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2) Explain why the esterification reaction of carboxylic acids with bulky alcohols(eg tBuOH) does not generate...

2) Explain why the esterification reaction of carboxylic acids with bulky alcohols(eg tBuOH) does not generate products. What would be an alternative method to obtain these esteres?

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Answer #1

2)

In Fischer esterification, the bulky alcohols such as tBuOH undergoes elimination reaction to give isobutene in presence of acid catalyst.

The alternative method is to use Steglich esterification reaction which employs DCC (dicyclohexylcarbodiimide) as a coupling agent and DMAP (4-dimethyaminopyridine) as a catalyst.

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