contain at least one double bond between carbon-carbon atoms. The general molecular formula for alkenes with one double bond is C n H 2n .

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