Dolbier HW Solutions 470

Dolbier HW Solutions 470 - 564 CARBOXYLIC ACID DERIVATIVES:...

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( f ) Steric crowding increases more when hydroxide adds to the axial carbonyl group. 20.32 Compound A is the p -toluenesulfonate ester (tosylate) of trans -4- tert -butylcyclohexanol. The oxygen atom of the alcohol attacks the sulfur of p -toluenesulfonyl chloride, and so the reaction proceeds with retention of con f guration. The second step is a nucleophilic substitution in which benzoate ion displaces p -toluenesulfonate with inversion of con f guration. Saponi f cation of cis -4- tert -butylcyclohexyl benzoate in step 3 proceeds with acyl oxygen cleav- age to give cis -4- tert -butylcyclohexanol. 20.33 Reaction of ethyl tri F uoroacetate with ammonia yields the corresponding amide, compound A. Com- pound A undergoes dehydration on heating with P 4 O 10 to give tri F uoroacetonitrile, compound B. Grignard reagents react with nitriles to form ketones. tert -Butyl tri F uoromethyl ketone is formed from tri F uoroacetonitrile by treatment with tert -butylmagnesium chloride followed by aqueous hydrolysis.
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This note was uploaded on 09/30/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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