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Chapter 17

front 1

1) Which molecule is a carboxylic acid?

back 1

Answer: D

front 2

2) Which functional group contains a carbonyl group and a hydroxyl group bonded to the same carbon atom?

A) aldehyde

B) amide

C) carboxylic acid

D) ester

E) ketone

back 2

Answer: C

front 3

3) Which functional group contains a carbonyl group and an ether linkage bonded to the same carbon atom?

A) aldehyde

B) amide

C) carboxylic acid

D) ester

E) ketone

back 3

Answer: D

front 4

4) Which molecule is an ester?

back 4

Answer: C

front 5

5) Which molecule is an amide?

back 5

Answer: B

front 6

6) The similarities in properties of carboxylic acids, esters, and amides can best be explained by

A) their polarity and structural similarities.

B) their similarities in molar mass.

C) hydrogen bonding.

D) the ease with which they form ions.

E) none of these.

back 6

Answer: A

front 7

7) The most common reactions of carboxylic acids or their derivatives involve

A) addition across the double bond between carbon and oxygen.

B) replacement of the oxygen atom in the carbonyl group.

C) replacement of the group bonded to the carbonyl atom.

D) oxidation of the R group.

E) reduction of the R group.

back 7

Answer: C

front 8

8) Which molecule shown is β-hydroxy butyric acid?

back 8

Answer: C

front 9

9) Which molecule is formic acid?

back 9

Answer: C

front 10

10) All of the statements concerning citric acid are true except

A) it contains three carboxylic acid groups because its carbon skeleton is branched.

B) it is very soluble in water.

C) its salts are used in many consumer products.

D) it is produced only by plants.

E) it is a weak acid.

back 10

Answer: D

front 11

11) Which of the following bonds is not present in a carboxylic acid functional group?

A) C=C

B) C=O

C) C-O

D) O-H

E) none of the above

back 11

Answer: A

front 12

12) The pleasant, characteristic odor of fruit flavorings is often associated with the presence of

A) esters

B) carboxylic acids

C) carboxylate salts

D) ketones

back 12

Answer: A

front 13

13) Which compound is a carboxylic acid?

A) CH3COO-K+

B) CH3COOH

C) (CH3)2CHOOCH3

D) (CH3CO)2O

E) (CH3)2O

back 13

Answer: B

front 14

14) All of the statements about carboxylic acids are true except

A) they undergo substitution reactions involving the -OH group.

B) at low molecular weights they are liquids with sharp stinging odors.

C) they form hydrogen bonds, causing their boiling points to be higher than expected on the basis of molecular weight.

D) they react with bases to form salts which are often more soluble than the original acid.

E) when they behave as acids, the -OH group is lost leaving the CO-

back 14

Answer: E

front 15

15) Which acid would be expected to have the lowest boiling point?

A) acetic, CH3CO2H

B) benzoic, C6H5CO2H

C) formic, HCO2H

D) oxalic, (CO2H)2

E) stearic, CH3(CH2)16CO2H

back 15

Answer: C

front 16

16) Which acid would be expected to have the highest boiling point?

A) acetic, CH3CO2H

B) benzoic, C6H5CO2H

C) formic, HCO2H

D) oxalic, (CO2H)2

E) stearic, CH3(CH2)16 CO2H

back 16

Answer: E

front 17

17) Which of the following has the highest boiling point?

A) ethane, CH3CH3

B) dimethyl ketone, CH3COCH3

C) ethyl alcohol, CH3CH2OH

D) acetic acid, CH3COOH

E) formaldehyde, HCHO

back 17

Answer: D

front 18

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

A) 1-butanoic acid

B) 4-butanoic acid

C) 1-butenoic acid

D) 3-butenoic acid

E) none of the above

back 18

Answer: D

front 19

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

A) 3-hexanoic acid

B) 2-ethyl pentanoate

C) 2-ethylpentanoic acid

D) 3-heptanoic acid

E) 4-heptanoic acid

back 19

Answer: C

front 20

20) What is the common name of the molecule shown?

A) γ-amino-α-hydroxybutyric acid

B) 4-amino-2-hydroxybutanoic acid

C) α-amino-γ-hydroxybutyric acid

D) 1-amino-3-hydroxybutanoic acid

E) none of these

back 20

Answer: A

front 21

21) What is the IUPAC name of the molecule shown?

A) γ-amino-α-hydroxybutyric acid

B) 4-amino-2-hydroxybutanoic acid

C) α-amino-γ-hydroxybutyric acid

D) 1-amino-3-hydroxybutanoic acid

E) none of these

back 21

Answer: B

front 22

22) What is the IUPAC name of the molecule shown?

A) ethyl butanoate

B) butyl ethanoate

C) acetyl butyrate

D) butyl acetate

E) 2-hexanoic ester

back 22

Answer: A

front 23

23) What is the common name of the molecule shown?

A) ethyl butanoate

B) butyl ethanoate

C) ethyl butyrate

D) butyl acetate

E) 2-hexanoic ester

back 23

Answer: C

front 24

24) What is the IUPAC name of the molecule shown?

A) diethanoic acid

B) ethanedioc

C) dibutanoic acid

D) butanedioic acid

E) pentanedioic acid

back 24

Answer: D

front 25

25) An acyl group is a group in which
A) an amine and a carbonyl are bonded to the same carbon atom.
B) a hydroxyl and an alkene are bonded to the same carbon atom.
C) an alpha carbon is bonded to an alkyl group.
D) an alkyl group is bonded to a carbonyl carbon atom.
E) an acidic group is bonded to an aromatic group.

back 25

Answer: D

front 26

26) When common names are used for acids, the underlined carbon atom in the molecule shown would be designated as the ________ C atom.

A) alpha

B) beta

C) gamma

D) #1

E) #2

back 26

Answer: B

front 27

27) Which molecule is acetic acid?

back 27

Answer: A

front 28

28) Which molecule is oxalic acid?

back 28

Answer: D

front 29

29) What is the common name of the molecule shown?

A) acetic acid

B) butyric acid

C) formic acid

D) lactic acid

E) oxalic acid

back 29

Answer: B

front 30

30) Which acid would be expected to have the lowest boiling point?

A) acetic

B) benzoic

C) formic

D) oxalic

E) stearic

back 30

Answer: C

front 31

31) Which acid would be expected to have the highest boiling point?

A) acetic

B) benzoic

C) formic

D) oxalic

E) stearic

back 31

Answer: E

front 32

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

CH3CH2COOCH3

A) 2-butanoic acid

B) 3-butanoic acid

C) methyl ethanoate

D) propyl methanoate

E) methyl propanoate

back 32

Answer: E

front 33

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

A) 2-methyl propanamide

B) N-methyl propanamide

C) 2-methyl butanamide

D) 3-methyl butanamide

E) N-methyl butanamide

back 33

Answer: D

front 34

34) An alpha hydroxy carboxylic acid has an additional -OH group attached to the molecule at which location?

A) the carbonyl carbon atom

B) the #2 carbon atom

C) the carbon atom farthest from the carboxyl group

D) the carbon atom that contains the amine group

E) none of the above

back 34

Answer: B

front 35

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

A) 1-methylpropanamide

B) N-methylpropanamide

C) N-butylethanamide

D) N-methylbutanamide

E) N-butylformamide

back 35

Answer: D

front 36

36) Carboxylic acids generally taste ________.

A) sour

B) sweet

C) bitter

D) salty

E) spicy

back 36

Answer: A

front 37

72) This compound is

A) an anhydride only.

B) an ester only.

C) both an ester and an anhydride.

D) neither an ester nor an anhydride.

E) phosphoric acid.

back 37

Answer: C

front 38

38) The solubility of compounds containing the carboxylic acid group can be increased by reaction with

A) sulfuric acid.

B) nitric acid.

C) sodium hydroxide.

D) water.

E) benzoic acid.

back 38

Answer: C

front 39

39) Which equation correctly represents the dissociation of a carboxylic acid in water?
A) CH3COOH + H2O CH3CHCOOH2+ + OH-
B) CH3COOH CH3COO- + H+
C) CH3COOH + H2O CH3COO- + H3O+
D) CH3COOH + H3O+ CH3COOH2+ + H2O
E) CH3COOH + 2 H2O CH3COO2- + 2 H3O+

back 39

Answer: C

front 40

40) The ion formed from a carboxylic acid is called the

A) carboxylate anion.

B) carboxylate cation.

C) ester anion.

D) ester cation.

E) amide cation

back 40

Answer: A

front 41

41) Which formula correctly illustrates the form which acetic acid would take in a basic solution?

back 41

Answer: D

front 42

42) Reaction of a carboxylic acid with a base like sodium hydroxide, NaOH gives ________

A) a carboxylate salt.

B) an alkoxide salt.

C) an ester.

D) an alcohol.

E) none of the above.

back 42

Answer: A

front 43

43) Which of the following conditions would favor the carboxylate ion form of a carboxylic acid?

A) low pH

B) high pH

C) both A and B

D) neither A nor B

back 43

Answer: B

front 44

44) Which of these compounds is the most soluble in water?

A) CH3CH2CH2CH2CH2COOH

B) CH3CH2CH2CH2CH2COO-Na+

C) CH3CH2CH2CH2CH2OH

D) CH3CH2CH2CH2CH2CH3

E) CH3CH2OCH2CH2CH3

back 44

Answer: B

front 45

45) In the production of an ester, the carboxylic acid loses which atom or group of atoms?

A) oxygen from the C=O

B) H from the OH group

C) the OH group

D) the entire COOH group

E) oxygen from the OH

back 45

Answer: C

front 46

46) When an alcohol reacts with a carboxylic acid the major product is

A) an amide.

B) an amine.

C) an ester.

D) a salt.

E) a soap.

back 46

Answer: C

front 47

47) Reaction of butanoic acid with ethanol produces

A) butyl ethanoate.

B) ethyl butanoate.

C) butyl ethanamide.

D) ethyl butanamide.

E) butyl ethyl ester.

back 47

Answer: B

front 48

48) Which carboxylic acid is used to prepare the ester shown?

back 48

Answer: D

front 49

49) What is the major organic product of the reaction shown?

back 49

Answer: B

front 50

50) When an amine reacts with a carboxylic acid at high temperature the major product is

A) an ester.

B) an amide.

C) a thiol.

D) an ether.

E) an alcohol.

back 50

Answer: B

front 51

51) The common chemical name of aspirin is

A) acetamide.

B) acetylsalicylic acid.

C) phenylalanyl aspartic acid.

D) acetaminophen.

E) lidocaine.

back 51

Answer: B

front 52

52) The reactants needed to produce simple polyamides (nylons) are

A) diacids and dialcohols.

B) diacids and diamines

C) diamines and dialcohols.

D) alkenes and catalysts.

E) diacids and phosphates.

back 52

Answer: B

front 53

53) The reactants needed to produce simple polyesters are

A) diacids and dialcohols.

B) diacids and diamines

C) diamines and dialcohols.

D) alkenes and catalysts.

E) diacids and phosphates

back 53

Answer: A

front 54

54) The functional groups in the aspirin molecule shown are

A) aromatic, carboxylic acid.

B) aromatic, ester.

C) carboxylic acid, ester.

D) aromatic, carboxylic acid, ester.

E) amide, aromatic, carboxylic acid.

back 54

Answer: D

front 55

55) The products of acid hydrolysis of an ester are

A) another ester + water.

B) alcohol + acid.

C) alcohol + water.

D) acid + water.

E) salt + water.

back 55

Answer: B

front 56

56) The products of basic hydrolysis of an ester are

A) another ester + water.

B) alcohol + acid.

C) alcohol + water.

D) acid + water.

E) carboxylate salt + alcohol.

back 56

Answer: E

front 57

57) What are the major organic products of the reaction shown?

A) CH3CH2CH2COOH + HOCH2CH3

B) CH3CH2CH2COO- + +H2OCH2CH3

C) CH3COOH + HOCH2CH2CH2CH3

D) CH3CH2CH2CH2OH + CH3CH2OH

E) CH3CH2CH2COOH + CH3COOH

back 57

Answer: A

front 58

58) Reaction of an ester with a strong base is called

A) reverse esterification.

B) esterification.

C) saponification.

D) oxidation.

E) condensation.

back 58

Answer: C

front 59

59) Hydrolysis of the ester ethyl acetate produces

A) ethanol and acetic acid.

B) butanol.

C) butanal and ethanol.

D) ethanal and acetic acid.

E) butanoic acid.

back 59

Answer: A

front 60

60) The potassium or sodium salt of a long chain carboxylic acid is called a

A) soap.

B) triglyceride.

C) ester.

D) emollient.

E) none of the above

back 60

Answer: A

front 61

61) When an amide is hydrolyzed under acidic conditions, the products are

A) an amine and a carboxylic acid.

B) an amine and a carboxylate ion.

C) an ammonium ion and a carboxylate ion.

D) an ammonium ion and a carboxylic acid.

E) There is no reaction.

back 61

Answer: D

front 62

62) The amide produced from pentanoic acid and ammonia is

A) N-pentanamide.

B) N-methylpentanamide.

C) pentanoicamide.

D) pentanamide.

back 62

Answer: D

front 63

63) When an amide is hydrolyzed under basic conditions, the products are

A) an amine and a carboxylic acid.

B) an amine and a carboxylate ion.

C) an ammonium ion and a carboxylate ion.

D) an ammonium ion and a carboxylic acid.

E) There is no reaction.

back 63

Answer: B

front 64

64) Hydrolysis of a carboxylic acid ester using base is called ________.

A) saponification

B) decarboxylation

C) detoxification

D) alcoholysis

E) extraction.

back 64

Answer: A

front 65

65) Which of the following might be obtained as one of the products in this reaction?

back 65

Answer: B

front 66

66) What are the products of this reaction?

back 66

Answer: D

front 67

67) The two monomers used to make Dacron polyester fabric are

A) ethylene glycol and mylar.

B) terephthalic acid and mylar.

C) propylene glycol and mylar.

D) ethylene glycol and terephthalic acid.

E) none of the above

back 67

Answer: D

front 68

68) Nylons and proteins are both referred to as polyamides because

A) each reactant molecule contains an amide group.

B) they are produced by reaction between an amide and an ester.

C) they are formed when an acid reacts with ammonia.

D) they are produced by basic hydrolysis of an amine.

E) they are formed when an acid functional group reacts with an amine functional group.

back 68

Answer: E

front 69

69) One requirement for the reactants in the formation of polyester is that each molecule contain

A) at least one carbon-carbon double bond.

B) one aromatic ring.

C) at least two functional groups that can form ester linkages.

D) an amine group somewhere on the carbon skeleton.

E) none of these

back 69

Answer: C

front 70

70) When an alcohol reacts with phosphoric acid, the product is referred to as a

A) phosphate salt.

B) phosphate ester.

C) phosphate anion.

D) pyrophosphate.

E) none of the above

back 70

Answer: B

front 71

71) Phosphate esters are prepared from

A) phosphoric acid + alcohol.

B) phosphoric acid + ester.

C) phosphoric acid + carboxylic acid.

D) phosphate + ester.

E) phosphate + alcohol.

back 71

Answer: A