2004winter-finalexambsolns

2004winter-finalexambsolns - Chemistry 140C (Tor) Winter...

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1 Chemistry 140C (Tor) Winter 2004 – Final Exam (V.2) This exam accounts for 50% of the final grade. Time 11:30 AM –2:30 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 clearly indicate if your final answer should be found at the end of the exam. Good Luck! Your Name (Please Print):_____________________________ Your ID # : _____________________________ Question # 1:. ...................................................................... /25 Question # 2:. ...................................................................... /90 Question # 3:. ...................................................................... /35 Question # 4:. ...................................................................... /20 Question # 5:. ...................................................................... /30 Question # 6:. ...................................................................... /25 Question # 7:. ...................................................................... /30 Question # 8:. ...................................................................... /20 Question # 9:. ...................................................................... /10 Question # 10: . ................................................................... /15 Total ...................................................................................... /300
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Name: ________________________ ID# _________________ 03-15-04 2 1. Treatment of ketone 1 with dilute base leads to product 2 as shown: O 12 NaOH, H 2 O O O O O Write a detailed stepwise mechanism that accounts for the formation of product 2 . (Show all intermediates! Transfer H’s intermolecularly!). O 1 O O HO H H H O O O O O O H O H O O OH HO HH O O OH 2 O O
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Name: ________________________ ID# _________________ 03-15-04 3 2. For each one of the following reactions, circle the product that is formed. CN O O O H OH HO O O NH 2 O OH Cl NaOH H 2 O H 3 O + CO 2 H O O O O O CO 2 H HO HO 2 C HO NH 2 O O OH O CO 2 H HO OO OH CN HO HO 2 C CO 2 H HO O HCl, H 2 O, (d) HCl, H 2 O, (c) (b) (a)
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Name: ________________________ ID# _________________ 03-15-04 4 H OH OH HBr 1. TsCl, pyridine 1. (CH 3 ) 3 CO K , (CH 3 ) 3 COH, Br 3. H 2 SO 4, H 2 O, O O S 2. NaCN, DMSO OH HO HO O HO OH O OO N OCOCH 3 HO HO O HO OH OH CH 3 COO CH 3 COO O CH 3 COO OCOCH 3 Br H COOH COOH H H CH 2 NH 2 OCOCH 3 CH 3 COO CH 3 COO O CH 3 COO OCOCH 3 O CH 2 NH 2 H (f) (g) (e) (h) Ts = excess O 2. CH 3 I O O OH
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Name: ________________________ ID# _________________ 03-15-04 5 H 3 CO O OCH 3 O N Li + O O OCH 3 O O OCH 3 O OCH 3 O (k) (j) (i) LDA = LDA, Ether (slight excess, low temperature) 1. CH 3 O Na + , CH 3 OH 2. H 3 O + , H 2 O Br O O O O OCH 3 O O H 3 CO Cl O OCH 3 HO O O OH HO O O OH HO O O OH 2.
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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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2004winter-finalexambsolns - Chemistry 140C (Tor) Winter...

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