Br2, H3O+ གོ་ཤི་ན་ཤི་ H3C CH3 CH3 CH3 Aldehydes and ketones can be halogenated at their a-position by reaction with Cl₂, Br2, or 12, 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. Arrow-pushing Instructions :OH :OH Br-Br H3C H3C. Br Br CH₂ H₂ H3C CH3 H3C CH3 2b

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
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Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
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Br2, H3O+
གོ་ཤི་ན་ཤི་
H3C CH3
CH3
CH3
Aldehydes and ketones can be halogenated at their a-position by reaction with Cl₂, Br2, or 12, 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.
Arrow-pushing Instructions
:OH
:OH
Br-Br
H3C
H3C.
Br
Br
CH₂
H₂
H3C CH3
H3C CH3
2b
Transcribed Image Text:Br2, H3O+ གོ་ཤི་ན་ཤི་ H3C CH3 CH3 CH3 Aldehydes and ketones can be halogenated at their a-position by reaction with Cl₂, Br2, or 12, 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. Arrow-pushing Instructions :OH :OH Br-Br H3C H3C. Br Br CH₂ H₂ H3C CH3 H3C CH3 2b
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