Q19P - Organic Chemistry (Mcmurry)

Question

What products would result after hydrolysis from the reaction of the enamine prepared from cyclopentanone and pyrrolidine with the following 𝛂-𝛃-unsaturated acceptors? 

(a) $H_{2}C=CHC{O}_{2}Et$ 

(b) $H_{2}C=CHCHO$

(c)$C{H}_{3}CH=CHCOC{H}_3$

Step-by-Step Solution

Answer

The net effect of the Stork reaction is the Michael addition of a ketone to an α, β-unsaturated carbonyl compound and after hydrolysis, it give diketone products.

Enamines

Enamines are readily prepared by a reaction between a ketone and a secondary amine. Enamines behave in much the same way as enolate ions and enter into many of the same kinds of reactions that are given by enolate ions.

Product forms after hydrolysis of given compounds are: