Questions with Answers on Elementary Organic Chemistry II - Exam 4 | CH 231, Exams of Chemistry

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RBxam #4 Chemistry 231(Blackstock) April 20, 2011 Name: leo ae (print) Honor Pledge: a (sign) Partial credit will often be given for partially correct answers. Clarity in drawings helps earn points. 1, General Knowledge (24 pts) 1. (19 pts) Provide the corresponding structures for the items listed below. G 5 ) 4. veN < re wT, © ce the highest E oceupied pi MO of cyclopentene - show H's and thiony! chloride allyl cation (sketch if} circle weakest CH bond(s} QS n eo tos aN Ce Li Xgl HOr---C-- O-Ts ke 2 iz it tt Gilman reagent derived from Grignard reagent derived from the # (3D) for Sy2 reaction of bromobenzene neopenty! iodide hydroxide with methyl tosylate \ 9306 g 1 @ , ° Y ca ch cH ch I a z — 2b 2 cae oo 2 Ch-cH-O- 5 8 cH Oe oer gy were Hs aoe (ths p3i7} the tosylate derived from ethanol all important resonance structures of benzyl cation, C;H,* Cs pS oe 38 2.(5 pts) Provide the requested information. oH cae Olle. XX + aor Hs + 1,0 Tanenn st. a balanced rxn for methanolysis of 2-methyl-2-butanol in acidic methanol. He— ~Tppm ad pee FX a ho ae Hap—< Ott HO CH; <— ~\ pps the approx H-NMR chemical shifts for the indicated H's.