Chemistry_2220_-_Maguire_-_Summer_2005_-_Exam_2_Makeup

Chemistry_2220_-_Maguire_-_Summer_2005_-_Exam_2_Makeup -...

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Chem 2220 Exam 2 100pts Name_______________ SpringSummer 2005 Makeup Circle your TA / Quiz section (4pt) 1 M 915 STAT 111 Chitnis 2 M 915 STAT 114 Parajuli 3 T 1030 STAT 131 Hoffman 4 R 1030 STAT 131 Chitnis 5 M 915 STAT 219 Hoffman 6 T 1030 STAT 219 Parajuli 1. (6pt) Name the following molecules: O O O O H C 2. (12pt) Write a complete mechanism that describes the acid-catalyzed formation of an acetal when ethanol reacts with ethanol.
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3. (12pt) Rank the following molecules in order of decreasing reactivity towards nucleophiles. C H 3 Br O C H 3 H O C H 3 C 6 H 5 O A B C Rank the following molecules in order of decreasing reactivity by nucleophilic acyl substitution. C H 3 O O CH 3 C H 3 N H O CH 3 C H 3 O O C 6 H 5 A B C Rank the following nucleophiles in order of decreasing strength: - CH 2 CH 3 - OCH 2 CH 3 HOCH 2 CH 3 A B C 4. (12pt) Write conditions that can carry out the individual conversions in the following cycle. C 6 H 5 O OH C 6 H 5 O Cl C 6 H 5 O NH 2 C 6 H 5 O OH C 6 H 5 O H C 6 H 5 CH 2 OH
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5. (12pt) Write a complete mechanism that describes the Wittig reaction between acetophenone and a phosphonium ylide formed from triphenylphosphine and
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Unformatted text preview: bromoethane in base. O CH 3 P(Ph) 3 , CH(CH 3 ) 2 Br BuLi a). Show preparation of phosphonium ylide b) Show reaction of phosphonium ylide with ketone c) How many isomers can be prepared by this reaction? 6. (6pt) Predict the outcome of these reactions CH 3 CH 2 OH KMnO 4 PBr 3 i) Br 2 ii) H + , H 2 O 7. (12pt) Write a mechanism that describes the aldol condensation of 2,2-dimethyl-5-(3-oxobutyl)-cyclopentanone with base. Show only the major product. O O-OH 8. (6pt) Predict the outcome of these reactions O i) P(Ph) 3 (CH 3 ) 2 CHBr ii) BuLi KMnO 4-OH, H 2 O HIO 4 9. (12pt) Write a complete mechanism that describes the Baeyer-Villiger reaction of benzaldehyde (C 6 H 5 CHO), with peroxyethanoic acid (CH 3 COOOH). 10. (6pt) Predict the outcome of these reactions O CH 3 CH 2 NH 2 O O O i. NaBH 4 ii. H + , H 2 O...
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Chemistry_2220_-_Maguire_-_Summer_2005_-_Exam_2_Makeup -...

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