malo H3C H3C CH3 CH3 rrow-pushing Instru Br2, H3O+ H3C CH₂Br H3C CH3 Aldehydes and ketones can be halogenated at their a-position by reaction with Cl₂, Br₂, or I₂, under acidic conditions. Using Br₂ under acidic conditions, an intermediate enol is formed which adds bromine at the a-position. The reaction stops after the addition of one bromine because the electron-withdrawing halogen decreases the basicity of the carbonyl oxygen, making the protonation less favorable. Draw curved arrows to show the movement of electrons in this step of the mechanism.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter26: Aldol And Claisen Reactions
Section: Chapter Questions
Problem 26E
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H3C
Arrow-pushing Instructions
NOC XT
H3C
H3C CH3
H3C CH3
Aldehydes and ketones can be halogenated at their a-position by reaction with Cl₂, Br₂, or I2, under acidic conditions.
Using Br₂ under acidic conditions, an intermediate enol is formed which adds bromine at the a-position. The reaction stops
after the addition of one bromine because the electron-withdrawing halogen decreases the basicity of the carbonyl oxygen,
making the protonation less favorable.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
:OH
H3C CH3
CH3
Submit Answer
H
Br₂, H3O+
H₂O
H3C
H3C
:OH
H3C CH3
FCH₂
CH₂Br
Retry Entire Group 9 more group attempts remaining
H30
Transcribed Image Text:H3C Arrow-pushing Instructions NOC XT H3C H3C CH3 H3C CH3 Aldehydes and ketones can be halogenated at their a-position by reaction with Cl₂, Br₂, or I2, under acidic conditions. Using Br₂ under acidic conditions, an intermediate enol is formed which adds bromine at the a-position. The reaction stops after the addition of one bromine because the electron-withdrawing halogen decreases the basicity of the carbonyl oxygen, making the protonation less favorable. Draw curved arrows to show the movement of electrons in this step of the mechanism. :OH H3C CH3 CH3 Submit Answer H Br₂, H3O+ H₂O H3C H3C :OH H3C CH3 FCH₂ CH₂Br Retry Entire Group 9 more group attempts remaining H30
H3C
Arrow-pushing Instructions
NA
H3C
H3 C
CH3
H3C CH3
Aldehydes and ketones can be halogenated at their a-position by reaction with Cl₂, Br₂, or I2, under acidic conditions.
Using Br₂ under acidic conditions, an intermediate enol is formed which adds bromine at the a-position. The reaction stops
after the addition of one bromine because the electron-withdrawing halogen decreases the basicity of the carbonyl oxygen,
making the protonation less favorable.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
:OH
H3C CH3
Submit Answer
CH3
XT
FCH₂
Br₂, H3O+
Br-Br
H3C
H3C.
:OH
H3C CH3
CH₂Br
Retry Entire Group 9 more group attempts remaining
Br Br
Transcribed Image Text:H3C Arrow-pushing Instructions NA H3C H3 C CH3 H3C CH3 Aldehydes and ketones can be halogenated at their a-position by reaction with Cl₂, Br₂, or I2, under acidic conditions. Using Br₂ under acidic conditions, an intermediate enol is formed which adds bromine at the a-position. The reaction stops after the addition of one bromine because the electron-withdrawing halogen decreases the basicity of the carbonyl oxygen, making the protonation less favorable. Draw curved arrows to show the movement of electrons in this step of the mechanism. :OH H3C CH3 Submit Answer CH3 XT FCH₂ Br₂, H3O+ Br-Br H3C H3C. :OH H3C CH3 CH₂Br Retry Entire Group 9 more group attempts remaining Br Br
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