CHM 201 Fall 2008 Test 3 Answer Key

CHM 201 Fall 2008 Test 3 Answer Key - OM - PR EME D41 1.C P...

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Unformatted text preview: OM - PR EME D41 1.C P - PR EME D41 1.C OM O rganicChemistryI (CHM201C) The Third In-ClassExamination OM December 2008 5th, 11" ASwer - PR EME D41 1.C print): Name(please D41 1.C OM Signature: COM - PR EME Cane #: ID - PR EME D4 11. Theexamwill beginat 10:10AM andendat 1l:00 AM. PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EME D4 11. COM Directions: (l) Pleasedo not start the test till 10:10AM. Instead,pleasestart bubbling in the for scantron your name, student ID number, andthe consentbubble if you want your posted your I.D. number. grade by to (2) Please accordingly the instructiongiven on it. on recordyour answers the scantron papers attached at that be It is stronglyrecommended the answers workedout on scratch to the endof this examinationandthen transferred the scantron. (3) Periodic Table and Schematic Energy Diagram are provided at the end of this examination. OM - PR EME D41 1.C P - PR EME D41 1.C OM Questions 1.C OM contributor makes the greater contribution to the 1. (4 points). Which resonance resonance hybrid,A or B? - PR EME D41 Ao tl rl OM Il - PR EME D41 1.C \,/ ,r^ - PR EME D4 11. COM from the information determine (a) Af (b) B ) (c) A & B contribute equally (d) cannot given\-/ B - PR EME D4 o 11. A COM 2. (4 points). Which canlosea protonmorereadily,A or B? 11. COM ?r. ED4 11. COM - PR EM ED4 ,/-(a) A ((b) B / (c) A and B lose a proton at the samerate. (d) cannot determinefrom the informltioffiven. ( Diels-Alder reacilon - PR EM ED4 O ll 11. COM - PR EM 3. (4 points). What is the major product of the following Diels-Alder reaction? fn+ o\ ED4 11. COM tl PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM (a) (b) o @ _oe]l' q." /'o H (d) -o OM - PR EME D41 1.C P + - PR EME D41 I OM CHgO (a) - PR EME D41 1.C T Br 1.C OM 4. (4 points). What is the major product of the following Sn2 reaction? (b) I D41 1.C ./\.-\./ OMe COM - PR EME T OMe OM i .-\.-\./ I OMe (c) - PR EME D4 11. o F' COM - PR EME D4 11. in wasmeasured 5. (4 points). The rateof reactionof isopropyliodidewith quinuclidine and nitrobenzene, then the rate of reactionof isopropyliodide with triethylaminewas had solvent. Whichreaction the largerrateconstant? in measured the same quinuclidine ) triethylamine ED4 11. COM iodide isopropyl [*^ - PR EM (b) tiethylamine (c) both rate constantsare about same. 11. COM given. ilterminefrom the information COM 11. ED4 - PR EM EtOH 11. COM o,, - PR EM ED4 from the solvolysis of the following 6. (4 points). What is the major productobtained in compound ethanol? (c) (b) Oo,, O*, Go=, - PR EM ED4 11. COM - PR EM ED4 O*, (d) 11. COM 7. (4 points). Which reacts faster in an El reaction, 3-bromocyclohexene bromocyclohexane? MPRE M ED4 ( (a) 3-bromocyclohexene) PRE MED 411 .CO \pproiihaei@e-rate. (c) both react at the (b) bromocyclohexane (d) cannot determinefrom the information given. OM - PR EME D41 1.C P 1.C OM 8. (4 points).What is the majorproductof thefollowing E2 reaction? + - PR EME D41 --rJ--- CHgO (a) D41 1.C OM cl - PR EME ; '/ - PR EME D41 1.C OM \, 11. I OH - PR EME D4 rffi+ e' \2 COM 9. (4 points).Whatis the majorproductof thefollowing E2rcaction? - PR EME D4 11. COM q**r( ED4 11. COM U 11. COM - PR EM 10. (4 points). Rank the following compoundsin order of decreasingreactivity in anE2 reaction (high reactivity > low reactivity): - PR EM ED4 A r^./CHg t )( t''. CHg c G*' - PR EM ED4 11. COM aY'cHs V,,,. B (b)B>A>C (c)A:B>C (d)c>A>B 11. COM (a)A:C>B - PR EM ED4 ll. (4 points). What is the major product of the following reaction? COM - PR EM ED4 11. COM ,Mon PBr3 o PRE MED 411 .CO MPRE M ED4 11. (").,^.--rr,., MBr OM - PR EME D41 1.C P 11. COM - PR EME D41 1.C OM - PR EME D41 1.C OM - PR EME D41 1.C OM 12. (4 points). What is the major product of the following reaction? 11. COM o A - PR EME D4 13.(4 points).Whatis the majorproductof thefollowing reaction? - PR EME D4 2. H+,H2O 'G,-,' tt' o-oto'h, COM - PR EM ED4 11. COM tu'o--o* ED4 11. L4.(4 points).Whatis the majorproductof the followingreaction? H2CrO4 t COM t - PR EM OH I ED4 11. \-/ COM - PR EM (a) oH - PR EM ED4 11. \-/ ED4 11. COM 15.(4 points).Whatis the majorproductof the following reaction? COM - PR EM X^.- PRE MED 411 .CO MPRE M ED4 11. 9",, HBr,A ,0, x,. (c) BrA (d) -l"J.- OM - PR EME D41 1.C P - PR EME D41 1.C OM 1 6. (8 points). Which diagram shows the ground-state n molecularorbitalsof 1,3butadiene? l 1.C OM 1,3-butadiene ft ll OM 1.C D41 - PR EME rlt4 - v1 - f,h fe fr ft , 1 1 ft trE 1l ,,, tl frh 1l /l oll *, )J- 1l vo JJ- 1l w, ll n1l . 1l ll - PR EME D4 11. COM . f* COM f,h ft *ll ft tl ,,' || f{ v3- - PR EME D4 fr\ - PR EME ft oll 11. f\ w4- (d) D41 (b) (a) - PR EM ED4 11. COM (an 17. (S points). (R)-2-methyloxirane epoxide)reactedin methanol under basic underacidic conditionsto give a product. to conditions give a product. It alsoreacted or isomers, diastereomers, enantiomers? or products identical,or constitutional these Are (R)-2-methyloxirane COM - PR EM ED4 11. COM . cH3oH /,<r" lT'=1', (b) constitutional isomers/ (c) diastereomers (d) enantiomers - PR EM ED4 11. (a) identical COM A is 18.(8 points).Which carbocation morestable, or B? ED4 11. A - PR EM / - PR EM ED4 11. COM L/X PRE MED 411 .CO MPRE M ED4 11. COM (b) B B Y A/ \<A ,N (c) A and B are equally stable (d) cannot determine from the information OM - PR EME D41 1.C P o Diels-Alder reaction 1.C OM + Ao"" ( - PR EME D41 1.C OM does the following Diels-Alder reaction 19. (8 points). How many stereoisomers provide? - PR EME D41 \ (c) 3 (d) 4 - PR EME D41 1.C OM (a) I COM SNl 20. (S points).Doesvinyl bromideundergo andSN24 (c) both SNI and Sr.r PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EME D4 11. COM - PR EME D4 11. (b) SN2only (a) Snl only ...
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