CHAPTER 1

CHAPTER 1Multiple ChoiceIdentify the letter of the choice that best completes the statement or answers the question.____ 1. An amine is characterized by what functional group?a. -CO2CH3 d. -CHOb. -NH2 e. -OHc. -CO2H____ 2. Which of the following is an alcohol?a. NaOH d.b. e.c.____ 3. When two alcohols undergo a self condensation, what is formed?a. liquid alcohol d. an aldehydeb. a ketone e. an etherc. an ester____ 4. How many actual double bonds does the benzene ring possess?a. 4 d. 1b. 3 e. 0c. 2____ 5.____ 6.The correct name for the compound given above is which of the following?a. 2-methyl-1-butene d. 3-methyl-2-buteneb. pentene e. 2-ethyl-1-pentenec. 2-ethyl-1-propeneWhat is the correct name for the above compound?a. 2,3-dimethylbutane d. 2,2-dimethylbutaneb. hexane e. isohexanec. 2-methylpentane

____ 7.The compound above is classified as a(n)a. alkane d. ketoneb. carboxylic acid e. alkenec. aldehyde____ 8. Which of the following is a secondary alcohol?a. d. CH3OHb. e. CH3CH2OHc.____ 9.What is the correct name for the above compound?a. 2-methyl-3-butanol d. 3-methyl-2-butanolb. 2-pentanol e. none of thesec. isobutanol____ 10. What results when a secondary alcohol is oxidized?a. a ketone d. an acidb. an amine e. no reactionc. an aldehyde

____ 11. Which statement is incorrect concerning these two molecules with the same formula, C2H6O?I. II.a. compound (II) will more likely be soluble in water than compound (I)b. compound (I) will have a lower boiling point than compound (II)c. hydrogen bonding will be the most likely for compound (II)d. the vapour pressure of compound (II) will be lower than that of compound (I) at a giventemperaturee. compound (I) would be a better solvent____ 12. The general formula for a cycloalkane can be represented by which of the following?a. CnHn c. CnH2nb. CnH2n+2 d. CnH2n-2____ 13.____ 14.The correct name for compound above is which of the following?a. chloropropylbenzene c. 1-chloro-3-phenyl-3-propeneb. 3-phenyl-1-choloropropyne d. 3-chloro-1-phenyl-1-propeneThe correct name for the compound given above is which of the following?a. 3-amino-3-hexanone c. N-propylpropanamideb. ethyl ethanamide d. N-ethylethanamide

____ 15.____ 16.The correct name for the compound given above is which of the following?a. 1,3-cyclopentadiene c. 1,4-cyclopenteneb. 1,4-cyclopentadiene d. 1,3-cyclopentene____ 17.The correct name for the compound given above is which of the following?a. 1-amino-3-ethoxyhexane c. 1-amino-3-methoxycyclohexaneb. 1-methoxy-3-amidecyclohexane d. 1-amino-3-methoxyhexaneThe correct name for the compound given above is which of the following?a. 1-propyl-3-ethyl-4-methylbenzeneb. 4-cyclopropyl-2-ethyl-1-methylbenzenec. p, - methyl, ethylcyclopropylbenzened. 1-propyl-3-ethyl-4-methylcyclohexane

____ 18. The correct structure for 1,4-dicyclopropylcyclohexane is which of the following?a.b.c.d.

____ 19. The correct structure for 1-methyl-2,4,6-trinitrobenzene(TNT) is which of the following?a. c.b. d.____ 20.The correct name for the compound given above is which of the following?a. 2-cycloproproxylcyclobutane c. 2-cyclobutoxycyclopropaneb. cyclobutylpropoxy ether d. cyclopropoxycyclobutane____ 21. Of the five names listed below, four contain deliberate errors. Which is the only name is correct?a. 2-pentanal d. 1,2-dimethylpropanoateb. 2,3-dichloropentane e. n-methylpropanamidec. 3-methylpropanoic acid____ 22. The reaction of CH3CH=CH-CH=CH 2 with excess bromine gives chiefly

a. 1,2-dibromo-3-penteneb. 3,4-dibromo-1-pentenec. 1,4-dibromo-2-pentened. a mixture of the above three compoundse. none of the above three compounds____ 23. The number of isomers of chlorodibromobenzene is which of the following?a. three d. sixb. four e. sevenc. five____ 24. The nitration of benzene with nitric acid is best done in which of the following?a. water d. ethanolb. sulfuric acid e. carbon tetrachloridec. sodium hydroxide____ 25. Considering the following compounds:I II IIIThe order of acid strength isa. I>II>III d. III>II>Ib. II>III>I e. II>I>IIIc. III>I>II____ 26. The formula for methyl ethanoate is which of the following?a. c.b. d.____ 27. The condensed formula of 2,3,4-trimethylpentane is which of the following?

a. c.b. d.____ 28.____ 29.The correct IUPAC name for above compound is which of the following?a. fluorobutanoic acid c. 2-fluoro-2-nitrobutanoic acidb. 3-fluoro-3-nitrobutanoic acid d. 3-fluoro-2-nitropropanoic acidThe correct IUPAC name of the above structure is which of the following?a. 1-bromo-2-butene c. 4-bromo-2-butyneb. 1-bromo-2-butyne d. 4-bromo-1-methyl-1-propyne____ 30. Which of the following compounds contains 10 carbon atoms?a. 2,2,3-trimethylheptane c. 2-methyldecaneb. octane d. 2,3-dimethylheptane____ 31. 1-amino-4,4-difluoro-2-pentanol is the correct name for which of the following compounds?a. c.b. d.____ 32. 2-methyl-4-ethyl-3,3-dicyclopropyl-1-hexene is the correct name for which of the following?

a. c.b. d.____ 33.The correct IUPAC name for the compound above is which of the following?a. 5-ol-2-ethylpentane ether c. 3-propoxypentanalb. 2-ethoxy-5-pentanone d. 4-ethoxypentanal____ 34. Which of the following is the correct name for the compound below?a. benzene-ethanol c. methylbenzenalb. phenylmethanoate` d. phenylmethanol____ 35. Which of the following is the correct name for the structure below?a. trans-4-nonyne c. trans-4-noneneb. cis-5-nonene d. cis-4-nonene____ 36. Which of the following is the correct name for the diagram below?a. propylcyclohexylcyclohexanoate c. dicyclohexanylpropanoateb. 2-cyclohexoxycyclohexylpropanoate d. methylcycloxypropanoate____ 37. Which of the following is the correct IUPAC name for the compound below?

a. 4-phenyl-6-cyclobutylhexanoic acidb. 3-phenyl-6-cyclobutylhexanoic acidc. 3-cyclohexyl-6-cyclobutylhexanoic acidd. 4-cyclohexyl-5-cyclobutylpentanoic acid____ 38. In a chemistry lab test, you are asked to react a solution of bromine with each of the following unknownliquids. Which one decolourizes the bromine solution?a. 2,3-dimethylbutane c. cyclohexeneb. ethanoic acid d. n-methylmethanamide____ 39. Which type of reaction will an alkene not undergo?a. addition d. dehydrationb. polymerization e. hydrationc. oxidation____ 40. Which of the following classes of organic compounds does not contain oxygen?a. aldehydes d. ethersb. amines e. amidesc. amino acids____ 41. The primary product of the following reaction is which of the following?a. c.b. d.

____ 42. The most abundant isomer following the double bromination of benzene by the reactionis which of the these below?a. c.b. d.____ 43. Which group of these compounds tends to be the most reactive?a. alkanes c. alkynesb. alkenes d. aromatics____ 44. The correct synthesis of n-octane would involve which of the following reactions?a. dehydrogenation of 2-octene c. hydrogenation of 3-octeneb. halogenation of 4-octene d. reduction of isooctane____ 45. When excess hydrogen bromide is added to pentyne, the possible product is which of the following?a. 1,1-dibromopentane c. 1,1,2,2-tetrabromopentaneb. 1,2-dibromopentane d. 2,2-dibromopentane____ 46. The primary product of the reaction below which uses excess HBr is which of the following?a. c.b. d.____ 47. Butane and fluorine gas would react by which of the following?

a. addition c. substitutionb. combustion d. single displacement____ 48. The correct IUPAC name for the compound below is which of the following?a. 1,1-diiodo-2-fluoro-3-cycloproplycyclobutaneb. 1-cyclopropyl-2-fluoro-3,3-diiodocyclobutanec. 1,1-diiodo-3-cyclopropyl-4-fluorocyclobutaned. 1-fluoro-2,2-diiodo-4-cyclopropylcyclobutane____ 49. When CH4 is reacted with excess Cl 2(g) in the presence of light, the reaction mixture contains which ofthe following?a. CH3Cl c. CH3Cl, CH2Cl 2, CHCl3b. CH2Cl2 d. CHCl3____ 50. The compound with the highest boiling point will be which of the following?a. CH3Cl c. CH4b. CH Br d. CH F3 3____ 51. The common name for the compound given below is which of the following?a. CFC c. Teflonb. DDT d. PCB____ 52. Name the following compound:a. 2-chloro-6-ethyl-3-methyloctane d. 2-chloro-6-propyl-3-methyloctaneb. 2-chloro-6-ethyl-3-methyldecane e. 2-chloro-6-ethyl-3-methylheptanec. 2-chloro-6-methyl-3-ethyloctane____ 53. Which of the following compounds can exist as geometric isomers?, , ,I II III IV

a. I and IV d. I, II, IVb. II and III e. IV onlyc. II and IV____ 54. The alcohol below is classified as which of the following?a. primary alcohol c. tertiary alcoholb. secondary alcohol d. aromatic alcohol____ 55. Which one of the following compounds is not expected to be completely soluble in water at roomtemperature?a. CH3CH2CH2OH c. CH 3(CH 2) 16CO2Hb. CH3CO2H d. CH3OH____ 56. Esters area. found in some medicines d. found in some types of flavoringsb. often fragrant e. all of the abovec. essential oils in fruits and flower____ 57. As a chemist you are trying to identify an unknown substance. It turns red litmus paper blue, has noeffect on blue litmus paper, and reacts with methanoic acid to form a product which is insoluble in water.This unknown is most likely which of the following?a. d.b. e.c.____ 58. What is the proper name for the structure given below?a. 3-methyl-2-butanone c. 1-ethyl-1-propanoneb. 3-pentanone d. 1,1-dimethyl-1-propanone____ 59. The synthesis sequence shown here is best described as which of the following?

1. 2. 3.a. (1) Dehydration; (2) halogenation; (3) hydrogenationb. (1) Hydrogenation; (2) dehydration; (3) halogenationc. (1) Hydrogenation; (2) halogenation; (3) dehydrationd. (1) Halogenation; (2) hydrogenation; (3) dehydratione. (1) Dehydration; (2) hydrogenation; (3) halogenation____ 60. Which of the reactions shown are reductions?a. (1), (2), and (3) d. (4) onlyb. (1) and (3) only e. (1) and (4) onlyc. (2) and (4) only____ 61. Select the compound with the highest boiling point at standard pressure.a. d.b. e.c.____ 62. As a chemist in an automotive research company, you are asked to make a substitute for ethylene glycol,the major component of antifreeze used in cars. Which of these reactions would you use to provide aproduct that has similar properties?a.

.c.d.Unknown B.P Red LitmusPaperBlue LitmusPaperOdourSolubility inH2OReactionwith anoxidizerI 48°C Turns blue No reaction Fishy smell Yes WeakreactionII 161°C No reaction Slightly red None Yes VigorousreactionIII 38°C No reaction No reaction None No WeakreactionIV 164°C No reaction Turns red Unpleasant, Yes No reactionrancid odour____ 63. A forensic scientist is trying to identify the functional groups in some unknowns. After several tests, sheproduces the above chart. Unknown I is most likely which of the following?a. d.b. e.c.____ 64. A forensic scientist is trying to identify the functional groups in some unknowns. After several tests, sheproduces the above chart. Unknown II is most likely which of the following?a. d.b. e.

c.____ 65. A forensic scientist is trying to identify the functional groups in some unknowns. After several tests, sheproduces the above chart:Unknown III is most likely which of the following?a. d.b. e.c.____ 66. A forensic scientist is trying to identify the functional groups in some unknowns. After several tests, sheproduces the above chart. Unknown IV is most likely which of the following?a. d.b. e.c.____ 67. How many double bonds would be in one of the resonance structure of aromatic napthalene?a. 5 c. 4b. 6 d. 12

____ 68.Which of the following is an oxidation product of the above compound?a. c.b. d.____ 69. In order to determine the identity of an alcohol, a chemist reacts it with excess sulphuric acid, then reactsit with HCl, and then finally with benzene. A gas chromatograph (an analytical test) determines thatisopropylbenzene has been produced. The identity of the alcohol was most likely which of the following?a. c.b. d.____ 71. What is the correct IUPAC name for compound below?____a. 2-ethyl-5-hexanone d. 5-methyl-2-heptanoneb. 5-ethyl-2-hexanone e. 2-heptanonec. 3-methyl-6-heptanone

____ 73. Which one of the following statements is incorrect?a. a primary amine contains the amino group, NH 2b. a secondary amine has a nitrogen which makes three single bondsc. a 3º amine will have a positive charged. a secondary amine can behave as a basee. amines can undergo hydrogen bonding____ 74. Which of the follwing compounds is 4-iodo-6-cyclopropyl-3-hexanone?a. c.b. d.____ 75. In order to prepare the molecule shown below, which organic compounds must a chemist react under theappropriate catalyst/conditions?a.b.c.d.

____ 76. A chemist is able to use a HPLC (analytical test) to distinguish between 2º amines. She receives a sampleof food that has been contaminated by an unknown alkene. She reacts this alkene with HCl. Two molesof this product is then reacted with 1 mole of NH3 to form:The unknown alkene is which of the following?a. c.b. d. 2-octene____ 77. In order to determine the identity of an unknown alcohol 'P', a chemist reacts some of it with a strongoxidizer to produce a product 'Q', which has a pH less than 6.9. Another quantity of 'P' is reacted withHCl, and then with NH3 in a 1:1 mole ratio to make 'R'. 'Q' and 'R' are reacted with H2SO4 to makeand H20. What is the identity of the alcohol?a. c.b. d.____ 78. The product formed by the reaction of CH3CO2H withis properly nameda. N-ethyl-N-methylethanamide c. N,N-diethylmethanamideb. N,N-diethylaminomethane d. N-ethyl-N-methylmethamide____ 79. Amines will not react with which of the following?a. alkyl halides c. Ketonesb. carboxylic acids d. hydrogen chloride____ 80. Which statement below is incorrect?a. the smallest aldehyde has the formula HCOHb. a carbonyl carbon consists of a carbon-oxygen double bondc. in an aldehyde, the carbonyl carbon is always bonded to a hydrogen atomd. Ketones are more soluble in water than alcohols with the equivalent number of carbons____ 81. Which of following chlorine compounds has had a negative influence on Earth's ozone layer?a. chlorofluorocarbons (CFC's)b. hexachlorobenzenec. dichlorodiphenyltrichloroethane (DDT)d. tetrachloromethane (carbon 'tet')

____ 82. The correct name for the compound given below is which of the following?a. 1-phenyl-1-butanone c. 4-phenyl-4-butanoneb. phenylbutanal d. butanonebenzene____ 83. The functional group of a molecule does not affect a compound'sa. solubility c. reaction with other moleculesb. melting point d. carbon chain length____ 84. Which compound is most likely to be a gas at room temperature?a. propane c. propanalb. 2-chloropropane d. propanone____ 85. The melting point of a compound is not influenced by which of the following?a. polarity d. hydrogen bondsb. electronegativity of its atoms e. isotope of carbonc. Van der Waals forces____ 86. From the following list, select the two molecules that are isomers:1. CH3CH2CH2CH2CH 2. CH33CH2CH2CH(CH 3)23. CH CH CH CH 4. CH3CH2CH2-C(CH 3)23 2 2 3a. (1) and (2) only d. (2) and (3) onlyb. (1) and (3) only e. (2) and (4) onlyc. (1) and (4) only____ 87. Which of the following compounds is a secondary alcohol?a. 1-pentanol c. 2-pentanoneb. 2-pentanol d. 2-methyl-2-butanol____ 88. The compound shown below can be prepared by which of the following?a. substitution of benzene with chlorobenzeneb. condensation of hydroxybenzene (phenol)c. hydrogenation of diphenylmethanoned. oxidation of diphenylmethane____ 89. Which of the following compounds is an isomer of the other three identical molecules?a. c.b. d.

____ 90. The symbol shown below is which of the following?a. an empirical formula c. a structural formulab. a molecular formula d. a stick formula____ 91. TNT, properly called trinitrotoluene, is shown in the structure below.It is best prepared bya. the reaction of benzene with chloromethane, followed by 3 successive reactions withHNO 3 in the prescence of H2SO4b. the reaction of benzene with chloromethane, followed by 3 successive reactions withHNO 2 in the prescence of H2SO4c. the reaction of benzene with excess Br 2, then bromomethane, then successive reactionswith HNO 3 in the prescence of H2SO4d. the reaction of benzene with excess chloromethane followed by successive reactions withHNO 2____ 92. A chemist is designing a new fuel using cyclohexane as a starting material. The cyclohexane is exposedto Cl 2(g) and light. The resulting substance is reacted with H2O. A dehydration reaction is thenaccomplished with H2SO 4. The resulting product is slightly soluble in polar and non-polar substances.The product is:a. c.b. d.____ 93. Ethanoic acid (vinegar) when diluted to low concentrations by water can be prepared from ethene bya. reduction with H 2, followed by reaction with a strong oxidizerb. addition of HCl, followed by reaction with H2Oc. addition of H2O followed by reaction with a strong oxidizerd. addition of Br , followed by reduction with H2 2

____ 94. A cosmetic company wants to produce nail polish remover, also known as acetone,,from propene. An efficient method would involve the following series of reactions in which order?a. halogenation, oxidation c. reduction, halogenation, eliminationb. reduction, hydration d. hydration, oxidation____ 95. A chemist wishes to identify an unknown alkene. She does the following series of reactions with theunknown alkene:i. hydrationii. oxidationproducing the 1-cyclohexyl-2-propane. The unknown alkene's structure is which of the following?a. c.b. d.____ 96. Which of the following trivial or common names do not match the IUPAC names?a. 1,2-ethanediol and ethyleneglycol c. hydroxybenzene and phenolb. propanal and formaldehyde d. ethyne and acetylene____ 97. In a combustion reaction with O 2(g), which compound would produce the greatest release of energy?a. c.b. d.____ 98. Carbon is able to form large numbers of organic compounds because carbon cana. form 4 bondsb. form single, double and triple bondsc. form chains, rings, spheres and sheetsd. the carbon-carbon bond is very stablee. all of the above

____ 99. Oil of jasmine is a naturally occurring substance. A chemist wishes to synthesize this compound usingbenzene and ethane as starting materials. In order to do this, the following procedure is done. Benzene isreacted with methyl chloride followed by exposure to Cl 2(g) and light. The result of these reactions isreacted with water and the product is called 'R'. The ethane is reacted with Cl 2(g) and light, followed byreaction with water. The product of these reactions is exposed to a strong oxidizer and the result is called'S'. 'R' and 'S' are reacted together in the prescence of H2SO 4 to form oil of jasmine. The structure of thecompound is which of the following?a. c.b. d.____ 100. Name CH3CH(OH)CH 3.a. iso-ethanolb. tertiary-propanolc. butanold. propanole. 2-propanol____ 101. Which organic compound is unsaturated?a. ethylcyclopentaneb. 2-methyl-3-ethylpentynec. 1,1-dimethylhexaned. cyclohexanee. 1,3,5-trimethyloctane____ 102.Name the following compound.

____ 103.____ 104.____ 105.a. 4-ethyl-3-methylheptaneb. 4-methyl-3-propylhexanec. 3-propyl-4-methylhexaned. 4-ethyl-3-methylhexenee. 3-ethyl-4-propylheptaneWhich alkane would most likely be a liquid at room temperature?a. methaneb. ethanec. propaned. butanee. pentaneWhich feature do all aromatic hydrocarbons have?a. an amine groupb. halogensc. a benzene ring structured. an aldehyde groupe. all double bonds in a ringTo which family of organic compounds does CH3COCH2CH2CH 3 belong?a. alcoholb. aldehydec. alkyned. ketonee. carboxylic acid____ 106.Name the following compound.

____ 107.a. 1-methyl-3,4-dibromocyclopenteneb. 3-methyl-1,2-dibromocyclopentenec. 3-methyl-4,5-dibromocyclopentened. 3-methyl-3,4-dibromocyclopentenee. 2-methyl-3,4-dibromocyclopenteneWhich compound is a structural isomer of the compound shown below?____ 108.____ 109.____ 110.____ 111.____ 112.a. propaneb. butanec. methaned. pentanee. hexaneWhich class of organic compounds does not contain a carbon-oxygen double bond?a. amidesb. ethersc. ketonesd. esterse. carboxylic acidsWhat is the difference between an amine and an amide?a. There is no carbon-oxygen bond in an amine, but there is in an amide.b. Amines are non-polar molecules.c. Amines always have a larger molecular weight than amides.d. Amines always have a nitrogen atom attached to two carbon atoms.e. Amines can be found in proteins, but amides can not.Which molecule is polar?a. carbon dioxideb. carbon tetrachloridec. propaned. methyl chloridee. butaneWhat is the shape of an alkyne molecule?a. bentb. linearc. tetrahedrald. trigonal planare. cyclicTo predict whether or not an organic molecule contains a polar bond, what do you not need to do?

____ 113.____ 114.____ 115.____ 116.a. Consider the three-dimensional shape of the moleculeb. Consider the bond dipoles within the molecule.c. Determine if there is more than one single bond within the molecule.d. Determine if there is an imbalance in charge within the molecule.e. Use the electronegativity values of each atom to determine the polarity of each bond.Which compound is not an aliphatic hydrocarbon?a. propaneb. hexynec. 1,2-dimethylbenzened. 2,2-dimethylheptanee. iso-butaneWhen numbering the main chain or ring of an organic compound, which functional group gets the highestpriority?a. methylb. hydroxylc. halogend. aminee. hydrogenWhich substance is not a structural isomer of hexyne?a. 2-hexyneb. 3-hexynec. 2,2-dimethylpentyned. 4-methyl-1-pentynee. 2,3-dimethylbutadieneWhy does the boiling point of an alkane increase as its chain length increases?a. There is more hydrogen bonding.b. There are more hydrogen atoms available for hydrogen bonds to form.c. The number of dipole-dipole interactions increases.d. The strength of the dispersion forces increases with increased molecular size.e. Heavier molecules cannot float on the surface of water as well.____ 117. How many unshared electron pairs are found in a molecule of formaldehyde, HNCHO? Hint: Draw aLewis structure to help you answer this question.a. noneb. threec. twod. foure. one____ 118. Which shape is used to represent cyclobutane?a. triangleb. squarec. hexagond. octagone. cube____ 119. How many isomers have the molecular formula C H O?5 10

____ 120.____ 121.____ 122.____ 123.a. fourb. fivec. sixd. sevene. threeWhich compounds do perfumers mix to obtain distinctive and attractive scents?a. alcoholsb. ketonesc. aldehydesd. alkanese. cyclic compoundsInfrared spectroscopy allows researchers to determine the kinds of bonds and the functional groups thatare present in a molecule. What does infrared spectroscopy measure?a. the absorption of white lightb. bond stretching, bending, and vibratingc. the degree of absorption of infrared lightd. the emission of infrared light from the organic moleculee. the emission of full-spectrum light from a sampleWhich two compounds react to form an ester?a. a carboxylic acid and an alcoholb. an alcohol and an aldehydec. an alcohol and a ketoned. a carboxylic acid and a ketonee. an aldehyde and a carboxylic acidTo which class does CH3CH2NH 2 belong?a. secondary amineb. primary aminec. secondary amided. primary amidee. tertiary amine