Justify the use of NaOH rather than a stronger base to deprotonate guaiacol. Wha

Question

Justify the use of NaOH rather than a stronger base to deprotonate guaiacol. What special problems are introduced by using a stronger base than NaOH?

I've looked in my textbook and online and everything explains that you need a base that's strong enough, but nothing explains what happens when you use a base that's stronger than what is needed. This is for Williamson ether synthesis of guaifenesin (deprotonate guaicol with NaOH then react with  (±)-3-chloro-1,2-propane-diol to produce guaifenesin).

Explanation / Answer

If you use an stronger base than NaOH, in fact you will deprotonate the -OH group in position 2, but also it will produce secondary products from the attack of the base on the methoxy group in position 1. You not just need to think in terms of the stronger base, you also need to meditate about stearic hindrance, solvent and possible counterproducts.

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