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Final 2010 keys - NAME STUDENT ID NUMBER LAB TIME TA NAME...

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NAME: STUDENT ID NUMBER LAB TIME TA NAME CHEMISTRY 112A Final March 19, 2010 I. --------------------- (25) II.--------------------- (25) III.-------------------- (25) IV--------------------- (20) V. --------------------- (15) VI. -------------------- (15) VII---------------------(15) VIII---------------------(25) IX----------------------(15) X ----------------------(10) XI ----------------------(10) Bonus ---------------- (10) Total -------------------(200)
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I) Complete the following reactions. Only one organic product is obtained. Do not show the mechanism. I CH 3 SNa Br LDA Br 1) Mg 2) H 3 O + OH HBr NBS CCl 4 , h ν ΣΧΗ 3 Βρ Βρ
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II) Complete the following reactions and show stereochemistry when required. Do not show the mechanism.
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CH 3 C OTs H H OTs CH 3 CH 2 CH 3 CH 3 H A D OTs B NaCN CH 3 SNa (CH 3 ) 2 CuLi rate = k[ B ][NaCN] rate = k[ A ][CH 3 SNa] rate = k[ D ][(CH 3 ) 2 CuLi] H CH 3 CH 2 CH 3 Br CH 3 H E tBuOK rate = k[ E ][tBuOK] H OTs CH 3 CH 2 CH 3 CH 3 H C LDA rate = k[ C ][LDA] CH 3 C H SCH 3 H CN CH 3 CH 2 CH 3 CH 3 H CH 3 CH 3 CH 3 CH 2 H CH 3 H CH 3 CH 2 CH 3 III) Complete the following reactions by showing the starting materials or reagents. Show stereochemistry when required. Do not show the mechanism.
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-TsONa RSNa NaCN 1) BH 3 2) H 2 O 2 / OH - HO H CH 3 H CH 2 CH 3 CH 3 Br CH 3 CH 2 H CH 3 SR CH 2 CH 3 CH 3 CH 3 C CN H -TsONa Br 2 Br H CH 3 Br CH 2 CH 3 CH 3 NBS, CCl 4 h ν ΧΗ 3 ΧΗ 2 Η ΧΗ 3 ΟΤσ ΧΗ 2 ΧΗ 3 ΧΗ 3 ΧΗ 3 Χ Η ΟΤσ ΧΗ 2 ΧΗ 3 ΧΗ 3 ΧΗ 3 Η ΧΗ 3 ΧΗ 2 ΧΗ 3
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