Oragnic Chemistry 112A

Oragnic Chemistry 112A - NAME STUDENT ID NUMBER LAB TIME TA...

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NAME: STUDENT ID NUMBER LAB TIME TA NAME CHEMISTRY 112A Final March 23, 2006 I. --------------------- (20) II.--------------------- (20) III.-------------------- (20) IV--------------------- (10) V. --------------------- (10) VI. -------------------- (20) VII----------------------(10) VIII----------------------(30) IX----------------------(20) X ----------------------(10) XI----------------------(10) XII----------------------(20) Bonus ---------------- (10) Total -------------------(200)
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CH 2 Br OTs Br CH 3 CH 2 CuLi NaCN LDA I) Complete the following reactions. Do not show the mechanism. 2 1) Mg 2) H 3 O + HBr OH Br CN Br CH 2 CH 2 CH 3
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C C CH 3 H OTs CH 3 CH 2 CH 3 H H Br CH 3 CH 2 CH 3 CH 3 H A NH 3 , Li LDA CH 3 SNa B 1) BH 3 2) H 2 O 2 , / OH - II) Complete the following reactions and show stereochemistry when required. Do not show the mechanism. rate = k[ A ][LDA] rate = k[ B ][CH 3 SNa] OTs C rate = k[ B ][(CH 3 ) 2 CuLi] (CH 3 ) 2 CuLi CH 3 CH 3 CH 2 CH 3 CH 3 H H SCH 3 CH 3 CH 2 CH 3 H B H OH
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Br 2 OsO 4 - TsONa CH 3 SNa Br H CH 3 Br H CH 2 CH 3 HO OH CH 3 CH 2 CH 3 CH 2 CH 3 CH 3 III) Complete the following reactions by showing the starting materials. Show stereochemistry when required. Do not show the mechanism. CH 3 CH 3 S H CN NaCN - TsONa CH 3 I CH 3 CH 2 H H NaI - TsONa H H CH 3 CH 2 CH 3 CH 3 CH 2 CH 3 CH 3 CH 2 CH 3 OTs H 3 C H OTs
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IV) Draw all the possible resonance structures for the following radical.
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