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Draw or provide each of the following: a) The anionic intermediate formed in the

ID: 506451 • Letter: D

Question

Draw or provide each of the following: a) The anionic intermediate formed in the last step (EICB) of the Knoevenagel condensation shown below: b) The structure and IUPAC name of the aldol product obtained by treatment of butanal with a catalytic amount of NaOMe in MeOH at room temperature. c) A specific example [reactant, reagent(s), d) A specific example [reactant(s), reagent, product] of a Michael reaction. d) A specific example [reactant(s), reagent, product] of a viable mixed aldol reaction (i.e. can only give one product).

Explanation / Answer

2. 2- ethyl-2-hexenal

3. The Michael addition is an organic reaction used to convert an activated methylene and a conjugated olefin to the corresponding addition product using a base catalyst followed by an acid work-up. The activated methylene is essentially a methylene bonded to electron withdrawing groups that would stabilize the negative change that forms after deprotonation by the base. This deprotonation results in an enolate which in turn does a 1,4 addition to the conjugated olefin. An acid work-up then provides the final Michael addition product.

4.Mixed aldol reactions between an aldehyde with no -hydrogens and a ketone generally give good yields of a single product

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