CHE 232-1, Spring 2008Dr. HarrisName (please print)___________________________________Student ID #______________________________________Short Answer (20 pts, 2pts. each)CHE 232-1, Spring 2008Dr. HarrisName (please print)___________________________________Student ID #______________________________________Short Answer (20 pts, 2pts. each)1) Which of the following alkanes will give more than one monochlorination product when treated with chlorine and light?a) 2,2’-dimethylpropane, b) cyclopropnae, c) ethane, d) 2,3-dimethylbutane 2) Which type of halogenation is most selective? 3) Which of the following absorbs at the highest frequency?a) 1,3,5-hexatriene, b) 1,3,5,7-octatetraene, c) 1,7-diphenyl-1,3,5-heptatiene, d) 1,6-diphenyl-1,3,5-heptatriene 4) Draw 3,5-difluoroanisole.5) Circle each of the following compounds that is aromatic.6) Which of the following compounds will undergo fredal-Crafts alkylation?a) benzoic acid, b) nitrobenzene, c) aniline, d) toluene 7) Which of the following compounds is most acidic?OOHH2NOOHO2NOOHOOH8) Which of the following gives a secondary alcohol when treated with methyl grignard?a. butyl formate, b) 3-pentanone, c)pentanal, d) methyl butanoate9) Draw N-ethyl-N-propylformamide.10) What does a positive iodoform test tell you is present?Predict the Products.-Show stereochemistry (20 pts., 2 pts. each) 11) OOClOONaOHH2O12)OOOOH3O+H2O13) OOHONaBH4, MeOHH+, H2O, heat14) OI2NaOH15)OBr2aq. NaOH16)OHClH2O17)OONaOHheat18)OO+OONaOCH2CH3H+, H2O, heat19) OCH3O ONaOCH2CH3H3O+20) O+OH3COOOCH3NaOCH2CH3CH3CH2OHFill in the missing parts of this synthesis. (20 pts., 2 pts. each)21)O OOCH2CH3NaOCH2CH3CHCCH2BrABOHOCH2CH2OHTsOHCNaOHCH3IDOOEH3O+F22)OBr2CH3COOHALi2CO3LiBrDMFBNaOCH2CH3O OOCH2CH3H2OCDOOMechanism: (Show and label all steps) (20 pts.)23) OOOCH2CH3+OOO1) NaOEt, EtOH2) H+, H2O, heatSpectroscopy: Give the formula and structure. Circle your final answers. (20 pts.)24)Exam Score1.10 _________ (/20)11-20_________ (/20)21.22 ________ (/20)22 _________ (/20)23 _________ (/20)Total________
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