2005spring-finalexam

2005spring-finalexam - Chemistry 140C (Tor) Spring 2005...

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1 Chemistry 140C (Tor) Spring 2005 – Final Exam (V.1) This exam accounts for 50% of the final grade. Time 7:00 – 10:00 PM. Mark your final answer clearly and completely erase irrelevant information! Remember: Exams written in pencil will not be regraded! Additional pages are at the end for your convenience. Please indicate if your final answer should be found at the end of the exam. Good Luck! Your Name (Please Print): _____________________________ Your ID # : _____________________________ Question # 1:. .................................................................... /20 Question # 2:. .................................................................... /32 Question # 3:. .................................................................... /80 Question # 4:. .................................................................... /32 Question # 5:. .................................................................... /08 Question # 6:. .................................................................... /34 Question # 7:. .................................................................... /16 Question # 8:. .................................................................... /30 Question # 9:. .................................................................... /12 Question # 10:. .................................................................. /12 Question # 11:. .................................................................. /08 Question # 12:. .................................................................. /16 Total ................................................................................... /300
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Name: ________________________ ID# _________________ 06-08-05 2 1. Treatment of the compound 1 with aqueous base gives the diketone 2 : O 1 HO ! H 2 O 2 O O O O Write a detailed , arrow-pushing , stepwise mechanism that accounts for this transformation. !!! Note : Show all intermediates! Transfer H’s intermolecularly!
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Name: ________________________ ID# _________________ 06-08-05 3 2. Treatment of ketoester 3 with sodium ethoxide in ethanol, followed by a reaction with ethyl iodide gives ketoester 4 : O O OEt Me 3 O O OEt EtO ! Na + EtOH CH 3 CH 2 I Et 4 Me Write a detailed stepwise mechanism that accounts for the formation of 4 .
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Name: ________________________ ID# _________________ 06-08-05 4 3. For each one of the following reactions, circle the product that is formed. (a) O MeO ! Na + , MeOH, 25 o C (b) H 3 O + , H 2 O Br O O O O O THF, ! 78 o C Br O O O O N Li O O O O (c) O 1. MeO ! Na + , MeOH O MeO 2. H 3 O + O O O O O O (d)
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Name: ________________________ ID# _________________ 06-08-05 5 (e) H 3 CO O OCH 3 O O O OCH 3 O O OCH 3 1. CH 3 O ! Na + , CH 3 OH 2. H 3 O + , H 2 O O O OCH 3 OEt EtO O O HO (f) 1. EtO ! Na + , EtOH 2. CH 3 CH 2 Br O 3. HCl, H 2 O, " 1. EtO ! Na + , EtOH (g) O O OCH 3 O O O HO O HO O 2. NaOH, H 2 O, " O O O O O O O O O
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Name: ________________________ ID# _________________ 06-08-05 6 (h) CN O O H 3 O + , H 2 O, ! NH 2 H 2 N O (i) t-BuOH, Et 3 N O O HO O OH O HO O OH O HO O OH OH O excess CH 3 CH 2 OH, H + OCH 3 O O O OCH 3 O OH OCH 2 CH 3 O OH OH O O O OCH 2 CH 3 O O O O O O O O H N H 2 N O O O H N N H O O O O O H N H 2 N O O NH 2 N H O (j) O O
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Name: ________________________ ID# _________________ 06-08-05 7 (k) NH 2 N H O (l) O OH (m) O MeO !
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2005spring-finalexam - Chemistry 140C (Tor) Spring 2005...

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