Practice Test Answer Key
Practice Test Answer Key CHM 211 - 003
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This 28 page Study Guide was uploaded by Alexandra Borog on Monday January 25, 2016. The Study Guide belongs to CHM 211 - 003 at University of North Carolina - Wilmington taught by Paulo F Almeida in Fall 2015. Since its upload, it has received 96 views. For similar materials see LEC:Organic Chemistry (must register for LAB) in Chemistry at University of North Carolina - Wilmington.
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Date Created: 01/25/16
Organic Chemistry CHM 211 NAME Test 2 Fall 2014 1 Which ONE of the statements below is correct OH QH QH OH 3 NH2 NH2 a I and II are enantiomers b I and II are the same compound I and III are enantiomers d I and III are diastereomers 2 Which ONE of the statements below is correct 0 m CH3 H30 CH3 a I is chiral II is meso c II and IV are chiral 1 III is meso 3 Menthol has an optical rotation ocD of 490 rotation of 49O CH3 CH3 9H3 HO K Ho Ho menthol 091D 490 a b 0 H3Ch39 CH3 0 pro Choose the compound below that has an optical H06 9H3 0 4 Which E of the following substituents has the highest priority according to the Cahn Ingold Prelog rules system used for priority in RS determination a d 5 5 The correct name for the compound shown below is a 2R3S2 bromo3chloropentane 253R2 bromo3chloropentane c 2R3R2bromo3chloropentane d 253S2bromo3chloropentane 6 Classify the type of reaction below 0 H20 gt OH HCI a Elimination Substitution c Rearrangement 1 Addition 7 In the reaction below which of the atoms indicated by arrows is the nucleophilic atom Helpful Hint try drawing the mechanistic curved arrows rst O H W l i e H C H gt Cl Eff C H30 H H H b 8 The reaction between dihydrofolate DHF and NADPH to yield tetrahydrofolate THF and NADP shown in the figure below is one of the most important oxidationreduction reactions in biochemistry However in the figure shown one of the arrows was drawn incorrectly Which arrow is incorrect H O NHR NH H 2 O I OC N HN IIIIIIquot H NR1 H2N N DHF NADPH THF NADP 9 Which of the following mechanisms is correct H H2 H2 0 c H N C CH3 gt C CH3 HBr Br H I I H H H H H 2 2 c c C CH gt C CH HBr 3 3 Br H I I H H H I g2 g2 CH3 gt CH3 HBr Br H I I H H Q H d C CHs a BrC CHs H Br H I I H H 10 The following are four free energy profiles Which of these reactions has the most favorable AG has the largest equilibrium constant Keq In ifin 5 EL quoth air E if quot Hr 5 Friml l al I r g a f 5 is r uni If s Hquot I TL If r r a a h i 39 I Fr a w a 4 39 I 11 In the mechanism of lactate dehydrogenase which arrow is incorrect G e 2 O O O O lt Sic CH3 lt c 0 NH2 7 No I R1 12 Which is a major product in the following allvlic bromination reaction O NBS NBS N Br hV O a i b c j 13 When 2chlorobutane is treated with magnesium metal a Grignard reagent is produced Which of the following is the best representation of the Grignard reagent CI A Mg 7 ether lt9 lt9 9 e 14 Which one of the following radicals is most stable H a39 c k d M H H H H H 15 Which one of the following transformations is an oxidation 0 B CI 0 r a gtlt H OH 0 c A d gt gt OH OH Br OH 16 Which is the worst substrate for the SNl reaction 17 Which solvent would give the best rate for the following reaction 3 9 Na CzN N Br gt NaBr solvent 0 if 0 O S a HBCJKOH b H H C H3Cth Hsc CH3 me ano acetic acid water DMSO 18 Which is the strongest nucleophile VS 86 SH b d Jam 9 19 Which alkene is not a possible product in the E1 elimination 1966 20 An alkyl iodide undergoes substitution by SNl when it is heated in water The IR and MS spectra of the product are shown below What is the major product IIEH39ltl39H391L39lI OH 0 o MW136 MW136 MW136 MW134 HSHlJ EESS BC 3 quotE E 50 5 m E E 40 3911 Di 2C C39 Illlllllllllililllllllilillllllllllllilllill1lilllllllriilllllllllilillllllliiIillllliilllllllllllllilill 25 5D 75 lCICI 125 mfz Writein questions 21 4 pts Using the skeletal template below draw the meso form of a molecule with a molecular formula of C4H8F2 Be sure to indicate stereochemistry using wedge and dash notation HHH F F Both uorine atoms must be either wedged or dashed 22 3 pts Add three curved arrows to the following reaction to obtain its mechanism 9 S M 0230 ltI W CI gt 039 CI39 23 4 pts Draw the mechanism of the reaction below using curved arrows Draw the structures of the products ea 6 CH3 H CH3 H H Na gCH3 CH3 H a I CH3 H H CH3 H30 CI HBC H HQCH3 H H H CH3 NaCI 24 9 pts When the following alkyl bromide is reacted with water it undergoes both a substitution reaction by SNl mechanism and an elimination reaction by El mechanism to form a mixture of products as shown below a Using curved arrows show the SNl mechanism for the formation of the substitution product Include all intermediates if any H gr H O H H OH H20 gt H 043 2C ltCH3 H H l HIOIH T H Hp COO H H C H H20 9 CH3 Br H 9 Br b Using curved arrows show the El mechanism for the formation of the elimination product Include all intermediates if any Organic Chemistry CHM 211 NAME Test 1 Fall 2014 1 Which of the following statements about oxygen is NOT true a Oxygen has the electron configuration 1s2 2s2 2p4 Q Oxygen has four valence electrons c Oxygen forms two bonds to achieve a full octet 1 Oxygen typically gains electrons to achieve a noble gas configuration Ne 2 Which of the following Lewis structures is correct b c d HoH Hue IHoH csce 939 a CH3 CH3 CH3 3 Which of the following Lewis structures is NOT correct 39 39 b d O H C CH3 H C 0 H l 39Br IH HC C 0 Cf C CC N3 H I H CC H H 39 H C N H I H H H 4 How many sp3 hybridized carbon atoms are present in a molecule of Naproxen 0quot gr t 5 Which of the following representations of orbital overlap would best illustrate the 0 H bond in the molecule of Naproxen a b 9 off d 00 6 Which compound is NOT a Lewis base a EH3 c 0 d 0 H C N CH 3 3 N 3 7 Which reaction below will proceed largely to products the equilibrium lies to the right 0 0 6 II a HCN H3C C O CN H3C C OH pKa 93 pKa 48 9 e b CH30HZOH CN CH3CH20 HCN pKa 160 pKa 93 e A e c HCECH 0H HCEC H20 pKa 25 pKa 157 0 ll 9 II we ch C CH3 NHZ NH3 pKa 193 pKa 35 8 What are the formal charges on the atoms indicated by the arrows CH3 I oo P1 1 H3C IID H2 c POC l d P 1C0 CH3 9 Which of the following does NOT have a net dipole moment u 0 Ir Ir Ill 0 a H C Br Br C Br c H C CI d g I I I H H H Br CI 10 Which structure below has an amide functional group a bJTKGDJIL H 11 The following arrows are supposed to indicate the change from one resonance form to another But one of the arrows is wrong to indicate resonance Which one is wrong CL 0 a C my T H c c o chG 393 H b 0 CH3 12 What type of hydrogen atom is explicitly shown below H s r B a primary 1 secondary 2 c tertiary 3 d quaternary 4 13 What is the name of the alkyl group substituent shown in the structure below a butyl propyl c chloryl d methyl CI 14 Which of the following molecules is consistent with the IR spectrum shown Hint focus on the region from 4000 to 1500 cm39l DD 5D IHHflbl39lll IHHLtllll 39 39 39 39 39 39 39 39 39 39 39 39 39 E l l E HHVEHUHBERIHI I d i OH O a 0H 0 6 onto a M O 15 Which of the following is the correct name for the skeletal structure shown below SI 5chloro7methyl3isopropyloctane 4chloro6ethyl27dimethyloctane 5chloro3ethyl27dimethyloctane b c d 2methyl3ethyl5chloro7methyloctane 16 What is the correct name for the following substituted cyclic alkane a cislbromo3ethylcyclohexane b translethyl3bromocyclohexane c cislethyl3bromocyclohexane trans l bromo3 ethylcyclohexane Br 17 Below is the mass spectrum of a cycloalkane What is the molecular formula based on the molecular ion 13930 HS HLIJ IUE l EU 15H 2 E 3911 EU E m 3 2 4o 3911 CE EU U illlll 1393 ED a C5H24 b C6H10 C6H12 C7H14 39 40 ED TE ED 18 From the following Newman projections choose the one that represents the gauche conformation of butane CH3 H H H H CH3 a II HCH3 CH3 CH3 H CH3 H CH3 H H H CH3 19 Which choice accurately predicts the ring ip of the disubstituted cyclohexane below ring ip m a 0 d 20 Which statement about the relative stabilities of chair 1 and chair 2 is true n Chair 1 is lower in energy Chair 2 is lower in energy c Chair 1 and Chair 2 are equal in energy d There is not enough information to decide which chair is lower in energy Writein Problems 21 4 pts Propose a structure of a chloroalkene with molecular formula C4H7Cl You MUST use skeletal notation to draw the compound CI C39W A M CV q CI Others are possible 22 6 pts Using the chair skeletons below dr the two conformations of cis1bromo2 methylcyclohexane Circle which is most abundant ie most stable lowest energy at equilibrium Draw only the substituents and the hydrogens attached to carbons l and 2 and the corresponding bonds Clearly show the correct orientation axial or equatorial for the bonds originating from carbons l and 2 to receive full credit Note The 13diaxial interaction strain for a bromine substituent is 10 kJmol and for a methyl substituent is 38 kJmol Br CH3 H Br CH3 H H most stable because the larger methyl group is equitorial 23 6 pts Phenol has a relatively low pKa compared to a regular alcohol it loses a proton more easily because the phenolate ion formed shown below is stabilized by resonance There are several more resonance forms in addition to the one shown Write the structure of two of those the other resonance forms and indicate the movement of electrons by using curved arrows 5 59 lt gt O O G 4 o39 4 6 Others are possible 24 4 pts Below is the IR and mass spectrum of an unknown hydrocarbon contains only carbon and hydrogen that contains ONE oxygen Propose a possible structure based upon spectra provided and draw it in the indicated box n W t SE DD TFHHEHETTHHEEIEI I I I E l l E HHVEHUHEEHIqI I d i 100 MSNwUEEI ECJ an 3 Relative Intensity L D Pd 3 Cl Iililll1llllllilill IiIllililiilIIillllillli 10 ED 30 4O 50 60 TD 80 90 100 mz Others are possible Organic Chemistry CHM 211 NAME Test 3 Fall 2014 1 What is the correct IUPAC name for the compound shown below Br AM a cis4bromo5ethy1 2hexene b trans4bromo3methy1 5heptene c trans3bromo2ethy1 4hexene rans4bromo5methy1 2heptene 2 Which of the following has E stereochemistry Br CI H CI H H I H F Br H3C CH3 a b c 3 The compound C8H11C1 has what degree of unsaturation a 2 3 c 4 d 6 4 Rank the following alkenes in order of decreasing stability W N I II a I gt 11 gt 111 b 111 gt 11 gt I I gt 111 gt I d I gt 111 gt 11 H3C H3C 111 5 All four of the alkenes shown below will undergo electrophilic addition upon treatment with HCl Which one will undergo a hydride shi producing a mixture of products p M O M b d 6 Which one of the following shows the correct formation of a carbocation intermediate HgOH Hg I 3 HquotCH3 HCH3 c d 2 8 What is the product of the following reaction 1 BH3 2 H202 OH39HZO a b c CD 9 What is the product of the following hydrogenation reduction 0 H30 CH3 00 H2 gt H3C PdC O OH H3C CH3 H3C CH3 H3C H3C b OH O H3C i I I CH3 H3C CH3 H3C H30 0 d 10 What is the major product formed in the following reaction CI2 7 gt0 H20 CI CI OH OH O CI iquot c 3 11 The MS A and IR B spectra of an unknown compound as shown below What is the structure of the compound Hints 1 In the MS spectrum think about what fragment is lost to decrease the mass from 214 to 171 2 In the IR spectrum think of the peaks that are not there Br 0 Br 0 Br Br 0 o 1 100 80 3 g 60 E E 40 o 214 20 BMW 50 100 150 200 250 mz ill 2 I I I I I I I I I I I I I I I I I I I I I 1000 EDEN 2000 1500 IDDIII EDD 100 IREIJIJEI EI41IIITK WavenumbedcmH 4 12 One of the following compounds is produced as a synthetic intermediate in the following synthesis Which one 0304 H104 H20 0 2 NaHSO3 H SD gt0 I O l quot0 I 0 C 3 b 9 N C I 13 Which of the following reaction conditions will lead to the product shown OH GA o C02 0 OOH a CI mCPBA b l 03 2 211 H30 KMIIO4 H30 d l BH3 THF 2 H202 14 Choose the correct monomer used to synthesize polystyrene shown below 7 2 polystyrene a b d 15 What is the correct IUPAC name for the compound shown below FHB ch csc q H CCI H H a lchloro2methyl3pentyne 5chloro4methyl2pentyne c 1chloro24dimethyl3butyne d 4chloro l 3 dimethyl l butyne 16 What is the product in the following reaction 1 BH3 THF 9 H CEC 2 H202 H20 OH o 0 AA J HOW HJJ6 a b c 17 Which of the following reaction conditions will lead to the product shown CEc gt cc H H a H2 H2 Lindlar catalyst Pdlead acetatequinoline C H2 C d Li NH3 18 Which of the indicated hydrogens would be removed preferentially by the strong base NaNHz bH H Hlt c a gtH O Hlt H NaNH2 H 19 Which arrow is drawn incorrectly 4 9quot RCEC R39 R39 a39 H92SO4239 2 l HgSO4 H Q H HJC H R39 O R39 C C l R HgSO4239 C C R HgSO4239 H30 20 Choose the correct alkyne starting material for the synthesis shown below M2 2Brgt W M b M cV d Writein questions 21 5 pts Draw the complete mechanism for the reaction shown below For full credit draw the structures of the intermediateg s if any and productg s formed and use curved arrows to show the movement of all electrons I O O H Br 3quot Br 22 6 pts Draw the mechanism of the following halogenation reaction using curved arrows Include intermediates if any formed during the process and draw the final product including the correct stereochemistry v CW BrBr M gt x 3 Br Br gtltBr 23 4 pts Provide the structures of compound A and compound B in the synthetic scheme below Draw your structures in the boxes provided Show all relevant stereochemistry for ill credit 0 v Cl oo OH O mCPBA 0 H20 0 O H3O quot oH Compound A Compound B 24 5 pts Starting from alkyne A propose a synthesis of epoxide B Show the reagents and structures of the intermediates Mechanism arrows are NOT necessary Hint This synthesis requires more than one step O A gt gt A B 1 NaNH2 NH3 2 CH3Br mCPBA 39 I Lmdlars cat gt m H2 ethanol CH3 Li NH3 alternate acceptable route mCPBA can be substituted with 1 C12 H20 2 NaOH 1 Circle any conjugated double bonds in the molecules below 0 CCH ltO 2 O 2 Match the IR spectrum to the correct structure below INFRARED SPEC RUM 03 1 LU U 2 E 06 E E 04 I 12 7 I I u n n I I u n Il 4000 3000 moo moo Wauenumber Email MHST Chenilletry Webaook httpNwebbcoknigtgou chemiigtry 6 C o j 3 Predict and brie y explain how UVVis spectroscopy can be used to distinguish between the following pair of isomers which isomer would you expect to have the highest kmax and why H3C CH3 0 CH3 CH3 vs This molecule has more conjugation 4 Which one of the following represents the l4addition product for the reaction shown below i Br Br Br Br Br b c d 5 Write the structures of the diene and dienophile for the following compounds a CO20HzCHa COZCHZCH3 gt J HsCHzCozC COZCHZCH3 b O 0 BC H3O CH3 H3C H30 6 For a diene to undergo a Diels Alder reaction it M a be substituted with electronwithdrawing groups b be able to adopt and strans conformation c be substituted with electrondonating groups be able to adopt an scis conformation 7 For Diels Alder cycloaddition reactions to take place most rapidly and in highest yield the dienophile should be substituted with electronWithdrawing groups b be able to adopt and strans conformation c be substituted with electrondonating groups d be able to adopt an scis conformation
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