Ch 16 Answers - Answers to Ch. 16 Extra problems 1. Show...

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1 Answers to Ch. 16 Extra problems 1. Show the major product (or products if more than one is formed in significant amount. Show stereochemistry if it is important. a. 1. NaBH4, EtOH 2. H + ,H 2 O(neutralize) (we say that NaBH 4 reduces aldehydes & ketones, not esters or amides.) Both diastereomers of the alcohol will form. O H CO 2 CH 3 b. 1. Excess PrMgBr 2) neutralize (H + ) Similar to addition to esters; Cl - leaves after first addition and the ketone reacts with more Grignard. + HO H CO 2 CH 3 H 1. BuLi 2. O Cl A Wittig reaction c. d. OH Thioacetal formation e. H 3 C P(C 6 H 5 ) 3 OCH 3 1. PhNHNH 2 , HCl O CH 3 OCH 3 SH SH CH 3 O CH 3 S S O Br - H + N N H 2. neutralize Phenylhydrazone formation + HO H CO 2 CH 3 H although you have not seen Grignard addition to acid chlorides, you should be able to predict this result because you know that Cl - is a much better leaving group than RO -
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2 2. Show the major product (or products if more than one is formed in significant amount. Show stereochemistry if it is important. 1. Ph 3 P 2. BuLi 3) O H OCH 3 O a. (+ Ph 3 P=O) Wittig Br b. NaCN, H + , H 2 O C C cyanohydrin formation CO 2 Me c. NaCN, H + (less than 1 eq.) hemiacetals show the chemistry of the O opened form (aldehyde and alcohol) cyanohydrin d. OH C H + , separate H 2 O N e. H + (catalytic) acetal formation, does not affect stereochem. at the backbone, so the methyls are trans when the oxygens are cis O OH phenylhydrazone formation OH OH CN H O CH 3 HO OH CH 3 O O H 3 C CH 3 O N N H (HCN is not a reactive nucleophile, so a whole equivalent of acid removes the NC - ) PhNHNH 2 cis C C CO 2 Me H H H H
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3 3. Show reagents and intermediate compounds that would be isolated for the following
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This note was uploaded on 02/14/2011 for the course ORGANIC CH 341 taught by Professor Idk during the Spring '11 term at Wisconsin.

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Ch 16 Answers - Answers to Ch. 16 Extra problems 1. Show...

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