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Unformatted text preview: Chemistry 233 March 13, 2010 Organic I George A. ODoherty Prac. Exam #1.6 (AK) Name: ID# (Please also put your name and ID# on the last page) There is a total of 150 points for this exam. Answer all questions on this exam in the space provided. [I] (30 points/3 points each) Please indicate which C-H -bond is the weakest in each molecule by drawing it in. If there are two or more identical C-H bonds you only need to draw in one of them. Draw in the weakest C-H bond in each molecule 1) 2) 3) 4) 5) 6) 7) 8) 9) 10) O H H H H H H H H H H [II] (30 points total/6 points each) a) On the next two pages please draw the products ( A- E ) for the following reactions. b) Label all stereocenters in the products with an R or S . c) Circle chiral or achiral where appropriate d) Circle the term, which most appropriately indicates the mechanism for the reactions. a) Me LiCuEt 2 only one optically active product with NO IR stretchs at 1600 cm-1 A ( R ) ( S ) Br ( R ) Et ( R ) Et ( R ) ( R ) H H b) two diastereomeric achiral products with IR stretches at 1760 cm-1 + Br CH 3 B C H 3 C H 3 C O CH 3 O Na OAc CH 3 H 3 C H 3 C CH 3 OAc H 3 C H 3 C ( S ) ( R ) ( S ) ( R ) not a chiral cener c) one optically active product is formed with IR stretch at 1610 cm-1 (C=C) D KO t-Bu ( R ) ( R ) Br ( R ) ( R ) d) LUME 2 y E PTy TvE PDUT WT NO STETS T 6...
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