Ch 24 answers - Answers to Extra Problems for Chapter 24...

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Answers to Extra Problems for Chapter 24 Chem. 345 1. Show the major organic product (or products if more than one will be formed in significant amount) for the following reactions: Ph CO 2 H 3 N _ + Et 3 N, heat CMe 3 O O O Me 3 C Ph CO 2 H N H O O Me 3 C 1. 2. (excess) HO - , H 2 O; neutralize + CO 2 H Br N - K + O O CO 2 - NH 3 1. DCC, 2. F 3 CCO 2 H O O Me 3 C N H OH O H N H N O H O O O H 2 N OEt S N O N Ph H H H + , heat NOT complete hydrolysis, but the last step of an Edman degradation N N Ph S O H H O OEt O NaBH 3 CN NH 3 (HOAc cat.) OEt O NH 2 OH O NH 2 1. H 3 O + ,H 2 O 2. neutralize S N O N Ph H H not a mechanism, but the CS bond breaks, and an NC bond forms at the same CO group book, p. 1182 shows: CH NH N S Ph O R (rotated 180 o about the N-Ph bond, which is a confusing thing to do!) a. b. c. d. e. g. Show the use of phenyl isothiocyanate in peptide chemistry (no mechanism required). It is used for removal of the N-terminal amino acid unit: R H 2 N N O Peptide H 1. 2. H + , H 2 O N Ph C S N N CHR O Ph S H H 2 N Peptide a phenylthiohydantoin
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2 2. Show reagents and any intermediate compounds that would be isolated for the following conversion. Any reagents stable enough to buy may be employed.
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Ch 24 answers - Answers to Extra Problems for Chapter 24...

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