2
$\begingroup$

Question

  1. List item

Attempt I think the product A would be as I have attempted below, but I am getting the answer as A but book says D. enter image description here Where am I wrong? Please help.

$\endgroup$
6
  • $\begingroup$ if there was excess I2 present would it add across the double bond of the iodoform product that you have drawn? $\endgroup$
    – Waylander
    Apr 30 '20 at 15:34
  • $\begingroup$ But still even if I2 adds I+ and OH- across double bond, how would we get d? $\endgroup$ Apr 30 '20 at 15:45
  • $\begingroup$ The intermediate hydroxy acid gets oxidised to keto acid by I2 perhaps? $\endgroup$
    – Waylander
    Apr 30 '20 at 15:48
  • 2
    $\begingroup$ Alpha keto acids readily decarboxylate pubs.acs.org/doi/full/10.1021/acs.orglett.6b01964 $\endgroup$
    – Waylander
    Apr 30 '20 at 15:59
  • 2
    $\begingroup$ Form the hydroxy iodide by addition to the double bond then OH opening the iodonium giving the tertiary iodide/alpha hydroxy acid. I2 oxidises the hydroxy to the keto acid which decarboxylates. OH- eliminates I- to form double bond. $\endgroup$
    – Waylander
    Apr 30 '20 at 18:35

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.