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Dolbier HW Solutions 351 - 445 ALDEHYDES AND KETONES...

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bulkier the alkyl groups that are attached to the carbonyl, the more strained and less stable will be the cyanohydrin. ( d ) Steric effects in fl uence the rate of nucleophilic addition to these two ketones. Carbon is on its way from tricoordinate to tetracoordinate at the transition state, and alkyl groups are forced closer together than they are in the ketone. The transition state is of lower energy when R is smaller. Acetone (for which R is methyl) is reduced faster than 3,3-dimethyl-2-butanone (where R is tert -butyl). ( e ) In this problem we examine the rate of hydrolysis of acetals to the corresponding ketone or aldehyde. The rate-determining step is carbocation formation. Hybridization at carbon changes from
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