Print Name: Ex le Organic Chemistry II Summer 2014 Test 3 Honor Code: Students must abide by the Tennessee Wesleyan Honor System. You have pledged, on your honor, to conduct yourself with the foremost level of academic integrity. As such, you ‘must sign the certification below: Thereby certify that I have neither given nor received unauthorized aid on this exam. Student SignatureMultiple Choice: (2 points each) 4 1) The correct name for the compound shown below is: wh a a) m-chorophenol _) o-chorophenol__¢) p-chorophenol 4) o-chorobenzyl alcohol ¢) 2-chlorophenyl alcohol » D2) which ofthese is the rate-determining step in the nitration of benzene? a) Protonation of nitric acid by sulfuric acid 'b) Protonation of sulfuric acid by nitric acid ©) Loss of a water molecule by the protonated species to produce the nitronium ion 4) Addition of the nitronium to benzene to produce the arenium ion ©) Loss of a proton by the arenium ion to form nitrobenzene [2 __ 3) What is the correct IUPAC name for the following compound? ° a)2-Methyl-5-heptanone —_b) 7-Methyl-4-octanone __c) 6-Isopropyl-4-octanone d) Isobutyl propyl ketone ) 1,1-Dimethyl-4-heptanone iC E 4) Xylene is the name commonly assigned to: 'a) Hydroxybenzene b) Aminobenzene ©) Dimethylbenzene 4) Ethylbenzene ) Methoxybenzene 5) Which of the following structures contribute(s) to the resonance hybrid of the intermediate formed when bromobenzene undergoes para-chlorination? Bre Q a Hcl Wor Ho I 0 m Vv a)I_ b) I c)I d)IV_e) Allof these choices. iy) 6) Which of the compounds listed below would you expect to have the highest boiling point? (They all have approximately the same molecular weight.) a)Pentane —b)I-Butanol¢)Butanal_—d)I-Fluorobutane —_e)DiethyletherCo 14 cyctopentadiene is unusually acidic for a hydrocarbon. An explanation for this is the following statement. a) The carbon atoms of cyclopentadiene are all sp*-hybridized. b) Cyclopentadiene is aromatic. c) Removal of a proton from cyclopentadiene yields an aromatic anion. 4) Removal of a hydrogen atom from cyclopentadiene yields a highly stable free radical. ) Removal of a hydride ion from cyclopentadiene produces an aromatic cation, 8) Undesired polysubstitution of an aromatic compound is most in the case of: a) Friedel-Crafts alkylation b) Friedel-Crafts acylation ©) Nitration <) Sulfonation ©) Chlorination ely to be encountered A 9) The migratory aptitude for groups attached to a ketone or aldehyde carbonyl during the Baeyer-Villiger oxidation is: a) H>Ph- > 3° alkyl > 2° alkyl > 1° alkyl > methyl b) Ph- > H>3° alkyl>2° alkyl>1° alkyl>methyl ©) 3° alkyl > 2° alkyl > 1° alkyl > methyl>H >Ph- 4) 3° alkyl > 2° alkyl > 1° alkyl > methyl>Ph>H ©) H> 3° alkyl > 2° alkyl > 1° alkyl > methyl>Ph- { 10) Which eyctization(s) should oceur with a decrease in pi-lectron energy? eel re~e™ — [D> * Te ocd Pe, e a)I b)IT c) IM d)IV_e) All of these choices.