H r cn o h r cn o h me3si r cn cn osime3 cn problem

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Unformatted text preview: rocess. H R H Me3SiCN catalytic KCN O CN R OSiMe3 Purpose of the problem To help you get used to mechanisms involving silicon and revise an important way to promote additions to the carbonyl group. Suggested solution The silyl cyanide is an electrophile while the cyanide ion in the catalyst is the nucleophile. Cyanide adds to the carbonyl group and the oxyanion product is captured by silicon, liberating another cyanide ion for the next cycle. H R CN O H R CN O H Me3Si R CN CN OSiMe3 + CN PROBLEM 4 There are three possible products from the reduction of this compound with sodium borohydride. What are their structures? How would you distinguish them spectroscopically, assuming you can isolate pure compounds? O H O Purpose of the problem To let you think practically about reactions that may give...
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This document was uploaded on 02/10/2014.

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