Denniston Ch.13 Test Bank Aldehydes and Ketones

General, Organic, and Biochemistry, 10e (Denniston)

Chapter 13 Aldehydes and Ketones

1) Salicin is a naturally occurring pain reliever isolated from the bark of willow trees. Which of the following statements concerning the structure of salicin is correct?

A) It contains a hemiacetal.

B) It contains an acetal.

C) It contains both a hemiacetal and an acetal.

D) It contains a phenol.

E) It contains a hemiacetal, an acetal, and a phenol.

2) Which statement best describes the structural difference between aldehydes and ketones?

A) Aldehydes contain a hydroxyl group; ketones contain a carbonyl group.

B) Aldehydes contain a carbonyl group on an end carbon of the carbon chain; ketones contain a carbonyl group on a carbon within the carbon chain.

C) Ketones are cyclic compounds; aldehydes are acyclic compounds.

D) The carbonyl group of a ketone is bonded to an oxygen atom; the carbonyl group of an aldehyde is bonded to a hydrogen atom.

E) The carbonyl group of an aldehyde is bonded to two carbon atoms; the carbonyl group of a ketone is bonded to at least one hydrogen atom.

3) Nandrolone is an anabolic steroid sometimes taken by athletes to build muscle mass. Which of the following correctly describes the organic families to which nandrolone belongs?

A) ketone, alkene, alcohol

B) aldehyde, alkene, phenol

C) ketone, alkene, phenol

D) aldehyde, aromatic, alcohol

E) keto, enol, aromatic

4) The presence of a carbonyl group has which effect on the physical properties of a compound?

A) The carbonyl group decreases the polarity of the compound.

B) The carbonyl group increases the boiling point of the compound.

C) The carbonyl group decreases the water solubility of the compound.

D) The carbonyl group increases the ability of the compound to form ionic bonds.

E) The carbonyl group decreases the melting point of the compound.

5) What is the common name of the simplest aldehyde?

A) acetal

B) methal

C) acetaldehyde

D) formaldehyde

E) formal

6) What is the structure of ethyl isopropyl ketone?

A)

B)

C)

D)

E)

7) Methanol is toxic if ingested. The toxicity is due to the aldehyde produced when methanol is oxidized in the liver. Which of the following is the aldehyde formed by the oxidation of methanol?

A)

B)

C)

D)

E)

8) What is the name of the aqueous solution of formaldehyde that is available commercially as a tissue preservative?

A) acetone

B) formalin

C) acetaldehyde

D) glycerol

E) enol

9) What class of compounds is formed by oxidation of aldehydes?

A) enols

B) carboxylic acids

C) ketones

D) acetals

E) Aldehydes do not undergo oxidation.

10) What is the structure of the compound produced by the oxidation of ethanal?

A)

B)

C)

D)

E)

11) The compound decanal contributes to the odor and flavor of an orange. Which of the following statements about decanal is FALSE?

A) It is an aldehyde.

B) It contains a saturated chain of ten carbons.

C) It contains a carbonyl group on the first carbon of the carbon chain.

D) It can form intermolecular hydrogen bonds with other molecules of decanal.

E) It is insoluble in water.

12) An unknown compound is highly water soluble, forms a silver mirror in the Tollens' test, and forms a red precipitate in the Benedict's test. Which of the following compounds is consistent with this data?

A)

B)

C)

D)

E)

13) What type of compound is produced in the reaction of a ketone with two alcohol molecules in the presence of a trace of acid?

A) hemiacetal

B) aldehyde

C) carboxylic acid

D) enol

E) acetal

14) What is the structure of the hemiacetal produced in the following reaction?

A)

B)

C)

D)

E)

15) What is the structure of the acetal produced in the following reaction?

A)

B)

C)

D)

E)

16) Which of the following is the enol tautomer of the keto form shown?

A)

B)

C)

D)

E)

17) Which of the following compounds would be expected to react similarly in a chemical reaction?

A) I and III

B) II and IV

C) I and IV

D) I, II, and IV

E) I, III, and IV

18) Which of the statements concerning the compound shown below is FALSE?

A) Its name is cyclopentanone.

B) Its molecular formula is C5H8O.

C) Molecules of this compound are held together in a collection by dipole-dipole attractions.

D) It may be formed by the oxidation of cyclopentanol.

E) It can be oxidized to produce a carboxylic acid.

19) Propylene glycol, shown below, is a nontoxic diol used as a solvent for pharmaceutical drugs, and as a moisturizing agent for foods. When ingested, both alcohol functional groups are oxidized by enzymes in the liver to produce pyruvic acid, a compound with the formula C3H4O3. What is the structure of pyruvic acid?

A)

B)

C)

D)

E)

20) What compound is produced when 2-methyl-3-pentanol is oxidized?

A) 2-methyl-3-pentanone

B) 2-methyl-3-pentanal

C) 2-methyl-3-pentene

D) 2-methylpentone

E) It does not undergo oxidation.

21) What is the general formula of a ketone?

A) R-O-R

B) R-O-H

C)

D)

E) None of the choices are correct.

22) What is the proper IUPAC name of the three carbon aldehyde?

A) propanal

B) butanal

C) acetal

D) propanone

E) propanol

23) What is the common name of the following compound?

A) propanone

B) propanal

C) 2-propyl ketone

D) 1-propyl ketone

E) acetone

24) Where in the body is ethanol oxidized to produce ethanal?

A) stomach

B) liver

C) small intestine

D) large intestine

E) Both small intestine and large intestine are correct.

25) What is the IUPAC name of the aldehyde produced when ethanol is oxidized?

A) acetal

B) acetone

C) ethanal

D) ethanone

E) None of the choices are correct.

26) What alcohol undergoes oxidation to produce acetic acid?

A) methanol

B) ethanol

C) propanol

D) isopropyl alcohol

E) acetone

27) The compound butanone does not need a number to specify the location of the carbonyl group on the parent carbon chain. Which of the following best explains why?

A) The C=O is assumed to be on C-1 of the parent chain if it is not specified.

B) The C=O can only be on C-2 of the parent chain in this compound for it to be a ketone.

C) The C=O is on an end carbon in this compound, and therefore does not need to be specified.

D) The location of a C=O does not need to be specified for a cyclic ketone.

E) The location of the C=O in this compound is not significant to the name.

28) What type of compound is formed in the following reaction?

A) acetal

B) aldehyde

C) hemiacetal

D) enol

E) ketone

29) Acetone is the simplest ketone. Not only is it used industrially as a solvent, but it is also produced by the body as a product of lipid metabolism. What is the structure of acetone?

A)

B)

C)

D)

E)

30) Which of the following best describes the structure of an enol?

A) contains a triple bond and a carbonyl group

B) contains only single bonds and a hydroxyl group

C) contains a double bond and a hydroxyl group

D) contains a double bond and a carbonyl group

E) contains only single bonds and a carbonyl group

31) Which structure/name combination is incorrect?

A) A

B) B

C) C

D) D

E) E

32) What class of compounds is represented by the general formula RCHO?

A) ketones

B) carboxylic acids

C) alkenes

D) alcohols

E) aldehydes

33) Which of the following does NOT represent an oxidation reaction?

A) ethanal → ethanol

B) benzaldehyde → benzoic acid

C) 2-propanol → propanone

D) 1-propanol → propanal

E) All of the reactions are oxidation reactions.

34) What is the IUPAC name of the compound shown?

A) formaldehyde

B) acetone

C) propanone

D) propanal

E) ethanal

35) What is the IUPAC name of the compound shown?

A) 2-methylpropanone

B) 2-butanal

C) 2-butanyl

D) butanone

E) 2-methyl-2-propanone

36) What is the IUPAC name of the compound shown?

A) 4-octanone

B) 1-propyl butanal

C) 4-heptanone

D) dipropyl ether

E) 4-heptanal

37) What simple ketone is commonly used as a solvent?

A) acetal

B) formalin

C) acetone

D) benzanal

E) butanone

38) What is the IUPAC name of the compound produced in the liver that is responsible for the symptoms of a hangover?

A) acetone

B) acetic acid

C) ethanol

D) ethanal

E) 2-propanol

39) What is the IUPAC name for the product of the reaction shown?

A) acetone

B) methanal

C) acetic acid

D) acetal

E) propanone

40) What type of compound is produced by the oxidation of an aldehyde?

A) carboxylic acid

B) alcohol

C) alkane

D) hemiacetal

E) acetone

41) Which of the following will give a silver mirror when treated with Tollens' reagent?

A) 2-pentanone

B) propanone

C) hexanal

D) 1-pentanol

E) 2-pentanol

42) What is the name of the organic product formed when the compound, CH3CH2CH2CHO, is reduced by addition of H2?

A) butane

B) 1-butanol

C) 1-butanone

D) butanal

E) butanoic acid

43) What is the name of the organic product formed when the compound shown is oxidized?

A) 2-butanol

B) butanone

C) butanal

D) butyl ketone

E) methyl ethyl ether

44) Which of the following is a hemiacetal?

A)

B)

C)

D)

E)

45) What kind of compound is produced by the reaction of an aldehyde with an alcohol in the presence of a trace of acid?

A) ether

B) ketone

C) carboxylic acid

D) hemiacetal

E) alkyne

46) Which of the following pairs of reactant molecules can react in the presence of a trace of acid to give a hemiacetal molecule?

A) a ketone and an aldehyde

B) an aldehyde and an alkene

C) an aldehyde and an alcohol

D) two ketones

E) two aldehydes

47) Which of the following sets of reactant molecules can react in the presence of a trace of acid to give an acetal molecule?

A) one ketone molecule and two aldehyde molecules

B) one ketone molecule and two alcohol molecules

C) one ketone molecule and one aldehyde molecule

D) one ketone molecule and one alcohol molecule

E) one alcohol molecule and two ketone molecules

48) The reduction of acetaldehyde is an important biochemical reaction. Which of the following is the product of its reduction?

A)

B)

C)

D)

E)

49) When a hemiacetal reacts with an alcohol, an acetal is formed. This is how disaccharides and polysaccharides are formed. What is the structure of the acetal formed in the following reaction?

A)

B)

C)

D)

E)

50) Cyclopentanone reacts with one molecule of ethanol to yield a hemiacetal product. Which of the following correctly represents the structure of the hemiacetal product?

A)

B)

C)

D)

E)

51) Small (low molecular weight) aldehyde molecules are generally more water-soluble than large ones.

52) Pure formaldehyde is a liquid at room temperature.

53) Formaldehyde is used to kill viruses without damaging their genetic information.

54) The oxidation of isopropyl alcohol produces propanone.

55) The most oxidized organic form of a primary alcohol is a ketone.

56) Benedict's test can be used to distinguish between an aldehyde and a ketone.

57) A ketone will react with Tollens' reagent to produce a silver mirror, but an aldehyde will not.

58) A ketone can be reduced to a primary alcohol.

59) Aldehydes are easily oxidized to carboxylic acids.

60) A hemiacetal contains two ether functional groups.

61) An acetal contains two ether functional groups.

62) In any pair of keto-enol tautomers, the keto form is generally more stable than the enol form.

63) The compound shown below is the enol form of butanal.