Midterm_2-2008keys

Midterm_2-2008keys - NAME: STUDENT ID NUMBER LAB TIME TA...

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NAME: STUDENT ID NUMBER LAB TIME TA NAME CHEMISTRY 112A Second Midterm February 25, 2008 I. --------------------- (25) II.--------------------- (25) III.-------------------- (10) IV--------------------- (10) V. --------------------- (10) VI. -------------------- (10) VII. -------------------- (10) VIII. -------------------- (10) IX. -------------------- (10) Bonus ---------------- (10) Total -------------------(120)
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1) Hg(OAc) 2 , H 2 O 1) O 3 2) Zn HCl C C H 1) strong base 2) RCH 2 Br C C H HgSO 4, H 2 O/H + I) Complete the following reactions. Do not show the mechanism. R 2) NaBH 4 OH Cl O O C C CH 2 R R C 3 O
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C C H 2 II) Complete the following reactions and show stereochemistry. Do not show the mechanism. 1) BH 3 2) H 2 O 2 / OH - CH 3 3 H 3 2 H Br 2 H 2 H 3 C 3 2 3 3 2 H Lindlar catalyst NBS (or Br 2 ) / H 2 O OH Pd/C H Br Br C C H H Br 3 CH 2 H 3 C 2 3 3 3 2 H 3 C 3 H
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III) Propose a synthesis of derivative B from compound A . You may choose your reactants from those indicated in the box only. 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. B OsO 4 KOH You can use: O 3 HBr Br A BH 3 H 2 O 2 OH NaHSO 3 H 2 0 Hg(OAc) 2 NaBH 4 Br A KOH 1) Hg(OAc) 2 , H 2 O 2) NaBH
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Midterm_2-2008keys - NAME: STUDENT ID NUMBER LAB TIME TA...

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