2006spring-finalexamsolns

2006spring-finalexamsolns - Chemistry 140C (Tor) Spring...

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Chemistry 140C (Tor) Spring 2006 – Final Exam 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): ________ KEY _____________________ Your ID # : _____________________________ Question # 1:. .................................................................... /28 Question # 2:. .................................................................... /20 Question # 3:. .................................................................... /80 Question # 4:. .................................................................... /32 Question # 5:. .................................................................... /14 Question # 6:. .................................................................... /30 Question # 7:. .................................................................... /12 Question # 8:. .................................................................... /10 Question # 9:. .................................................................... /12 Question # 10:. .................................................................. /30 Question # 11:. .................................................................. /16 Question # 12:. .................................................................. /16 Total ................................................................................... /300
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Name: _____ KEY ___________________ ID# _________________ 06-13-06 2 1. Acid hydrolysis of the ketoester 1 gives product 2 : OCH 3 O 1 2 O H 3 O + ,H 2 O, ± O Write a detailed stepwise mechanism that accounts for the formation of 2 from 1 . ± Note: show all intermediates! Transfer protons intermolecularly! Ester hydrolysis, followed by a decarboxylation reaction and acid-catalyzed isomerization of the unsaturated ketone. O 2 OCH 3 1 O O H H O H OCH 3 O O H H O H OCH 3 O O H H O H H O H OCH 3 O O H O H H H O H O O O H O H H CH 3 O O H CH 3 OH H O H O H O OH O O O O H ± CO 2 OH H H O H O H H O H
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Name: _____ KEY ___________________ ID# _________________ 06-13-06 3 2. Treatment of the diester 3 with sodium ethoxide in ethanol, followed by a reaction with methyl iodide gives product 4 : OEt O O 3 4 OEt 1. EtO ± Na + 2. CH 3 I EtOH OEt O O Write a detailed and stepwise mechanism that accounts for the conversion of 3 to 4 . ± Note: show all intermediates! Transfer protons intermolecularly! 4 OEt O 3 OEt O H H EtO OEt O OEt O OEt O EtO O EtO OEt O O H OEt O O H 3 C I O 4 OEt O
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Name: _____ KEY ___________________ ID# _________________ 06-13-06 4 3. For each one of the following reactions, circle the product that is preferentially formed. (a) O H + ( ± H 2 O) (c) O O O O O THF, ± 78 o C N Li O OMe H + ( ± MeOH) (d) HO OH O O O O O O O O O OH ± , H 2 O O O (b) O O O Br O HO O O O O O O O
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Name: _____ KEY ___________________ ID# _________________ 06-13-06 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 O O O O O O (f) 1. EtO ± Na + , EtOH 2. H 3 O + , H 2 O O O (g) O O OCH 3 O O O O O O H 3 O + , H 2 O, ² CN HO O O O O HO OH O HO OH O
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Name: _____ KEY ___________________ ID# _________________ 06-13-06 6 OMe O O MeO Br O HO O 2. 4. HCl, H 2 O, ± 1. MeO ² Na + (h) O 1. N 3 ² , DMSO (i) (j) Cl 3. MeO ² Na + 2. H 2 (catalyst) OH HO O O O O 1. EtO ² Na, EtOH O + 2. NaOH, H 2 O, ± O O O O O O O O Br O NH NH NH 2 NH 2
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Name: _____ KEY ___________________ ID# _________________ 06-13-06 7 NH 2 H 2 N (k) O t-BuOH, Et 3 N O excess CH 3 CH 2 OH, H + O O O O O O H N H 2 N O O H N N H O O O O H N H 2 N O NH 2 N H (l) O O O O O O O O OH O O OH O O O O O O O O O NH 2 (m) HO
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2006spring-finalexamsolns - Chemistry 140C (Tor) Spring...

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