Question

Complete the curved arrow pushing mechanism for the following Michael (conjugate) addition reaction.

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I can't figure out what I'm doing wrong in the second step. Please help!

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Answer #1
Concepts and reason

The reaction of nucleophile (Michael donor) with the α,β{\rm{\alpha ,}}\,{\rm{\beta }} -unsaturated ketone (Michael acceptor) at the alkene site will be resulting in the formation of a new carbon-carbon single bond is called as Michael addition reaction.

Arrow pushing mechanism:

Is a technique to indicate the movement of electrons during the course of the organic reaction.

Fundamentals

Michael addition reaction:

Michael adduct
Michael acceptor
Michael donor
R
R
NaOH
CH,ОН
R1
R
R
R
н
0,B-unsaturated ketone
Acidic alpha hydrogens
Additio

Michael donor: Is an electron rich species, which can donate electrons easily.

Michael acceptor: Is an α,β{\rm{\alpha ,}}\,{\rm{\beta }} -unsaturated ketone, with electron deficient alkene, which can accept electron rich specie (Michael donor).

Michael adduct: The product in which C=C{\rm{C = C}} is converted into CC{\rm{C - C}} .

Но
CH3
CH3
CH3
Нас
Н
Нэс
CHз
carbanion
н
CHз
Нас
enolate

CH3
CH3
Н
Hас
CHз
СH
Hас
O:
о:

CH3
CHз
Н*
CHз
Нас
CHЗ
Hас
о:
о:
о:

Ans:

The complete arrow pushing mechanism for the given Michael conjugated addition reaction is shown below.

-CHз
CHз
н
CHз
|Нзс
CHз
Нас
CHз
- СH3ОН
CHз
CHз
H*
Hас
CHз
CHз
Hас
о:
о:
о:
о:

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