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Midterm 2keys-2005 - NAME STUDENT ID NUMBER LAB TIME TA...

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NAME: STUDENT ID NUMBER LAB TIME TA NAME CHEMISTRY 112A Second Midterm February 23, 2005 I. --------------------- (25) II.--------------------- (25) III.-------------------- (10) IV--------------------- (5) V. --------------------- (20) VI. -------------------- (10) VII. -------------------- (5) Bonus ---------------- (10) Total -------------------(100)
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H-Cl 1) O 3 2) Zn 1) BH 3 2) H 2 O 2 / NaOH H 3 C-C C H 1) strong base 2) CH 3 CH 2 CH 2 Br C C H HgSO 4 , H 2 O / H + I) Complete the following reactions. Do not show the mechanism. Cl OH H 3 C-C C CH 2 -CH 2 -CH 3 O O C CH 3 O
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H 2 , Pd CHCl 3 , KOH C C CH 3 Li / NH 3 OsO 4 II) Complete the following reactions and show stereochemistry when required. Do not show the mechanism. 1) BH 3 2) H 2 O 2 / OH - H 3 C CH 3 H H HO OH (H 2 0) OH Cl Cl C C CH 3 H H H H 3 C H CH 3
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III) Propose a synthesis corresponding to the following transformation. You may use some or all reactants indicated below. Show all steps, but do not show mechanisms. Do not use the space below as scrap paper - place only your final answer on this page. Be neat - illegible markings will be considered incorrect. R multiple steps R CH 2 CH 3 Reactants: CH 3 CH 2 Br, BH 3 , H 2 O, NaNH 2 , Br 2 , KOH, HCl R Br 2 R Br Br KOH R H 1) NaNH 2 2) CH 3 CH 2 Br R CH 2 CH 3
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