Which reaction will not give the indicated product? 1. CH, CHO 2. H₂O OH O CH₂CH₂OH, H* N H OH CH₂CH₂OH, H* 1. CH,CHO 2. H₂O O O HO HO H

Pushing Electrons
4th Edition
ISBN:9781133951889
Author:Weeks, Daniel P.
Publisher:Weeks, Daniel P.
Chapter1: Lewis Structures
Section: Chapter Questions
Problem 73EQ
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Step 4: In an
acid-catalyzed
epoxide ring opening, the
epoxide is first protonated and can then be attacked by
weak nucleophiles.
H
HO:
:Nuc
Nuc
Weak nucleophiles such as water and alcohols can react
with the protonated epoxide.
One of the main differences between base-catalyzed and
acid-catalyzed epoxide ring openings is the regiochemical
product expected. In an acid-catalyzed reaction, if one of
the epoxide carbons is tertiary and the other primary, the
nucleophile will attack at the more substituted carbon. If the
epoxide is monosubstituted, the nucleophile will attack
preferentially at the primary carbon vs. the
secondary carbon.
Which reaction will not give the indicated product?
N
1. CH,CH,O
2. H₂O
OH
CH₂CH₂OH, H*
N
CH₂CH₂OH, H
1 CHICH,O
2. H₂O
HO
HO
H-
H
Transcribed Image Text:Step 4: In an acid-catalyzed epoxide ring opening, the epoxide is first protonated and can then be attacked by weak nucleophiles. H HO: :Nuc Nuc Weak nucleophiles such as water and alcohols can react with the protonated epoxide. One of the main differences between base-catalyzed and acid-catalyzed epoxide ring openings is the regiochemical product expected. In an acid-catalyzed reaction, if one of the epoxide carbons is tertiary and the other primary, the nucleophile will attack at the more substituted carbon. If the epoxide is monosubstituted, the nucleophile will attack preferentially at the primary carbon vs. the secondary carbon. Which reaction will not give the indicated product? N 1. CH,CH,O 2. H₂O OH CH₂CH₂OH, H* N CH₂CH₂OH, H 1 CHICH,O 2. H₂O HO HO H- H
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