1. In step I the alpha bromination of ketones is acid catalyzed. 3 pts a. What a
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Question
1. In step I the alpha bromination of ketones is acid catalyzed. 3 pts a. What acid is formed as Step 1 progresses? b. Why are alpha bromination reactions acid catalyzed? 2. Substitution of bromine by t-butyl amine is the second step of the reaction today. Secondary alkyl halides can undergo substitution by Snl or Sn2 mechanisms. Explain (in terms of electronic interactions) why an Sn2 mechanism is favored when the halogen is alpha to a carbonyl. (Hint: Like charges on adjacent atoms are unfavorable) 2 ptsExplanation / Answer
1.
(a)
During acid catalyzed alpha-bromination of ketone, as the step-1 progress HBr is formed.
(b)
During alpha-bromination, H+ reacts with O - atom attached to carbonyl carbon and forms enol. The -C=C- double bond in enol is reactive and reacts with Br2 to form alpha-brominated ketone and HBr.
Hence the reaction is acid catalyzed.
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