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Chapter 15 Amines and Amides

Chapter 15: Amines and Amides 1. Lidocaine is used as a local anesthetic and a cardiac depressant. Which of the following best describes the organic families to which lidocaine belongs?

A) phenol, amide B) aromatic, amine C) aromatic, ketone, amine D) aromatic, amide, amine E) phenol, ketone, amine Ans: D 2. Socrates used coniine, an alkaloid extracted from the poison hemlock plant, to end his life. How is this nitrogen-containing compound best classified?

A) cyclic amide B) primary, aromatic amine C) secondary, heterocyclic amine D) tertiary amine E) lactam Ans: C

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Chapter 15 Amines and Amides

3. Benzphetamine (trade name Didrex) is a habit-forming diet pill with many of the same properties as amphetamines. Which of the following statements concerning this compound is FALSE?

A) It is a tertiary amine. B) It has low water solubility. C) It is a largely nonpolar, hydrophobic compound. D) It reacts with a strong base like NaOH to produce an amine salt. E) It will not produce an amide upon reaction with a carboxylic acid chloride. Ans: D 4. What is the IUPAC name of the simplest amine? A) ammonia B) ethamine C) methamine D) methanamine E) formamine Ans: D 5. What is the common name of 2-propanamine? A) propylamine B) isopropylamine C) aminopropane D) propylammonia E) propylammonium Ans: B

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Chapter 15 Amines and Amides

6. 4-Amino butanoic acid (common name GABA) is a neurotransmitter found in the brain’s nerve cells. Which of the following properly represents the structure of this compound?

A)

B)

C)

D)

E) Ans: B 7. Which of the following is NOT a medical use of amphetamines? A) appetite suppressant B) antihistamine C) antidepressant D) treatment of epilepsy E) diet pills Ans: B 8. What type of product results from the neutralization reaction between an alkylamine and an acid such as HCl? A) an amine B) an amide C) an alkylammonium salt D) ammonia E) ammonium chloride Ans: C

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Chapter 15 Amines and Amides

9. What compound is produced when ethylamine reacts with HCl? A) ethylammonium chloride B) diethylamine C) ammonium chloride D) ammonia E) ethyl chloride Ans: A 10. What compound is produced by the reduction of the amide shown below?

A) ammonia B) ethylmethylamine C) methylpropylamine D) methylamine E) butylamine Ans: C 11. Which of the statements concerning the compound below is INCORRECT?

A) It is a tertiary amine. B) Its molecular formula is C6H15N. C) Its name is 2-methyl-2-pentanamine. D) It is able to form intermolecular hydrogen bonds. E) It can act as a base. Ans: A 12. Which of the following is a true statement concerning the properties of nitrogencontaining compounds? A) All amines are water-soluble compounds because the N-H group can hydrogen bond with water. B) Primary and secondary amines can form intermolecular hydrogen bonds, but tertiary amines cannot. C) Amides form strong ionic bonds with each other and therefore have higher boiling points than hydrocarbons. D) The water solubility of an amine increases with an increase in the hydrocarbon chain. E) Amides are basic compounds that act as hydrogen ion acceptors. Ans: B

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Chapter 15 Amines and Amides

13. Bupropion is used medicinally as an antidepressant, and as an aide in smoking cessation. The carbonyl group in this compound is part of what functional group family?

A) amide B) carboxylic acid chloride C) ketone D) ester E) lactam Ans: C 14. What is the IUPAC name of the compound shown?

A) N-propylhexamide B) aminohexyl propanamide C) aminopropyl pentanamide D) N-hexylpropamide E) N-propylhexanamide Ans: E 15. What is the common name of the compound shown?

A) formamide B) aniline C) benzamide D) acetate E) acetamide Ans: E 16. Which of the following is NOT a neurotransmitter in the human body? A) serotonin B) acetylcholine C) histamine D) aspartame E) epinephrine Ans: D

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Chapter 15 Amines and Amides

17. What type of organic compound is formed in the reaction between an acid chloride and an amine? A) ammonium chloride B) amide C) quaternary ammonium salt D) secondary amine E) anhydride Ans: B 18. The active ingredient in the insect repellant DEET is the amide formed by the reaction shown below. What is the structure of DEET?

A)

B)

C)

D)

E) Ans: B

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Chapter 15 Amines and Amides

19. What acid chloride is required to form the amide shown below?

A) butylammonium chloride B) propanoyl chloride C) propylammonium chloride D) butanoyl chloride E) HCl Ans: B

20. What product is formed when the amide below is hydrolyzed by a strong base?

A)

B)

C)

D)

E) Ans: C

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Chapter 15 Amines and Amides

21. What two products are formed in the hydrolysis reaction shown below?

A) B) C) D) E) Ans: D 22. What class of biological compounds contains amide bonds as the central feature in their structure? A) lipids B) carbohydrates C) proteins D) nucleic acids E) None of the above. Ans: C 23. What is another name for the amide bond that joins amino acids together in a protein? A) glycosidic linkage B) hydrogen bond C) peptide bond D) salt bridge E) acetal bond Ans: C 24. 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 nine carbons in a continuous chain. D) It contains a carbonyl group on the fourth carbon of the carbon chain. E) It is largely nonpolar. Ans: D

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Chapter 15 Amines and Amides

25. Amines are organic derivatives of what inorganic compound? A) nitrous oxide D) sodium nitrite B)

ammonia

C)

nitrogen dioxide

E)

sodium nitrate

Ans: B 26. What is the general structure of a secondary amine? A) NH3 B) RNH2 C) R2NH D) R3N E) R3NH Ans: C 27. How many hydrogen atoms are directly attached to the nitrogen atom of a tertiary amine? A) 0 B) 1 C) 2 D) 3 E) 4 Ans: A 28. What is the systematic name of ethylamine? A) N-ethanamine D) B)

ethyleneamine

C)

ethanamine

E)

1-ethaneamine None of the choices are correct.

Ans: C 29. What is the systematic name of the compound, CH3CH2CH2 — NH — CH3? A) propyl ammonia methane D) propylmethylamine B)

N-propylmethanamine

C)

methylpropylamine

E)

Ans: E

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N-methyl-1-propanamine

Chapter 15 Amines and Amides

30. N-Methylformamide is an organic compound used to kill insect larvae in cereal and dried fruit. What is its structure? A) B) C) D) E) Ans: A 31. What is the systematic name of the product formed by the reduction of methanamide? A) N-methylmethanamine D) N-methylamine B)

methanamine

C)

ammonia

E)

ammonia methane

Ans: B 32. When the amine RNH2 (where R is a 12-carbon alkyl chain) is neutralized with aqueous HCl, the compound RNH3+Cl- forms. Briefly predict, with reasons, the solubilities of RNH2 and RNH3+Cl- in water. A) Both are insoluble due to the hydrophobic long carbon chain. B)

Both are soluble because both contain polar N-H bonds.

C)

RNH2 is insoluble due to the long hydrophobic carbon chain, but RNH3+Cl– is soluble due to the ionic part of the compound. RNH2 is soluble due to the polarity of the N-H bond. The salt is insoluble because most chloride salts are insoluble in water. None of the choices are correct.

D) E)

Ans: C 33. Which of the following would NOT be classified as a primary amine? A) aniline B) 1-pentanamine C) 2-pentanamine D) N-methyl-2-pentanamine E) 3-methyl-2-pentanamine Ans: D

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34. What is the physical state of most amides at room temperature? A) solid B)

liquid

C)

gas

D)

Some amides are solid, some are liquids, and some are gases

E)

Amides are solid or liquids, but never gases.

Ans: A 35. What is the common name of the compound shown?

A)

N-formic acid

D)

acetamide

B)

formamide

E)

benzamide

C)

methanamide

Ans: B 36. Why is the bond between N and H in amines a polar bond? A) Hydrogen is more electronegative. D) Hydrogen is electrophilic. B)

Nitrogen is more electropositive.

C)

Nitrogen is more electronegative.

E)

Nitrogen is electrophilic.

Ans: C 37. What term best describes the following compound?

A)

primary amine

D)

amide

B)

secondary amine

E)

alkaloid

C)

tertiary amine

Ans: B 38. Ammonia is best described as which of the following? A) a primary amine D) a quaternary amine B)

a secondary amine

E)

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a weak base

Chapter 15 Amines and Amides

C)

a tertiary amine

Ans: E 39. For compounds of similar molecular weight, which of the following types would have the highest boiling point? A) alkane B) ether C) primary amine D) secondary amine E) tertiary amine Ans: C 40. What is the systematic name of the following compound?

A)

dimethylmethanamine

D)

trimethylamine

B)

dimethylaminomethane

E)

N,N-dimethylmethanamine

C)

N-methylethanamine

Ans: E 41. When heated up with propanoyl chloride, which of the following nitrogen-containing compounds would NOT result in an amide? A) triethylamine B) aniline C) ammonia D) dibutylamine E) methylamine Ans: A 42. What is the common name of the following compound?

A)

triethylamine

D)

N-methylethanamine

B)

N,N-diethylethanamine

E)

N,N-dimethylethanamine

C)

diethylaminoethane

Ans: A 43. Which synthetic amine compounds stimulate the central nervous system and are often used in diet pills? A) nitrates B) serotonins C) epinephrines D) amphetamines E) barbiturates Ans: D

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44. What two kinds of organic compounds can be reduced in the laboratory to prepare amines? A) amides and purines B)

nitrosamines and amides

C)

phenylamines and phenylnitro compounds

D)

amides and nitro compounds

E)

amides and aldehydes

Ans: D 45. What is the systematic name of the compound produced by the reduction of pentanamide? A) 1-pentanamine D) methylpentanal B)

2-pentanamine

C)

hydroxylaminopentane

E)

methylpentanamine

Ans: A 46. What product, in addition to a hydroxide ion, is formed when an amine reacts with water? A) hydronium ion D) quaternary ammonium ion B)

alkylammonium ion

C)

alkylammonium salt

E)

Ans: B

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amide

Chapter 15 Amines and Amides

47. A chemist needs to reflux a reaction mixture at high temperature. This requires the use of a high-boiling organic solvent. Of the following solvents available for use, which would have the highest boiling point? A) B)

C) D) E) NH3 Ans: C 48. What is the charge usually found on a quaternary ammonium ion? A) +1 B) +2 C) +4 D) -1 E) -4 Ans: A 49. What is the name of the species represented by the structure R4N+Cl−? A) a quaternary ammonium salt D) an alkylammonium salt B)

an alkaloid

C)

an amine

E)

a porphyrin

Ans: A 50. Which class of naturally occurring compounds has one or more nitrogen containing heterocyclic rings and includes many compounds that have medicinal and physiological effects? A) analgesics B) alkaloids C) pheromones D) nitrosamines E) carcinogens Ans: B 51. What subclass of amines contains at least one nitrogen atom in a ring structure? A) cyclic B) aliphatic C) secondary D) tertiary E) heterocyclic Ans: E 52. Which of the following is NOT a general characteristic of amides? A) They have high boiling points. B)

Intermolecular hydrogen bonds are present.

C)

Solutions in water are basic.

D)

Most are solids at room temperature.

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Chapter 15 Amines and Amides

E)

C=O and C-N bonds involve resonance.

Ans: C 53. What is the IUPAC name of the following compound?

A)

ethanamide

D)

formamide

B)

acetamide

E)

N-methanamide

C)

methanamide

Ans: A 54. What is the IUPAC name of the following compound?

A)

N-ethylpropanamide

D)

N-ethylbutanamide

B)

N-butylethanamide

E)

N-ethylbutyramide

C)

N-ethylbutylamine

Ans: D 55. Which of the following correctly represents how ethylamine would exist when dissolved in an acidic solution? A) CH3CH2NH2 B) CH3CH2NH−

C) D)

E) Ans: E 56. Which of the following amines is involved in the transmission of nerve impulses that control the contraction of muscles? A) epinephrine B) alkaloid C) amide D) aminoethane E) acetylcholine Ans: E

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Chapter 15 Amines and Amides

57. What disease results from a deficiency of dopamine? A) Wilson's disease D) cancer B)

K-Factor disease

C)

Parkinson's disease

E)

mental depression

Ans: C 58. Which of the following amines is involved in the breakdown of glycogen to glucose? A) epinephrine B) serotonin C) cephalin D) sphingomyelin E) cortisone Ans: A 59. Which synthetic amide compounds are used as sedatives and as anticonvulsants? A) amides B) serotonins C) epinephrines D) amphetamines E) barbiturates Ans: E 60. In addition to an amine, what other type of compound is formed in the amide hydrolysis reaction shown? amide + strong base  amine + ? A) amine D) amino acid B)

alkylammonium ion

C)

carboxylic acid salt

E)

nitro compound

Ans: C 61. Acid-catalyzed hydrolysis of amides is an important reaction because it represents the first step in the digestion of dietary protein. Which of the following compounds is formed as a result of the acid-catalyzed hydrolysis of N-methylbutanamide?

A) CH3CHCH2CH2CH2CH3 B) NH2CH2CH2CH2CH3 C) CH3NH3+ D) CH3NH2

E) Ans: C 62. What is the intermolecular force between primary amine molecules? A) London forces D) ionic bonds

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Chapter 15 Amines and Amides

B)

dipole-dipole force

C)

hydrogen bonding

E)

None of the choices are correct.

Ans: C 63. Which of the following does NOT have hydrogen bonding between molecules? A) ammonia D) tertiary amines B)

primary amines

C)

secondary amines

E)

All of the choices are correct.

Ans: D 64. Which of the following is a property of amphetamines? A) central nervous system stimulant D) decongestant B)

analgesic

C)

anesthetic

E)

Both B and C are correct.

Ans: A 65. Which of the following is a property of ephedrine? A) central nervous system stimulant D) decongestant B)

analgesic

C)

anesthetic

E)

Both B and C are correct.

Ans: D 66. Which best describes the chemical behavior of amines? A) weak acids D) strong bases B)

weak bases

C)

strong acids

E)

neutral compounds

Ans: B 67. Which of the following is a quaternary ammonium salt? A) NH4Cl D) (CH3)3NHCl B)

CH3NH3Br

C)

(CH3)2NH2F

E)

Ans: E

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(CH3)4NCl

Chapter 15 Amines and Amides

68. Lidocaine is used as a local anesthetic and a cardiac depressant. When Lidocaine is administered, it is administered as the alkylammonium salt Lidocaine HCl. Why is the alkylammonium salt, rather than the free amine, used?

A) The alkylammonium salt has a higher solubility in water and bodily fluids than the free amine. B) The alkylammonium salt is not as addictive as the free amine. C) The alkylammonium salt is more basic than the free amine. D) The alkylammonium salt is a gas at room temperature and can be readily inhaled. E) None of the above. Ans: A 69. Which statement concerning amines and amides is false? A) Amines and amides are both weak bases. B)

Amines and amides both contain a nitrogen atom.

C)

Amides have a carbonyl group, amines do not.

D)

Amines and amides can both have hydrogen atoms connected to the nitrogen.

E)

Amines and amides can both have hydrogen bonding between molecules.

Ans: A 70. What is a medical use for barbiturates? A) analgesic B)

anticonvulsant

C)

sedative

D)

stimulant

E)

Both B and C are correct.

Ans: E 71. Amides may be prepared by which of the following methods? A) the reaction of an acid chloride with an amine B)

the reaction of an acid anhydride with ammonia

C)

the reaction of a carboxylic acid and a nitrate

D)

the reaction of a carboxylic acid and an ammonium salt

E)

Both A and B are correct.

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Chapter 15 Amines and Amides

Ans: E 72. A primary amide has two carbons bonded to the nitrogen. Ans: False 73. N-methyl-1-propanamine contains a methyl group, hydrogen, and a propyl group attached to a nitrogen atom. Ans: True 74. Aniline is another acceptable name for benzenamine. Ans: True 75. Amines react with water to form alkylammonium salts. Ans: False 76. Hydrolysis of an amine produces an amide. Ans: False 77. Purine and pyrimidine rings are found in DNA. Ans: True 78. The amine morphine is an analgesic. Ans: True 79. In solid amides, the oxygen atom of the C=O group can form strong hydrogen bonds with the hydrogen of the N-H group on a neighboring molecule. Ans: True 80. Amines behave as bases when dissolved in water. Ans: True 81. Serotonin is a neurotransmitter. Ans: True 82. Barbiturates are used as anticonvulsants. Ans: True

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