3. Provide a clear arrow-pushing mechanism for each of the following reactions. Do not skip proton transfers, do not combine steps, and make sure your arrows are clear enough to be interpreted without ambiguity. a. Sulfur can form ylides just like phosphorus, but the products they form are different from phosphorus ylides Ph H. H3C + Ph,S Ph `CH3 predict relative stereochemistry (Hint: think about orbital alignment) b. Dicarbonyls can be used to synthesize interesting heterocycles Ph Ph H* N-N H3C `CH3 H2N-NH -Ме Me

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Chapter1: Chemical Foundations
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3.
Provide a clear arrow-pushing mechanism for each of the following reactions. Do not skip proton
transfers, do not combine steps, and make sure your arrows are clear enough to be interpreted
without ambiguity.
a. Sulfur can form ylides just like phosphorus, but the products they form are different from phosphorus ylides
Ph
H.
+ H3C
+ Ph2S
CH3
Ph
predict relative
stereochemistry
(Hint: think about
orbital alignment)
b. Dicarbonyls can be used to synthesize interesting heterocycles
Ph
Ph
H+
N-N
-Me
H2N
H.N-NH
H3C
°CH3
Ме
Transcribed Image Text:3. Provide a clear arrow-pushing mechanism for each of the following reactions. Do not skip proton transfers, do not combine steps, and make sure your arrows are clear enough to be interpreted without ambiguity. a. Sulfur can form ylides just like phosphorus, but the products they form are different from phosphorus ylides Ph H. + H3C + Ph2S CH3 Ph predict relative stereochemistry (Hint: think about orbital alignment) b. Dicarbonyls can be used to synthesize interesting heterocycles Ph Ph H+ N-N -Me H2N H.N-NH H3C °CH3 Ме
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