Question 9: [30 pts] 0 Illustrated below is the mechanism of (A) base-catalyzed hydrolysis of a cyclic anhydride and (B) bromolactonization. Clearly describe each elementary step (-i) shown of the mechanism. In CHE 232 lecture, we are currently discussing carboxylic acid derivatives, so you should be able to thoroughly describe (in words!) the anhydride hydrolysis. SAc-Base Catalyzed H Anhydride Hydrolysis H H +[H₂O]/[HCO₂H] H Na / OH L Na Collapse of tetrahedral intermediate with Ring opening -[H] OH Na°/0° Br Br 11. Na/ AdE- Electrophilic Additon of Bromine +[Br III. H O/Na Br H Br Br H H Na H -0°/Na Lactonization —[NaBr] Na bridged bromonium ion

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Question 9: [30 pts]
0
Illustrated below is the mechanism of (A) base-catalyzed hydrolysis of a cyclic anhydride and (B)
bromolactonization. Clearly describe each elementary step (-i) shown of the mechanism. In CHE
232 lecture, we are currently discussing carboxylic acid derivatives, so you should be able to
thoroughly describe (in words!) the anhydride hydrolysis.
SAc-Base Catalyzed
H
Anhydride Hydrolysis
H
H
+[H₂O]/[HCO₂H]
H
Na /
OH
L
Na
Collapse of tetrahedral
intermediate with
Ring opening
-[H]
OH
Na°/0°
Br
Br
11.
Na/
AdE- Electrophilic
Additon of Bromine
+[Br
III.
H
O/Na
Br
H
Br
Br
H
H Na
H
-0°/Na
Lactonization
—[NaBr]
Na
bridged bromonium ion
Transcribed Image Text:Question 9: [30 pts] 0 Illustrated below is the mechanism of (A) base-catalyzed hydrolysis of a cyclic anhydride and (B) bromolactonization. Clearly describe each elementary step (-i) shown of the mechanism. In CHE 232 lecture, we are currently discussing carboxylic acid derivatives, so you should be able to thoroughly describe (in words!) the anhydride hydrolysis. SAc-Base Catalyzed H Anhydride Hydrolysis H H +[H₂O]/[HCO₂H] H Na / OH L Na Collapse of tetrahedral intermediate with Ring opening -[H] OH Na°/0° Br Br 11. Na/ AdE- Electrophilic Additon of Bromine +[Br III. H O/Na Br H Br Br H H Na H -0°/Na Lactonization —[NaBr] Na bridged bromonium ion
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