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So, the picture I showed above asks for which reagents can form the ester product. I was wondering why D can't form it? I was thinking that first, the $\ce{NaH}$ would react with the carboxylic acid to form the basic form of the carboxylic acid (where the $\ce{-OH}$ becomes $\ce{-O^-}$). Then, the $\ce{-O^-}$ of the carboxylic acid would attack the tert-butyl bromide in a $\mathrm{S_N1}$ reaction where the bromide would leave first. Why is this not possible?

Also, does F not work because Fischer esterification does not occur in basic/neutral conditions?

  • $\begingroup$ For conditions F, all you are doing is deprotonation of the benzoic acid with a strong base. Carboxylate is a poor nucleophile because of the delocalisation of the charge. Conditions B is a much better source of tBu+ than tBu-Br. $\endgroup$
    – Waylander
    Aug 3 '19 at 22:00
  • 2
    $\begingroup$ For condition D, the carboxylate will effect E2 elimination of the tertiary bromide.. $\endgroup$
    – user55119
    Aug 3 '19 at 23:58

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