2004spring-finalexamsolns

2004spring-finalexamsolns - Chemistry 140C (Tor) Spring...

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1 Chemistry 140C (Tor) Spring 2004 – 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):_____________________________ Your ID # : _____________________________ Question # 1:. ...................................................................... /15 Question # 2:. ...................................................................... /24 Question # 3:. ...................................................................... /75 Question # 4:. ...................................................................... /45 Question # 5:. ...................................................................... /20 Question # 6:. ...................................................................... /10 Question # 7:. ...................................................................... /12 Question # 8:. ...................................................................... /30 Question # 9:. ...................................................................... /24 Question # 10: . ................................................................... /15 Question # 11: . ................................................................... /30 Total ...................................................................................... /300
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Name: ________________________ ID# _________________ 06-08-04 2 1. Upon treatment of the ketoester 1 with sodium methoxide in methanol, followed by a mild acidic workup, the diketone 2 is obtained: O O 1 . 1. CH 3 O Na + , CH 3 OH 2. H + , H 2 O 2 . O CH 3 O O Write a detailed , arrow-pushing, stepwise mechanism that accounts for this transformation. 4 4 4 Note : Show all intermediates! Transfer H’s intermolecularly! O O OCH 3 O O CH 3 O H H H CH 3 O O O H H OCH 3 O O CH 3 O O O O O O O O O CH 3 O O O 1 2 End of part 1 Part 1 Part 2 H 3 O + , H 2 O . . .
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Name: ________________________ ID# _________________ 06-08-04 3 2. Upon treatment of diketone 2 with acidic ethanol, water is lost and product 3 is obtained: O CH 3 CH 2 OH, H + 3 . OCH 2 CH 3 O 2 O Write a detailed , arrow-pushing, stepwise mechanism that accounts for this transformation. 4 4 4 Note : Show all intermediates! Transfer H’s intermolecularly! O O O OCH 2 CH 3 CH 3 CH 2 OH, H + 3 2 OH O HOEt H H OH O O Et O Et H H OH OH H OH OH OEt H O Et H OH OH OEt OH O OEt O Et H H H OH OCH 2 CH 3 O Et H
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Name: ________________________ ID# _________________ 06-08-04 4 3. For each one of the following reactions, circle the product that is formed. O H O HO O O OH H O HO O (b) (c) (a) (d) NaOH, H 2 O, 5 0 C H 3 O + , H 2 O O 1. (CH 3 ) 3 CO K , (CH 3 ) 3 COH, 2. CH 3 I O O O O O O H 3 CO O OCH 3 O O O OCH 3 O O OCH 3 O OCH 3 O 1. CH 3 O Na + , CH 3 OH 2. H 3 O + , H 2 O
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Name: ________________________ ID# _________________ 06-08-04 5 O O OCH 3 O O O CN OO O OH O O O N H HO CO 2 H HO OCH 2 CH 3 O O O O OH N H OCH 2 CH 3 O OH HO CN OH O HO CO 2 H OCH 3 O OH OH OH O N O excess CH 3 CH 2 OH, H + (f) (e) CH 3 CH 2 NH 2 , HCl, H 2 O, (g) (h) H 2 O,
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Name: ________________________ ID# _________________ 06-08-04 6 NH 2 O O t -BuOH, Et 3 N O O O O O t -Bu t -Bu HN t -Bu O 1. CH 3 CH 2 O Na , CH 3 CH 2 OH, -5 o C HN O t -Bu O OH HO HO O HO OH NH 2 HO O OH CH 3 O H 3 CO O CH 3 O OCH 3 NH O O NH O OCH 3 CH 3 O H 3 CO O CH 3 O OCH 3 OCH 3 HO HO O HO OH HN O OO O t -Bu NH O O O O CH 3 OH, 0.25% HCl, H 2 O (i) (j) (k) 2. NaOH, H 2 O, (l) DCC
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This note was uploaded on 04/14/2009 for the course CHEM140C 234234 taught by Professor Nefzi during the Spring '09 term at UCSD.

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2004spring-finalexamsolns - Chemistry 140C (Tor) Spring...

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