Practice_Final_F (Key)

Practice_Final_F (Key) - Practice Final Examination C...

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Final Examination Chemistry S-20 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 ____________ / 16 ____________ / 18 ____________ / 18 Total Score: ______________ / 300 Problem 10. 11. 12. 13. 14. 15. 16. 17. 18. Score ____________ / 18 ____________ / 18 ____________ / 18 ____________ / 18 ____________ / 18 ____________ / 16 ____________ / 16 ____________ / 16 ____________ / 16 Tue AM Tue PM (circle one) Section Time: SOLUTIONS
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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. CH 2 I 2 , Zn 1. H 2 , Lindlar 3. X 2. CrO 3 1. OsO 4 , H 2 O 3. X 2. NaNO 2 , HCl 1. Sn 0 , HCl 3. H 2 O 2. AlCl 3 1. SOCl 2 3. N 2 H 4 , KOH, Δ H 3 C CH 3 NO 2 O OH CH 3 H 3 C H 3 C CH 3 CH 3 H 3 C CH 3 CH 3 O HO OH May also do 2. H 2 CrO 4 May also do 3. Zn(Hg), HCl
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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. pH 5, 1. DIBAL Chemistry S-20 2. H 3 O + workup 2 2. 1. Δ , 3. 1. NaN 3 2. H 2 , Pd/C 3. AcCl, py a) b) c) d) 1. Hg 2+ , H + , H 2 O 2. CH 3 MgBr 3. H 3 O + work up H 3 C O OEt Br N H O CH 3 N H 3 C CH 3 CH 3 CH 3 CH 3 CO 2 CH 3 CO 2 CH 3 H 3 C H 3 C OH CH 3 CH 3 Ph NH 2 CO 2 CH 3 CO 2 CH 3 May do stepwise. 1. Δ , 2. Δ , dimethyl maleate
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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)
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