Deck 10: Amines

Question 1

Arrange the basicities of the four amines in decreasing order (highest first).

A) II, III, I, IV
B) IV, III, II, I
C) I, III, IV, II
D) III, IV, I, II

Answer 1

II, III, I, IV

Question 2

Which compound is the strongest base?

A) I
B) II
C) III
D) IV

Answer 2

IV

Question 3

Which is the name for the following compound?

A) 4-carboxy aniline
B) 1-amino-4-carboxybenzene
C) benzylamine carboxylic acid
D) 4-aminobenzoic acid

Answer 3

4-aminobenzoic acid

Question 4

Which is the IUPAC name for the following structure?

A) N-methyl-tert-butylamine
B) 2,N-methyl-1,1-dimethylethylamine
C) 2,N-dimethyl-2-propanamine
D) tert-butyl methyl amine

Question 5

Arrange the amines in order of increasing boiling point (lowest first).

A) I, III, II, IV
B) II, IV, I, III
C) IV, II, III, I
D) II, III, IV, I

Question 6

Hydrocodone is a semi-synthetic opioid, which is an orally active narcotic analgesic (painkiller), often found (together with acetaminophen (N-(4-hydroxyphenyl)acetamide)) in Vicodin and other brands. What is the classification of the amine?

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

Question 7

Which is the classification of the following compound?

A) 1°
B) 2°
C) 3°
D) 4°

Question 8

Arrange the amines in order of increasing solubility in water (least first).

A) II, III, I, IV
B) IV, II, III, I
C) IV, III, II, I
D) I, III, II, IV

Question 9

Arrange the amines in order of increasing boiling point (lowest first).
Methylamine ethylamine propylamine cyclohexylamine
I II III IV

A) IV, III, II, I
B) I, II, III, IV
C) III, II, I, IV
D) II, I, IV, III

Question 10

Which is the structure for N,N-dimethyl-3-hexanamine?

A) I
B) II
C) III
D) IV

Question 11

Which is the correct structure for diphenylamine?

A) I
B) II
C) III
D) IV

Question 12

Dopamine is a neurotransmitter occurring in a wide variety of animals, including both vertebrates and invertebrates. What is the classification of the amine?

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

Question 13

Which pairs of names and structures match correctly?

A) I and II and III
B) II and IV and IV
C) II and IV and V
D) I and III and V

Question 14

Arrange the amines in order of increasing boiling point (lowest first).

A) II, III, I, IV
B) III, I, IV, II
C) IV, II, III, I
D) IV, III, I, II

Question 15

Arrange the amines in order of increasing solubility in water (least first).

A) III, I, IV, II
B) II, I, III, IV
C) I, III, IV, II
D) IV, II, III, I

Question 16

Arrange the following in order of increasing strength of the hydrogen bonds (weakest first).

A) I, II, III, IV
B) II, I, IV, III
C) II, IV, I, III
D) I, IV, II, III

Question 17

Which compound is the strongest base?

A) I
B) II
C) III
D) IV

Question 18

Procaine is a local anesthetic drug. What is the classification of the amines I and II?

A) I: primary aliphatic; II: primary aromatic
B) I: tertiary aliphatic, II: primary aromatic
C) I: tertiary aliphatic, II: tertiary aromatic
D) I: tertiary aromatic, II: tertiary aliphatic

Question 19

Which is the name for the following compound?

A) aniline hydrochloride
B) phenyltrihydrogenammonium chloride
C) aniline chloride
D) benzylammonium chloride

Question 20

Order the following bases according to increasing basicity (weakest base first):

A) I, III, II, IV
B) III, II, IV, I
C) IV, II, III, I
D) II, IV, I, III

Question 21

Which structures are secondary amines?

A) I, II
B) II, III
C) III, IV
D) II, IV

Question 22

The name of the following compound is _______________________________.

Question 23

The name of the following compound is ______________________________.

Question 24

The order of increasing basicity of the following compounds is (1 is the least basic),

Question 25

The starting material needed to complete the following reaction is,

Question 26

The name of the following compound is _________________________________.

Question 27

The major product of the following reaction is,

Question 28

At pH 5.0, the ratio of morpholine and morpholinium ion is 1:1622. Which is the pK_b of morpholine?

A) 3.21
B) 5.79
C) 8.21
D) 9.25

Question 29

When the following compounds are dissolved in water at the same concentrations, which one will have the lowest pH (i.e., most acidic)?

A) I
B) II
C) III
D) IV

Question 30

Which reactions will proceed predominantly to products as written?

A) I, II
B) III, IV
C) II, IV
D) I, III

Question 31

The following mixture was extracted with 1 M HCl, followed by 1 M NaOH, followed by ether. Which compound is recovered from the acid solution?

A) I
B) II
C) III
D) None of the above

Question 32

The starting material needed to complete the following reaction is,

Question 33

Which is the product of the following reaction?

A) I
B) II
C) III
D) IV

Question 34

The starting material and reactants needed to complete the following reaction are?

Question 35

The order of decreasing basicity of the following amines is (1 is the most basic),

Question 36

Arrange the amines in order of increasing basicity (weakest first).

A) IV, II, III, I
B) II, I, III, IV
C) I, II, III, IV
D) II, I, IV, III

Question 37

The order of increasing boiling point of the following compounds is (1 is lowest boiling),

Question 38

When guanidine (at left) and imidazole (at right) undergo protonation, which nitrogen atoms are protonated preferentially?

A) I, III
B) II, IV
C) I, IV
D) II, III

Question 39

Guanidine has a pK_b value of 0.4. Which is the ratio of guanidine to its conjugate acid at blood pH of 7.4?

A) 10^-6.2:1
B) 10^+6.2:1
C) 1:1
D) 2.5:1

Question 40

Trinitrotoluene (TNT) reacts with large quantities of hydrogen in the presence of a nickel catalyst. Which reaction product is formed?

A) I
B) II
C) III
D) IV

Question 41

The pKa for ethyl ammonium ion is 10.8 (ethyl amine pK_b is 3.2).

Question 42

The reactants and solvents needed to complete the following reaction are?

Question 43

The starting material and reactants needed to complete the following reaction are?

A) I
B) II
C) III
D) IV

Question 44

The strongest base in the following group is methylthiocyclohexane.

Question 45

The strongest base in the following group is aniline.

Question 46

The equilibrium for the reaction of p-nitroaniline and acetic acid lies to the right.

Question 47

Many d-block metals are suitable catalysts for the reduction of aromatic nitro-compounds by molecular hydrogen.

Question 48

Tertiary amines are generally stronger bases than secondary amines.

Question 49

The name of the following compound is N-cyclopentylethanamine.

Question 50

Metal catalysts are the more reactive the larger their surface is that is accessible to both, the aromatic nitro-compounds and molecular hydrogen.

Question 51

Cyclohexanamine is a 2º amine.

Question 52

The name of the following compound is 3,5-dimethylpiperidine.

Question 53

The reduction of aromatic nitro-compounds using metallic iron requires a basic aqueous reaction medium.

Question 54

tert-Butyl methyl amine is a 3º amine.

Question 55

The reduction of aromatic nitro-compounds using molecular hydrogen requires a metal catalyst.