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EK ICE 3 Question 62 (Glycerol + Acetic anhydride)
Korolos_5348
#1 Posted : Monday, July 06, 2020 1:41:12 PM
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Hello,

I initially thought the answer either C or D. I was just wondering if someone would be able to explain why C is not the correct answer because the question stem says that the reaction only uses "One" equivalent of Acetic anhydride. Wouldn't this mean that only 1 ester forms and not 2 like in answer C?

Thank you in advance
INSTR_Katerina_102
#2 Posted : Monday, July 06, 2020 5:03:27 PM
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Hi,

The key here is the acid catalysis - you can substitute the acetic anhydride with nucleophilic acyl substitution, liberate a carboxylic acid (because you have some acid around) and then do a fischer esterification resulting in 2 acetyl units being added (please let me know if this is unclear and I can draw a mechanism). It is actually mechanistically possible to do the two additions this way.

The crux of the matter for this question is that A B and C show the addition of acetyl units derived from acetic anhydride, while D only provides a formyl unit (one carbon instead of 2). This means that D is the most unlikely because it would require the breaking a C-C bond, which isn't really possible under these conditions.

I hope this helps!
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