The following question was given in FIITJEE study material:

enter image description here

I guess (i) step is de-esterification, which gives the compound of option (A).

In next step, I wouldn't expect it to decarboxylate, instead I guess it'll dehydrate. So, according to me, final product is:

enter image description here

which I can't see in the options. Then, what should be the final product?

The correct answer given was: (C)

  • 2
    $\begingroup$ The conditions for the first step specify base but not water present, so you are not going to get hydrolysis which means the product is not A . What might a sufficiently strong base do to the starting material? $\endgroup$
    – Waylander
    Jan 13 '20 at 15:11
  • 1
    $\begingroup$ @Waylander: Ok, so this is Claisen condensation. And, then this is the product, which converts into acid on hydrolysis and finally decarboxylate on ∆. Thanks for helping. $\endgroup$ Jan 13 '20 at 15:32
  • $\begingroup$ Correct. Depending on how strong the acid is, how long you heat it and to what temperature. $\endgroup$
    – Waylander
    Jan 13 '20 at 16:16
  • $\begingroup$ The answer is B. You use NaOEt as the base to avoid trans-esterification. $\endgroup$
    – joehua
    Jan 15 '20 at 15:32
  • $\begingroup$ @joehua: I agree with your expl. But, I think we get (B) in the first step itself, what about the second one? $\endgroup$ Jan 16 '20 at 8:22

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