Fundamentals of General, Organic, and Biological Chemistry

John McMurry, David S. Ballantine, Carl A. Hoeger

Chapter 16 Amines - all with Video Answers

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Chapter Questions

02:12

Problem 1

Identify the following compounds as primary, secondary, or tertiary amines.

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03:31

Problem 2

What are the names of these amines?

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02:49

Problem 3

Draw structures corresponding to the following names:
(a) Octylamine
(b) $N$ -Methylpentylamine
(c) $N$ -Ethylaniline
(d) 4-Aminobutan-2-ol

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02:56

Problem 4

Classify the amines in Problem 16.3 (a)-(c) as primary, secondary, or tertiary.

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01:33

Problem 5

Draw the structure of the tetramethylammonium ion. Why does this species have a permanent positive charge?

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01:22

Problem 6

Draw the condensed and line formula of the molecule in the margin. Is it a primary, secondary, or tertiary amine? Why?

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02:21

Problem 7

Arrange the following compounds in order of increasing boiling point. Explain why you placed them in that order.

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01:52

Problem 8

Draw the structures of (a) ethanamine and (b) trimethylamine. Use dashed lines to show how they would form hydrogen bonds to water molecules.

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03:32

Problem 9

Provide compounds that fit the following descriptions:
(a) Two amines that are gases at room temperature
(b) A heterocyclic amine
(c) A compound with an amine group on an aromatic ring

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01:24

Problem 10

Consult Table 16.1 and write the molecular formulas for pyrimidine and purine.

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01:36

Problem 11

Which of the following compounds are heterocyclic nitrogen compounds?

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01:48

Problem 12

Write an equation for the acid-base equilibrium of:
(a) Pyrrolidine and water
(b) Pyridine and water
Label each species in the equilibrium as either an acid or a base.

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01:24

Problem 13

Complete the following equations:

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01:49

Problem 14

Name the organic ions produced in reactions (a)-(c) in Problem 16.13.

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01:15

Problem 15

Which is the stronger base in each pair?
(a) Ammonia or ethanamine
(b) Triethylamine or pyridine

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01:19

When each of the following biologically active amines is placed into the body, they immediately pick up an $\mathrm{H}^{+}$ to form an ammonium ion. Draw the structures of the ammonium ions formed by the following amines:

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02:19

Problem 17

Write the structures of the following compounds:
(a) Butyldiethylammonium bromide
(b) Tetrabutylammonium hydroxide
(c) Propylammonium iodide
(d) Isopropylmethylammonium chloride

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02:43

Problem 18

Identify each compound in Problem 16.17 as the salt of a primary, secondary, tertiary, or quaternary amine.

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01:29

Problem 19

Write an equation for the formation of the free amine from butylammonium chloride by reaction with aqueous $\mathrm{OH}^{-}$.

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01:38

Problem 20

The general structure of an antihistamine is shown in the margin. Does Benadryl (p. 547 ) have that general structure? Explain your comparison of the two structures.

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02:16

Problem 21

Write the structure of benzylamine hydrochloride in two different ways, and name the hydrochloride as an ammonium salt.

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02:43

Problem 22

Provide the products expected from the following reactions:

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01:34

Problem 23

(a) For the compound above, identify each nitrogen as either a primary, secondary, tertiary, quaternary, or aromatic amine.
(b) Which amine group(s) would be able to provide a hydrogen bond? Which could accept a hydrogen bond?

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01:22

Problem 24

The structure of the amino acid lysine (in its uncharged form) is shown below.
(a) Which amine groups would be able to participate in hydrogen bonding?
(b) Is lysine likely to be water-soluble? Explain.

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01:57

Problem 25

Draw structures to illustrate hydrogen bonding (similar to those on p. 541 ) between the following compounds.

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01:48

Problem 26

Explain what bonds must be made or broken and where the electrons go when the hydrogen-bonded water between the two amines shown on page 541 reacts to form an amine, ammonium ion, and $\mathrm{OH}^{-}$.

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01:35

Problem 27

Which of these amines is the strongest base? The weakest?

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01:28

Problem 28

Complete the following equations:

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01:24

Problem 29

Draw the structures corresponding to the following names:
(a) $N$ -Methylcyclohexylamine
(b) Dipropylamine
(c) Pentylamine

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01:52

Problem 30

Draw the structures corresponding to the following names:
(a) $N$ -Methylpentylamine
(b) $N$ -Ethylcyclobutylamine
(c) $p$ -Propylaniline

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01:04

Problem 31

Name the following amines, and classify them as primary, secondary, or tertiary:

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01:27

Problem 32

Name the following amines, and identify them as primary, secondary, or tertiary:

Ronald Prasad

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01:48

Problem 33

Is water a weaker or stronger base than ammonia?

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01:18

Problem 34

Which is a stronger base, diethyl ether or diethylamine?

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01:26

Problem 35

Give names or structures for the following ammonium salts. Indicate whether each is the ammonium salt of a primary, secondary, or tertiary amine.
(a)
(b)
(c) $N$ -Propylbutylammonium bromide
(d) Cyclobutylammonium bromide

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02:20

Problem 36

Give names or structures for the following ammonium salts. Indicate whether each is the ammonium salt of a primary, secondary, or tertiary amine.
(a)
(b)
(b) Pyridinium chloride
(c) $N$ -Butyl- $N$ -isopropylhexylammonium chloride

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02:15

Problem 37

The compound lidocaine is used medically as a local anesthetic. Identify the functional groups present in lidocaine.

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02:25

Problem 38

Identify the functional groups in cocaine.

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02:06

Problem 39

Draw the structures of the ammonium ions formed when the amines in Problem 16.29 are treated with acid.

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01:16

Problem 40

Draw the structures of the ammonium ions formed when the amines in Problem 16.30 are treated with acid.

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02:20

Problem 41

Complete the following equations.

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02:05

Problem 42

Complete the following equations.

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01:33

Problem 43

Many hair conditioners contain an ammonium salt such as the following to help prevent "fly-away" hair. These ions will react with neither acid nor base. Provide a reason why.

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01:09

Problem 44

Choline has the following structure. Do you think that this substance reacts with aqueous hydrochloric acid? If so, what is the product? If not, why not?

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02:46

Problem 45

Propose structures for amines that fit these descriptions:
(a) A secondary amine with formula $\mathrm{C}_{5} \mathrm{H}_{13} \mathrm{~N}$
(b) A tertiary amine with formula $\mathrm{C}_{6} \mathrm{H}_{13} \mathrm{~N}$
(c) A cyclic quaternary amine that has the formula $\mathrm{C}_{6} \mathrm{H}_{14} \mathrm{~N}^{+}$

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01:20

Problem 46

para-Aminobenzoic acid (PABA) is a common ingredient in sunscreens. Draw the structure of PABA (refer to Table 13.2).

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02:38

Problem 47

PABA (Problem 16.46) is used by certain bacteria as a starting material from which folic acid (a necessary vitamin, Table 19.3) is made. Sulfa drugs such as sodium sulfanilamide work because they resemble PABA. The bacteria try to metabolize the sulfa drug, fail to do so, and die due to lack of folic acid. (a) Describe how this structure is similar to that of PABA.
(b) Why do you think the sodium salt, rather than the neutral compound, is used as the drug?

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02:45

Problem 48

Acyclovir is an antiviral drug used to treat herpes infections. It has the following structure:
(a) What heterocyclic base (Table 16.1) is the parent of this compound?
(b) Label the other functional groups present.

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01:47

Problem 49

Which is the stronger base, trimethylamine or ammonia? In which direction will the following reaction proceed?

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01:29

Problem 50

How do amines differ from analogous alcohols in (a) odor,
(b) basicity, and (c) boiling point?

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01:19

Problem 51

Name at least two undesirable characteristics are often associated with alkaloids.

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03:09

Problem 52

Name the following compounds:

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01:24

Problem 53

Complete the following equations.

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01:57

Problem 54

Hexylamine and triethylamine have the same molar mass. The boiling point of hexylamine is $129^{\circ} \mathrm{C}(402 \mathrm{~K}),$ whereas that of triethylamine is only $89^{\circ} \mathrm{C}(362 \mathrm{~K})$. Explain these observations.

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01:29

Problem 55

Baeocystin is a hallucinogenic compound that is isolated from the mushroom Psilocybe baeocystis and has the structure shown below. What heterocyclic base (Table 16.1 ) is the parent of this compound?

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01:52

Problem 56

Why is cyclohexylamine not considered to be a heterocyclic nitrogen compound?

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01:55

Problem 57

Benzene and pyridine are both single-ring, aromatic compounds. Benzene is a neutral compound that is insoluble in water. Pyridine, with a similar molar mass, is basic and completely miscible with water. Explain these phenomena.

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04:31

Problem 58

Name the organic reactants in Problem 16.41 .

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01:01

Problem 59

1-Propylamine, propan-1-ol, acetic acid, and butane have about the same molar masses. Which would you expect to have the (a) highest boiling point, (b) lowest boiling point,
(c) least solubility in water, and (d) least chemical reactivity? Have each member of your group chose a part to answer, and then discuss with each other why those answers were chosen.

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01:31

Problem 60

Which of the two amines, decylamine or ethanamine, would you expect to be more soluble in water and why?

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01:13

Problem 61

Lemon juice, which contains citric acid, is traditionally recommended for removing the odor associated with cleaning fish. What functional group is responsible for a "fishy" odor, and why does lemon juice work to remove the odor? If possible, test this at home using a piece of fish.

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