Deck 16: Amines

Question 1

Phentermine, also called Fastin, is an example of which type of amine?

A) primary aliphatic
B) primary aromatic
C) tertiary aliphatic
D) tertiary aromatic

Answer 1

A

Question 2

Which of the following compounds is a heterocyclic aliphatic amine?

A) (i) only
B) (ii) only
C) (iii) only
D) (ii) and (iii) only

Answer 2

C

Question 3

Which of the following is a not a primary amine?

A) Benzedrine
B) Fastin
C) Methedrine
D) None, they are all primary amines.

Answer 3

C

Question 4

Which of the following is not a heterocyclic aromatic amine?

A) piperidine
B) purine
C) pyrimidine
D) pyridine

Question 5

What is the basis for classifying amines as primary, secondary, or tertiary?

A) the number of carbon atoms bonded directly to the nitrogen atom
B) the number of carbon atoms bonded to a carbon bearing nitrogen
C) the number of nitrogen atoms present
D) the number of hydrogen atoms present

Question 6

Which element is the fourth most common element in organic compounds?

A) N
B) O
C) P
D) S

Question 7

Which of the following is a heterocyclic amine?

A) aniline
B) benzylamine
C) piperidine
D) none of these

Question 8

Which of the following amines serve as a building block for the amine bases of DNA and RNA?

A) purine
B) pyrimidine
C) both a and b
D) neither a nor b

Question 9

What is the IUPAC name of the following compound?

A) 1-amino-4-methylbenzene
B) 4-aminotoluene
C) 4-methylaniline
D) p-toluidine

Question 10

Which of the following is not an alkaloid?

A) cocaine
B) coniine
C) nicotine
D) phentermine

Question 11

Which of the following amines serve as a building block for the amine bases of DNA and RNA?

A) purine
B) pyridine
C) both a and b
D) neither a nor

Question 12

Which of the following compounds are primary aliphatic amines?

A) (i) and (ii) only
B) (i) and (iii) only
C) (ii) and (iii) only
D) (i) only

Question 13

What is the IUPAC name of the following compound?

A) 1,2-dimethylaniline
B) 1,2-dimethyl-4-aminobenzene
C) 3,4-dimethylaniline
D) 3,4-dimethylcyclohexanamine

Question 14

Which of the following is the simplest aromatic amine?

A) anilamine
B) aniline
C) anisole
D) benzylamine

Question 15

(S)-Methamphetamine, also called Methedrine, is an example of which type of amine?

A) primary aliphatic
B) primary aromatic
C) secondary aliphatic
D) secondary aromatic

Question 16

Which of the following is not a chiral molecule?

A) Amphetamine
B) Phentermine
C) Methedrine
D) None of these, they are all chiral.

Question 17

Which of the following compounds is a secondary aromatic amine?

A) (i) only
B) (ii) only
C) (iii) only
D) (i) and (ii) only

Question 18

Amphetamine, also called Benzedrine, is an example of which type of amine?

A) primary aliphatic
B) primary aromatic
C) secondary aliphatic
D) secondary aromatic

Question 19

Nitrogen's abundance among organic compounds is primarily the result of the wide distribution of which class of compounds?

A) alcohols
B) amides
C) amines
D) imides

Question 20

Which of the following is not a heterocyclic aliphatic amine?

A) piperidine
B) pyrrolidine
C) pyrimidine
D) They are all heterocyclic aliphatic amines.

Question 21

What is the IUPAC name of sec-butylamine?

A) 1-butanamine
B) 2-butanamine
C) N-methyl-2-propanamine
D) 2-methyl-2-propanamine

Question 22

What is the IUPAC name of the following compound?

A) methylisopropylamine
B) isopropylmethylamine
C) N-methyl-2-propanamine
D) none of these

Question 23

What is the IUPAC name of tert-butylamine?

A) 1-methyl-2-propanamine
B) 2-methyl-2-propanamine
C) 1,1-dimethylethanamine
D) 2,2-dimethylethanamine

Question 24

What is the IUPAC name of isobutylamine?

A) 1-methyl-1-propanamine
B) 2-methyl-1-propanamine
C) N-methyl-1-propanamine
D) 2,2-dimethylethanamine

Question 25

Which of the following compounds is (S)-N-methyl-2-butanamine?

A) (i) only
B) (ii) only
C) (iii) only
D) (i) and (ii) only

Question 26

What is the common name of CH₃−NH−C₂H₅?

A) ethylmethylamine
B) methylethylamine
C) N-methylethanamine
D) propanamine

Question 27

What is the IUPAC name of the following compound?

A) ethylpropylmethylamine
B) N-ethyl-N-methylpropanamine
C) N-ethyl-N-methyl-1-propanamine
D) N-ethyl-N-methyl-2-propanamine

Question 28

What is the common name of the following compound?

A) methylisopropylamine
B) isopropylmethylamine
C) N-methyl-2-propanamine
D) none of these

Question 29

When N,N- is part of the IUPAC name of an amine which of the following is true?

A) The amine is a 1° amine.
B) The amine is a 2° amine.
C) The amine is a 3° amine.
D) The amine has more than one N atom.

Question 30

What is the common name of the following compound?

A) ethylmethylpropylamine
B) N-ethyl-N-methylpropanamine
C) N-ethyl-N-methyl-1-propanamine
D) N-ethyl-N-methyl-2-propanamine

Question 31

What is the IUPAC name of the following compound?

A) 1-ethylaminobenzene
B) N-ethylaniline
C) N-ethylcyclohexanamine
D) N-ethyltoluidine

Question 32

What is the IUPAC name of the following compound?

A) N-ethylcyclohexanamine
B) N-cyclohexylethanamine
C) N-ethylaniline
D) N-cyclohexylethylamine

Question 33

What is the IUPAC name of the following compound?

A) ethylmethylpropylamine
B) ethylisopropylmethylamine
C) N-ethyl-N-methyl-1-propanamine
D) N-ethyl-N-methyl-2-propanamine

Question 34

What is the common name of (CH₃)₂NC₂H₅?

A) ethyldimethylamine
B) dimethylethylamine
C) N,N-dimethylethanamine
D) none of these

Question 35

What is the IUPAC name of isopropylamine?

A) propanamine
B) 1-propanamine
C) 2-propanamine
D) 2-propylamine

Question 36

What is the IUPAC name of (CH₃)₂NC₂H₅?

A) ethyldimethylamine
B) dimethylethylamine
C) N,N-dimethylethanamine
D) none of these

Question 37

What is the IUPAC name of the following compound?

A) N-propylpentanamine
B) N,N-diethyl-1-propanamine
C) diethylpropylamine
D) N,N-ethylpropanamine

Question 38

What is the common name of the following compound?

A) ethylmethylpropylamine
B) ethylisopropylmethylamine
C) N-ethyl-N-methyl-1-propanamine
D) N-ethyl-N-methyl-2-propanamine

Question 39

What is the IUPAC name of CH₃−NH−C₂H₅?

A) ethylmethylamine
B) methylethylamine
C) N-methylethanamine
D) propanamine

Question 40

What is the IUPAC name of the following compound?

A) 5-aminopentylamine
B) 1,5-pentanediamine
C) 1,5-diaminopentane
D) 5-amino-1-pentanamine

Question 41

What is the name of (CH₃)₃NH⁺Br−?

A) trimethylamine bromine
B) trimethylamine bromide
C) trimethylammonium bromine
D) trimethylammonium bromide

Question 42

What is the name of the following compound?

A) aniline bromine
B) aniline bromide
C) anilinium bromine
D) anilinium bromide

Question 43

Which of the following amines will be most soluble in water?

A) 1-hexanamine
B) N,N-dimethyl-1-hexanamine
C) 1-butanamine
D) 1,4-butanediamine

Question 44

Which of the following amines does not have a pungent odor?

A) (i) only
B) (ii) only
C) (iii) only
D) none, they all have a pungent odor

Question 45

Which of the following is closely associated with the smell of rotting fish?

A) NH₃
B) CH₃NH₂
C) (CH₃)₂NH
D) (CH₃)₃N

Question 46

What is the name of the following compound?

A) N,N,N-trimethylanilinium chloride
B) N,N,N-diethylanilinium chloride
C) N,N,N-triethylanilinium chloride
D) N,N,N-triethylaniline chlorine

Question 47

In a pure sample of which of the following is there no hydrogen bonding?

A) CH₃NH₂
B) (CH₃)₂NH
C) (CH₃)₃N
D) None, pure samples of all these have hydrogen bonds.

Question 48

What is the IUPAC name of the following compound?

A) (R)-2,5-dimethylpentanamine
B) (S)-5-methyl-2-hexanamine
C) (R)-5-methyl-2-hexanamine
D) (S)-2,5-dimethylpentanamine

Question 49

Which of the following gives the correct order of boiling points?

A) C₂H₅OH > C₃H₈ > C₂H₅NH₂
B) C₂H₅OH > C₂H₅NH₂ > C₃H₈
C) C₃H₈ > C₂H₅OH > C₂H₅NH₂
D) C₃H₈ > C₂H₅NH₂ > C₂H₅OH

Question 50

Which of the following has the highest boiling point?

A) butane
B) 1-propanamine
C) 1-propanol
D) 2-propanamine

Question 51

Which of the following has the lowest boiling point?

A) butane
B) 1-propanamine
C) 1-propanol
D) 2-propanamine

Question 52

Which of the following will have the highest boiling point?

A) CH₃CH₂CH₂OH
B) CH₃CH₂CH₂NH₂
C) NH₂CH₂CH₂OH
D) NH₂CH₂CH₂NH₂

Question 53

Which of the following is true?

A) No amines form hydrogen bonds.
B) The N−H- - - -N hydrogen bond is stronger than the O−H- - - -O hydrogen bond.
C) The N−H- - - -N hydrogen bond is the same strength as the O−H- - - -O hydrogen bond.
D) The N−H- - - -N hydrogen bond is weaker than the O−H- - - -O hydrogen bond.

Question 54

Which type of amines cannot hydrogen bond with water?

A) 1°
B) 2°
C) 3°
D) None, they can all hydrogen bond with water.

Question 55

What is the name of (CH₃)₄N⁺Br−?

A) tetramethylamine bromide
B) tetramethylammonium bromide
C) tetramethylamine bromine
D) tetramethylammonium bromine

Question 56

Which of the following is true?

A) The N−H bond is nonpolar.
B) The polarity of the N−H bond is less than that of the O−H bond.
C) The polarity of the N−H bond is the same as that of the O−H bond.
D) The polarity of the N−H bond is greater than that of the O−H bond.

Question 57

Which of the following is true of the solubility of amines?

A) All amines are insoluble in water.
B) All amines are soluble in water.
C) Most low molecular weight amines are soluble in water.
D) Amines decompose when water is added to them.

Question 58

Which of the following is characteristic of relatively low molecular weight amines?

A) They are odorless.
B) They have mild, pleasant odors.
C) They have strong, pleasant odors.
D) They have pungent, unpleasant odors.

Question 59

Which of the following will have the highest boiling point?

A) CH₂CH₂CH₂OH
B) HOCH₂CH₂OH
C) NH₂CH₂CH₂OH
D) NH₂CH₂CH₂NH₂

Question 60

Trimethylamine, ethylmethylamine, and propylamine are constitutional isomers. Based on their shapes and hydrogen bonding ability, which of the following is true regarding their boiling points?

A) They all have very nearly the same boiling points, so it is hard to predict the order.
B) The predictions based on shape are opposite to those based on hydrogen bonding considerations, so it is hard to predict the order.
C) propylamine < ethylmethylamine < trimethylamine
D) propylamine > ethylmethylamine > trimethylamine

Question 61

The following is the formula for gabapentin used in the treatment of epilepsy. How many stereocenters are there in this compound?

A) 1
B) 2
C) 3
D) There are no stereocenters.

Question 62

Which of the following occurs when amines react with water?

A) The amine loses a hydrogen atom.
B) The amine loses a lone pair of electrons.
C) The lone pair of electrons of the amine forms a covalent bond with a hydrogen atom of water and a hydronium ion is displaced.
D) The lone pair of electrons of the amine forms a covalent bond with a hydrogen atom of water and a hydroxide ion is displaced.

Question 63

Which of the following is the correct equation for the reaction of dimethylamine with hydrochloric acid?

A) (CH₃) ₂NH + HCl(aq) 2CH₄(g) + NH₂Cl(l)
B) 2(CH₃)₂NH + 2HCl(aq) 2(CH₃)₂NH₂(aq) + Cl₂(g)
C) (CH₃)₂NH + HCl(aq) (CH₃)₂NH₂⁺(aq) + Cl−(aq)
D) (CH₃)₂NH + 2HCl(aq) 2CH₃NHCl(l) + H₂ (g)

Question 64

Which of the following gives the correct order of solubility in water?

A) (i) > (ii) > (iii)
B) (ii) > (i) > (iii)
C) (iii) > (ii) > (i)
D) (iii) > (i) > (ii)

Question 65

Which of the following is a reasonable value for the pK_b of an aromatic amine?

A) 1.5
B) 3.5
C) 6.5
D) 8.5

Question 66

Which of the following is a primary amine?

A) albuterol
B) epinephrine
C) isoproterenol
D) none of these

Question 67

In what form do aromatic amines exist at physiological pH (pH= 7.4)?

A) largely as neutral molecules
B) largely as their conjugate acids
C) as a mixture of neutral molecules and their conjugate acid, but with a slight predominance of the conjugate acid
D) as a 50/50 mix of neutral molecules and their conjugate acids

Question 68

Which of the following gives the correct order of solubility in water?

A) C₂H₅NH₂ < C₄H₉NH₂ < C₆H₁₃NH₂
B) C₂H₅NH₂ < C₆H₁₃NH₂ < C₄H₉NH₂
C) C₆H₁₃NH₂ < C₄H₉NH₂ < C₂H₅NH₂
D) C₆H₁₃NH₂ < C₂H₅NH₂ < C₄H₉NH₂

Question 69

Which of the following gives the correct order of solubility in water?

A) (i) > (ii) > (iii)
B) (ii) > (i) > (iii)
C) (iii) > (ii) > (i)
D) (iii) > (i) > (ii)

Question 70

In what form do aliphatic amines exist at physiological pH (pH= 7.4)?

A) largely as neutral molecules
B) largely as their conjugate acids
C) as a mixture of neutral molecules and their conjugate acid, but with a slight predominance of the conjugate acid
D) as a 50/50 mixture of neutral molecules and their conjugate acids

Question 71

Which of the following will be the strongest base?

A) (i)
B) (ii)
C) (iii)
D) none of these compounds are basic

Question 72

Although many amines are insoluble in water they can be dissolved in which of the following?

A) aqueous acid
B) aqueous base
C) both a and b
D) neither a nor b

Question 73

Methadone is which of the following?

A) an anesthetic
B) a bronchodilator
C) a narcotic analgesic
D) none of these

Question 74

Which of the following structural features is found in all catecholamines?

A) the presence of two hydroxyl group in meta positions on a benzene ring
B) the presence of two hydroxyl groups in ortho positions on a benzene ring
C) the presence of two hydroxyl groups in para positions on a benzene ring
D) none of the above

Question 75

Which of the following is a primary amine?

A) albuterol
B) epinephrine
C) norepinephrine
D) all of these

Question 76

Select the strongest base in each pair of compounds.

A) A and C
B) A and D
C) B and C
D) B and D

Question 77

Which of the following is a reasonable value for the pK_b of an aliphatic amine?

A) 1.5
B) 3.5
C) 6.5
D) 8.5

Question 78

Procaine hydrochloride is marketed as Novocaine. Which of the following is true when comparing Procaine and Novocaine?

A) Neither is susceptible to oxidation.
B) Both compounds are very susceptible to oxidation.
C) Novocaine is very susceptible oxidation, but Procaine is not.
D) Procaine is very susceptible to oxidation, but Novocaine is not.

Question 79

Which of the following is a useful approach for separating cyclopentanamine and cyclopentanol which are both dissolved in a solution of diethyl ether?

A) Wash the ether solution with aqueous HCl.
B) Wash the ether solution with aqueous NaOH.
C) Wash the ether solution with an aqueous ammonia solution.
D) None of these would affect the separation.

Question 80

Which of the following will be the strongest base?

A) (i)
B) (ii)
C) (iii)
D) none of these compounds are basic