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Michael addition reaction
Natasha_4902
#1 Posted : Friday, August 07, 2020 6:17:11 PM
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HI,

The Michael addition reaction came up on AAMC fl 3 CP question 4 and I am just wondering why the enolate attacks a carbon that isn't the carbonyl carbon?

Thank you
INSTR_Katerina_102
#2 Posted : Saturday, August 08, 2020 2:51:50 AM
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Hi Natasha,

I do not see a michael addition in question 4 of CP of the Altius FL 3.

However, Michael additions are an exception to the carbonyl selectivity - there is some competition between the addition at the carbonyl (1,2) and addition at the alkene (1,4) addition, but generally the (1,4) addition occurs because the product formed following addition to the alkene is less sterically hindered then the product following the addition to the carbonyl. However, the effect is slight and can be changed with other competing factors.

I would expect that to be a bit beyond the scope of the MCAT however, and lower yield as a result.

I hope this helps,

Katt


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