Final 2009defkeys

Final 2009defkeys - NAME: STUDENT ID NUMBER LAB TIME TA...

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N A M E : K E Y S STUDENT ID NUMBER LAB TIME TA NAME CHEMISTRY 112A Final March 18, 2009 I. --------------------- (25) II.--------------------- (25) III.-------------------- (25) IV--------------------- (20) V. --------------------- (10) VI. -------------------- (10) VII----------------------(20) VIII----------------------(25) IX----------------------(10) X ----------------------(15) XI ----------------------(15) Bonus ---------------- (10) Total -------------------(200)
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I) Complete the following reactions. Only one organic product is obtained. Do not show the mechanism. OH PBr 3 Br t -BuOK NaCN CH 2 CH 2 CuLi 2 CH 3 CH 2 CH 2 Br OTs CH 3 H 3 CC CH 3 CH 3 C CH 3 CH 3 CH 3 Cl 2 h ν Br H 3 CH 3 CH 3 C CH 3 CH 3 CH 2 Cl CN
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NaCN LDA (CH 3 CH 2 ) 2 CuLi II) Complete the following reactions and show stereochemistry.Only one organic product is obtained. Do not show the mechanism. CH 3 C OTs H D H CH 2 CH 3 CH 3 E rate = k[ E ][LDA] B rate = k[ B ][(CH 3 CH 2 ) 2 CuLi] OTs A rate = k[ A ][NaCN] RSNa OTs CH 3 CH 2 CH 3 H D C rate = k[ C ][RSNa] CH 3 CH 3 CH 2 Br tBuOK Br CH 2 CH 3 CH 3 D rate = k[ D ][tBuOK] CH 3 CH 3 CH 2 H CH 3 C H CN D CH 2 CH 3 SR CH 3 CH 2 CH 3 H D CH 3 CH 2 CH 2 CH 3 CH 3 CH 3 CH 3 CH 2 CH 2 CH 3 CH 3 CH 3
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III) Complete the following reactions by showing the starting material, the final product or the reagent. Show stereochemistry when required. Do not show the mechanism.
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Final 2009defkeys - NAME: STUDENT ID NUMBER LAB TIME TA...

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