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Final-Key. - Student Name Problem 1 Propose synthetic...

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Unformatted text preview: Student Name: Problem 1: Propose synthetic strategies for the following reactions. Provide all reagents needed and show all the intermediates. (Kpoints each) H&JZO(HQ)J A Student Name: Problem 2 Complete the following reactions. ()(points;)(each)) 02“ CIZIAICI3 ‘3.” \J‘n —* - \3/ 1) HN03, H2504 ; 0—4 ——-—-—)-— __l:l.> 2) SnCl2_2H20 E / . H+ I an; H o c: cicH HCEC'Li+ —...+ H+IH20 0‘4 C” o \ 3 1) CH3MgBr _—._..>_ 2)HCIIH20 0 0 1 H+ )H/ Br ) L—— LDAITHF 2) Brz Mo” 0 1)OH'IH20 é ———-—-—)> f CH5 2) 5°) in DMSO 3) H+IH20 0 ,Br 3* {a ”C3 M9 _>,_ —___* d Ether __ 2) H+IH20 OH Student Name: Problem 3 F0 the following reaction, give the structures of compounds A, B, C and D. Show the stereochemistry. ( oints) a) . Hso,Ho,Hso 0—: fl A i“... B Li; C + D A = (W—ECQ ”a4 —- b) o __ A ”NaOH H 1)CH3MgBr _ ——)-— B —-—).. —__._>.. C 2) CH3-l + 2) H IHzo pt = )3. 5H GD 2. J H,- 2. J 0H 0 \\ Problem 4 Complete the following reactions: Cl _ 1)03 b) o<—+ A 2) CHg-S-CHg O. . A, _ ' H Aggy»; 0 2| ' H O 1) OH'IH20 _.b. 2) H+ Student Name: H+, Heat Student Name: Problem 5 , ' Prognose reasonable structures for the compoundrA and B on the basis of the given molecular formulas and the H NMR spectras. Assign the signals to specific hydrogens in the molecule. l 1) 14= C7H70Bl‘ Br Hl, ' ”L \W 'Hm/%/\ Ha. O\CH UN F ‘0 a 0 Student Name: Problem 6 1) What are the major products for the following reactions? 0'9 / B Dr G‘s—Cu_m “(ml-aw b) M I‘2! l ' col4 Br B!“ .+ N‘s/MK ( 3f — HBr 1 6, ¢ a >2? A 1)o3 > 00 d) —)-> 2)(CH3)25 e) HBr ('3 v.43.“ ::CH 5r = —-—>'- ROOR 2) Name the following compounds: 5: v a- gw-a-mwenmc ...
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