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prob_04 - O OH OH H OH b Based on the number of atoms you...

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Problem Set #4, 5.12 Spring 2003 Due Monday, March 10, 4pm 1. a) Label each pair as enantiomers , diastereomers , or same molecule. b) Label each stereocenter with its R or S configuration. Br and F D H F D Br H OH O Br HO CH 3 and HO CH 3 O Br OH Cl Cl Cl and Cl Ph H H OH CH 3 and H 3 C H 3 C Ph OH CH 3
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2. a) Label each molecule as chiral or achiral . b) Label each stereocenter with its R or S configuration. c) Label all of the meso compounds . H N H Et Me Me C O Me O Br Br H 2 C N CH 3 CH 3
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3. a) There are three different constitutional isomers of dichlorocyclopentane. Draw them. b) There are seven different stereoisomers of dichlorocyclopentane. Draw all of them. c) Label each stereocenter as R or S . d) Label each structure as chiral or achiral . e) Label any meso compounds.
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4. The following molecule A is drawn in such a way that the 3-D structure is ambiguous. a) Circle the atoms that are stereocenters.
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Unformatted text preview: O OH OH H OH b) Based on the number of atoms you circled in part a , what is the maximum number of stereoisomers possible for A ? c) Draw all of the possible stereoisomers of A and label their stereoisomeric relationships (diastereomers, enantiomers). d) Label each stereocenter with its R or S configuration. 5. a) Provide a complete detailed mechanism for the following reaction (including initiation, propagation, and termination steps). Remember to use fishhook arrows! hv H 3 C CH 3 Br Br H 3 C CH 2 Br H Br b) Using the BDE table on p. 134 in Wade, calculate Δ H for each of the propagation steps. c) Draw a reaction-energy diagram for the propagation steps from part a. d) Label H° for each step, H° overall , and the rate-determining step . e) Is the overall reaction endothermic or exothermic?...
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