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General, Organic & Biological Chemistry, 5e (Timberlake) Chapter 13 Alcohols, Phenols, Thiols, and Ethers 13.1 Multiple-Choice Questions 1) Which one of the following compounds is an alcohol? A) OH | CH3 - CH - CH3 B) O CH3 - CH2 - CH C) CH3 - CH = CH - CH2 - CH3 D) CH3 - CH2 - O - CH2 - CH3 E) CH3 - SH Answer: A Objective: 13.1 Global Outcomes: GO2 2) The compound CH3 - CH2 - SH is in the organic family known as A) ethers B) thiols C) alcohols D) sulfides E) amino acids Answer: B Objective: 13.1 Global Outcomes: GO2 3) Alcohols contain which functional group? A) amine B) amide C) hydroxyl D) thiol Answer: C Objective: 13.1 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 4) What is the IUPAC name for this compound? A) 3-methyl-1-hexanol B) 3-methyl-1-pentanol C) 3-methyl-5-pentanol D) 3-methyl-6-hexanol E) 3-methylpentanol Answer: B Objective: 13.1 Global Outcomes: GO2 5) Which of the following is the IUPAC name for the compound below? A) 5-methyl-4-hexanol B) 5-methyl-4-pentanol C) 2-methyl-3-hexanol D) 2-methyl-3-pentanol E) 2-methyl-3-heptanol Answer: C Objective: 13.1 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 6) The condensed structural formula for 2,3-dichloro-4-methylcyclohexanol is A) B) C) D) E) Answer: D Objective: 13.1 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 7) What is the IUPAC name of this compound? OH | CH3 - C - CH3 | CH3 A) butanol B) propanol C) 2-propanol D) 2-methylbutanol E) 2-methyl-2-propanol Answer: E Objective: 13.1 Global Outcomes: GO2 8) Which one of the following compounds is a thiol? A) OH | CH3 - CH - CH3 B) O CH3 - CH2 - CH C) CH3 - CH = CH - CH2 - CH3 D) CH3 - CH2 - O - CH2 - CH3 E) CH3 - SH Answer: E Objective: 13.1 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 9) What is the name for this compound? A) 2-bromo-5-ethylcyclohexanol B) 2-bromo-5-ethylphenol C) 4-bromo-1-ethyl-5-phenol D) 6-bromo-3-ethylphenol E) 2-bromo-5-methylphenol Answer: B Objective: 13.1 Global Outcomes: GO2 10) What is the name for this compound? A) cyclopentanol B) cyclohexanol C) cyclobenzenol D) phenol E) glycerol Answer: D Objective: 13.1 Global Outcomes: GO2 11) A phenol has an -OH group bonded to a(n) A) singly substituted or unsubstituted carbon B) disubstituted carbon C) trisubstituted carbon D) aromatic carbon E) tetrasubstituted carbon Answer: D Objective: 13.1 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 12) Thiols have structures similar to alcohols except that they contain A) three alcohol groups B) more than one carbon C) sulfur in place of oxygen in the functional group D) lithium in place of oxygen in the functional group E) nitrogen in place of oxygen in the functional group Answer: C Objective: 13.1 Global Outcomes: GO2 13) Methanol is used in all the following except A) making plastics B) racing fuel C) alcoholic beverages D) solvents E) paint remover Answer: C Objective: 13.1 Global Outcomes: GO2 14) 1,2-ethanediol (ethylene diol) has uses that include A) antifreeze B) solvent for paint C) production of synthetic fibers D) solvent for ink E) All of the above Answer: E Objective: 13.1 Global Outcomes: GO2 15) What is the IUPAC name for CH3 - CH2 - CH2 - SH? A) 1-propanethiol B) 2-propanethiol C) 1-butanethiol D) 2-butanethiol E) propyl thiol Answer: A Objective: 13.1 Global Outcomes: GO2 16) Thiols are strong-smelling compounds responsible for A) fruity odors B) sharp odors C) flowery odors D) skunky or bad smelling odors E) salty odors Answer: D Objective: 13.1 Global Outcomes: GO2 17) What is the name of this compound? Copyright © 2016 Pearson Education, Inc A) cyclopentyl propyl ether B) cyclopentyl propyl ketone C) 1-cyclopropyl-1-propylalcohol D) propylcyclopentanol E) 3-cyclopentylpropanol Answer: A Objective: 13.2 Global Outcomes: GO2 18) The common name for the compound CH3 - CH2 - CH2 - O - CH2 - CH3 is A) 3-pentanol B) ethyl propyl ether C) 3-hexanol D) 3-ether pentane E) ethyl propyl ketone Answer: B Objective: 13.2 Global Outcomes: GO2 19) The common name of CH3 - CH2 - O - CH2 - CH3 is A) dimethyl ether B) diethyl ether C) 2-etherbutane D) butyl ether E) dibutyl ether Answer: B Objective: 13.2 Global Outcomes: GO2 20) Why has diethyl ether been replaced as a general anesthetic? A) It causes unpleasant side effects in many patients B) It is slightly polar C) It can hydrogen bond to water D) It is not very reactive E) It is slightly soluble in water Answer: A Objective: 13.2 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 21) What is the common name of the ether that is an isomer of 2-propanol? A) isopropyl ether B) diethyl ether C) dimethyl ether D) ethyl methyl ether E) 1-propanol Answer: D Objective: 13.2 Global Outcomes: GO2 22) What is the common name of the ether that is an isomer of 1-butanol? A) isopropyl ether B) diethyl ether C) dimethyl ether D) ethyl methyl ether E) butyl ether Answer: B Objective: 13.2 Global Outcomes: GO2 23) The alcohol in this list that would be most soluble in water is A) ethanol B) 1-butanol C) 1-pentanol D) 1-hexanol E) 1-heptanol Answer: A Objective: 13.3 Global Outcomes: GO2 24) Which of the following compounds is a weak acid? A) ethanol B) ethanal C) phenol D) cyclohexanol E) acetone Answer: C Objective: 13.3 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 25) Which of the following compounds is a secondary alcohol? A) CH3 - CH - O - CH3 | CH3 B) CH3OH C) OH | CH3 - CH2 - C - CH3 | CH3 D) CH3 | CH3 - C - CH3 | OH E) CH3 - CH - OH | CH3 Answer: E Objective: 13.3 Global Outcomes: GO2 26) In a tertiary alcohol, how many alkyl groups are attached to the carbon atom bonded to the -OH group? A) none B) one C) two D) three E) four Answer: D Objective: 13.3 Global Outcomes: GO2 27) A primary alcohol has a hydroxyl group bonded to a(n) A) singly substituted or unsubstituted carbon B) disubstituted carbon C) trisubstituted carbon D) aromatic carbon Answer: A Objective: 13.3 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 28) A secondary alcohol has a hydroxyl group bonded to a(n) A) singly substituted or unsubstituted carbon B) disubstituted carbon C) trisubstituted carbon D) aromatic carbon Answer: B Objective: 13.3 Global Outcomes: GO2 29) A tertiary alcohol has a hydroxyl group bonded to a(n) A) singly substituted or unsubstituted carbon B) disubstituted carbon C) trisubstituted carbon D) triple-bonded carbon E) double bonded carbon Answer: C Objective: 13.3 Global Outcomes: GO2 30) What kind of bonds alcohols form between individual molecules? A) oxygen bonds B) hydrogen bonds C) single bonds D) carbon bonds E) ionic bonds Answer: B Objective: 13.3 Global Outcomes: GO2 31) The dehydration of an alcohol in the presence of a strong acid yields A) an alkane B) an alkene C) a ketone D) an alcohol E) an aldehyde Answer: B Objective: 13.4 Global Outcomes: GO2 32) The dehydration product of CH3 - CH2 - CH2 - OH in the presence of acid is A) CH2 = C = CH2 B) cyclopropane C) cyclopropene D) propene E) propyne Answer: D Objective: 13.4 Global Outcomes: GO2 33) When 2-methyl-2-butanol undergoes dehydration in acid, one product is A) 2-methyl-2-butene B) 2-methylbutanone C) 2-pentanone D) 2-methylbutanal E) hexene Answer: A Objective: 13.4 10 Copyright © 2016 Pearson Education, Inc Global Outcomes: GO2 34) In the oxidation of an alcohol to a ketone, there is A) a loss of hydrogen B) a loss of oxygen C) a loss of carbon D) a gain of hydrogen E) a gain of oxygen Answer: A Objective: 13.4 Global Outcomes: GO2 35) What is the product when this compound undergoes oxidation? CH3 | CH3 - C - CH2 - CH2 - OH | CH3 A) hexanal B) 2,2-dimethylbutanal C) 2,2-dimethyl-4-butanone D) 3,3-dimethyl-1-butanone E) 3,3-dimethylbutanal Answer: E Objective: 13.4 Global Outcomes: GO2 36) What type of alcohol undergoes oxidation to yield a ketone? A) primary alcohol B) both primary and secondary alcohols C) secondary alcohol D) all classes of alcohols E) both secondary and tertiary alcohols Answer: C Objective: 13.4 Global Outcomes: GO2 11 Copyright © 2016 Pearson Education, Inc 37) Tertiary alcohols cannot be oxidized because A) there are no oxygen atoms to remove from the alcohol carbon B) there are no hydrogen atoms attached to the alcohol carbon C) the alcohol carbon is bonded to four groups so no oxygen can be added to it D) the alcohol carbon is bonded to four groups so no hydrogen can be added to it E) the alcohol carbon is too electronegative to have hydrogen removed from it Answer: B Objective: 13.4 Global Outcomes: GO2 38) What type of alcohol is resistant to oxidation? A) primary B) secondary C) tertiary D) quaternary E) none Answer: C Objective: 13.4 Global Outcomes: GO2 39) What is the product when the following compound is oxidized? A) a ketone B) an alkene C) an aldehyde D) an ether E) an alkane Answer: A Objective: 13.4 Global Outcomes: GO2 12 Copyright © 2016 Pearson Education, Inc 40) Which compound will undergo oxidation to yield the following? A) pentanol B) cyclopentane C) cyclopentanol D) methylcyclobutanol E) cyclopentene Answer: C Objective: 13.4 Global Outcomes: GO2 41) In the dehydration of an alcohol to an alkene, what is produced in addition to the alkene? A) water B) hydrogen C) oxygen D) carbon dioxide E) carbon monoxide Answer: A Objective: 13.4 Global Outcomes: GO2 42) When a primary alcohol is completely oxidized, the product is A) another alcohol B) a carboxylic acid C) an aldehyde D) an alkane E) a ketone Answer: B Objective: 13.4 Global Outcomes: GO2 43) Methanol is toxic because it is by the liver to carboxylic acids A) reduced B) protonated C) oxidized D) conjugated E) hydrated Answer: C Objective: 13.4 Global Outcomes: GO2 13 Copyright © 2016 Pearson Education, Inc 44) Secondary alcohols are oxidized to A) carboxylic acids B) ketones C) aldehydes D) esters E) ethers Answer: B Objective: 13.4 Global Outcomes: GO2 45) Tertiary alcohols are oxidized to A) secondary alcohols B) ketones C) aldehydes D) carboxylic acids E) None of the above Answer: E Objective: 13.4 Global Outcomes: GO2 46) Thiols can be gently oxidized to A) disulfides B) aldehydes C) ketones D) carboxylic acids E) thioethers Answer: A Objective: 13.4 Global Outcomes: GO2 47) The dehydration product of OH │ CH3 - CH- CH3 in the presence of acid is A) CH2 = C = CH2 B) cyclopropane C) cyclopropene D) propene E) propyne Answer: D Objective: 13.4 Global Outcomes: GO2 14 Copyright © 2016 Pearson Education, Inc 13.2 True/False Questions 1) Alcohols, ethers, and phenols contain oxygen with only single bonds Answer: TRUE Objective: 13.1 Global Outcomes: GO2 2) Alcohols, ethers, and thiols contain oxygen atoms Answer: FALSE Objective: 13.1 Global Outcomes: GO2 3) Thiols usually have sweet odors Answer: FALSE Objective: 13.1 Global Outcomes: GO2 4) 1,2,3-propanetriol is obtained during the manufacture of soap Answer: TRUE Objective: 13.1 Global Outcomes: GO2 5) Glycerin strongly attracts and holds water, a property that makes it useful as a skin softener in cosmetics Answer: TRUE Objective: 13.1 Global Outcomes: GO2 6) Diethyl ether has been replaced by halogenated anesthetics, which have fewer side effects Answer: TRUE Objective: 13.2 Global Outcomes: GO2 7) Ethers can only be straight chain compounds Answer: FALSE Objective: 13.2 Global Outcomes: GO2 8) The following compound is ethyl propyl ether Answer: TRUE Objective: 13.2 Global Outcomes: GO2 15 Copyright © 2016 Pearson Education, Inc 9) Alcohols form hydrogen bonds; this accounts for their higher boiling points when compared to similar-sized alkanes Answer: TRUE Objective: 13.3 Global Outcomes: GO2 10) The oxygen atom in alcohols decreases water solubility of the molecule Answer: FALSE Objective: 13.3 Global Outcomes: GO2 11) Phenols behave as weak acids in water Answer: TRUE Objective: 13.3 Global Outcomes: GO2 12) Alcohols can form hydrogen bonds Answer: TRUE Objective: 13.3 Global Outcomes: GO2 13) Heptanol is a water soluble alcohol Answer: FALSE Objective: 13.3 Global Outcomes: GO2 14) A secondary alcohol can be easily oxidized to a carboxylic acid Answer: FALSE Objective: 13.4 Global Outcomes: GO2 15) Cycloalkanols are straight chain alcohols Answer: FALSE Objective: 13.4 Global Outcomes: GO2 16) Alcohols can be dehydrated to form alkenes Answer: TRUE Objective: 13.4 Global Outcomes: GO2 17) Primary alcohols can be oxidized to either aldehydes or ketones Answer: FALSE Objective: 13.4 Global Outcomes: GO2 18) Secondary alcohols can be oxidized to ketones Answer: TRUE Objective: 13.4 Global Outcomes: GO2 19) Tertiary alcohols are easily oxidized Answer: FALSE Objective: 13.4 Global Outcomes: GO2 13.3 Matching Questions Identify the product, if any, that would form in each of the following reactions 16 Copyright © 2016 Pearson Education, Inc A) O CH3 - CH2 - C - CH3 B) O CH3 - CH2 - CH 1) CH3 - CH2 - CH2 - OH Objective: 13.4 Global Outcomes: GO2 2) CH3 - CH2 - CH - OH | CH3 Objective: 13.4 Global Outcomes: GO2 Answers: 1) B 2) A Match the structural formula with the correct functional group A) thiol B) alcohol C) ether 3) CH3 - CH2 - OH Objective: 13.1 Global Outcomes: GO2 4) CH3 - CH2 - O - CH3 Objective: 13.1 Global Outcomes: GO2 5) CH3 - CH2 - SH Objective: 13.1 Global Outcomes: GO2 Answers: 3) B 4) C 5) A Select the correct name for the following A) propanethiol B) 1-ethyl-3- hydroxycyclohexene C) propane sulfide D) 3-ethylphenol E) diethyl ether 6) CH3 - CH2 - CH2 - SH Objective: 13.2 Global Outcomes: GO2 7) CH3 - CH2 - O - CH2 - CH3 Objective: 13.2 17 Copyright © 2016 Pearson Education, Inc Global Outcomes: GO2 8) Objective: 13.2 Global Outcomes: GO2 Answers: 6) A 7) E 8) D 18 Copyright © 2016 Pearson Education, Inc Classify the alcohols shown in column as primary, secondary, or tertiary A) secondary B) primary C) tertiary 9) CH3 - CH2 - OH Objective: 13.3 Global Outcomes: GO2 10) CH3 | CH3 - C - CH2 - OH | CH3 Objective: 13.3 Global Outcomes: GO2 11) OH | CH3 - CH - CH3 Objective: 13.3 Global Outcomes: GO2 12) Objective: 13.3 Global Outcomes: GO2 13) CH3 | CH3 - C - CH2 - CH3 | OH Objective: 13.3 Global Outcomes: GO2 Answers: 9) B 10) B 11) A 12) A 13) C 19 Copyright © 2016 Pearson Education, Inc ... 13. 1 Global Outcomes: GO2 2) Alcohols, ethers, and thiols contain oxygen atoms Answer: FALSE Objective: 13. 1 Global Outcomes: GO2 3) Thiols usually have sweet odors Answer: FALSE Objective: 13. 1... Objective: 13. 3 Global Outcomes: GO2 12) Alcohols can form hydrogen bonds Answer: TRUE Objective: 13. 3 Global Outcomes: GO2 13) Heptanol is a water soluble alcohol Answer: FALSE Objective: 13. 3 Global... Objective: 13. 3 Global Outcomes: GO2 10) CH3 | CH3 - C - CH2 - OH | CH3 Objective: 13. 3 Global Outcomes: GO2 11) OH | CH3 - CH - CH3 Objective: 13. 3 Global Outcomes: GO2 12) Objective: 13. 3 Global
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