{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

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

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
( 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 fi guration. The second step is a nucleophilic substitution in which benzoate ion displaces p -toluenesulfonate with inversion of con fi guration. Saponi fi 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 fl uoroacetate with ammonia yields the corresponding amide, compoundA. Com- pound A undergoes dehydration on heating with P 4 O 10 to give tri fl uoroacetonitrile, compound B. Grignard reagents react with nitriles to form ketones. tert -Butyl tri fl uoromethyl ketone is formed from tri fl uoroacetonitrile by treatment with tert -butylmagnesium chloride followed by aqueous hydrolysis.
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

{[ snackBarMessage ]}

Ask a homework question - tutors are online