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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?

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  • $\begingroup$ 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

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