A student performs a sodium borohydride reduction of 3, 3-dimethyl-2-butanone us

Question

A student performs a sodium borohydride reduction of 3, 3-dimethyl-2-butanone using excess reducing agent at 0 C. After isolating the product mixture, an 1H nmr is taken. Integration of the t-butyl groups in the alkyl region shows 2 singlets. Instead of just the one at 0.8 ppm that was expected, there is also a pk at 1.2 ppm. Integration of the 2 peaks shows the ht of the integral at 1.2 ppm to be 4 mm and the ht of the pk at 0.8 ppm to be 16 mm. a. What is the ratio of starting material to product? b. what was the percent conversion to product?

Explanation / Answer

(a) ratio of starting material to product = 1:4

(b) percent conversion = (4/5) * 100 = 80 %

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