Midterm 2 keys-2006

Midterm 2 keys-2006 - NAME: STUDENT ID NUMBER LAB TIME TA...

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NAME: STUDENT ID NUMBER LAB TIME TA NAME CHEMISTRY 112A Second Midterm February 27, 2006 I. --------------------- (35) II.--------------------- (10) III.-------------------- (10) IV--------------------- (10) V. --------------------- (10) VI. -------------------- (5) VII. -------------------- (8) VIII. -------------------- (4) IX. -------------------- (8) Bonus ---------------- (5) Total -------------------(100)
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I) Complete the following reactions and show stereochemistry when required. Do not show the mechanism. 1) O 3 2) Zn 1) BH 3 2) H 2 O 2 / NaOH O O NBS / H 2 O C C CH 3 Li / NH 3 HgSO 4 , H 2 O / H + C CH 3 O CHCl 3 , KOH HO OH H 2 O / H + or 1) Hg(OAc) 2 , H 2 O 2) NaBH 4 Cl Cl Br OH C C H
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II) Show the alkyl bromide and terminal alkyne from which the following product can be obtained. C C CH 2 C H 3 C H 3 C H 3 C CH 3 C C H C H 3 C H 3 C H 3 C Br CH 2 CH 3 III) Propose a synthesis of derivative A starting from B. 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. A OH OH OsO 4 NaHSO 3 , H 2 0 KOH You can use: O 3 H 2 HBr Br B BH3 H 2 O 2 Br B KOH 1) OsO 4 2) NaHSO 3 , H 2 0 A OH OH
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IV) Propose a synthesis of derivative C. You may use some or all reactants indicated. Show all
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Midterm 2 keys-2006 - NAME: STUDENT ID NUMBER LAB TIME TA...

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