The following problem is from Paper-2 of JEE Advanced 2016. enter image description here

The answer given to the problem is A. The solution given by various sources suggests an Aldol addition, followed by a cross cannizaro in the first step(i). In the second step (ii) the oxygen of formaldehyde is protonated and acetal formation takes place.

I am doubtful about the answer for various reasons:

1) The carbon anion formed is really bulky and thus Aldol seems unreasonable to me.

2) Acetals are supposed to hydrolyze in acidic conditions, hence option A seems improbable.

Are my arguements correct? If yes, then what should be the correct product?

  • $\begingroup$ Comments are not for extended discussion; this conversation has been moved to chat. $\endgroup$ – jonsca Feb 10 at 1:57
  • $\begingroup$ While the discussion was nice and productive, it's better to move it to a chatroom once it starts getting beyond just a few comments back and forth. Thanks! $\endgroup$ – jonsca Feb 10 at 1:57
  • $\begingroup$ Please explain the downvote $\endgroup$ – Akshat Joshi Feb 10 at 4:36

Your Answer

By clicking "Post Your Answer", you acknowledge that you have read our updated terms of service, privacy policy and cookie policy, and that your continued use of the website is subject to these policies.

Browse other questions tagged or ask your own question.