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Final Exam-2010

Final Exam-2010 - MCMP 205 Final...

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Name _________________________________ Lab TA ________________________________ Lab Period (Day & Time) ___________________ Monday, May 3, 2010 7:00 - 9:00 pm EE 129 This exam contains 16 problems on 14 pages (numbered 1-14) in addition to the cover and scoring pages (i and ii). Please write your name at the top of every page. MCMP 205 Final Exam 150 pts - i -
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Scoring page Question Possible points Score Total Points __________ Name ______________________________ - ii - 1 16 __________ 3 4 __________ 4 14 __________ 5 10 __________ 6 6 __________ 7 10 __________ 8 15 __________ 9 6 __________ 10 24 __________ 11 7 __________ 2 4 __________ 12 7 __________ 13 7 __________ 14 6 __________ 15 8 __________ 16 6 __________
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Name __________________________ page 1 1. (16 pts.) Draw the structure of each of the molecules specified in parts a. - g. a.) ethyl 5-oxopentanoate = b.) 3-(dimethylamino)benzoic acid = d.) enolate anion of 3,3-dimethyl-2-butanone NaOH e.) E -conformation of N -ethyl- N -methylpropionamide CH 3 CH 2 CON(CH 3 )CH 2 CH 3 = 3,3-dimethyl-2-butanone c.) 5-fluoropentanamine = f.) β -D-glucopyranose in the chair form = O OH HO HO HO OH O O O H OH O F H 2 N O or ONa N O N
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Name __________________________ page 2 f.) The ethyl α -pyranoside of glucose in the chair or Haworth form = g.) Pyridine-3-carboxylic acid = 2. (4 pts.) The protons circled below have pKa values of 1.2, 4.6, 10.6, and 25. Write the correct pKa value in the space below each compound. NH 2 3. (4 pts.) The protons circled below have pKa values of 4.2, 7.7, 13, and 18. Write the correct pKa value in the space below each compound. O MeO O OMe O H H 2 N H F F O O H OEt O H H H O O H C NH 2 H N O OEt HO HO HO OH or OH O OEt OH OH CH 2 OH N CO 2 H 1.2 4.6 10.6 25 18 4.2 7.7 13
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Name __________________________ page 3 4. (14 pts.) Fill in the missing reagents and structures in the boxes a - g in the following synthetic scheme. OH CrO 3 , pyridine NMe 2 MeI Ag 2 O NaOH K 2 Cr 2 O 7 , aq. H 2 SO 4 Cl O HNMe 2 , pyridine a.) c.) e.) f.) C 7 H 12 O 2 g.) d.) b.) Hofmann Elimination Borch Reduction H O OH O NMe 2 O NMe 2 Me LiAlH 4 SOCl 2 or PCl 5 HNMe 2 and NaBH(OAc) 3 or NaBH 3 CN
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Name __________________________ page 4 5 (10 pts.) Fil in the missing reagents and structures in the boxes a - e in the following synthetic scheme.
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