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Ch14 PTMULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.1) Compounds with the -OH group attached to a saturated alkane-like carbon are known asA) alcohols.B) phenols.C) ethers.D) alkyl halides.E) hydroxyls.1)2) Compounds with an oxygen atom bonded to two organic groups are known asA) ethers.B) hydroxides.C) hydroxyls.D) phenols.E) alcohols.2)3) None of the following organic compounds is very likely to form hydrogen bonds exceptA) alkanes.B) ethers.C) alkenes.D) aromatics.E) alcohols.3)4) Alcohols, ethers, and phenols can be considered organic derivatives of the inorganic compoundA) sodium hydroxide.B) water.C) carbon dioxide.D) ammonia.E) none of these4)1

5) Which molecule shown is an ether?A)5)B)C)D)E)SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.6) What is the inorganic compound that can be considered the structural basis for alcoholsand ethers? Discuss two ways in which the physical properties of alcohols and ethers aresimilar to properties of this compound.6)MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.7) The alcohol which contains only one carbon atom and has the common name of wood alcohol isA) methanol.B) glycol.C) glycerol.D) ethanol.E) phenol.7)8) The common name of CH3 OH is8)A) antifreeze.B) grain alcohol.C) wood alcohol.D) rubbing alcohol.E) glycerol.9) The alcohol which contains two carbon atoms and has the common name of grain alcohol isA) glycol.B) ethanol.C) glycerol.D) phenol.E) methanol.29)

10) The common name of CH3 CH2OH is10)A) wood alcohol.B) grain alcohol.C) antifreeze.D) rubbing alcohol.E) glycerol.11) The molecule with three carbon atoms with an -OH group on each, and used as a moisturizer isA) glycerol.B) methanol.C) ethanol.D) phenol.E) glycol.11)12) The common name of CH2 (OH)CH2 OH is12)A) rubbing alcohol.B) antifreeze.C) wood alcohol.D) grain alcohol.E) glycerol.13) Which molecule shown is a glycol?A)13)B)C)D)E)3

14) The common name of 1,2-ethanediol isA) wood alcohol.B) glycerol.C) antifreeze.D) rubbing alcohol.E) grain alcohol.14)15) The common name of CH3 CH(OH)CH3 in water solution is15)A) wood alcohol.B) rubbing alcohol.C) grain alcohol.D) antifreeze.E) glycerol.16) What is the IUPAC name of the compound shown?16)A) 2,2-dimethyl-4-butanolB) 4-methyl-2-pentanolC) 2-methyl-4-pentanolD) 4,4-dimethyl-2-butanolE) 2-isohexanol17) The IUPAC name of the alcohol shown is17)A) primary 2,3-dimethylpentanol.B) 2,3-dimethyl-5-pentanol.C) 3,4-dimethyl-1-pentanol.D) 3,4-dimethyl-5-pentanol.E) 2,3-dimethyl-1-pentanol.18) What is the IUPAC name of the compound shown?18)A) isooctanolB) 3-ethyl-1-hexanolC) 4,4-diethyl-1-butanolD) 3-ethyl-6-hexanolE) 4-ethyl-1-hexanol4

19) The name of the alcohol shown is19)A) branched 3-octanolB) secondary 2,4,4-pentanolC) 2,2,4-trimethyl-3-pentanolD) 2,4,4-trimethyl-3-pentanolE) trimethyl-3-pentanol20) What is the IUPAC name of the compound shown?20)A) 2-hydroxy-1,4-butanediolB) butylene glycolC) butanetriolD) 1,3,4-butanetriolE) 1,2,4-butanetriol21) Compounds of the type R3 C-OH are referred to as alcohols.21)A) secondaryB) primaryC) quaternaryD) tertiaryE) none of the above22) Compounds of the type R2 CH-OH are referred to as alcohols.22)A) quaternaryB) tertiaryC) primaryD) secondaryE) none of the above23) Compounds of the type RCH2-OH are referred to as alcohols.A) secondaryB) tertiaryC) quaternaryD) primaryE) none of the above523)

24) Which molecule shown is a primary alcohol?A)24)B)C)D)E)6

25) Which molecule shown is a secondary alcohol?A)25)B)C)D)E)7

26) Which molecule shown is a tertiary alcohol?A)26)B)C)D)E)27) Which compound is a tertiary alcohol?A) 1-propanolB) 3-methyl-2-hexanolC) 2-methyl-2-hexanolD) 2-methyl-1-hexanolE) 3-hexanol27)28) The molecule shown is a alcohol because .28)A) primary; its -OH group is on the end of the moleculeB) tertiary; the -OH is bonded to the number 3 carbonC) secondary; each group bonded to the hydroxyl carbon contains two carbon atomsD) secondary; the carbon bonded to the -OH group is bonded to two other carbonsE) primary; it has one -OH group8

29) An alcohol is classified as primary, secondary or tertiary based onA) the number of carbon atoms bonded to the carbon bearing the OH group.B) the number of hydrogens present in the alcohol.C) the mass of the alcohol.D) the number of carbon atoms in the molecule.E) the number of OH groups present in the molecule.29)30) How many isomeric alcohols exist with the formula C4 H10OA) 3B) 4C) 530)D) 1E) 231) The relatively high boiling point of alcohols in relation to their molecular weights is the result ofA) ionic bonding.B) London forces.C) dipolar forces.D) covalent bonding.E) hydrogen bonding.31)32) All of the following properties of alcohols are affected by hydrogen bonding exceptA) boiling point.B) molecular weight.C) miscibility with water.D) ability to dissolve polar substances.E) none of the above32)33) Which compound is the most soluble in water?A) CH3 CH2 CH2 OH33)B) CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH3C) CH3 CH2 CH3D) CH3 CH2 CH2 CH3E) CH3 CH2 CH2 CH2 OH34) Which compound is the least soluble in water?A) CH3 CH2 CH334)B) CH3 CH2 CH2 CH2 OHC) CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH3D) CH3 CH2 CH2 OHE) CH3 CH2 CH2 CH335) Which compound has the lowest boiling point?A) CH3 CH2 CH2 CH2 CH335)B) CH3 CH2 CH2 CH3C) CH3 CH2 CH2 CH2 CH2 OHD) CH3 CH2 CH2 OHE) CH3 CH2 CH2 CH2 OH9

36) Which compound has the highest boiling point?A) CH3 CH2 CH2 CH2 CH2 OH36)B) CH3 CH2 CH2 OHC) CH3 CH2 CH2 CH2 OHD) CH3 CH2 CH2 CH3E) CH3 CH2 CH2 CH2 CH337) Which of the following is the most soluble in water?A) methanolB) 1-butanolC) 1-decanolD) diethyl etherE) decane37)38) Which of the following is the most soluble in water?A) CH3 CH2 CH2 O CH338)B) CH3 CH2 O CH2 CH3C) CH3 CH2 CH2 CH2 OHD) CH3 CH2 CH2 CH3E) OH CH2 CH2 CH2 OH39) Which of the following would be the least soluble in water?A) CH3 CH2 CH2 CH2 OH39)B) OH CH2 CH2 CH2 OHC) CH3 CH2 O CH2 CH3D) CH3 CH2 CH2 O CH3E) CH3 CH2 CH2 CH340) Which compound has the lowest boiling point?A) CH3 CH2 O CH2 CH340)B) CH3 CH2 CH2 O CH3C) CH3 CH2 CH2 OHD) CH3 CH2 CH2 CH2 OHE) CH3 CH2 O CH341) Which compound has the highest boiling point?A) CH3 CH2 O CH341)B) CH3 CH2 CH2 O CH3C) CH3 CH2 CH2 CH2 OHD) CH3 CH2 O CH2 CH3E) CH3 CH2 CH2 OH10

42) Which compound would you expect to have the lowest boiling point?A) dimethyl etherB) ethanolC) waterD) methanolE) methane42)43) Which alcohol is most soluble in waterA) ethanolB) 1-hexanolC) 1-pentanolD) 1-propanolE) 1-butanol43)SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.44) Describe and explain the change in water solubility of straight-chain primary alcohols asmolar mass increases.44)MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.45) The product of dehydration of an alcohol is anA) alkane.B) alkene.C) ether.45)D) aldehyde.46) Oxidation of an alcohol group results in formation of a(an) group.A) aromaticB) carbonylC) etherD) hydroxylE) aromatic.46)E) alkyl47) The symbol [O] written above a reaction arrow meansA) oxygen is removed from one of the reactants during the reaction.B) that a reduction reaction is occurring and oxygen is liberated.C) the reaction consumes oxygen from the atmosphere.D) that an oxidation reaction is occurring.E) none of the above47)48) Oxidation of R2 CH OH will produce48)A) a ketone.B) a carboxylic acid.C) an aldehyde.D) an alkene.E) no reaction.49) Oxidation of a tertiary alcohol will produceA) a carboxylic acid.B) an aldehyde.C) a ketone.D) an alkene.E) no reaction.49)11

50) Treatment of CH3 CH2 CH2 OH with a limited amount of oxidizing agent will produce50)A) an alkene.B) an aldehyde.C) a ketone.D) a carboxylic acid.E) no reaction.51) Treatment of CH3 CH2 OH with an excess amount of oxidizing agent will produce51)A) a carboxylic acid.B) an aldehyde.C) a ketone.D) an alkene.E) no reaction.52) Gentle oxidation of a primary alcohol will produceA) an ether.B) an alkene.C) a ketone.D) an aldehyde.E) a carboxylic acid.52)53) Gentle oxidation of a secondary alcohol will produceA) a carboxylic acid.B) a ketone.C) an alkene.D) an aldehyde.E) an ether.53)54) Strong oxidation of a primary alcohol will produceA) an alkene.B) an ether.C) a ketone.D) an aldehyde.E) a carboxylic acid.54)55) Treatment of the molecule shown with a strong oxidizing agent will produce55)A) an aldehyde.B) an alkene.C) a ketone.D) a carboxylic acid.E) no reaction.12

56) Treatment of the molecule shown with a dehydrating agent will produce56)A) a carboxylic acid.B) an alkene.C) a ketone.D) an aldehyde.E) no reaction.57) The major product obtained from dehydration of 2-hexanol isA) 2-hexene.B) 1-hexene.C) 3-hexene.D) 2-hexanone.E) 2-hexanal.57)58) Which alcohol should be used to produce 2-methyl-3-pentene by dehydration?A) 4-methyl-2-pentanolB) 2-methyl-3-pentanolC) 1-propanol and 2-propanolD) 2-methyl-1-pentanolE) 4-methyl-1-pentanol58)59) The major product resulting from the dehydration of59)will beA) 1-pentene.B) n-pentane.C) 2-pentene.D) 1,3-pentanediol.E) 1,2-pentanediol.60) What is the product of the oxidation of a secondary alcohol?A) ketoneB) carboxylic acidC) aldehydeD) alkyneE) alkene60)SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.61) Oxidation reactions are defined differently in organic chemistry than they are in inorganicchemistry. Give the definition of both and explain their similarities.1361)

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.62) The simplest aromatic alcohol, recognized by its strong medicinal odor and used as a disinfectant isA) glycol.B) methanol.C) phenol.D) ethanol.E) glycerol.62)63) Which compound is sometimes called carbolic acid?A) phenolB) ethanolC) glycerol63)D) etherE) methanol64) Compounds with the -OH group attached to an aromatic ring are known asA) alkyl halides.B) alcohols.C) ethers.D) hydroxyls.E) phenols.64)65) Which molecule would be considered a derivative of phenol?A)65)B)C)D)E)66) Which molecule would be the most acidic?A) 1-hexanolB) dimethyl etherC) waterD) phenolE) ethanol66)67) When phenol acts as an acid, a ion is produced.A) phenolateB) benzylC) phenyl1467)D) phenoxideE) phenolic

68) The molecule CH3 CH2 CH2 O CH2 CH3 can be classified as68)A) an ether.B) an alcohol.C) an aldehyde.D) an alkane.E) a ketone.69) All of the following are properties of ethers exceptA) Except for flammability, ethers are relatively unreactive.B) Low molecular weight ethers are flammable and evaporate easily.C) The molecules are polar, but do not form hydrogen bonds with other ether molecules.D) Ethers dissolve readily in water in all proportions.E) Ethers dissolve many organic compounds readily.69)70) What is the IUPAC name of the compound shown?CH3 CH2 CH2 O CH370)A) isobutyl etherB) 1,2-etherbutaneC) butyl etherD) methyl propyl etherE) propyl methyl ether71) Ether molecules are polar, but do not form hydrogen bonds with other ether molecules becauseA) ether molecules are so reactive that they never have an opportunity to form hydrogen bonds.B) the molecules are generally too large.C) there are too many hydrogen atoms on the molecules to bond with just one oxygen atom.D) there is no hydrogen atom bonded to the oxygen.E) only binary compounds form hydrogen bonds.71)72) Organic compounds which are sulfur analogs of alcohols are referred to asA) halides.B) sulfuric alcohols.C) thiols.D) carbonyls.E) disulfides72)73) Which property of thiols makes them useful as additives to natural gas?A) disinfectantB) colorC) solubilityD) odorE) flammability73)74) The reaction conditions which would result in formation of disulfides from thiols areA) strong acid.B) mild oxidizing.C) gentle heat.D) strong heat.E) none of these74)15

75) What is the IUPAC name of the compound shown?75)A) 1-methyl-1-propanethiolB) 3-thiobutanolC) 2-thiobutaneD) 1-methyl-1-thiopropaneE) 2-butanethiol76) When a thiol is oxidized the product isA) a ketone.B) an alkeneC) sulfuric acid.D) a disulfide.E) an aldehyde.76)77) The most characteristic feature of thiols isA) odorB) solubility in waterC) colorD) reactivity with waterE) boiling point77)78) What is the IUPAC name of the compound shown?78)A) 1,2-dichloro-1,2-dimethylethaneB) di(chloroethane)C) 2,3-dichlorbutaneD) 1,2-dichloro-1-methylpropaneE) 2,3-dichlorobutane79) What is the IUPAC name for the compound shown?A) 3-bromo-2-chloro-3-methylpentaneB) bromochlorohexaneC) 3-bromo-4-chloro-3-methylpentaneD) 3-bromomethyl-2-chloro-pentaneE) none of these1679)

80) All of the following can be classified as alkyl halides exceptA) styrene, the monomer used to make foam coffee cups.B) CFC's used as refrigerants.C) chloroform, an anesthetic.D) thyroxine, a thyroid hormone.E) methyl bromide, an insecticide.80)MATCHING. Choose the item in column 2 that best matches each item in column 1.Match the following.81) glycolA) -OC2 H581)82) alkoxy groupB)82)83) disulfide84) thiol83)C)D) CH3 CH2 CH2 S S CH2 CH31784)

Answer KeyTestname: UNTITLED11)2)3)4)5)6)AAEBCAlcohols and ethers can be considered to be derivatives of water. Similar physical properties include:Polarity: Water is a very polar molecule; alcohols and ethers also display polarity.Boiling point: Water has a higher boiling point than predicted on the basis of its molar mass. Alcohols also share thischaracteristic, but ethers do not.Solubility: Water is miscible with other polar liquids; alcohols and ethers of low molar mass are miscible with waterand with each other because of their polarity.7) A8) C9) B10) B11) A12) B13) C14) C15) B16) B17) C18) E19) C20) E21) D22) D23) D24) A25) C26) A27) C28) D29) A30) B31) E32) B33) A34) C35) B36) A37) A38) E39) E40) E41) C42) E43) A18

Answer KeyTestname: UNTITLED144) As the molar mass of these alcohols increases, the water solubility decreases. This occurs because the polarity of thehydroxyl group, which is the reason for the interaction with the polar water molecules, becomes less important as thesize of the nonpolar hydrocarbon portion of the molecule increases.45) B46) B47) D48) A49) E50) B51) A52) D53) B54) E55) E56) B57) A58) A59) C60) A61) The inorganic definition of oxidation is loss of electrons. The organic definition is formation of additional bondsbetween carbon and oxygen (or a decrease in the number of carbon-hydrogen bonds). These are similar because whencarbon forms a bond with electronegative oxygen, it essentially loses some of its attraction for its electrons.62) C63) A64) E65) C66) D67) D68) A69) D70) D71) D72) C73) D74) B75) E76) D77) A78) E79) A80) A81) C82) A83) D84) B19

7)The alcohol which contains only one carbon atom and has the common name of wood alcohol is A)methanol. B)glycol. C)glycerol. D)ethanol. E)phenol. 7) 8)The common name of CH3OH is A)antifreeze. B)grain alcohol. C)wood alcohol. D)rubbing alcohol. E)glycerol. 8) 9)The alcohol which contains two carbon atoms and has the common name of grain .

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