Chemistry 108A final 2006

Chemistry 108A final 2006 - C F Bernasconi Final Exam...

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C. F. Bernasconi Chemistry 108A Winter 2006 Final Exam – March 22, 2006 This exam consists of nine (9) questions for a total of 150 points. Try to answer all questions. Write your answers in a Blue Book. Put your name and that of your TA on the cover page. 1. ( 18 points ) Which of the following compounds are aromatic? (a) (d) (b) (e) (c) (f) N N H Cl CH 3 NO 2 O 2. ( 32 points ) Show the major organic products of the following reactions (no mechanisms please). Indicate the stereochemistry where relevant. Note that in some cases there may be no reaction. (a) Br + HNO 3 H 2 SO 4 ? (b) Cl CCH 2 CH 2 CH 3 O H 2 /Pd ? (c) NO 2 + (CH 3 ) 3 CCl AlCl 3 ? (d) DBr ?
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C. F. Bernasconi Chemistry 108A Winter 2006 Final Exam March 22, 2006 Page 2 (e) O O + ? (f) CHCH 3 I S-form NaCN H 2 O ? (g) CH 3 CH 2 CH 2 C CH 1. BH 3 2. H 2 O 2 /NaOH ? (h) CH 3 1. Hg(OAc) 2 2. NaBH 4 ? 3. ( 30 points ) What reagents would you use to achieve the following transformations? Note that more than one reagent might be necessary, i.e. it may be necessary to carry out more than one reaction.
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