Practice_Final_D (Key)

Practice_Final_D (Key) - Final Examination Chemistry S-20...

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Final Examination Chemistry S-20 August 16, 2007 8:30 — 11:30 a.m. Last Name: First Name: Section TF: Important Notes: 1. This exam consists of 18 problems on 18 pages, plus this cover sheet, and two pages for scratch work at the end of the exam. 2. All answers must be written in the spaces provided. Do not write anything in red ink. Answers written on the back of a page will not be graded. Anything written on the scratch pages will not be graded. 3. You are allowed to use a set of molecuar models for this exam. Problem 1. 2. 3. 4. 5. 6. 7. 8. 9. Score ____________ / 16 ____________ / 16 ____________ / 16 ____________ / 16 ____________ / 16 ____________ / 14 ____________ / 18 ____________ / 16 ____________ / 18 Total Score: ______________ /300 Problem 10. 11. 12. 13. 14. 15. 16. 17. 18. Score ____________ / 18 ____________ / 16 ____________ / 18 ____________ / 18 ____________ / 18 ____________ / 16 ____________ / 16 ____________ / 16 ____________ / 18 Tue AM Tue PM (circle one) Section Time: Answer Key
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Name: _______ / 16 Chemistry S-20 1 a) b) c) d) 1. Each of the following transformations can be carried out in no more than three steps. (If an acid workup is required, please indicate this explicitly as a separate step.) Fill in the reagents required for each step. If a step is not needed, please put an "X" through that step. 2. 1. 3. 1. 1. 1. C C H HO OH H Br O OH H 2 , Lindlar OsO 4 HBrorHC lorH I KO t Bu Also OK: 1. H + ,H 2 O 2. conc. H 2 SO 4 H 2 ,Pd/C Br 2 ,FeBr 3 SOCl 2 AlCl 3 KOH, H 2 NNH 2 , Δ Or, for 3: HCl, Zn Also OK: 1) Na/NH 3 2) mCPBA 3) H 3 O + or 3) H 2 O, OH A lsoOK :1 .H + 2 O 2. TsCl, py (or MsCl Py, or HBr, or HI, or HCl) 3. KOtBu
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Name: _______ / 16 2. Each of the following transformations can be carried out in no more than three steps. (If an acid workup is required, please indicate this explicitly as a separate step.) Fill in the reagents required for each step. If a step is not needed, please put an "X" through that step. 3. 1. Chemistry S-20 2. 2 2. 3. 2. 3. a) b) c) d) 2. 3. O NH 2 N H OH NH 2 O OTs N H CH 3 CH 3 NC NC LiAlH 4 H + PhCHO, pH 5 CrO 3 ,dry 4 C O 1D& N H 3 O + H 3 O + H 2 N Δ CN Δ O NaCN , DCC
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Chemistry S-20 3 Name: _______ / 16 3. Fill in each box with the single major product of the indicated transformation. (You do not need to worry about the stereochemistry of any product.) a) b) c) d) heat O CH 3 Cl KO t Bu H 3 CC CH Ph 3 PC H 2 1. H
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This note was uploaded on 01/22/2012 for the course CHEM CHEM E-2B taught by Professor Loganmccarty during the Fall '09 term at Harvard.

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Practice_Final_D (Key) - Final Examination Chemistry S-20...

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