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.

  • $\begingroup$ 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, 2020 at 15:34
  • $\begingroup$ But still even if I2 adds I+ and OH- across double bond, how would we get d? $\endgroup$ Apr 30, 2020 at 15:45
  • $\begingroup$ The intermediate hydroxy acid gets oxidised to keto acid by I2 perhaps? $\endgroup$
    – Waylander
    Apr 30, 2020 at 15:48
  • 2
    $\begingroup$ Alpha keto acids readily decarboxylate pubs.acs.org/doi/full/10.1021/acs.orglett.6b01964 $\endgroup$
    – Waylander
    Apr 30, 2020 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, 2020 at 18:35


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