Full Test Bank Chapter 18 Amines and Neurotransmitters

General, Organic and Biological Chemistry, 4e (Smith)

Chapter 18 Amines and Neurotransmitters

1) Which compound is a secondary amine?

A)

B)

C)

D)

E)

2) Which compound is a primary amine?

A)

B)

C) CH3CH2NHCH2CH3

D)

3) Which compound is a tertiary amine?

A)

B)

C)

D)

4) What is the IUPAC name of the compound shown below?

A) Propylhexylamine

B) N-hexyl-1-propanamine

C) N-propyl-1-hexanamine

D) Hexylpropylamine

5) What is the IUPAC name of the compound shown below?

A) Butylheptylamine

B) N-4-heptyl-1-butanamine

C) N-butyl-4-heptanamine

D) Dibutylpropylamine

6) What is the IUPAC name of the compound shown below? 

A) Propylheptylcyclobutylamine

B) N-cyclobutyl-N-heptyl-1-butanamine

C) N-butyl-N-cyclobutyl-1-heptanamine

D) Dibutylheptylamine

7) Which structure is N-methyl-2-ethylpentylamine?

A)

B)

C)

D)

8) What is the name of the heterocyclic amine shown below? 

A) Aniline

B) Pyridine

C) Pyrrole

D) Pyrrolidine

E) Piperidine

9) What is the structure of piperidine?

A)

B)

C)

D)

10) Which compound has the highest boiling point?

A) (CH3)2CHCH2COOCH3

B) CH3CH2CH2CH2CH2CH2CH2NH2

C) (CH3)2CHCH2CH2CH2CH2OH

D) CH3(CH2)6CH3

E) All of the compounds have the same boiling point.

11) Which amine has the lowest boiling point?

A) (CH3)2CHNHCH2CH2CH2CH3

B) CH3CH2CH2CH2CH2CH2CH2NH2

C) (CH3)2NCH2CH2CH2CH2CH3

D) All of the compounds have the same boiling point.

12) Hygrine (structure shown) is an alkaloid found mainly in coca leaves. What type of nitrogen heterocycle is present in hygrine?

A) Pyridine

B) Pyrrole

C) Pyrrolidine

D) Piperidine

13) Dipicolinic acid is an interesting amino acid. What type of nitrogen heterocycle is present in dipicolinic acid?

A) Pyridine

B) Pyrrole

C) Pyrrolidine

D) Piperidine

14) Which compound has the highest boiling point?

A) (CH3)2CHCH2CH2CH2NH2

B) CH3CH2CH2CH2CH2COOH

C) (CH3)2CHCH2CH2CH2OH

D) CH3(CH2)6CH3

15) Which amine has the highest boiling point?

A) CH3(CH2)5CH2NH2

B) CH3CH2CH2N(CH2CH2CH2CH3)2

C) CH3CH2CH2CH2CH2NHCH2CH3

D) All of the amines are expected to have a similar boiling point.

16) Lobeline (structure shown) is a natural alkaloid found in a number of plants including "Indian tobacco" (Lobelia inflata) and "Devil's tobacco" (Lobelia tupa). Lobeline has been used as a smoking cessation aid. How many chirality centers are in lobeline?

A) 0

B) 1

C) 2

D) 3

E) There are four or more chirality centers in lobeline.

17) Albuterol is a drug used to treat asthma, drawn below. How many chirality centers are in albuterol?

A) 0

B) 1

C) 2

D) 3

E) There are four or more chirality centers in lobeline.

18) Fexofenadine, drawn below, is a nonsedating antihistamine with a single amine functional group. Classify the amine in fexofenadine.

A) 1o

B) 2o

C) 3o

D) 4o

E) This amine is impossible to classify.

19) Norepinephrine is an important neurotransmitter. Classify the amine in norepinephrine.

A) 1o

B) 2o

C) 3o

D) 4o

E) This amine is impossible to classify.

20) What products are formed when the amine below reacts with HCl?

A)

B)

C)

D)

21) What are the products in the acid–base reaction shown below? 

A)

B)

C)

D)

E) No reaction occurs.

22) What is the IUPAC name of the amine salt shown below? 

A) Ethylmethylpropylammonium chloride

B) N-ethyl-N-methyl-1-propanammonium chloride

C) N-ethyl-N-methyl-N-propylammonia chloride

D) N-methyl-N-propylethanammonium chloride

23) What is the IUPAC name of the amine salt shown below?

A) Ethylammonium acetate

B) Ethylamine carbonate

C) Dimethylammonium acetate

D) Dimethylammonium chloride

24) Which compound is the most soluble in water?

A) Trihexylamine

B) N-ethyl-1-heptanamine

C) Dibutylamine

D) N-ethyl-1-pentanammonium bromide

25) What product is formed when tripropylamine is treated with acetic acid?

A) Tripropylammonium acetate

B) Acetamide

C) Tripropylammonia acetate

D) Tripropylamide

26) What is the name of the class of compounds with the general formula of R4N+ X–?

A) Tertiary ammonium salts

B) Tetraammonium salts

C) Quaternary ammonium salts

D) Tertiary ammonia salts

27) In what way may drugs be used to affect neurotransmitters?

A) A drug may prevent the binding of a neurotransmitter to a receptor.

B) A drug may increase the amount of neurotransmitter released.

C) A drug may prevent the release of a neurotransmitter.

D) A drug may affect the degradation of a neurotransmitter.

E) Drugs may affect neurotransmitters using all of the mechanisms listed.

28) Which is not a neurotransmitter?

A) Serotonin

B) Norepinephrine

C) Tryptophan

D) Dopamine

E) Acetylcholine

29) Which does not occur as a result of the release of epinephrine?

A) Dilation of lung passages

B) An increase in heart rate

C) A decrease in glucose synthesis

D) An increase in blood pressure

30) Which is not a derivative of 2-phenylethylamine?

A)

B)

C)

D)

E) All of the compounds are derivatives of 2-phenylethylamine.

31) Kainic acid is a natural product found in some seaweed varieties. Which type of nitrogen heterocycle is present in kainic acid?

A) Pyridine

B) Pyrrole

C) Pyrrolidine

D) Piperidine

32) Methylphenidate (Ritalin) is a drug used to treat attention deficit hyperactivity disorder (ADHD). Which type of nitrogen heterocycle is present in methylphenidate? 

A) Pyridine

B) Pyrrole

C) Pyrrolidine

D) Piperidine

33) What are the small packets that store neurotransmitters?

A) Dendrites

B) Synapses

C) Axons

D) Vesicles

34) What is the long stem that protrudes from a cell body at one end and ends in numerous small filaments at its opposite end?

A) A dendrite

B) A synapse

C) An axon

D) A vesicle

35) Which statement is not true?

A) Once a chemical message is delivered, the neurotransmitter is degraded or returned to the presynaptic neuron to begin the process again.

B) All neurotransmitters are quaternary ammonium ions.

C) Norepinephrine, dopamine, and serotonin are important neurotransmitters.

D) Norepinephrine and dopamine are both synthesized from the amino acid tyrosine.

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

A) N-pentyl-N-propyl-4-nonanamine

B) N-pentyl-N-propyl-N-nonylamine

C) Pentylpropylnonylamine

D) N-pentyl-N-propylnonanamine

37) How is the amine shown below classified? 

A) Secondary amine

B) Primary amine

C) Tertiary amine

D) Quaternary amine

38) Atorvastatin (structure shown) is the active ingredient in Lipitor, a drug classified as a statin, used for lowering blood cholesterol. Which type of nitrogen heterocycle is present in atorvastatin? 

A) Pyridine

B) Pyrrole

C) Pyrrolidine

D) Piperidine

39) Which of the following structures is aniline?

A)

B)

C)

D)

40) Atorvastatin (structure shown) is the active ingredient in Lipitor, a drug classified as a statin, used for lowering blood cholesterol. Which of these functional groups is not present in atorvastatin? 

A) Carboxylic acid

B) Benzene

C) Ketone

D) Amine

E) Amide

41) The hallucinogen known as LSD is drawn below. Which of these functional groups is not present in LSD?

A) Amine

B) Benzene

C) Amide

D) Ketone

42) Which is a possible correct name for an amine?

A) N,N-dipropylmethylamine

B) 1,3-diethylaniline

C) N,N,N-tributylaniline

D) N-ethylpyrrolidine

E) N-ethylpyridine

43) Which type of nitrogen heterocycle(s) is/are present in nicotine (structure shown)?

A) Only pyridine

B) Only pyrrole

C) Only pyrrolidine

D) Pyridine and pyrrolidine

E) Pyridine and pyrrole

44) How many chirality centers are present in the amine shown below?

A) 0

B) 1

C) 3

D) 7

45) How many chirality centers are present in pseudoephedrine, the amine shown below?

A) 0

B) 1

C) 2

D) 3

46) When heated up with propanoic acid, which nitrogen-containing compound would NOT result in the formation of an amide?

A) Ammonia

B) Aniline

C) Dibutylamine

D) Triethylamine

47) What are the products in the acid–base reaction shown below? 

A)

B)

C)

D)

48) What are the products in the acid–base reaction shown below?

A)

B)

C)

D)

49) Arecoline is used in veterinary medicine to treat parasitic worms. Which of the following correctly describes the types of functional groups present in Arecoline? 

A) Amide, ether, alkene

B) Ester, amine, aromatic

C) Alkene, ketone, amide

D) Amine, alkene, ester

50) Serotonin is drawn below. Which of the following correctly describes the types of functional groups present in serotonin?

A) Amide, ether, alkene

B) Alcohol, amine, aromatic

C) Alkene, ketone, amide

D) Amine, alkene, ester

51) Which of the following is not a valid statement about the compound 4-nonanamine?

A) It is a nitrogen-containing compound.

B) It is a primary amine.

C) It contains a carbonyl group on the fourth carbon of a nine carbon saturated chain.

D) It is largely nonpolar, and is insoluble in water.

52) Coniine, shown below, is an alkaloid extracted from poison hemlock. How is this nitrogen-containing compound most appropriately classified? 

A) Heterocyclic, primary amine

B) Secondary amine

C) Primary, heterocyclic amide

D) Lactam

53) Benzphetamine, shown below, is a habit-forming diet pill. How is this nitrogen-containing compound most appropriately classified?

A) Primary

B) Secondary

C) Tertiary

D) Quarternary

54) 4-amino butanoic acid (common name GABA) is a neurotransmitter found in 30% of the brain's nerve cells. Which of the following properly represents the structure of this compound?

A)

B)

C)

D)

55) Which structure should have the IUPAC name N-methyl-N-propylcyclopentanamine?

A)

B)

C)

D)

56) Lidocaine is an amine used as a local anesthetic and cardiac depressant. When Lidocaine is administered, it is administered as its amine salt. Why is the amine salt, rather than the free amine, used?

A) The amine salt is more basic than the free amine.

B) The amine salt is a gas at room temperature and can be rapidly inhaled.

C) The amine salt has a higher solubility in water and bodily fluids than the free amine.

D) The amine salt is not as addictive as the free amine.

57) At the pH of the aqueous environment of the cells, amines exist in their ionized (charged) form. Which of the following properly represents how epinephrine exists in the cell?

A)

B)

C)

D)

58) Which of the following properly represents how methamphetamine, drawn below, reacts with a strong acid?

A)

B)

C)

D)

59) Spermine is a compound isolated from sperm. Which of the following statements correctly describes an aqueous solution of spermine? 

A) The pH of the solution would be equal to that of pure water.

B) The hydronium ion concentration in the solution would be greater than that in pure water.

C) The hydroxide ion concentration in the solution would be greater than that in pure water.

D) The solution would be acidic.

60) Spermine (structure shown) is a compound isolated from sperm. Which of the following statements correctly describes an aqueous solution of spermine?

NH2(CH2)3NH(CH2)4NH(CH2)3NH2

A) The pH of the solution would be equal to that of pure water.

B) The hydronium ion concentration in the solution would be greater than that in pure water.

C) The hydroxide ion concentration in the solution would be greater than that in pure water.

D) The solution would be acidic.

61) Strychnine (structure shown) is a very toxic alkaloid used as a pesticide. There are two amine groups in strychnine. 

62) The following acid-base reaction occurs when piperidine is dissolved in water.

63) Only ammonium salts with less than six carbon atoms are water soluble.

64) The IUPAC name of the compound below is dimethylammonia iodide.

65) The conversion of an amine to an ammonium salt is an irreversible process.

66) When the compound below is treated with KOH the products are N-propyl-1-hexanamine, potassium chloride, and water. 

67) Many amines with useful medicinal properties are sold as their ammonium salts.

68) The postsynaptic neuron contains the receptors that bind the neurotransmitter.

69) Neurotransmitters are stored in small packets called vesicles in the filaments of the axon near the synapse.

70) A person can get sleepy after eating a turkey dinner on Thanksgiving because the unusually high level of tryptophan in turkey is converted to norepinephrine.

71) Dopamine affects brain processes that control movement, emotions, and pleasure.

72) The hormone epinephrine is commonly called noradrenaline.

73) Histamine is a biologically active amine formed in many tissues from the amino acid histidine.

74) Both albuterol and salmeterol are derivatives of 2-phenylethylamine.

75) Histamine is a bronchodilator.

76) Too little dopamine causes schizophrenia.

77) Derivatives of 2-phenylethylamine contain a benzene ring bonded to a two-carbon chain that is bonded to a nitrogen atom.

78) SSRIs are antidepressants that effectively increase the concentration of serotonin.

79) Fentanyl (structure shown) is a drug used for anesthesia and analgesia. There are two 2-phenylethylamine units in fentanyl. 

80) The compound shown below is a derivative of 2-phenylethylamine. 

81) The compound below is a tertiary amide. 

82) The compound below is a quarternary amine.

83) The two compounds below are expected to have approximately the same boiling point.

84) The two compounds below are expected to have approximately the same boiling point.

85) 2-ethyl-1-heptanamine is an alternative name for N-ethyl-1-heptanamine.

86) Dextromethorphan (structure shown) is a cough suppressant found in many over-the-counter cold and cough medicines. Dextromethorphan is a derivative of 2-phenylethylamine.  

87) All neurotransmitters contain nitrogen atoms.

88) Cyclohexylammonium fluoride is soluble in water.

89) Derivatives of 2-phenylethylamine may be used to treat asthma.

90) The compound below is named N-methylcyclopentylamine. 

91) Nicotine (structure shown) is a derivative of 2-phenylethylamine.

92) The compounds 1-pentanamine, 2-pentanamine, and 3-methyl-2-pentanamine are all classified as primary amines.

93) When an amine dissolves in water, the hydroxide ion concentration of the solution increases.

94) Hydrogen bonding between two methylamine molecules is indicated by the dotted line. 

95) Common names are generally used for simple amines.

96) Heptylamine is the common name for 1-heptanamine.

97) The name of the compound below is N-ethylaniline. 

98) The name of the compound below is N,N-diethylcyclohexanamide.

99) (CH3)2NCH2CH2CH2CH3 has a lower boiling point than CH3CH2CH2CH2NHCH2CH3.

100) Alkaloids are naturally occurring amines derived from plant sources.

101) Caffeine and nicotine are alkaloids.

102) Primary (1°) and secondary (2°) amines have higher boiling points and melting points than tertiary (3°) amines of comparable size.

103) In an acid–base reaction of an amine, the amine nitrogen always forms a new bond to a proton forming a/an ________ ion.

104) A water-insoluble amine can be converted to a water-soluble ammonium salt by treatment with a/an ________.

105) A/An ________ is a chemical messenger that transmits nerve impulses from one nerve cell (neuron) to another cell.

106) _____ are the chemical messengers of the endocrine system.

107) Amines act as proton ________ in water and acid.

108) In nicotine (structure shown) the shape of the nitrogen in the pyridine ring is ________ and the shape of the nitrogen in the pyrrolidine ring is ________.

109) Several studies suggest that pregnant women should limit their intake of caffeine, and that excessive caffeine consumption increases the risk of ________.

110) The IUPAC name of the compound below is ________. 

111) The IUPAC name of the compound below is ________.

112) The ________ neuron releases the neurotransmitter, and the ________ neuron contains receptors that bind the neurotransmitter.

113) The neurotransmitter ________ plays an important role in addiction, and affects brain processes that control movement, emotions, and pleasure

114) The neurotransmitter ________ plays an important role in mood, sleep, perception, and temperature regulation. Improper levels of this neurotransmitter in the brain have been linked to migraine headaches.

115) The hormone ________ is produced in the endocrine gland in response to physical or emotional stress that causes the heart rate and blood pressure to increase.