# Why can't carboxylic acid + NaH + tert-butyl bromide react to create an ester?

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?

• 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. – Waylander Aug 3 at 22:00
• For condition D, the carboxylate will effect E2 elimination of the tertiary bromide.. – user55119 Aug 3 at 23:58