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Organic Chemistry Testbank History of Organic Chemistry The first organic chemical to be synthesized in a lab from inorganic chemicals was a. ethanol c. methane b. sugar d. urea The first person to synthesis an organic chemical from inorganic chemicals was a. August Kekulé c. Friedrich Wöhler b. John Dalton d. Raymond LeMieux The Avitalism@ theory in organic chemistry held that a. organic chemicals can only be obtained from living organisms b. organic chemicals can only be obtained from dead organisms c. organic chemicals can only be obtained from living or dead organisms d. organic chemicals can be obtained from any source of chemicals, organic or inorganic. Long Answer: Explain why Wöhlers synthesis of urea by heating ammonium cyanate crystals was a landmark event in the study of organic compounds. Definition of Organic Chemistry Organic chemicals a. are all the compounds of carbon including the ionic compounds b. are all the molecular compounds of carbon except the oxides c. are all the ionic compounds of carbon including the oxides d. can only be made by living organisms Throughout history there have been many definitions of organic chemistry. The modern definition of organic chemistry refers to the study of a. ionic compounds of carbon b. molecular compounds of carbon c. non-living substances only d. substances derived from living things. Which is an organic chemical? a. CaCO3 c. Cl2 b. CCl4 d. CO2 Which is NOT an organic chemical? a. CH3COOH c. C4H7O b. CO2 d. CCl4 Which is NOT an organic chemical? c. CH3CHO c. C2H6O d. CBr4 d. CO Which substance is organic? a. AgCl c. NH4CN b. AgOCN d. (NH2)2CO Multitude of Organic Chemicals 1 Organic Chemistry Testbank 2 Which statement is true? a. Carbon can bond in chains with branches, but cannot form rings b. Carbon can form single bonds, but not double and triple bonds. c. Carbon can bond in chains with branches, in rings, and with single, double and triple bonds d. Carbon cannot form rings with double bonds or branches on them Which statement is true? a. Over 90% of all known compounds are organic b. Over 90% of all known compounds are inorganic c. There are about 2 times as many inorganic compounds as organic compounds d. There are about 2 times as many organic compounds as organic compounds There are thousands of times more organic than inorganic compounds. The enormous number of carbon compounds is believed to be due, in large part, to the a. high bonding capacity of a carbon atom. b. ability of carbon atoms to form covalent bonds with hydrogen. c. high number of lone pairs of electrons of a carbon atom. d. large variety of chemical reactions of elemental carbon Short Answer: List three factors that contribute to the tremendous diversity of carbon compounds relative to the number of inorganic compounds. Give two (good) reasons why carbon has its own branch of chemistry. Homologous Series Each member of the alkane series differs from the preceding member by one additional carbon atom and a. 1 hydrogen atom c. 2 hydrogen atoms b. 3 hydrogen atoms d. 4 hydrogen atom The alkane family is referred to as a homologous series because each member of the family a. becomes more soluble in water as they get larger b. can have more isomers as they get larger c. has a boiling point that increases as they get larger d. increases by A-CH2" as they get larger Which of the following is part of a homologous series: a. CH4, C2H4, C4H8 b. CH4, C2H2, C3H6 c. C3H8, C3H6, C3H4 d. C2H4, C3H6, C4H8 Which term describes this group of compounds? chloromethane, chloroethane, 1-chloropropane, 1-chlorobutane a. aldehydes c. functional isomers b. aromatics d. homologous series Alkanes/Straight chain alkanes Alkanes are: Organic Chemistry Testbank 3 a. organic compounds containing one or more carbon-carbon double bonds b. special group of unsaturated cyclic hydrocarbons c. organic compounds containing one or more carbon-carbon triple bonds d. hydrocarbons that contain only single covalent bonds How many double covalent bonds are in an alkane? a. none c. one b. two d. The number varies How many carbons are in a molecule of hexane? a. 3 b. 4 b. 5 d. 6 What is the name of the alkane having five carbons? a. hexane c. methane b. octane d. pentane What increment of change occurs between propane and butane in the alkane series? B a. -CHb. -CH2b. -CH3d. -CH2= Which of the following is a condensed structural diagram for propane? H H H a. C3H8 H C C C H b. CH3-CH2-CH3 d. c. C-C-C H H H What is the name of the molecule on the right? CH2 CH3 a. butane H C CH b. pentane 3 2 c. propane d. tetrane What is the name of the molecule on the right? CH2 CH2 CH3 a. butane H3C CH2 CH2 b. pentane c. propane d. hexane What is the IUPAC name of the compound on the right? H H H H H a. butane b. decane H C C C C C c. propane H H H H H d. pentane What is the name of the straight chain alkane with 7 carbons? a. pentane c. hexene b. heptane d. octyne Branched Alkanes - Nomenclature Which condensed structural formula represents the alkyl group called ethyl? a. CHCH c. CH2CH3 H Organic Chemistry Testbank 4 b. CH2CH2 d. CH3CH3 What is the name of an alkyl group that contains two carbon atoms? a. diphenyl c. dimethyl b. ethyl d. propyl What prefix is used to represent the substituent CH3-CH2-CH2-? a. ethylc. methylb. propyld. pentyl If a substituent appears four times in an organic compound, what prefix is used? a. dic. monob. pentad. tetraWhat is the name of the compound on the right? a. 2,4-diethyl-2-methylhexane b. 3-ethyl-5,5-dimethylheptane c. 5-ethyl-3,3-dimethylheptane d. 3,5-diethyl-5-methylhexane What is the IUPAC name of compound on the right? a. 2-ethyl-3-dimethylhexane b. 2-ethyl-3,3-diemethylhexane c. 4,4,5-trimethylheptane d. 3,4,4-trimethylheptane What is the IUPAC name of compound on the right? a. 2,3-dimethylpentane b. 3,4-dimethylpentane c. 3,4,4 -trimethylbutane d. 2,3,4-trimethylbutane What is the IUPAC name of compound on the right? a. trimethylpentane b. 2-methyl-3-methyl-4-methylpentane c. 2,2-dimethyl-3-methylpentane d. 2,3,4-trimethylpentane H3C CH3 CH H3C CH What is the IUPAC name of compound on the right? a. 2-ethyl-2,4,5-trimethylpentane b. 2-ethyl-2,4-dimethylhexane CH2 CH2 CH2 c. 3,5,5-trimethylheptane CH3 d. 3,3,5-trimethylheptane What is the correct IUPAC name for the compound shown below? CH3.CH(CH2.CH3).CH(CH3)2 a. 2,3-dimethyl pentane c. 1,1,2-trimethyl butane b. 2-ethyl-3-methyl butane d. 3,4-dimethyl pentane Which is the condensed structural formula for 2,2,3-trimethylbutane? CH CH3 CH3 CH3 C CH2 CH3 CH3 Organic Chemistry Testbank 5 a. CH3CH2(CH3)CH(CH3)2 c. CH3C(CH3)2C(CH3)3 b. CH3C(CH3)2CH(CH3)2 d. CH3CH2CH(CH3)C(CH3)3 What is the IUPAC name for this compound? CH3CH(CH3)C(CH3)3. a. 2,2,3-trimethylbutane c. tetramethylpropane b. 1,1,1,2-tetramethylpropane d. heptane Alkenes - Nomenclature Alkenes are: a. organic compounds containing one or more carbon-carbon double bonds b. special group of unsaturated cyclic hydrocarbons c. organic compounds containing one or more carbon-carbon triple bonds d. hydrocarbons that contain only single covalent bonds Which hydrocarbon contains a double carbon to carbon bond? a. 1-butene c. 2-methylbutane b. 1-butyne d. cyclobutane Which compound is an alkene? a. butyne c. pentane b. nonene d. propanone What is the name of the molecule on the right? CH2 CH3 a. 2-ethyl-3-propyl-1-pentene b. 2,3-diethyl-4-methyl-1-pentene CH3 CH2 C CH CH CH3 c. 3-ethyl-2,4-dimethyl4-hexene CH2 d. 3,4-diethyl-2-methyl-4-pentene What is the name of the molecule on the right? CH2 CH CH3 3 a. 2,3-dimethyl-4-propyl-4-pentene CH3 CH2 CH2 C CH CH CH3 b. 2,3-dipropyl-1-butene c. 3,4-dimethyl-2-propyl-1-pentene CH3 d. 4,5,6-trimethyl-4-heptene What is the IUPAC name of this compound? H H H a. 1,1-dimethyl-2-butene b. 2-methyl-3-pentene H C C H C H c. 4-methyl-2-pentene C C H d. methylhexane H H H C H H According to the rules established by chemists, what is the IUPAC name of the compound on the right? CH3 a. 1-methyl-1-pentene b. 5-methyl-4-pentene HC CH CH2 CH2 CH3 c. 2,3-hexene d. 2-hexene. Determine the IUPAC name for the following molecule: Organic Chemistry Testbank a. b. c. d. 6 2,5-dimethyl-2-hexene 2,5-dimethyl-4-hexene 2,5-dimethyl-2-heptene 2,5-dimethyl-4-heptene What is the name for the following molecule? H3C CH2 CH3 a. 2-ethyl-2-pentene C C b. 4-ethyl-3-pentene c. 3-methyl-3-hexene H CH2 CH3 d. 4-methyl-3-hexene The correct name for the compound (CH3)2CH.CH(CH3).CH2.CH:CH2 is: a. 4,5,5-trimethyl-1-pentene b. 4,5-dimethyl-1-hexene c. 2,3-dimethyl-5-hexene d. 4-propyl-4-methyl-1-butene Alkynes - Nomenclature Alkynes are: a. organic compounds containing one or more carbon-carbon double bonds b. special group of unsaturated cyclic hydrocarbons c. organic compounds containing one or more carbon-carbon triple bonds d. hydrocarbons that contain only single covalent bonds What is the name of the smallest alkyne? a. butyne c. ethyne b. methyne d. propyne CH2 CH3 What is the name of the molecule on the right? a. 4,4-diethyl-2-butyne H3C C C HC b. 4-ethyl-2-hexyne CH2 CH3 c. 3-ethyl-4-hexyne d. 1,1-diethyl-2-butyne What is the name of the molecule on the right? a. 1,6,6,6-tetramethyl-2-pentyne b. 2,2-dimethyl-4-heptyne c. 2,2,6-trimethyl-4-hexyne d. 6,6-dimethyl-3-heptyne CH3 H3C H3C HC C CH CH CH2 CH2 H3C CH3 C C CH3 Which is the condensed structural diagram for 4-methyl-2pentyne? a. CH2 C CH3 c. H3C C C CH3 Organic Chemistry Testbank 7 CH3 CH3 CH b. H3C CH CH CH CH3 H3C C What is the name of the molecule a. acetylene b. 1-butyne Cycloalkanes, cylcoalkene - Nomenclature d. CH c. d. H2C CH CH2 CH3 ? propyne propene What is the name of the molecule on the right? a. ethylbenzene b. ethylcyclohexane c. phenylethane d. propylcyclohexane What is the name of the molecule on the right? a. butylcyclohexane b. phenylpropane c. propylbenzene d. propylcyclohexane What is the name of the molecule on the right? a. ethylcyclopentane b. pentylcyclopropane c. propylcylclopentane d. propylcyclohexane What is the name of the molecule on the right? a. 2-ethylcyclopentene b. 3-ethylcyclopentene c. 2-ethyl-2-cyclopentene d. 5-ethyl-2-cyclopentene What is the name of the molecule on the right? a. 2-methylcyclohexene b. 3-methylcyclohexene c. 4-methylcyclohexene d. 5-methylcyclohexene CH3 Select the proper order of stability from least to most stable for the following cycloalkenes: Organic Chemistry Testbank B A a. b. 8 C A, B, C B, C, A c. d. C, A, B C, B, A Simple Aromatics - nomenclature What is the name of the molecule on the right? a. 2-butylbenzene b. butylbenzene c. phenylbutane d. propylbenzene What is the name of the molecule on the right? a. butylbenzene b. 2-pentylbenzene c. pentylbenzene d. phenylpentane What is the IUPAC name of the compound on the right? a. pentylcyclohexane b. cyclopentylhexane c. pentylbenzene d. hexylbenzene What is the IUPAC name of the compound on the right? a. butylbenzene b. phenylbutane c. propylbenzene d. phenylpropane CH2 CH2 CH2 CH2 CH3 CH2 CH2 CH3 CH2 Phenyl Branches - nomenclature What is the IUPAC name of the molecule on the right? a. 1,1,4-trimethyl-4-phenylbutane b. 2,4-dimethyl-5-phenylpentane c. 2,4-dimethyl-2-pentylbenzene d. 2,4-dimethyl-1-phenylpentane What is the IUPAC name of the molecule on the right? a. 2-methyl-3-ethyl-1-phenylbutane b. 2,3-dimethyl-1-phenylpentane c. 2,3-dimethyl-1-pentylbenzene d. 3,4-dimethyl-5-phenylpentane CH2 CH2 CH3 CH CH CH3 CH3 CH2 CH3 CH CH H3C CH3 CH2 Organic Chemistry Testbank 9 What is the IUPAC name for the molecule on the right? a. 2-pentylbenzene b. 2-phenypentane c. 1 -methyl-1-phenylbutane d. pentylbenzene How many phenyl groups does the following molecule have? a. 0 c. 2 b. 1 d. 6 Disubstituted benzenes What is another acceptable name for 1,3-dimethylbenzene? a. m-dimethylbenzene c. b. n-dimethylbenzene d. What is another acceptable name for 1,4-dimethylbenzene? a. m-dimethylbenzene c. b. n-dimethylbenzene d. What is another acceptable name for 1,2-dimethylbenzene? a. m-dimethylbenzene c. b. n-dimethylbenzene d. What is the name of the molecule on the right? a. ethylmethylbenzene b. o-ethylmethylbenzene c. m-ethylmethylbenzene d. p-ethylmethylbenzene What is the name of the compound on the right? e. diethylbenzene f. m-diethylbenzene g. o-diethylbenzene CH2 CH2 HC CH3 CH3 o-dimethylbenzene p-dimethylbenzene o-dimethylbenzene p-dimethylbenzene o-dimethylbenzene p-dimethylbenzene CH3 H3C h. p-diethylbenzene What is the name of the molecule on the right? a. ethylpropylbenzene b. o-ethylpropylbenzene c. m-ethylpropylbenzene d. p-ethylpropylbenzene What is the IUPAC name for the isomeric compound on the right? a. 1,2-dichlorobenzene b. 1,3-dichlorobenzene c. 2,2-dichlorobenzene d. 2,6-dichlorobenzene Which of the following molecules is p-ethylmethylbenzene? Cl Cl Organic Chemistry Testbank a. 10 b. c. d. Units of Unsaturation/general formulas What type of hydrocarbon is the compound on the right? CH3-CH2-CH2-CH2-CH2-CH3 a. aliphatic c. cyclic b. aromatic d. unsaturated Which hydrocarbon is saturated? a. C6H6 c. C6H12 b. C6H10 d. C6H14 Which is the formula of a saturated hydrocarbon? a. C2H2 c. C2H4 b. C5H8 d. C5H12 Which is the formula of a saturated hydrocarbon? a. CH2CH2 c. C6H6 b. CH3CHCH2 d. (CH3)3CH A saturated continuous-chain hydrocarbon with seven carbons is _____. a. cycloheptene c. heptene b. heptane d. heptyne Which of the following compounds is an unsaturated hydrocarbon? a. methane c. nonane b. propyne d. ethyl How many units of unsaturation does the molecular formula C5H8 have? a. none c. two b. one d. three How many units of unsaturation does the molecular formula C7H12 have? a. none c. two b. one d. three Which could be a molecular formula for an organic chemical with one ring and one double bond? a. C5H10 c. C5H8 b. C6H14 d. C6H12 Which could be a molecular formula for an organic chemical with one ring? a. C5H10 c. C5H8 b. C6H14 d. C6H10 Organic Chemistry Testbank Which could be a molecular formula for a non-cyclic hydrocarbon with two double bonds? a. C5H10 c. C5H8 b. C6H14 d. C6H12 What is the molecular formula for 3,3-diethyl-4-methyl-1-hexyne? a. C10H18 c. C11H22 b. C11H20 d. C12H22 Which formula represents a member of the alkene series? a. C3H6 c. C2H2 b. C2H6 d. C6H6 Which formula represents a member of the alkane family? a. C3H6 c. C2H2 b. C2H6 d. C6H6 What is the general formula for a continuous-chain alkane? a. CnHn c. CnH2n-2 b. CnHn+2 d. CnH2n+2 To which class of aliphatic hydrocarbons does C25H52 belong? a. alkanes c. alkynes b. alkenes d. aromatics Which of the following molecules is a saturated hydrocarbon? a. b. c. d. Isomers: Which molecule is NOT an isomer of C4H8? a. b. Which molecule is NOT an isomer of C5H12? c. d. 11 Organic Chemistry Testbank a. c. b. d. C8H16 could have isomers with a. one ring or one double bond c. one ring and one double bond b. one triple bond d two rings Which structural formula represents an isomer of 2-pentyne? a. c. b. d. Which compound is an isomer of methylpropane? a. butane c. pentane b. cyclopropane d. propane Which of the following compounds is a structural isomer of butane? a. 2-methylbutane c. 2,2-dimethylbutane b. 2-methylpropane d. 2,2-diethylpropane Which pairs of molecules are structural isomers? a. cyclohexane and 2,2-dimethylbutane b. cyclohexene and 3,3-dimethyl-1-butyne c. methylcyclobutane and 2-pentyne d. 2-methylpentyne and 2-methylpentene A structural isomer of hexane is _____. a. benzene c. cyclohexane b. 2,2-dimethylbutane d. 2-methylpentene Which compound can have isomers? a. C2H4 c. C2H2 b. C2H6 d. C4H8 How many structural isomers exist for the alkene CH2Br2? a. 1 c. 3 b. b. 2 d. 4 Which compound is an isomer of CH3.CH2.CH2.CH2.OH a. CH3CH2OCH3 c. CH3CH2CH2CH3 b. CH3CH2CH2OH d. CH3CH(OH)CH2CH3 Which of the following pairs of compounds are isomers? a. diethyl ether and 1-butanol b. 2-pentanone and 2-pentanol 12 Organic Chemistry Testbank c. pentanal and methyl butanoate d. Structural isomers have _____. a. the same molecular formula b. different physical and chemical properties c. the same elemental composition d. all of the above Which of the following pairs of compounds are isomers? a. propanal and 1-propanol b. propanoic acid and propyl propanoate c. propanone and propanal d. propyl ether and 1-propanol Isomer - Short Answer 13 propanoic acid and propanal 1a) A student is told to draw the structural diagram of the compound with formula C4H10 . Confused, the student tells the naive chemistry-challenged person that the task is impossible. a) Why can=t the student show the structure of C4H10? (2) b) Rephrase the question by changing one word so that the question can be answered, and then answer it. (Keep the flavor of the question - don't change it completely!) (4) 1a) Give a brief explanation, using two examples, as to why the numbers are necessary for identifying an organic compound sometimes, but not other times. (4) b) Identify which of the following names need numbers in front to identify them completely: butanol, propanal, pentanone, hexene, butanoic acid, methylpentane.(3) How many different answers should you get to the question, "What is the boiling point of C3H8O?" Explain with the use of structural diagrams, names and a brief discussion of intermolecular attractions. Draw structural formulas for and name four isomers of C4H7Cl. Halocarbons Which substituent would allow a compound to be classified as an alkyl halide? a. fluorine c. oxygen b. nitrogen d. sulfur The IUPAC name for the compound (CH3)2C(CH2.CH3).CH2.CHCl.CH3 is: a. 5-chloro-3,3-dimethylhexane c. 2-chloro-4-methyl-4-ethylpentane b. 4-chloro-2-ethyl-2-methylpentane d. 1-chloro-1,3,3,3-trimethylpentane What is the name of the molecule on the right? Cl CH3 a. 2-dichloro-3-methylpentane b. 2,2-dichloro-3-methylpentane CH3 C CH CH2 CH3 c. 4,4-dichloro-3-methylpentane d. 4,4-dichloro-3,5-dimethylbutane Cl What is the name of the molecule on the right? CH3 a. 2,3-dichloro-2-methylpentane CH3 C Cl CH Cl CH2 CH3 Organic Chemistry Testbank b. 1,2-dichloro-1,1-dimethylbutane c. 2,3-chloro-2-methylpentane d. 3,4-dichloro-4-methylpentane The correct name for the molecule on the right is: a. 1,4,4-trifluoro-2-bromopentane b. 2-bromo-1,4,4-trifluoropentane c. 2,2,5-trifluoro-4-bromopentane d. 4-bromo-2,2,5-trifluoropentane 14 Br F F CH C CH2 CH2 H3C F Alcohols What is the name of the molecule on the right? H3C CH2 a. butanone CH CH3 b. 2-butanol c. 2-butanal HO d. butyl ether What is the name of the molecule on the right? OH a. 3-pentanone b. 3-pentanal H3C CH CH3 c. 3-pentanol CH2 CH2 d. pentanoic acid What is the correct IUPAC name for the compound shown below? CH3.CH2.CH(CH2.CH3).CH(OH).CH3 a. 3-ethyl-4-pentanol b. 2-methyl-5-hexanol c. 3-ethyl-2-pentanol d. 3-ethyl-2-heptanol The correct IUPAC name for the compound CH3.CH2.CH2.C(CH3)2.OH is a. 1-hexanol c. 1- dimethylbutanol b. 1,1-dimethyl-1-butanol d. 2-methyl-2-pentanol Ethers Which molecule is an ether? OH O CH a. H3C CH2 CH2 C CH3 c. CH3 CH3 CH b. H3C H3C O CH2 C CH2 O CH2 O CH3 d. OH CH3 Organic Chemistry Testbank 15 Which of the following is an ether? OH CH3 CH2 CH3 CH2 CH2 CH2 C O a. O c. CH3 CH3 CH3 CH2 CH2 C CH3 CH2 CH2 CH O b. d. What is the name of the molecule on the right? a. butanal b. methylpropyl ether c. butanone d. methyl propanoate What is the name of the molecule on the right? H3C a. pentanal b. ethylpropyl ether c. pentanone d. ethyl propanoate O O CH2 CH3 O CH2 CH2 CH2 CH2 CH3 Aldehydes Which molecule is an aldehyde? CH3 O C a. O CH2 CH2 C CH3 c. H3C CH3 b. CH3 O CH H3C CH2 O CH2 O C CH3 d. CH2 H CH2 Which of the following is an aldehyde? OH CH3 CH2 CH3 CH2 CH2 CH2 C a. O c. O CH3 CH3 CH3 Organic Chemistry Testbank 16 CH3 CH3 CH2 CH2 C CH3 CH2 CH2 CH O b. O d. What is the IUPAC name of the molecule on the right? a. butanal b. 1-butanone c. butanoic acid d. propanal What is the IUPAC name of the molecule on the right? a. butanal b. 1-butanone c. butanoic acid d. propanal Which of the following is an aldehyde? a. butanone c. b. ethanol d. Which of the following is an aldehyde? a. butanal b. c. ethanol d. O CH CH2 CH2 CH3 O CH CH2 CH2 CH2 ethane pentanal ethanone pentanoic acid Ketones What is the IUPAC name of the molecule on the right? a. ethylpropyl ether b. 3-hexanal c. 3-hexanone d. methyl butanoate What is the IUPAC name of the molecule on the right? a. diethyl ether b. 2-pentanone c. 3-pentanone d. 3-pentanal Which of the following is a ketone? O O OH CH3 CH2 CH3 CH2 CH2 CH2 C O a. c. O CH3 CH3 CH3 CH2 CH2 C b. CH3 CH2 CH2 CH O d. CH3 O Organic Chemistry Testbank Which condensed structural formula represents a ketone? a. CH3CH2CH2OH c. b. CH3CH2CHO d. 17 CH3COCH3 CH3CH2COOH Carboxylic Acids What is the IUPAC name of the molecule on the right? a. butanone b. ethanoic acid c. methy propanoate d. propanoic acid What is the IUPAC name of the molecule on the right? a. butanal b. butanoic acid c. methy propanoate d. propanoic acid What is the IUPAC name of the molecule on the right? a. pentanal b. pentanoic acid c. methy butanoate d. pentanone OH O HO O CH3 CH2 CH2 O CH2 C OH Esters What is the IUPAC name of the molecule on the right? a. butyl ethanoate b. ethyl propanoate c. ethyl butanoate d. propyl ethanoate What is the IUPAC name of the molecule on the right? a. ethyl methanoate b. methyl ethanoate c. ethanoic acid d. propanoic acid What is the IUPAC name of the molecule on the right? a. ethyl propanoate b. methyl butanoate c. butyl methanoate d. methyl propanoate O O CH3 CH2 O O C H O O Trivial Names What is the IUPAC name of the molecule on the right? CH3 Organic Chemistry Testbank a. b. c. d. 18 acetylene formaldehyde phenol toluene What is the IUPAC name of the molecule on the right? a. acetylene b. formaldehyde c. phenol d. toluene OH Fractional Distillation/Sources of hydrocarbons Which molecule would condense closer to the top of a fractional distillation tower? a. C5H12 c. C14H30 b. C10H22 d. C20H42 Which molecule would condense closer to the bottom of a fractional distillation tower? a. C5H12 c. C14H30 b. C10H22 d. C20H42 Which is the correct statement regarding fractional distillation? a. The mixture of hydrocarbons in crude oil are converted into the various fractions (gasoline, furnace oil, etc.) by chemical reactions b. Substances with high boiling points will condense lower in the fractional distillation tower. c. Fractions with very low boiling points will condense before the fractions with high boiling points d. Crude oil from different sources, when distilled in a fractionating tower, will yield the same percent of gasoline Which compound in crude oil will be the first to evaporate relative to the other hydrocarbons listed? a. decane c. heptane b. nonane d. octane What is not a source of raw materials for petrochemical industries? a. coal deposits c. crude oil b. mineral deposits d. natural gas What is the main hydrocarbon component of natural gas? a. benzene c. ethane b. methane d. propane Which type of coal has the highest carbon content? a. anthracite c. lignite b. bituminous d. peat Which process involves the conversion of once living organic matter to fossil fuels? Organic Chemistry Testbank a. b. carbonization nuclear fusion c. d.. combustion photosynthesis Shapes of molecules The bonding shape around every carbon in propane is a. bent c. tetrahedral b. linear d. trigonal planar What is the shape of a methane molecule? a. bent c. pyramidal b. linear d. tetrahedral The bonding shape around both carbons in ethyne is a. bent linear tetrahedral trigonal planar Which of the following molecules is completely flat or planar? a. a. ethene b. ethane c. propene d. cyclohexane Which description best describes the boding shape around the carbons in the molecule on the right? a. trigonal planar b. linear c. tetrahedral d. cyclic Short Answer: 1. (a) Draw Lewis diagrams for ethane and ethyne. (b) Describe the shape around the carbon atoms in ethane versus ethyne. (c) How does the shape and arrangement of bonding electrons influence the reactivity of ethane versus ethyne? Solubility Which substance would be most soluble in water? a. propanoic acid c. propanal b. propanone d. propane Which substance would be least soluble in water? a. propanoic acid c. propanal b. propanone d. propane Which substance is immiscible with water? a. 2-butanol c. ethanal b. 2-methyl-3-heptene d. methanoic acid In which of the following solvents would candle wax, C25H52, dissolve in the best? a. H2O c. C9H18 b. CH3OH d. C3H7OH In which of the following compounds is hexane most likely to dissolve? 19 Organic Chemistry Testbank a. b. acetic acid decane c. d. 20 ethyl alcohol water nonane Boiling Points Which substance would have the highest boiling point? a. C7H12 c. C14H28 b. C9H16 d. C22H40 Which of the following compounds has the lowest boiling point? a. heptane c. 2,3-dimethylpentane b. 2-methylhexane d. 2,2,3-trimethylbutane Which substance would have the lowest boiling point? a. C7H12 c. C14H28 b. C9H16 d. C22H40 Which alkene has the highest boiling point at atmospheric pressure? a. C2H4 c. C4H8 b. C3H6 d. C5H10 What is the main force that influences boiling points in pure hydrocarbons? a. covalent bonding c. hydrogen bonding b. dipole-dipole attractions d. London Dispersion Forces Which property is generally accepted as an indicator of the strength of intermolecular forces within a substance? a. boiling point c. isomerism b. London dispersion force d. solubility Alkanes, alkenes, and alkynes with the same number of carbons have: a. similar boiling and melting points primarily because they have nearly the same molecular weight b. similar boiling and melting points primarily because they have similar polarities c. similar boiling and melting points primarily because they are nearly equal in stability d. vastly different boiling and melting points If alkenes of four carbons or less exist as gases at room temperature, how many alkenes exist as gases under these conditions? a. 2 c. 4 b. 3 d. 5 What is the physical state of the smallest alkanes (C1-C4) at room temperature? a. gas c. solid b. liquid d. gas or liquid Intermolecular Forces In which substance would London dispersion forces be the only intermolecular force of attraction? a. 1-pentanol c. pentanal Organic Chemistry Testbank 21 b. pentanoic acid d. pentyne Which substance would be able to form hydrogen bonds to water but would not have any hydrogen bonding between their own molecules? a. ethanol c. propanal b. propanoic acid d. propanol Hydrogen bonding is most noticeable in a. alkanes c. esters b. alkynes d. organic acids Why is a carbon-hydrogen bond essentially nonpolar? a. Neither atom is ionic. b. Free electrons cancel any polarity. c. The electron pair is shared almost equally. d. Van der Waals forces overcome polarity. Lewis Dot Diagrams/Carbon Bonding How many valence electrons surround a carbon atom? a. 1 c. 3 b. 2 d. 4 How many covalent bonds does each carbon atom participate in an organic compound? a. 1 c. 3 b. 2 d. 4 Which is the correct Lewis Dot diagram for acetylene, C2H2? a. c. HC CH H C C H c. d. HC CH H C C H Benzene Bonding What compound is the simplest of the arenes? a. benzene c. ethyne b. ethene d. methane Which of the following molecules does NOT have delocalized electrons? a. benzene c. cyclohexane b. 2-phenylpentane d. toluene The compound benzene puzzled chemists for many years. Empirical research indicates that carbon-carbon bonds in benzene are a. all carbon-carbon single bonds b. all carbon-carbon double bonds c. neither double nor single bonds Organic Chemistry Testbank 22 d. easily broken in chemical reactions. Which chemical has delocalized electrons? CH2 H3C a. H3C C CH b. CH3 c. d. What distinguishes benzene and benzene compounds from other organic compounds? a. benzene and benzene compounds are planar molecules b. carbon atoms in benzene have 120 bond angles c. carbon atoms in the benzene ring have just three bonding electrons d. carbon-carbon bonds in benzene involve delocalized bonding electrons Functional Groups/hydrocarbon derivatives Which of the following is a hydrocarbon derivative? a. C3H8 c. C9H18 b. CH4 d. C3H70H An arrangement of several atoms which gives characteristic properties to an organic molecule is known as a(an) a. carboxyl group c. group b. functional group d. alkyl group What is primarily responsible for the chemical properties of a hydrocarbon derivative like ethanol? a. its delocalized electrons c. its functional group b. its level of saturation d. its solubility in water In the general formula for alcohols, R-OH, the "R' represents a. radon c. the functional group b. CH3 only d. an alkyl group The functional group for aldehydes is: a. hydroxyl c. carboxyl b. carbonyl d. ester The functional group for ketones is: c. hydroxyl c. carboxyl d. carbonyl d. ester The functional group for alcohols is: e. hydroxyl c. carboxyl f. carbonyl d. ester The functional group for carboxylic acids is: Organic Chemistry Testbank 23 g. hydroxyl c. carboxyl h. carbonyl d. ester Which compound contains the functional group called hydroxyl? a. CH3OH c. HCOOH b. H2CO d. NH4CH3COO The functional group for alcohols is a. hydroxyl c. carboxyl b. carbonyl d. ester Organic Reactions Complete the following reactions by identifying reaction type, predicting products where necessary, drawing structures for ALL organic reactants and products and naming ALL products. Indicate if more than two products are possible. Respiration/Photosynthesis: Which biological process produces glucose from carbon dioxide and water? a. carbonization c. fusion b. photosynthesis d. respiration Cracking/Reforming Which reaction type uses ethene and low molecular weight hydrocarbons and converts them into gasoline grade hydrocarbons? a. cracking c. esterification b. elimination d. reforming What is the name of the process in which large molecules are broken down into smaller molecules in order to increase the yield of gasoline from petroleum? a. polymerization c. esterification b. hydrogenation d. cracking Which chemical reaction may be used to convert straight-chain aliphatic hydrocarbons to alkylated or branched hydrocarbons? a. elimination c. esterification b. reforming d. substitution n-decane + H2 butane + _______ + H2 Substitution Which is NOT a possible product in the reaction between benzene and 2 mol of bromine? Organic Chemistry Testbank a. 1,3-dibromobenzene c. 1,2,3,4-tetrabromobenzene b. o-dibromobenzene d. hydrogen bromide Which is NOT a possible product in the reaction between benzene and 2 mol of chlorine? a. 1,2-dichlorobenzene c. 1,2,4,5-tetrachlorobenzene b. p-dichlorobenzene d. hydrogen chloride Which pairs of reactants are most likely to react by a substitution reaction? I. H2 II. Cl2 III. C2H4 IV. C2H6 a. I and III c. I and IV b. II and III d. II and IV Which pairs of reactants are most likely to react by a substitution reaction? I. Br2 II. HBr III. C2H6 IV. C2H4 a. I and III c. I and IV b. II and III d. II and IV Which type of compound will undergo a substitution reaction with a halogen? a. an alkane c. an alkyne b. an alkene d. a ketone Based on the generalizations for reaction types, butane and fluorine gases react by a. addition c. combustion b. esterification d. substitution Short answer: propane + 1 mol chlorine pentane + 1 mol bromine benzene + 2 mol bromine m-dimethylbenzene + chlorine butane + 2 mol bromine pentane + Br2 hexane + chlorine Addition Which IS a product of the reaction between 2-butene and 1 mol of chlorine? a. 1,2-dichlorobutane c. 1,3-dichlorobutane b. 2,3-dichlorobutane d. 1-4-dichlorobutane Which IS a product of the reaction between propene and 1 mol of chlorine? a. 1,2-dichloropropane c. hydrogen b. 1,3-dichloropropane d. 1-chloropropane Which is NOT a product of the reaction between 1-pentyne and 2 mol of hydrogen bromide? a. 1,1-dichloropentane c. 1,3-dichloropentane b. 1,2-dichloropentane d. 2,2-dichloropentane What type of reaction is C2H4+ H2 C2H6 ? 24 Organic Chemistry Testbank 25 a. addition c. condensation b. substitution d. esterification Which equation represents an addition reaction? a. CH3CH3 + Cl2 CH3CH2Cl + HCl b. CH2CH2 + Cl2 CH2ClCH2Cl c. CH3CH2Cl + OHB CH2CH2 + H2O + ClB d. CH2CH2 + CH3CH3 (CH3)2CHCH3 How many products will result when 1-butene reacts with water? a. 1 c. 3 b. 2 d. 4 How many products will result when 2-butene reacts with water? a. 1 c. 3 b. 2 d. 4 Which organic reactant will produce 3-chloropentane when reacted with hydrogen chloride? a. pentane c. 2-pentene b. 1-pentene d. 2-pentyne Short answer 2-pentyne + excess HCl 2-pentyne + 2 mol HCl 2-butyne + 2 mol HBr 1-butyne + 2 mol HCl 3-octene + hydrogen iodide 1-pentene + water 1-butene + water 3-heptene + water 4-methyl-1-butyne + 1 mol hydrogen Esterfication Which of the following pairs of compounds could be combined to synthesize the compound responsible for the odor of pears, pentyl ethanoate? a. 1-pentanol and ethanol c. 1-pentanol and ethanoic acid b. ethanal and pentanoic acid d. ethanol and 1-pentene Which substance would be the best choice as a catalyst for a reaction between octanoic acid and ethanol? a. acetic acid c. methanol b. sodium hydroxide d. sulfuric acid What is the organic product of the reaction of methanol and ethanoic acid? a. propanone c. ethyl methanoate b. propanal d. methyl ethanoate Short answer ethanoic acid + 1-pentanol Organic Chemistry Testbank propanol + butanoic acid methanoic acid + 1-pentanol 1-butanol + _________________ 26 butyl propanoate Hydrocarbon Combustion When hydrocarbons are burned completely, which product is always formed? a. amorphous graphite c. limewater b. carbon dioxide d. methane Short answer 2-methyl-1-butene + oxygen (Balance this reaction) 2-methyl-1-hexene + oxygen (Balance this reaction) 3-methyl-1-pentyne + oxygen 3,4-diethyl-2-pentene + oxygen Elimination Which substance will undergo an elimination reaction when reacting with hydroxide ions? a. 2-fluoropropane c. ethanoic acid b. methyl methanoate d. propanal Which compound, when heated in the presence of a strong acid, will produce a second compound that will react quickly with bromine, even in the dark? a. acetylene c. 1-hexanol b. 2-butene d. pentane Which reaction will not produce an alkene? a. 2-chlorohexane is heated with sodium hydroxide b. 2-pentyne and hydrogen are mixed in the presence of a platinum catalyst c. 1-propanol is warmed with butanoic acid in the presence of a strong acid d. 3-propanol is warmed in the presence of a strong acid Short answer 2-chlorobutane + hydroxide ions 2-chlorobutane + sodium hydroxide 2-pentanol is warmed in the presence of a strong acid 2 4 ethanol H SO 2 4 H SO 3-heptanol Reaction type: _______________________ Identifying Polymerization Organic Chemistry Testbank 27 Identify the reaction type: O n C + C HO a. b. O O OH C n CH2 CH2 HO O C O OH addition polymerization esterification c. d. CH2 O CH2 + n condesation polymerization hydrocarbon combustion Identify the reaction type: H H C n C H a. b. CH3 H H C C H CH3 addition polymerization esterification n c. d. condesation polymerization hydrocarbon combustion What monomer was used to produce the polymer: CH3 CH3 CH3 ... ... H3C CH3 C a. H3C C H H C H b. C H H CH3 H3C CH3 C c. H H3C C CH3 C C CH3 d. H H n H2O Organic Chemistry Testbank 28 Condensation Polymerization Which polymer was produced by condensation polymerization? CH3 CH3 O O O O n a. CH3 CH3 CH3 CH3 .... b. CH3 .... CH3 CH CH CH3 H C n c. C CH3 H d. n Long answer: Proteins are the building blocks of the human body. They are composed of chains of amino acids, and make up our skin, nails, hair and connective tissue. The type of protein formed depends upon the sequence of the amino acids in the chain. Some amino acids are given below. CH3 O alanine NH2 NH2 glycine O Organic Chemistry Testbank O a. b. c. SH NH2 NH2 cysteine 29 O Threonine What type of reaction will link these amino acids into a long chained protein? What are the chemical characteristics of these molecules that allow them to form long chains? Pick one of the amino acids to illustrate your answer. The protein in hair will curl around in a helix shape, held together by hydrogen bonds. Draw a dotted line to show where hydrogen bonding could occur if cysteine and threonine were close together on two different protein chains. (2) O SH NH2 cysteine NH2 O OH threonine CH3 Addition Polymerization Which substance will undergo addition polymerization? a. 1-propanol c. propanal b. propanone d. propene Which monomer will produce the polymer on the right? a. 1-pentene b. 2-pentene c. ethylmethylethane d. pentane H H C C CH3 CH2 CH3 Which synthetic polymer is the product of addition polymerization? a. cellulose c. ribonucleic acid (RNA) b. protein d. teflon Short answer addition polymerization reaction with 1-pentene addition polymerization reaction with 1-butene n Organic Chemistry Testbank n 30 2-pentyne Long Answer Questions: When ethene reacts with chlorine in the absence of light, only one product forms. However, if ethene reacts with chlorine in the presence of light, over a long period of time, many products are formed. a. Identify the reaction type when ethene reacts in the absence of light, and write equation to show the product formed. Name and draw the product. (4%) b. Identify the two reaction types when ethene reacts in the presence of light, and write an equation to illustrate each. Name and draw all possible products. (8%)