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Prep101 Practice Sets: Class 4, Question 3
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Josh_4080
#1 Posted : Monday, June 22, 2020 5:26:35 PM
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I found this question hard because it required really understanding the mechanisms of saponification. If I forgot a mechanism on the MCAT, would there be another way to solve this problem? For example, how would you be able to predict if something has a tetrahedral intermediate? Or, how would I go about determining the mechanism if I did not know it.

Thanks!
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INSTR_Katerina_102
#2 Posted : Thursday, June 25, 2020 8:38:37 PM
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Is this the extra practice reaction package? With the protonated carboxylic acid and methoxid?

This would go through a tetrahedral intermediate, it's just not explicitly stated in the answer.

Pretty all nucleophilic acyl substitutions (those with acid chlorides and anhydrides, carboxylic acids etc) go through a tetrahedral intermediate, while Sn1 and Sn2 type reactions do not.

Sometimes we get lazy as chemists though and we don't draw the tetrahedral intermediate because it takes so much time (sadly me).

Please let me know if I have the wrong question!
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