Be sure to answer all parts. Explain why the addition of HBr to alkenes A and C is regioselective, forming addition products B and D, respectively. Br Br HBr HBr OCH3 OCH3 COOCH, COOCH3 A Addition to alkene A is regioselective because: Alkene A forms a primary carbocation, which is always more stable than a secondary carbocation. Alkene A forms a resonance stabilized carbocation on the C closest to the O atom. The Br atom is less crowded on a primary carbon than on a secondary carbon. Alkene A forms an inductively destabilized carbocation on the C closest to the O atom. Addition to alkene C is regioselective because: The Br atom is less crowded on the carbon that is farther away from the COOCH3 group. Alkene C forms a carbocation on the C farthest from the inductively destabilizing COOCH3 group. Alkene C forms a secondary carbocation, which is always more stable than a primary carbocation. Alkene C forms a carbocation that is resonance stabilized by the COOCH,3 group.

Be sure to answer all parts. Explain why the addition of HBr to alkenes A and C is regioselective, forming addition products B and D, respectively. Br Br HBr HBr OCH3 OCH3 COOCH, COOCH3 A Addition to alkene A is regioselective because: Alkene A forms a primary carbocation, which is always more stable than a secondary carbocation. Alkene A forms a resonance stabilized carbocation on the C closest to the O atom. The Br atom is less crowded on a primary carbon than on a secondary carbon. Alkene A forms an inductively destabilized carbocation on the C closest to the O atom. Addition to alkene C is regioselective because: The Br atom is less crowded on the carbon that is farther away from the COOCH3 group. Alkene C forms a carbocation on the C farthest from the inductively destabilizing COOCH3 group. Alkene C forms a secondary carbocation, which is always more stable than a primary carbocation. Alkene C forms a carbocation that is resonance stabilized by the COOCH,3 group.

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

100%

Be sure to answer all parts.
Explain why the addition of HBr to alkenes A and C is regioselective, forming addition products B and
D, respectively.
Br
Br
HBr
HBr
OCH3
OCH3
COOCH3
COOCH3
A
C
Addition to alkene A is regioselective because:
Alkene A forms a primary carbocation, which is always more stable than a secondary
carbocation.
Alkene A forms a resonance stabilized carbocation on the C closest to the O atom.
The Br atom is less crowded on a primary carbon than on a secondary carbon.
Alkene A forms an inductively destabilized carbocation on the C closest to the O atom.
Addition to alkene C is regioselective because:
The Br atom is less crowded on the carbon that is farther away from the COOCH3 group.
Alkene C forms a carbocation on the C farthest from the inductively destabilizing COOCH3
group.
Alkene C forms a secondary carbocation, which is always more stable than a primary
carbocation.
Alkene C forms a carbocation that is resonance stabilized by the COOCH, group.

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