CH3 CH3 1. ВНз, THF 2. NaOH, HzO, Н2О2 H3C °CH2 H3C Alkenes can be hydrated via the addition of borane to yield alcohols with non-Markovnikov regiochemistry. The boron atom is an electrophile and thus follows Markovnikov's rule in adding to the carbon containing the most hydrogens. Oxidation of the alkylborane with basic peroxide yields the product alcohol. Draw curved arrows to show the movement of electrons in this step of the mechanism.
CH3 CH3 1. ВНз, THF 2. NaOH, HzO, Н2О2 H3C °CH2 H3C Alkenes can be hydrated via the addition of borane to yield alcohols with non-Markovnikov regiochemistry. The boron atom is an electrophile and thus follows Markovnikov's rule in adding to the carbon containing the most hydrogens. Oxidation of the alkylborane with basic peroxide yields the product alcohol. Draw curved arrows to show the movement of electrons in this step of the mechanism.
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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Question
![CH3
CH3
1. ВНз, THF
2. NaOH, HzO, Н202
H3C
CH2
H3C
Alkenes can be hydrated via the addition of borane to yield alcohols with non-Markovnikov regiochemistry. The boron atom is an electrophile and thus follows Markovnikov's rule in adding to the
carbon containing the most hydrogens. Oxidation of the alkylborane with basic peroxide yields the product alcohol.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
OR
OR
RO-B-OH
RO-B
ÖR
OR
OH](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F3db69418-1d7a-4e58-ac88-0cf6e9e8bf86%2F87c23c9b-1b73-41ac-98c7-10d43ae84be6%2Fm77k3dr_processed.png&w=3840&q=75)
Transcribed Image Text:CH3
CH3
1. ВНз, THF
2. NaOH, HzO, Н202
H3C
CH2
H3C
Alkenes can be hydrated via the addition of borane to yield alcohols with non-Markovnikov regiochemistry. The boron atom is an electrophile and thus follows Markovnikov's rule in adding to the
carbon containing the most hydrogens. Oxidation of the alkylborane with basic peroxide yields the product alcohol.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
OR
OR
RO-B-OH
RO-B
ÖR
OR
OH
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