Draw the major organic product formed when the compound shown below undergoes a reaction with two equivalents of ch3ch2mgbr and

Question

PolarNik [594]

3 years ago

7

Draw the major organic product formed when the compound shown below undergoes a reaction with two equivalents of ch3ch2mgbr and

then is treated with water.

Chemistry

1 answer:

alekssr [168] · Answer 1 · 2022-07-06T07:34:23+03:00

I have attached an image showing the starting material required for the questions, which is a molecule with an ester functionality. Esters are very reactive towards Grignard reagents and the reagent will add twice to the carbonyl of the ester, as is implied by the question saying that 2 equivalents of the Grignard reacts.

The first Grignard reacts with the ester and adds the ethyl group to the carbonyl carbon of the ester, to undergo an addition-elimination reaction to form the ketone. However, ketones are also very reactive to Grignard reagents, and the carbon of the cabronyl will react once more with the second Grignard to add a second ethyl group. At this point the alkoxide is formed, which is why water is added as a work-up step, to protonate the alkoxide to isolate the final alcohol product.