CHAPTER 15 Aldehydes and Ketones Test Bank TYPE I MULTIPLE-CHOICE QUESTIONS In each of the following multiple-choice questions, place the letter of the correct response in the blank at the left. There is only one correct response for each question. 15.1 c Which of the following structural features is common to both aldehydes and ketones? O a) C OH O b) C H O c) C O d) 15.2 164 a C OR Which of the following structural features is possessed by aldehydes but not ketones? a) At least one hydrogen atom is bonded to the carbonyl carbon atom. b) At least one hydroxyl group is bonded to the carbonyl carbon atom. c) The carbonyl carbon atom is bonded to two other carbon atoms. d) The carbonyl carbon atom is part of a ring structure. Copyright Houghton Mifflin Company. All rights reserved. Test Bank Copyright Houghton Mifflin Company. All rights reserved. Chapter 15: Aldehydes and Ketones 165 166 Chapter 15: Aldehydes and Ketones 15.3 b [Algorithmic]Which of the following statements concerning aldehydes and ketones is correct? a) Cyclic aldehydes, but not cyclic ketones, exist. b) Cyclic ketones, but not cyclic aldehydes, exist. c) Both cyclic aldehydes and cyclic ketones exist. d) Neither cyclic aldehydes nor cyclic ketones exist. 15.4 b The simplest aldehyde and ketone contain, respectively, how many carbon atoms? a) 1 and 1 b) 1 and 3 c) 2 and 2 d) 2 and 3 Test Bank O 15.5 d The IUPAC name for the compound CH3 CH2 C a) acetaldehyde. b) propionaldehyde. c) 1-ethanal. d) propanal. O H is CH3 15.6 c The IUPAC name for the compound CH3 C CH2 CH CH3 is a) 2-methyl-2-pentanone. b) 2-methyl-4-pentanone. c) 4-methyl-2-pentanone. d) 2-methyl-4-pentaketone. 15.7 a [Algorithmic]What is the IUPAC name of the aldehyde whose common name is formaldehyde? a) methanal b) ethanal c) propanal d) 2-methylpropanal 15.8 c Two other acceptable names for the compound acetone are a) propanone and diethyl ketone. b) ethanone and methyl ethyl ketone. c) propanone and dimethyl ketone. d) ethanone and diethyl ketone. 15.9 c How many saturated noncyclic six-carbon ketones are there? a) two b) four c) six d) eight Copyright Houghton Mifflin Company. All rights reserved. Test Bank Chapter 15: Aldehydes and Ketones 167 15.10 d What two functional groups are never found at the end of a carbon chain? a) alcohol and aldehyde b) ether and aldehyde c) alcohol and ketone d) ether and ketone 15.11 d [Algorithmic]Which of the following statements concerning hydrogen bonding is correct? a) Ketone molecules can hydrogen bond to each other. b) Aldehyde molecules can hydrogen bond to each other. c) Both ketone molecules and aldehyde molecules can hydrogen bond to each other. d) Neither ketone molecules nor aldehyde molecules can hydrogen bond to each other. 15.12 d [Algorithmic]Comparison of the boiling points of aldehydes and ketones with those of other compounds of similar molecular mass shows that they are a) lower than those of alcohols and alkanes. b) higher than those of alcohols and alkanes. c) higher than those of alcohols but lower than those of alkanes. d) higher than those of alkanes but lower than those of alcohols. 15.13 b Ketones may be prepared by the oxidation of a) primary alcohols. b) secondary alcohols. c) tertiary alcohols. d) aldehydes. 15.14 a [Algorithmic]Which of the following statements concerning the oxidation of aldehydes and ketones is correct? a) Aldehydes readily undergo oxidation and ketones are resistant to oxidation. b) Ketones readily undergo oxidation and aldehydes are resistant to oxidation. c) Both aldehydes and ketones readily undergo oxidation. d) Both aldehydes and ketones are resistant to oxidation. 15.15 a The oxidizing agent in the Tollen’s test for the presence of an aldehyde is a) Ag+ b) Ag c) Cu2+ d) Cu2O Copyright Houghton Mifflin Company. All rights reserved. 168 Chapter 15: Aldehydes and Ketones Test Bank O 15.16 a What is the product when CH3 C CH3 is reduced using H2 gas and a Ni catalyst? OH a) CH3 CH CH3 OH b) CH2 C CH3 O c) CH3 C H d) CH2 CH CH3 15.17 c When an alcohol molecule adds across a carbon-oxygen double bond of an aldehyde or ketone, the a) H atom from the alcohol bonds to the carbonyl carbon atom. b) OH portion from the alcohol bonds to the carbonyl oxygen atom. c) OR portion from the alcohol bonds to the carbonyl carbon atom. d) OH portion from the alcohol bonds to the carbonyl carbon atom. 15.18 a A hemiacetal is a compound in which a) a hydroxy group and an alkoxy group are attached to the same carbon atom. b) a hydroxyl group and an alkoxy group are attached to adjacent carbon atoms. c) two alkoxy groups are attached to the same carbon atom. d) two alkoxy groups are attached to adjacent carbon atoms. 15.19 a The structural difference between a hemiacetal and an acetal is the replacement of a a) –OH group with an –OR group. b) H atom with an –OR group. c) H atom with a –OH group. d) –OR group with a –OH group. 15.20 d Hydrolysis of an acetal in an acid solution would yield a) an aldehyde, a ketone, and one alcohol. b) an aldehyde, a ketone, and two alcohols. c) an aldehyde or a ketone and one alcohol. d) an aldehyde or a ketone and two alcohols. Copyright Houghton Mifflin Company. All rights reserved. Test Bank Chapter 15: Aldehydes and Ketones 169 TYPE II MULTIPLE-CHOICE QUESTIONS In each of the following multiple-choice questions, place the letter of the correct response in the blank at the left. There may be more than one correct response for a question (choice d) or no correct response for a question (choice e). 15.21 b Which of the following statements concerning a carbonyl group is incorrect? a) It is polar. b) It contains two oxygen atoms and one carbon atom. c) It is present in both aldehydes and ketones. d) more than one correct response e) no correct response 15.22 d Which of the following is a correct notation for the aldehyde functional group? a) CHO O b) C H O c) C d) more than one correct response e) no correct response 15.23 a Which of the following aldehydes is paired with an incorrect IUPAC name? Cl O a) CH3 CH CH2 C Cl b) CH3 CH2 CH Cl c) CH3 CH H ; 2-chloro-4-butanal O C Cl O CH C H ; 2-chlorobutanal H ; 2,3-dichlorobutanal d) more than one correct response e) no correct response 15.24 b Which of the following pairings of aldehyde common and IUPAC names is correct? a) acetaldehyde and methanal b) 2-methylbutyraldehyde and 2-methylbutanal c) formaldehyde and ethanal d) more than one correct response e) no correct response Copyright Houghton Mifflin Company. All rights reserved. 170 Chapter 15: Aldehydes and Ketones 15.25 c Which of the following pairings of ketone IUPAC and common names is correct? a) 2-methyl-3-pentanone and methyl propyl ketone b) 3-methyl-2-pentanone and isopropyl methyl ketone c) propanone and dimethyl ketone d) more than one correct response e) no correct response 15.26 d Which of the following compounds is a constitutional isomer of 2-pentanone? a) 3-methyl-2-pentanone b) 3-methyl-2-butanone c) isopropyl methyl ketone d) more than one correct response e) no correct response 15.27 a Which of the following compounds contains 7 carbon atoms? a) benzaldehyde b) acetophenone c) benzophenone d) more than one correct response e) no correct response 15.28 b In which of the following pairs of compounds does the first listed compound have a greater water solubility than the second listed compound? a) butanal, methanal b) propanone, 2-pentanone c) hexanal, 2-butanone d) more than one correct response e) no correct response 15.29 b Oxidation of which of the following alcohols will produce a ketone? a) CH3 CH2 OH b) CH3 CH Test Bank CH3 OH CH3 c) CH3 C OH CH3 d) more than one correct response e) no correct response Copyright Houghton Mifflin Company. All rights reserved. Test Bank 15.30 c Chapter 15: Aldehydes and Ketones 171 Which of the following compounds would be resistant to oxidation with a mild oxidizing agent? a) CH3 CH2 CH2 OH O b) CH3 CH2 C H O c) CH3 C CH3 d) more than one correct response e) no correct response 15.31 d Hydrogenation, with a catalyst, of which of the following compounds would produce a four-carbon alcohol? a) butanal b) 2-butanone c) diethylketone d) more than one correct response e) no correct response 15.32 a In which of the following pairings of compound types does the first listed compound type contain more alkoxy groups than the second listed compound type? a) acetal, hemiacetal b) hemiacetal, acetal c) aldehyde, hemiacetal d) more than one correct response e) no correct response 15.33 a Which of the following is a product of the acid hydrolysis of the following compound? OH CH3 CH2 C H O CH3 a) b) c) d) e) 15.34 d methyl alcohol ethyl alcohol propanone more than one correct response no correct response Which of the following types of compounds contains a carbon-sulfur double bond? a) a thial (thioaldehyde) b) a thione (thioketone) c) a sulfoxide d) more than one correct response e) no correct response Copyright Houghton Mifflin Company. All rights reserved. 172 Chapter 15: Aldehydes and Ketones 15.35 c Test Bank Which of the following compounds would be named as a ketone? OH O a) CH3 CH CH2 C O O b) CH3 C CH2 C OH O c) CH3 CH CH2 C H H CH3 d) more than one correct response e) no correct response MULTIPLE-CHOICE FORMAT TRUE-FALSE QUESTIONS In each of the following multiple-choice questions, characterize EACH of the three given statements as being TRUE or FALSE and then indicate the collective true-false status of the statements using the choices a) All three statements are true. b) Two of the three statements are true. c) Only one of the statements is true. d) None of the statements is true. 15.36 b - TTF Statements: (1) Cyclic hemiacetals are usually more stable than noncyclic hemiacetals. (2) A carbonyl group consists of a carbon atom and an oxygen atom joined by a double bond. (3) The compound benzaldehyde contain six carbon atoms. a) All three statements are true. b) Two of the three statements are true. c) Only one of the statements is true. d) None of the statements is true. 15.37 a - TTT Statements: (1) The simplest aldehyde is formaldehyde and the simplest ketone is acetone. (2) Carbonyl group polarity makes dipole-dipole interactions between like aldehyde molecules or like ketone molecules possible. (3) Reaction of a hemiacetal with an alcohol produces an acetal. a) All three statements are true. b) Two of the three statements are true. c) Only one of the statements is true. d) None of the statements is true. Copyright Houghton Mifflin Company. All rights reserved. Test Bank 15.38 b - FTT Chapter 15: Aldehydes and Ketones 173 Statements: (1) Aldehydes and ketones readily undergo oxidation to carboxylic acids. (2) Propanone and dimethyl ketone are two names for the same compound. (3) The “silver mirror test” distinguishes between aldehydes and ketones. a) All three statements are true. b) Two of the three statements are true. c) Only one of the statements is true. d) None of the statements is true. 15.39 b - TTF Statements: (1) Acetals contain three oxygen atoms and hemiacetals contain two oxygen atoms. (2) Reduction of an aldehyde, using hydrogen gas, produces a primary alcohol. (3) In an aldehyde, the carbonyl group can be located on either carbon 1 or carbon 2. a) All three statements are true. b) Two of the three statements are true. c) Only one of the statements is true. d) None of the statements is true. 15.40 b - TTF Statements: (1) In a “dial” two aldehyde groups are present. (2) Formaldehyde readily participates in polymer formation. (3) Primary alcohol oxidation is a method for producing ketones. a) All three statements are true. b) Two of the three statements are true. c) Only one of the statements is true. d) None of the statements is true. 15.41 b - TFT Statements: (1) Butanal and 2-butanone are constitutional isomers. (2) The linear notation for an aldehyde is RCOH and that for a ketone is RCOR. (3) Water molecules can hydrogen bond with aldehyde and ketone molecules. a) All three statements are true. b) Two of the three statements are true. c) Only one of the statements is true. d) None of the statements is true. Copyright Houghton Mifflin Company. All rights reserved. 174 Chapter 15: Aldehydes and Ketones Test Bank 15.42 d - FFF Statements: (1) The compound 4-oxopentanal contains both an aldehyde and an ether functional group. (2) An alkoxy group and a hydroxy group attached to the same carbon atom are present in both hemiacetals and acetals. (3) Cyclic aldehyde structures are possible but cyclic ketone structures are not possible. a) All three statements are true. b) Two of the three statements are true. c) Only one of the statements is true. d) None of the statements is true. 15.43 c - FFT Statements: (1) Butanal and butanone are both correct IUPAC names. (2) The two alcohol molecules produced when an acetal molecule undergoes hydrolysis are always identical. (3) Aldehydes and ketones are both classified as carbonyl-containing compounds. a) All three statements are true. b) Two of the three statements are true. c) Only one of the statements is true. d) None of the statements is true. 15.44 a - TTT Statements: (1) In the IUPAC nomenclature system, an aldehyde group has priority over a ketone group. (2) Addition of an alcohol molecule across the carbon-oxygen double bond of an aldehyde produces a compound in which the carbonyl carbon atom bears both an alkoxy group and a hydroxy group. (3) 2-Propenal contains two fewer hydrogen atoms than propionaldehyde. a) All three statements are true. b) Two of the three statements are true. c) Only one of the statements is true. d) None of the statements is true. 15.45 b - TFT Statements: (1) The lachrymator in wood smoke is formaldehyde. (2) The skin pigment melanin is a polymeric substance containing many interconnected aldehyde units. (3) Benedict’s test can be used to detect glucose in urine (diabetes) because glucose contains an aldehyde group. a) All three statements are true. b) Two of the three statements are true. c) Only one of the statements is true. d) None of the statements is true. Copyright Houghton Mifflin Company. All rights reserved. Test Bank Chapter 15: Aldehydes and Ketones 175 MATCHING QUESTIONS Characterize each compound on the left in terms of functional groups present using the response list on the right. Responses on the right may be used more than once or need not be used at all. Copyright Houghton Mifflin Company. All rights reserved. 15.46 a Pentanal 15.47 c 3-Pentanone 15.48 b Pentanedial 15.49 c 3-Methylpentanone 15.50 d 3-Oxopentanal a) b) c) d) one aldehyde functional group two aldehyde functional groups one ketone functional group one aldehyde and one ketone functional group For each pair of compounds on the left, select a correct characterization from the response list on the right. Responses on the right may be used more than once or need not be used at all. 15.51 a Acetone Propanal 15.52 c Heptanal Benzaldehyde 15.53 a Diethylketone Pentanal 15.54 d Acetaldehyde Ethanal 15.55 c 2,2-Dimethylbutanal Cyclohexanone a) have the same molecular formula but are different compounds b) both contain a carbon ring system c) contain the same number of carbon atoms but have different molecular formulas d) two names for the same compound For each of the compound characterizations on the left, select from the response list on the right the number of constitutional isomers that exist. Responses on the right may be used more than once or need not be used at all. 15.56 a Saturated four-carbon aldehyde 15.57 d Saturated four-carbon monochloroaldehyde 15.58 b Methylcyclohexanone 15.59 b Saturated noncyclic five-carbon ketone 15.60 b Molecular formula of C4H8O a) b) c) d) two three four five Test Bank Chapter 15: Aldehydes and Ketones 181 For each set of reactants on the left, select a correct product characterization from the response list on the right. Responses on the right may be used more than once or need not be used at all. Copyright Houghton Mifflin Company. All rights reserved. 15.61 a Aldehyde Alcohol Acid catalyst 15.62 b Ketone Two alcohols Acid catalyst 15.63 b Hemiacetal Alcohol Acid catalyst 15.64 d Aldehyde Hydrogen Ni catalyst 15.65 d Ketone Hydrogen Ni catalyst a) b) c) d) hemiacetal acetal alkene alcohol For each of the reaction types on the left, select from the response list on the right the type of organic compound produced. Responses on the right may be used more than once or need not be used at all. O 15.66 a Oxidation of R C H a) b) c) d) O 15.67 d Oxidation of R C R OH 15.68 b Oxidation of R CH R O 15.69 c Reduction of R C R O 15.70 c Reduction of R C H carboxylic acid ketone alcohol no reaction occurs