Posted: October 30th, 2023

East Los Angeles College-CHEM 211-Chapters 17 and 18 Organic Chemistry Summer 2015

Name_______________________Date_______________________Chapters 17 and 18Organic ChemistrySummer 2015You must show work for all calculationsThis take-home test is open book! You may also work together.1) Which of the following statements about benzene is true?a) Benzene is a saturated hydrocarbon.b) Benzene undergoes addition reactions.c) Benzene has five degrees of unsaturation.d) Benzene undergoes substitution reactions.2) Which of the following statements about the structure of benzene is not true?a) Benzene is planar.b) Benzene has three short double bonds alternating with three longer single bonds.c) The electrons in the pi bonds are delocalized around the ring.d) Benzene has six pi electrons.3) What orbitals are used to form the bond indicated in the following molecule?Csp2 Csp2Csp2 C2pC2p C2pCsp3 Csp34) What is the IUPAC name of the following compound?a)b)c)d)a)b)c)d)3,6-Dichloroaniline2,5-Dichloroaniline2,5-Dichloroaminobenzene2,5-Dichloroanisole5) What is the IUPAC name of the following compound?a)b)c)d)Nitro-5-carboxychlorobenzeneChloro-4-carboxynitrobenzeneChloro-1-nitro-4-benzoic acid3-Chloro-4-nitrobenzoic acidPage 16) What is the IUPAC name of the following compound?a)b)c)d)1-Chloro-4-ethyl-3-propylbenzene1-Chloro-4-ethyl-5-propylbenzene4-Chloro-1-ethyl-2-propylbenzene4-Chloro-2-propyltoluene7) What is the IUPAC name of the following compound?a)b)c)d)3-Bromo-1-chloro-4-toluene2-Bromo-4-chlorotoluene4-Chloro-2-bromo-1-toluene2-Bromo-4-chloroanisole8) What is the correct assignment of the names of the following substituted benzenes?a)b)c)d)I = Phenol; II = anisole; III = toluene.I = Benzaldehyde; II = phenol; III = anisole.I = Benzaldehyde; II = phenol; III = toluene.I = Phenol; II = anisole; III = styrene.9) What is the correct assignment of the names of the following substituted benzenes?a)b)c)d)I = Styrene; II = aniline; III = anisole.I = Toluene; II = anisole; III = styrene.I = Styrene; II = anisole; III = phenol.I = Toluene; II = aniline; III = anisole.10) How many 13CNMR signals does the following compound exhibit?a)b)c)d)4568Page 211) What is the structure of a compound of molecular formula C10H14O2 that shows a strong IR absorption at 31502850 cm-1 and gives the following 1H NMR absorptions: 1.4 (triplet, 6H); 4.0 (quartet, 4H); and 6.8 (singlet, 4H)ppm.a) Ib) IIc) IIId) IV12) What is the correct assignment of the number of signals in the 13C NMR spectra of the followingdisubstituted benzene derivatives?a) I = 3 signals; II = 3 signals; III = 2 signals.b) I = 3 signals; II = 4 signals; III = 2 signals.c) I = 6 signals; II = 6 signals; III = 6 signals.d) I = 3 signals; II = 4 signals; III = 3 signals.13) What is the correct assignment of the names of the following aromatic heterocycles?a) I = pyridine; II = pyrimidine; III = furan.b) I = pyrimidine; II =pyrrole; III = furan.c) I = pyridine; II = pyrrole; III = furan.d) I = pyrimidine; II = pyrrole; III = tetrahydrofuran.14) What is the correct assignment of the names of the following fused aromatic compounds?a)b)I = naphthalene; II = anthracene; III = phenanthrene.I = naphthalene; II = phenanthrene; III = anthracene.Page 3c)d)I = naphthalene; II = phenanthrene; III = benzo[a]pyrene.I = anthracene; II = naphthalene; III = phenanthrene.15) Which of the following heterocycles is not aromatic?a) Ib) IIc) IIId) IV16) Which of the following ions is aromatic?a) Ib) IIc) IIId) IV17) Which of the following molecules has the most acidic hydrogen atoms?a) Ib) IIc) IIId) IV18) Rank the following compounds in order of decreasing acidity, starting with the most acidic.a) I > II > IIIb) III > II > Ic) III > I > IId) I > III > II19) Which of the following ions is aromatic?Page 4a)b)c)d)Only I and IIOnly II and IIIOnly III and IVOnly II and IV20) Which of the following statements about the molecular orbital (MO) theory is true?a) When two p orbitals of similar phase overlap side-by-side, a * antibonding molecular orbital isformed.b) When two p orbitals of opposite phase overlap side-by-side, a bonding molecular orbital is formed.c) A bonding molecular orbital is higher in energy than the two atomic p orbitals from which it isformed.d) A * antibonding molecular orbital is higher in energy than the two atomic p orbitals from which it isformed.21) What orbitals are used to form the indicated bond?a) sp3b) sp2c) pd) sp3 and sp222) What orbitals are used to form the indicated bond?sp3sp2psp3 and sp223) What is the name of the following compound?a)b)c)d)a) 2,6-dimethylbenzeneb) 5-methyltoluenec) anisoled) 1,3-dimethylbenzene24) What is the name of the following compound?a)b)c)meta-bromophenolpara-hydroxybenzene3-bromoanisolePage 5d)6-methoxy-2-bromobenzene25) What is the correct structure for aniline?a) Ib) IIc) IIId) IV26) . What is the correct structure for anisole?a) Ib) IIc) IIId) IV27) What is the correct structure for toluene?a) Ib) IIc) IIId) IV28) What is the correct structure for 1-bromo-2,4-dimethoxybenzene?a) Ib) IIc) IIId) IV29) Where do the protons in benzene appear in the 1H NMR spectrum?a) Around 1600 cm-1Page 6b)c)d)Around 120 ppmAround 0 ppmAround 7 ppm30) How many different proton signals would the following compound show in its 1H NMR spectrum?a) 1b) 3c) 5d) 631) What compound is consistent with the following 1H NMR spectrum?a) phenolb) anisolec) 4-bromoanisoled) 4-bromotoluene32) What is the correct structure for para-bromotoluene?a)b)c)d)IIIIIIIV33) . Which of the following compounds is not aromatic?Page 7a)b)c)d)IIIIIIIV34) Which of the following compounds is not aromatic?a) Ib) IIc) IIId) IV35) Which of the following compounds is aromatic?a) Ib) IIc) IIId) IV36) Which of the following compounds is aromatic?a) Ib) IIc) IIId) IV37) Why is the following compound not aromatic?a)b)c)d)It has 4n pi electrons.It is not cyclic.It has 4n+2 pi electrons.The electron system is not continuous.Page 838) Why is the following compound not aromatic?a)b)c)d)39)It has 4n electrons.It is not cyclic.It has 4n+2 electrons.The electron system is not continuous.What is the first step in the general mechanism for electrophilic aromatic substitution?a) Protonation of the aromatic ringb) Deprotonation of the aromatic ringc) Addition of the electrophile to the aromatic ringd) Loss of the electrophile from the aromatic ring40) . What is the driving force for losing a proton as the last step in electrophilic aromaticsubstitution?A) To neutralize the base that is present C) To make the ring more reactiveB)41)42) .43) .To make room for the electrophileD) To rearomatize the ring systemWhat is the electrophile in aromatic nitration?A) NO+ B) NO2+ C) NO3+ D) NO2HWhat is the electrophile in aromatic sulfonation?A) H2SO3 B) H2SO4 C) SO3+ D) HSO3+Why is sulfuric acid used in aromatic nitration?A) To keep the reaction from getting too basicB)To form the active electrophile NO2+C)To protonate the aromatic ringD) To keep the reaction from getting too acidic44)What is the electrophile in the Friedel-Crafts alkylation reaction with tert-butylchloride?A) the tert-butyl cationB)a complex of tert-butylchloride and aluminum chlorideC)a protonD) aluminum chloridePage 945) .46) .Which of the following halides will not work as an electrophile in a Friedel-Craftsalkylation reaction?A) I B) II C) III D) IVWhat are the two effects that have to be considered to determine the influence asubstituent will have on electrophilic aromatic substitution?A) Steric and electronicC) Inductive and resonanceB)47) .48) .Inductive and stericD) Resonance and electronicWhy is the nitro group a meta director?A) Because it is sterically very large.B)Because it adds electron density to the meta position, thus activating it.C)Because it stabilizes the intermediate cation.D) Because it removes more electron density from the ortho and para positions thanthe meta position, thus deactivating the meta position less.What is a major problem with Friedel-Crafts alkylation?A) It requires high temperatures.B)The conditions are too acidic.C)The starting material is frequently over-alkylated.D) The products coordinate with the aluminum chloride.49) .Which of the following statements about the mechanism of electrophilic aromaticsubstitution is not true?A) All electrophilic aromatic substitution reactions occur via a two-step mechanism.B)The transition state of the first step is lower in energy.C)The first step is the rate-determining step.D) The second step is the fast step.Page 1050)What will be the site that leads to the major mono substitution product for anelectrophilic aromatic substitution reaction of the following compound?51) .A) I B) II C) III D) IVWhat is the major organic product obtained from the following reaction?52) .A) I B) II C) III D) IVWhat is the major organic product obtained from the following reaction?A) I53) .B) IIC) IIID) IVWhat is the major organic product obtained from the following reaction?Page 11A) IB) IIC) IIID) IV54) .What is the major organic product obtained from the following reaction?55)A) I B) II C) III D) IVWhat is the major organic product obtained from the following reaction?56) .A) I B) II C) III D) IVWhat is the major organic product obtained from the following reaction?A) IB) IIC) IIID) IVPage 1257) .What is the major organic product obtained from the following reaction?58) .A) I B) II C) III D) IVWhat is the major organic product obtained from the following reaction?59) .60) .61) .62) .63) .A) I B) II C) III D) IVWhich of the following substituents are activators in electrophilic aromatic substitution?A) CH3O B) Cl C) NO2 D) HSO3Which of the following substituents are deactivators in electrophilic aromaticsubstitution?A) HO B) CH3NH C) CH3O D) (CH3)3N+Which of the following substituents is an ortho, para director?A) CHO B) COOH C) NHCOR D) CNWhich of the following substituents is a meta director?A) N(CH3)2 B) OCH3 C) NHCOCH3 D) SO3HWhat is (are) the product(s) of the following reaction?A) Only IB) Only IIC) Only IIID) Only I and IIIPage 1364) .What is (are) the product(s) of the following reaction?A) Only IB) Only IIC) Only IIID) Only I and II65) . Rank the following compounds in order of increasing reactivity in electrophilic aromaticsubstitution.66) .67) .A)I < II < III < IVC)III < IV < I < IIB)II < I < IV < IIID) II < I < III < IVRank the following compounds in order of decreasing reactivity in electrophilicaromatic substitution.A) II > IV > I > IIIC)B)D) IV > I > II > IIIII > III > IV > IIV > II > I > IIIRank the following activating groups in order of decreasing strength of activation,listing the most activating first.A) IV > II > III > IC)III > IV > II > IPage 14B)68) .69) .II > III > IV > ID) II > IV > III > IRank the following deactivating groups in order of increasing deactivating strength,listing the least deactivating first.A) I < II < III < IVC)B)D) IV < III < I < IIII < III < IV < III < I < III < IVWhat are the product(s) of the following reaction?A) Only I B) Only II C) Only I and II D) Only III70) . What are the product(s) of the following reaction?71) .A) Only I and II B) Only I and III C) Only II and III D) Only IVHow can polyalkylation be minimized in Friedel-Crafts alkylation?A) Use a large excess of alkyl halide relative to the aromatic compound.B)Use a large excess of benzene relative to the alkyl halide.C)Use an alkyl halide without a Lewis acid catalyst.D) Use a large excess of the Lewis acid catalyst.Page 1572) .What is the major product of the following reaction?73) .A) I B) II C) III D) IVWhat is (are) the product(s) of the following reaction?74) .A) Only I B) Only II C) Only III D) Only I and IIWhat are the two distinct pathways for nucleophilic aromatic substitution?A) Addition-substitution and substitution-additionB)Addition-elimination and elimination-additionC)Addition-addition and elimination-eliminationD) Elimination-substitution and substitution-elimination75) .76) .77) .78) .What is the reactive intermediate formed in the addition-elimination mechanism ofnucleophilic aromatic substitution?A) Carbocation B) Radical C) Benzyne D) CarbanionWhat is the reactive intermediate formed in the elimination-addition mechanism ofnucleophilic aromatic substitution?A) Carbocation B) Radical C) Benzyne D) CarbanionWhich of the following statements about nucleophilic aromatic substitution is not true?A) Increasing the electronegativity of the halogen increases the reactivity of the arylhalide.B) Increasing the number of electron-withdrawing groups increases the reactivity ofthe aryl halide.C) Electron-withdrawing groups stabilize the intermediate carbanion, and lower theenergy of the transition state.D) When a nitro group is located meta to the halogen, the negative charge of theintermediate carbanion can be delocalized onto the NO2 group, thus stabilizing it.Which of the following statements about nucleophilic aromatic substitution is true?A) For the addition-elimination pathway, the nucleophile may become attached eitherPage 16at the site bearing the leaving group or at the site bearing the ortho hydrogen atom.For the elimination-addition pathway, the nucleophile becomes attached only at thesite bearing the leaving group.C) The elimination-addition mechanism is not as common as the addition-eliminationmechanism.D) In the addition-elimination mechanism, the aromatic ring first accepts a pair ofelectrons from a nucleophile to form a cationic intermediate.B)Page 1779) .Rank the following compounds in order of increasing reactivity in nucleophilic aromaticsubstitution.80)A) III < II < I B) I < II < III C) III < I < II D) I < III < IIWhat is the major product of the following reaction?81) .A) I B) II C) III D) IVWhich aryl fluoride reacts the fastest with NaOH?82) .83) .A) I B) II C) III D) IVIn addition to the product shown, what other product is formed in the followingreaction?A) I B) II C) III D) IVWhich set of reagents would most likely bring about the following transformation?A) Br2 and FeBr3B) NBS and lightC) Br2 in CCl4Page 18D) NaBr and H2O84) .What is the product of the following sequence of reactions?A) I85) .C) IIID) IVWhat is the product of the following reaction?A) I86) .B) IIB) IIC) IIID) IVWhat is the product of the following reaction?A) IB) IIC) IIID) None of the abovePage 1987) .What is the best choice of reagent to bring about the following transformation?A) [1] LiAlH4; [2] H2O88) .D) H2, Pd-CWhat is the best choice of reagent to bring about the following transformation?A) [1] LiAlH4; [2]H2O89) .B) Zn (Hg), HCl C) NH3, NaOHB) Zn (Hg), HCl C) NH3, NaOHWhat is the product of the following reaction?A) IB) IIC) IIID) IVPage 20D) H2, Pd-C

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