Midterm Key - UCLA

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Chemistry 144, Fall 2004 Name: KEY Page 2 1A. (3) Label the prochiral faces of the ketone below as Re and Si. O Re Si OH B. (4) Label the indicated pairs of substituents as Homotopic, Enantiotopic, or Diastereotopic. OMe OMe C. (3) List the pKa values for the following. Homotopic Br Enantiotopic Acetylene Acetone Benzene 25 20 40 D. (5) Define the term Chemoselectivity. Use a drawing to illustrate your definition. Selective reaction at one functional group in a molecule containing two or more functional groups without using protecting groups. MeO O O OH NaBH4 MeOH MeO C. (5) Define the term Stereospecific. Use a drawing to illustrate your definition. A reaction where the stereochemistry of the starting material determines the stereochemistry of the product. OsO 4 OH OH O Cl Cl OsO 4 OH OH
Chemistry 144, Fall 2004 Name: KEY Page 3 2. (14) Draw the transition state models and products predicted for the following reactions. O O OBn H OSiEt 3 EtMgBr MgBr 2 Et2O NaBH 4 EtOH Nu - Br2 Mg BnO O H Et H Et O H Me OR Chelation OSiEt 3 Nu - Felkin-Anh Br2Mg BnO O H Nu - OH OSiEt 3 OBn OH
Page 1: CHEMISTRY 144 UCLA, FALL 2004 MIDTE
Page 5 and 6: HOOC 1) SOCl2 2) HNMe(OMe) Et3N 3)
Page 7 and 8: Chemistry 144, Fall 2004 Name: KEY

Midterm Key - UCLA

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