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sol_04 - 4W 67 Problem Set#4 5.12 Spring 2003 Due Monday...

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Unformatted text preview: 4W, 67% 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. ifl E?” g WW F——:—-D H 3. and D H OH 0 Br HO CH ' W 3 and H0)J\|S/'S\CH3 WM 0 Br OH Cl CI é Q/«Qp Cl Cl S $3 R Km? W E“ H /l:L\s/CH3 and ”$0“ ’91“)? = S aka/gm ”30 g H3C Ph _ 5 5H CH3 We - Lil” 2. a) Label each molecule as chiral or achiral. b) Label each stereocenter with its R or S configuration. c) Label all of the mesa compounds. a) There are three different constitutional isomers of dichlorocyclopentane. Draw them. 6 @/cl Q“ 02‘) (if) 0,5) 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. \1 Cl Cl / Q' d C‘ Ql / \ : {k Jig/d LLwZ S “\ s Cpl / L/ <___/ mCJ/vmvo “r Adam/0 (3ka Q’L‘AWVQ (H.503 u 02 9i a ill: i s . he following molecule A is drawn in such a way that the 3-D structure is ambiguous. a) Circle the atoms that are stereocenters. 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? lez ZW:ZL:4W\ 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. oil 0 (>14 0 W l 1 u/\\\Q‘:/;K/OH A H/lW/UH on 5;” Ki 5. a) Provide a complete detailed mechanism for the following reaction (including initiation, propagation, and termination steps). Remember to use fishhook arrows! hv HSC—CH3 + Br—Br —> H30—CHQBr + H—Br imhahovxl :U/EFW L B" 4, EF‘ .W mash» b) Using the BDE table on p. 134 in Wade, calculate AH for each of the propagation steps. 4M lye/dz EI II +0I75onQ/Im0 W I Bf _?2>J;u12/[email protected] Mir: + I0 Jaw/HI? 4” M Er—gv- + Lie limit/w? W JC+ Br _, 6‘8 W/M'p M1. = -2; JWQ/M? @ c) Draw a reaction-energy diagram for the propagation steps from part a. d) Label AH° for each step, AH°overa", and the rate-determining step. e) Is the overall reaction endothermic or exothermic? K‘ W~ WNW/5 54v? - ~— . s ‘ ARE; : ”2L ...
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