Package Title: Solomons Test Bank Course Title: Solomons 11e Chapter Number: 16 Question type: Multiple Choice 1) What is the correct IUPAC name for the following compound? O a) 2-Methyl-5-heptanone b) 7-Methyl-4-octanone c) 6-Isopropyl-4-octanone d) Isobutyl propyl ketone e) 1,1-Dimethyl-4-heptanone Answer: B Topic: Nomenclature Section: 16.2 Difficulty Level: Easy 2) What is the correct structure for 7-methyl-4-octanone? O I O II O III O O V IV a) I b) II c) III d) IV e) V Answer: D Topic: Nomenclature Section: 16.2 Difficulty Level: Easy 3) What is the correct IUPAC name for the following compound? O a) 5,5-Dimethyl-2-heptanone b) 5-Ethyl-5,5-dimethyl-Methyl-2-octanone c) 5-Ethyl-5-methyl- 2-hexanone d) 5,5-Dimethyl-2-octanone e) 3,3-Dimethyl-6-heptanone Answer: A Topic: Nomenclature Section: 16.2 Difficulty Level: Easy 4) What is the correct structure for 5,5-dimethyl-2-heptanone? O O I O II O III H O V IV a) I b) II c) III d) IV e) V Answer: B Topic: Nomenclature Section: 16.2 Difficulty Level: Easy 5) A correct name for the following compound would be which of those below? O H a) 2,5-Dimethyl-6-hexanal b) 2,5-Dimethylhexanal c) 2-Aldehydoisohexane d) 3,5-Dimethylheptanone e) 1-Hydro-2,5-dimethyl-1-hexanone Answer: B Topic: Nomenclature Section: 16.2 Difficulty Level: Easy 6) What is the correct structure for 2,5-dimethylhexanal? O O H I II III O O O H H IV V a) I b) II c) III d) IV e) V Answer: D Topic: Nomenclature Section: 16.2 Difficulty Level: Easy 7) What is the correct IUPAC name for the following compound? O a) 5,5-Dimethyl-2-heptanone b) 5-Ethyl-5,5-dimethyl-Methyl-2-octanone c) 5,5-Dimethylcycloheptanone d) 4,4-Dimethylcycloheptanone e) 3,3-Dimethylcycloheptanone Answer: D Topic: Nomenclature Section: 16.2 Difficulty Level: Medium 8) What is the correct IUPAC name for the following compound? O a) 2,4-dimethyl-2-pentenone b) 2,5-dimethylcyclopenten-3-one c) 2,4-dimethylcyclopent-2-enone d) 3,5-dimethylcyclopent-2-enone e) 2-methyl-5-methylcyclopent-2-enone Answer: C Topic: Nomenclature Section: 16.2 Difficulty Level: Medium 9) What is the correct IUPAC name for the following compound? O a) 1,1,2-Trimethyl-1,3-hexenone b) 1,2-Dimethyl-1,3-hexenone c) 2,3-Dimethyl-1,3-heptenone d) 2,3-Dimethyl-2-hepten-4-one e) 5,6-Dimethyl-5-hepten-4-one Answer: D Topic: Nomenclature Section: 16.2 Difficulty Level: Medium 10) What is the correct structure for 2,3-dimethyl-2-hepten-4-one? O I O II O III O IV O V a) I b) II c) III d) IV e) V Answer: E Topic: Nomenclature Section: 16.2 Difficulty Level: Medium O 11) A correct name for C6H5CH2CH2CH is? a) 3-Benzylpropanone b) 3-Phenylpropanal c) 3-Benzylpropanal d) Nonanone e) Nonanal Answer: B Topic: Nomenclature Section: 16.2 Difficulty Level: Medium 12) What is the correct structure for 3-phenylpropanal? O O H O II I III O H O IV V a) I b) II c) III d) IV e) V Answer: E Topic: Nomenclature Section: 16.2 Difficulty Level: Medium 13) What is the correct structure for 5-hydroxy-2-phenyl-3-hexanone? O Ph Ph OH II I Ph OH O III OH OH OH O O H IV V O Ph a) I b) II c) III d) IV e) V Answer: C Topic: Nomenclature Section: 16.2 Difficulty Level: Medium 14) Which is the proper name for the structure shown? CHO Cl CH3 a) 2-Chloro-5-aldehydotoluene b) 6-Chloro-3-aldehydotoluene c) 2-Methyl-4-aldehydochlorobenzene d) 4-Chloro-3-methylbenzaldehyde e) 4-Methyl-5-chloro-2-benzaldehyde Answer: D Topic: Nomenclature Section: 16.2 Difficulty Level: Medium 15) What is the correct structure for 4-chloro-3-methylbenzaldehyde? Ph O O H O H H Cl II I III Cl Cl O H H O Cl IV Cl V a) I b) II c) III d) IV e) V Answer: A Topic: Nomenclature Section: 16.2 Difficulty Level: Medium 16) What is the correct structure for 3-methyl-5-(2,5-dinitrophenyl)pentanal? NO2 O O H O2N NO2 II I O NO2 NO2 O O2N H O2N H NO2 III IV O2N H O NO2 V a) I b) II c) III d) IV e) V Answer: B Topic: Nomenclature Section: 16.2 Difficulty Level: Medium 17) What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal? O O H Cl Cl I II O O H H Cl IV III Cl Cl O H V a) I b) II c) III d) IV e) V Answer: D Topic: Nomenclature Section: 16.2 Difficulty Level: Medium 18) What is the correct structure for 7-bromo-1-octyn-4-one? Br Br Br O O O II I III Br Br IV O V O 10 166) In the total synthesis of the Cecropia juvenile hormone, the following sequence of reactions were used Draw the intermediate and final product formed HO / H+ H CH3Li O ? H+/H2O O Answer: HO O O / H+ H H O CH3Li H+/H2O O O HO H HO CH3 Topic: Reaction Sequence Section: 16.7 Difficulty Level: Hard 167) Complete the following reaction sequence, giving structural details of all significant intermediates O H OsO4 NaHSO3 ? H+ Answer: O OH H OsO4 NaHSO3 H+ O O OH Topic: Reaction Sequence Section: 16.7 96 Difficulty Level: Hard 168) Complete the following reaction sequence, giving structural details of all significantintermediates and the final product O KMnO4, OH-, heat H+ + HO H+ H ? H2 O O Answer: O O + H+ HO KMnO4, OH-, heat H O O O H O O H+ O O HO H2O O OH Topic: Reaction Sequence Section: 16.7 Difficulty Level: Hard 169) Complete the following reaction sequence, giving structural details of all significant intermediates X, Y, and final product Z CH3 KMnO4, OH-, heat H3O+ COOH X X SOCl2 COCl Y Y LiAlH(O-t-Bu)3 ether, -78 oC H2O Z CHO Z Answer: Topic: Reaction Sequence Section: 16.4 Difficulty Level: Hard 170) Complete the following reaction sequence, giving structural details of all significant intermediates 97 i Br2, hν ii Mg, CH3CH2CN iii H3O+ iv NaBH4 ? Answer: O NaBH4 Br i Mg, CH CH CN Br2, hν HO ii H3O+ Topic: Reaction Sequence Section: 16.5 Difficulty Level: Hard 171) Complete the following reaction sequence, giving structural details of all significant intermediates i O3 i EtMgBr ? + ii.Zn, CH3CO2H ii H3O , heat O O i EtMgBr ii H3O+, heat i O3 ii.Zn, CH3CO2H HO O O Answer: Topic: Reaction Sequence Section: 16.5 Difficulty Level: Hard 172) Complete the following reaction sequence, giving structural details of all significant intermediates and the final product Br2 Mg C6H5CHO H2Cr2O4 Benzene ? FeCl3 acetone ether H3O+ OH Br MgBr Answer: Topic: Reaction Sequence Section: 16.5 Difficulty Level: Hard 98 O 173) Complete the following reaction sequence, giving structural details of all significant intermediates and the final product Answer: Topic: Reaction Sequence Section: 16.5 and 16.12 Difficulty Level: Hard Question type: Essay 174) Aldehydes are more reactive than ketones towards nucleophilic substitution because of both steric and electronic factors Briefly explain a) Steric reasons: _ b) Electronic reasons: _ Answer: a) aldehydes have a small hydrogen substituent on one side, so less steric crowding than ketones with alkyl groups either side of the carbonyl carbon b) aldehydes have only one electron-releasing group to partly neutralize/stabilize the partial positive charge at the carbonyl carbon while ketones have two Topic: Relative Reactivity Section: 16.6 Difficulty Level: Medium Question type: fill-in-the-blank 175) A compound with an OH and OR group attached to the same carbon is known as a(n) _ Answer: hemiacetal Topic: Hemiacetals Section: 16.7 Difficulty Level: Easy 99 176) A compound with two OH groups attached to the same carbon is known as a(n) _ Answer: hydrate or gem-diol Topic: Hydrates Section: 16.7 Difficulty Level: Easy 177) A compound with two OR groups attached to the same carbon is known as a(n) _ Answer: acetal Topic: Acetals Section: 16.7 Difficulty Level: Easy 178) A compound with an OH and CN group attached to the same carbon is known as a(n) _ Answer: cyanohydrin Topic: Cyanohydrins Section: 16.9 Difficulty Level: Easy 179) A compound containing a C=N double bond is known as a(n) _ Answer: imine Topic: Imines Section: 16.8 Difficulty Level: Easy 180) 2,4-DNP is a reagent frequently used for functional group tests; it detects the presence of _ Answer: aldehydes and ketones Topic: Functional Group Tests Section: 16.8 Difficulty Level: Easy 100 181) Oximes are formed when aldehydes and ketones react with _ Answer:hydroxylamine, NH2OH Topic: Functional Group Tests Section: 16.8 Difficulty Level: Easy 182) The reaction between a phosphorus ylide and an aldehyde or ketone is called the _ reaction Answer: Wittig Topic: Wittig Reaction Section: 16.10 Difficulty Level: Easy 183) The driving force for the Wittig reaction is the formation of the very strong _ bond in _ Answer: P-O bond; triphenylphosphine oxide Topic: Wittig Reaction Section: 16.10 Difficulty Level: Easy 184) The conversion of a trans epoxide to a cis alkene using triphenylphosphine is an example of a _ reaction Answer: stereospecific Topic: General Section: 16.10 Difficulty Level: Hard 185) The conversion of a cis epoxide to a trans alkene using triphenylphosphine is an example of a _ reaction Answer: stereospecific Topic: General Section: 16.10 101 Difficulty Level: Hard Question type: Molecular Drawing 186) Draw a complete mechanism, using arrow convention to indicate electron movement, for the following transformation: Answer: H+ O O H H N H N H HO N ~H H2O + N H -H2O -H+ N 102 N Topic: Mechanisms Section: 16.8 Difficulty Level: Medium 187) Draw a complete mechanism, using arrow convention to indicate electron movement,for the following transformation: O H H H3C + PPh3 + CH3 H H H3 C Ph3P O CH3 Answer: O H3C O H H3C + O PPh3 H H PPh3 H3C CH3 H H H O PPh3 H PPh3 rotation 180o as shown CH3 H CH3 H + H3C H3C H3C Ph3P O CH3 H Topic: Mechanisms Section: 16.10 Difficulty Level: Hard 188) Draw a complete mechanism, using arrow convention to indicate electron movement, for the following transformation: O H H3 C H H3C + H PPh3 + CH3 H Answer: 103 CH3 Ph3P O O H3C O H H3C H + H O PPh3 CH3 H PPh3 H H3C CH3 O PPh3 H3C PPh3 rotation 180o as shown CH3 CH3 H CH3 H + H H Ph3P O CH3 H Topic: Mechanisms Section: 16.10 Difficulty Level: Hard Question type: fill-in-the-blank 189) The Tollens test, used in conjunction with 2,4-DNP, can distinguish between _ and _ Answer: aldehydes and ketones Topic: Functional Group Tests Section: 16.13 Difficulty Level: Easy Question type: Essay 190) What reagent would help you distinguish between acetophenone and 2methylbenzaldehyde? Answer: Tollen’s Reagent Topic: Functional Group Tests Section: 16.13 Difficulty Level: Easy 191) Explain clearly how you might use 1H NMR to distinguish between 2-phenylacetaldehyde and acetophenone 104 Answer: A quick inspection of 1H NMR of the two substances would allow easy identification and distinction between them: the expected 1H NMR spectra of the two substances are described below 2-Phenylacetaldehyde Acetophenone and C6H5COCH3 C6H5CH2CHO signals signals approximate δ ppm approximateδ ppm singlet (-CH3) 2.0 doublet (-CH2-) 2.5 multiplet (C6H5) 7.2 multiplet (C6H5) triplet(-CHO) Topic: Spectroscopy Section: 16.14 Difficulty Level: Medium 192) Propose a structure that fits the following spectroscopic data: C5H10O IR: 1720 cm−1 H NMR: 1.9δ (triplet, 3H), 1.7δ (sextet, 2H), 2.1δ (singlet, 3H), 2.4δ (triplet, 2H) O Answer: CH3CH2CH2CCH3 Topic: Spectroscopy Section: 16.14 Difficulty Level: Medium 193) Propose a structure that fits the following spectroscopic data: C5H10O IR: 1720 cm−1 H NMR: 1.1δ (triplet, 3H), 2.4δ (quartet, 2H) Answer: O Topic: Spectroscopy Section: 16.14 105 Difficulty Level: Medium 194) Propose a structure that fits the following spectroscopic data: C9H10O IR: 1680 cm−1 H NMR: 1.25δ (triplet, 3H), 3.0δ (quartet, 2H), 7-8δ (complexmultiplet, 5H) O Answer: Topic: Spectroscopy Section: 16.14 Difficulty Level: Medium 195) Propose a structure that fits the following spectroscopic data: C7H6O IR: 1703 cm−1 H NMR: 7-8δ (complexmultiplet, 5H), 10.0δ (singlet, 1H) O H Answer: Topic: Spectroscopy Section: 16.14 Difficulty Level: Medium 196) Propose a structure that fits the following spectroscopic data: C3H6O IR: 1730 cm−1 106 H NMR: 1.1δ (triplet, 3H), 2.5δ (doubletofquartets, 2H), 9.8δ (doublet, 1H) H Answer: O Topic: Spectroscopy Section: 16.14 Difficulty Level: Medium 197) Propose a structure that fits the following spectroscopic data: C5H10O IR: 1716 cm−1 Broadband decoupled 13C NMR: 7.93, 35.50, 212.07δ DEPT Experiments show: signal at 7.93 δ as CH3 and signal at 35.50 δ as CH2 Answer: O Topic: Spectroscopy Section: 16.14 Difficulty Level: Medium 198) Propose a structure that fits the following spectroscopic data: C5H10O IR: 1717 cm−1 Broadband decoupled 13C NMR: 13.70, 17.41, 29.78, 45.71, 208.93δ DEPT Experiments show: signals at 13.70, 29.78 δ as CH3 and signals at 17.41, 45.71 δ as CH2 O Answer: CH3CH2CH2CCH3 107 Topic: Spectroscopy Section: 16.14 Difficulty Level: Medium 199) Propose a structure that fits the following spectroscopic data: C4H8O IR: 1728 cm−1 Broadband decoupled 13C NMR: 13.71, 15.69, 45.82, 202.80δ DEPT Experiments show: signal at 13.71 δ as CH3 and signals at 15.69, 45.82 δ as CH2 O Answer: H Topic: Spectroscopy Section: 16.14 Difficulty Level: Medium 200) Propose a structure that fits the following spectroscopic data: C6H12O IR: 1708 cm−1 Broadband decoupled 13C NMR: 24.61, 26.42, 44.31, 213.81δ DEPT Experiments show: signals at 24.61, 26.42 δ as CH3 Answer: O Topic: Spectroscopy Section: 16.14 Difficulty Level: Medium 108 201) Propose a structure that fits the following spectroscopic data: C4H8O IR: 1737 cm−1 Broadband decoupled 13C NMR: 15.48, 41.07, 204.86δ DEPT Experiments show: signal at 41.07 δ as CH and signal at 15.48 δ as CH3 H Answer: O Topic: Spectroscopy Section: 16.14 Difficulty Level: Medium 202) Propose a structure that fits the following spectroscopic data: C5H10O IR: 1728 cm−1 Broadband decoupled 13C NMR: 22.59, 23.57, 52.66, 202.71 δ DEPT Experiments show: signal at 23.57 δ as CH, signal at 22.59 δ as CH3, and signal at 52.66 δ as CH2 O Answer: H Topic: Spectroscopy Section: 16.14 Difficulty Level: Medium 203) Acetaldehyde is reacted with excess methanol in acid The product was isolated and gave the following 1H NMR spectroscopic data: 1.3 δ (doublet, 3H) 3.4 δ (singlet, 6H) 109 4.6 δ (quartet, 1H) Propose a structure consistent with this information Answer: O O Topic: Spectroscopy Section: 16.14 Difficulty Level: Medium 110