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l. (10 points) Use the radical below to answer the following: a. Draw the resonance structures and the resonance hybrid . b. Among the resonance contributors in this prob lem, how many are allylic radica Is? c. Among the resonance contributors in t his problem, how many are benzylic radica Is? 2. (9 points) Name the molecules below using IUPAC nomenclature. a.--- --- ---- -- - ---- --- ---- --- -- --- -- --- b. -----=~ ¡\_ I ü= ----- - -- -- - --- ---- ---- --- ------------ -- H CI--- Bu c.-- ---------------------------- --- -- -- -- 3- (15 points) Answer the questions a - f for the reaction below: slow H O a. lnsert arrows into the reaction and identify the j fasi nucleophile and electr ophile for each step. b. Which step(s) have 6S > O? c. Which step(s) have 6H < O? o d. Is this reaction spontaneou s? e. Draw the trans ition state for each step. f . Considering the additional thermodynamic data {Keq< 1, óGstep1 > O and óGstep2 < O) and the rate descriptions above the arrows, sketch a reaction coordinate diagram. Label reactants, int ermediates, products , activation energies, tran sition states and LlGrxn• 4. (10 points) Use the reaction below to answer the following questions : a. How many monohalogenated products are generated from this reaction? b. Circle the carbon(s) that have the most reactive hydrogens. Explain why these hydrogens are so reactive. c. On a separate piece of paper, write the mechanism leading the major monohalgenated product (s), addressing stereochemistry where possible. 5. (15 points) Give the MAJOR product(s) for each of the following reaction s, noting stereoch emistry where possible. Write the name of the reaction in the space provided . a. 1. Hg(OAch , EtOH/THF b. c. j '-----'=;.;;.;;;_--< Ph d. //·o/1--,,-,r,--,----=-=-=-=---- // NBS, hv ,,,,,,,, e. f. g, h. i. answer from part h j. 2 eguiv HCI .. Li m-CPBA HBr, ROOR k. neutral l. --- ------- - ------- _l=(_ m. ___ _ _ _ _____________________ _ Lindlar's catalys t. H2 "·- -- - - - --- - --------------- answe r from part m o.---------- ---- o --0-~-0H o NaH 6. (28 po int s) Writ e the mechani sm for problem s Sa, Se, Sj and 51. 7. (4 points) Whi ch produ ct / product mixture s for Sa, Se, Sj and SI are optically active? 8. (9 point s) lndicate whether each of the following pairs of compound s are identical compound s, enantiomers , diastereomer s, structural isom ers, ar different (not isomer s). (a) __ _ __________________________ _ (b) ________________ _ _____ __ _ _ PhrhH H9-Ph OH HOA;H Ph-9-H Ph (e)----- - ------- -- ---------- - - c1 H (5 points) Answer Y for yes or N forno for questions 9 - 13 9. Would a 1: 1 mixture problem 8a have the same boiling point? 10. Would a 2:1 mixtur e of probl em 8a rotat e polarl zed light? 11. Would a 2:1 mixtur e of probl em 8b be opti cally active ? 12. Do the molecules in problem 8b have the same specific rotat ion? 13. Would a 1;1 mixt ure of probl em 8c have [cx]o = Oº?

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