1.

7 Carboxylic Acids and Esters

Organic acids are characterized by the presence of a carboxyl functional group, COOH,
and hence are called carboxylic acids. As with inorganic acids, carboxylic acids can react
with compounds containing OH groups to form an organic “salt” called an ester.

Figure 1
Tracking dogs, with their acute
sense of smell, are trained to iden-
tify odours in police work. As car-
boxylic acids have distinctive
odours, the dogs may follow the
characteristic blend of carboxylic
acids in a person’s sweat. Trained
dogs are also used to seek out
illegal drug laboratories by the
odour of acetic acid. Acetic acid is
formed as a byproduct when mor-
phine, collected from opium pop-
pies, is treated to produce heroin.
Carboxylic Acids
When wine is opened and left in contact with air for a period of time, it will likely turn
sour. The alcohol in the wine has turned into vinegar. Grocery stores sell wine vinegars
for cooking or for salad dressings. The chemical reaction in this souring process is the
oxidation of ethanol, and the vinegar produced belongs to a family of organic com-
pounds called carboxylic acids.
Carboxylic acids are generally weak acids and are found in citrus fruits, crab apples,
rhubarb, and other foods characterized by a sour, tangy taste. Sour milk and yogurt con-
tain lactic acid, produced by a bacteria culture. If you have ever felt your muscles ache
after prolonged exertion, you have experienced the effect of lactic acid in your muscles.
The lactic acid is produced when the supply of oxygen cannot keep up with the demand
during extended exercise. The gamey taste of meat from animals killed after a long hunt
is due to the high concentration of lactic acid in the muscles.
OH OH
CH3 C C O

carboxylic acid one of a family of lactic acid

organic compounds that is charac-
terized by the presence of a Carboxylic acids also have distinctive odours that can be used to advantage in law
carboxyl group; COOH enforcement (Figure 1).

TRY THIS activity Making Flavoured Vinegar

If vinegar (a carboxylic acid) can be made from ethanol (the
alcohol resulting from the fermentation of sugars), it should be
possible to make a nice flavoured vinegar at home starting with
apples, and a good supply of oxygen for oxidation.
Materials: apples; blender or food processor; sieve or cheese-
cloth; glass or plastic jars with lids, flavouring (e.g., ginger,
garlic, raspberries)
• Wash and chop the apples. Purée them, peel included, in the
blender.
• Pour the pulp into a sieve or a bowl lined with cheesecloth.
Strain out most of the pulp.
• Pour the juice into glass or plastic jars. Replace the lids
loosely to maintain a good oxygen supply. Keep at room tem-
perature and out of direct sunlight.
• Stir well each day to increase oxygen access. The yeast nor-
mally found in the fruit will start the fermentation process,
and vinegar should be produced in three to four weeks,
identifiable by smell.
(a) Write a series of chemical equations showing the
reactions that produce vinegar from ethanol.
(b) Describe a test to confirm that an acid is present in the
solution.
• Filter the vinegar through a coffee filter to remove any sedi-
ment, then pasteurize it by heating the filled jars (loosely
lidded) in a pan of hot water until the vinegar is between
60°C and 70°C.
(c) What is the purpose of the preceding step? Why does
it work?
• To add flavour, tie flavourings such as ginger, garlic, or rasp-
berries in a small cheesecloth bag and suspend in the
vinegar for several days. Enjoy the final oxidation product on
a salad.

58 Chapter 1 NEL
 Section 1.7

Naming Carboxylic Acids

The functional group of carboxylic acids is the carboxyl group, written in formulas as carboxyl group a functional group
COOH. This functional group combines two other functional groups already familiar consisting of a hydroxyl group
to us: the hydroxyl (OH) group in alcohols, and the carbonyl (CO) group in alde- attached to the C atom of a carbonyl
group; COOH
hydes and ketones.
The IUPAC name for a carboxylic acid is formed by taking the name of the alkane or
alkene with the same number of carbon atoms as the longest chain in the acid. Remember
to count the C atom in the carboxyl group in the total number of the parent chain. The
-e ending of the alkane name is replaced with the suffix -oic, followed by the word “acid.”
The simplest carboxylic acid is methanoic acid, HCOOH, commonly called formic acid;
the name is derived from the Latin word formica which means “ant,” the first source of
this acid (Figure 2). Methanoic acid is used in removing hair from hides and in coagu-
lating and recycling rubber.
O

H C O H
formic acid
Figure 2
Ethanoic acid, commonly called acetic acid, is the compound that makes vinegar taste Most ants and ant larvae are edible
sour. This acid is used extensively in the textile dyeing process and as a solvent for other and are considered quite delicious.
They have a vinegary taste because
organic compounds.
they contain methanoic acid,
The simplest aromatic acid is phenylmethanoic acid, better known by its common HCOOH, commonly called formic
name, benzoic acid. Benzoic acid is largely used to produce sodium benzoate, a common acid. In some countries, large ants
preservative in foods and beverages. are squeezed directly over a salad to
add the tangy ant juice as a dressing.
O

C OH

DID YOU KNOW ?

Water-Soluble Vitamins
Some acids contain multiple carboxyl groups. For example, oxalic acid, which is found With its many polar hydroxyl
naturally in spinach and in the leaves of rhubarb, consists of two carboxyl groups bonded groups, vitamin C ascorbic acid is
to each other; it is used in commercial rust removers and in copper and brass cleaners. highly water-soluble. The water-
soluble vitamins are not stored in
Tartaric acid occurs in grapes; it is often used in recipes that require a solid edible acid the body; rather, they are readily
to react with baking soda as a leavening agent. Citric acid is responsible for the sour excreted in the urine. It is therefore
taste of citrus fruits. Vitamin C, or ascorbic acid, found in many fruits and vegetables, important that we include these
is a cyclic acid. A familiar aromatic acid is acetylsalicylic acid (ASA), the active ingredient vitamins in our daily diet. However,
in Aspirin; you may have experienced its sour taste when swallowing a tablet. although taking too much vitamin
C is not dangerous, taking exces-
When naming acids with multiple carboxyl groups, the suffix -dioic acid is used for acids
sive amounts is truly sending
with a carboxyl group at each end of the parent chain. The compound HOOCCH2COOH money down the drain.
is named propanedioic acid; the carboxyl C atoms are counted in the parent chain. When
more carboxyl groups are present, all COOH groups may be named as substituents on the
parent chain; in this case, the parent chain does not include the carboxyl C atoms. An
example is citric acid, shown below; it is named as a tricarboxylic acid of propane.

COOH HO CH COOH CH2 COOH OH COOH

O
COOH HO CH COOH HO C COOH O CH CH2CH2OH OOCCH3

oxalic acid tartaric acid CH2 COOH

HO OH
citric acid ascorbic acid acetylsalicylic acid
(Vitamin C) (ASA)

NEL Organic Compounds 59

 SAMPLE problem Naming and Drawing Carboxylic Acids
Write the IUPAC name and the structural formula for propenoic acid.
The prefix propen- indicates that the acid contains three C atoms with one double bond;
the end C atom is in the carboxyl group. Since the carboxyl C atom can only form one
more single bond with its neighbouring C atom, the double bond is between carbon 2 and
carbon 3.
The structural formula for propenoic acid is
H H O

H C C C OH

Example
What is the IUPAC name for this carboxylic acid?
CH2 — CH — COOH

CH3 CH3

Solution
The structure represents 2-methylbutanoic acid.

Practice
Understanding Concepts
1. Draw a structural diagram for each of the following compounds:
(a) octanoic acid
(b) benzoic acid
(c) 2-methylbutanoic acid
2. Give IUPAC and, if applicable, common names for these molecules:
(a) O
H C OH
(b) O
CH3 CH2 CH CH2 C OH
CH2CH3
(c) CH3CH2 O
CH3 CH2 CH2 CH CH C OH
CH2CH3

Properties of Carboxylic Acids

The carboxyl group is often written in condensed form as COOH. However, the two
oxygen atoms are not bonded to each other. In fact, the carboxyl group consists of a
hydroxyl group (OH) attached to the C atom of a carbonyl group (CO).
O
C OH
carboxyl group

60 Chapter 1 NEL
 Section 1.7

As one would predict from the presence of both carbonyl (CO) and hydroxyl groups
(OH), the molecules of carboxylic acids are polar and form hydrogen bonds with each
DID YOU KNOW ?
Getting No Reaction
other and with water molecules. These acids exhibit similar solubility behaviour to that
of alcohols; that is, the smaller members (one to four carbon atoms) of the acid series
are soluble in water, whereas larger ones are relatively insoluble. Carboxylic acids have
the properties of acids: a litmus test can distinguish these compounds from other hydro-
carbon derivatives. They also react with organic “bases” in neutralization reactions to form
organic “salts,” as we will see later, in Chapter 2.
The melting points of carboxylic acids, as Table 1 shows, are higher than those of
their corresponding hydrocarbons (Figure 3). We can explain this by the increased inter-
molecular attractions of the polar carboxyl functional groups. This explanation is sup-
ported by the significantly higher melting points of analogous acids with an abundance
of carboxyl groups.
Cockroaches can swim happily in
Table 1 Melting Points of Some Carboxylic Acids and Their Parent Alkanes sulfuric acid because they have an
unreactive outer layer that consists
Number of Number of Compound Melting point of hydrocarbons. Human skin con-
C atoms COOH groups (°C) tains functional groups that react
1 0 methane –182 with acids, which is why we can
1 1 methanoic acid 8 be badly injured by contact with
concentrated strong acids.
2 0 ethane –183
2 1 ethanoic acid 17
2 2 oxalic acid 189
4 0 butane –138
4 1 n-butanoic acid -8
4 2 tartaric acid 206
6 0 hexane –95
6 1 hexanoic acid 13
6 3 citric acid 153 Figure 3
Oxalic acid, found in rhubarb, differs
from vinegar in that its molecule
Preparing Carboxylic Acids contains an additional carboxyl
group. This increased polarity
When an alcohol is mildly oxidized, an aldehyde is produced. Further controlled oxidation
explains why oxalic acid is a solid
of the aldehyde results in the formation of a carboxylic acid, containing a carboxyl group. while vinegar is a liquid at the same
The general oxidation pathway in this process is from alcohol to aldehyde to carboxylic temperature.
acid; the functional group in the parent molecule changes from the hydroxyl group to the
carbonyl group, then to the carboxyl group. As you can see in the example below, the dif-
ference between the carbonyl group and the carboxyl group is one additional O atom,
present in the OH group. In the case of ethanol, the aldehyde formed is ethanal (acetalde- INVESTIGATION 1.7.1
hyde), which is further oxidized to ethanoic acid, commonly known as acetic acid.
Properties of Carboxylic Acids
OH O (p. 87)
What gives a carboxylic acid its own
CH3CH2  (O) CH3C H + H2O unique properties? Compare many
properties of a large and a small
ethanol ethanal carboxylic acid, and draw your own
(acetaldehyde) conclusions.

O O
CH3C H  (O) CH3C OH

ethanal ethanoic acid

(acetic acid)

NEL Organic Compounds 61

 The active oxygen, (O), in these reactions is supplied by an oxidizing agent (one of
many compounds that itself becomes reduced). The clever selection of an oxidizing agent
that changes colour as this reaction proceeds is the basis of the breathalyzer test for
alcohol. In this system, the (O) is supplied by the chromate ion in its Cr6+ oxidation
state—an ion with an orange colour in aqueous solution. When a measured volume of air
containing ethanol passes through the breathalyzer tube, the ethanol is oxidized to acetalde-
hyde and then to acetic acid. The oxidation process is accompanied by a reduction of the
chromate ion to its Cr3+ oxidation state—an ion with a green colour in aqueous solution.
The extent of the green colour down the breathalyzer tube provides a measure of the
concentration of alcohol in the breath.

CH3CH2OH  (Cr6+) → CH3COOH  Cr3+

ethanol (orange) acetic acid (green)

Oxidation of Aldehydes to Carboxylic

SUMMARY Acids

aldehyde ketone
O O
R–C–H R – C – R′

(O)* (O)*

not readily oxidized

carboxylic acid
O
*(O) indicates controlled oxidation
R – C – OH
with KMnO4 or Cr2O72–, in H2SO4

SAMPLE problem Formation of Carboxylic Acids

Write an equation to show the controlled oxidation of an aldehyde to form
butanoic acid.
First, write the structural formula for butanoic acid.

CH3CH2CH2COOH

The aldehyde required must have the same number of C atoms, so must be butanal.

CH3CH2CH2CHO

The reaction equation is therefore

CH3CH2CH2CHO  (O) → CH3CH2CH2COOH

62 Chapter 1 NEL
 Section 1.7

Example
Write a series of equations to show the reactions needed to produce methanoic acid from
methanol. Write IUPAC names and nonsystematic names for the organic compounds in
the reactions.

Solution
O
CH3OH  (O) H C H  H2O
methanol methanal
(formaldehyde)

O O
H C H  (O) H C OH
methanal methanoic acid
(formaldehyde) (formic acid)

Practice
Understanding Concepts
3. Draw a structural diagram and write the IUPAC name of an alcohol that can be
used in the synthesis of oxalic (ethanedioic) acid.
4. The labels have fallen off three bottles. Bottle A contains a gas, bottle B contains a
liquid, and bottle C contains a solid. The labels indicate that the compounds have
the same number of carbon atoms, one being an alkane, one an alcohol, and the
other a carboxylic acid. Suggest the identity of the contents of each bottle, and give
reasons for your answer.
5. Write a series of chemical equations to illustrate the synthesis of a carboxylic acid
from the controlled oxidation of 1-propanol.
6. Name and draw a general structure for the functional group in a carboxylic acid.
Explain the effect of the components of this functional group on the molecule.
7. When a bottle of wine is left open to the air for a period of time, the wine often
loses its alcoholic content and starts to taste sour. Write a series of equations to
illustrate the reactions.

Applying Inquiry Skills

8. Suppose that you are given three colourless liquids whose identities are unknown.
You are told that one is an aldehyde, one a ketone, and the other a carboxylic acid.
What physical and chemical properties would you examine in order to identify
each compound? Give reasons for your strategy.

Making Connections
9. Think about common products in the home and identify several that contain alco-
hols other than ethanol. Do these alcohols also turn sour over time? Explain, and
illustrate your answer with structural diagrams.
10. Some cosmetic facial creams contain an ingredient manufacturers call “alpha
hydroxy,” which is designed to remove wrinkles. These compounds are carboxylic
acids that contain a hydroxyl group attached to the C atom adjacent to the car-
boxyl group.
(a) Explain why “alpha hydroxy” is an incorrect name for any compound.

NEL Organic Compounds 63

 (b) The alpha hydroxy acids in cosmetics may include glycolic acid, lactic acid,
malic acid, and citric acid. Research and draw structural diagrams for these com-
pounds.

GO www.science.nelson.com

Figure 4
Cosmetic treatment with carboxylic
acids to remove surface skin may
lead to irritation or sun sensitivity.
This patient is in the third day of a
skin-peeling treatment.
ester an organic compound charac-
terized by the presence of a car-
bonyl group bonded to an oxygen
atom
esterification a condensation reac-
tion in which a carboxylic acid and
an alcohol combine to produce an
ester and water
(c) In order to be absorbed through the skin, a substance must have both polar and
nonpolar components. Explain why these alpha hydroxy acids are readily
absorbed through the skin.
(d) Over-the-counter creams may contain up to 10% alpha hydroxy acids, while 25-
30% concentrations are used by cosmetologists for “chemical peels” (Figure 4).
In each case, the ingredients cause the surface of the skin to peel, revealing
younger-looking skin. Suggest reasons why physicians recommend daily use of
sun protection to accompany the use of these facial creams.
From Carboxylic Acids to Organic “Salts”:
Esterification
Carboxylic acids react as other acids do, in neutralization reactions, for example. A car-
boxylic acid can react with an alcohol, forming an ester and water. In this reaction, the
alcohol acts as an organic base and the ester formed may be considered an organic salt.
This condensation reaction is known as esterification. As we will see later in the chapter,
carboxylic acids also react with organic bases other than alcohols to form important
biological compounds.
The general reaction between a carboxylic acid and an alcohol is represented below.
An acid catalyst, such as sulfuric acid, and heat are generally required. It is interesting to
note that, by tracking the oxygen atoms using isotopes, it has been found that the acid
contributes the OH group to form the water molecule in the reaction.

O O
conc. H2SO4
RC OH  ROH RC O R  HOH
heat
acid alcohol ester water

Esters
Esters occur naturally in many plants (Figure 5) and are responsible for the odours of
Figure 5 fruits and flowers. Synthetic esters are often added as flavourings to processed foods,
The rich scent of the lily is at least and as scents to cosmetics and perfumes. Table 2 shows the main esters used to create
partially due to the esters produced certain artificial flavours.
in the flower.
Table 2 The Odours of Selected Esters
Odour Name Formula
apple methyl butanoate CH3CH2CH2COOCH3
apricot pentyl butanoate CH3CH2CH2COOCH2CH2CH2CH2CH3
banana 3-methylbutyl CH3
ethanoate
CH3COOCH2CH2CHCH3

cherry ethyl benzoate C6H5COOC2H5

orange octyl ethanoate CH3COOCH2CH2CH2CH2CH2CH2CH2CH3

64 Chapter 1 NEL
 Section 1.7

Table 2 The Odours of Selected Esters (continued)

Odour Name Formula
pineapple ethyl butanoate CH3CH2CH2COOCH2CH3
red grape ethyl heptanoate CH3CH2CH2CH2CH2CH2COOCH2CH3
LEARNING TIP
rum ethyl methanoate HCOOCH2CH3
Esters are organic salts, and are
wintergreen methyl salicylate OH named in a similar way to inorganic
salts:
sodium hydroxide  nitric acid →
sodium nitrate  water
—C O — CH3 methanol  butanoic acid →
methyl butanoate  water
O

Naming and Preparing Esters LEARNING TIP

As we learned earlier, esters are organic “salts” formed from the reaction of a carboxylic
Note that the names of carboxylic
acid and an alcohol. Consequently, the name of an ester has two parts. The first part is the acids and esters are written as two
name of the alkyl group from the alcohol used in the esterification reaction. The second separate words (e.g., propanoic
part comes from the acid. The ending of the acid name is changed from -oic acid to - acid, ethyl butanoate), unlike the
oate. For example, in the reaction of ethanol and butanoic acid, the ester formed is ethyl single names of most other organic
compounds (e.g., ethoxybutane,
butanoate, an ester with a banana odour.
2-methyl-3-pentanol).
O O
CH3CH2CH2C OH  CH3CH2OH CH3CH2CH2C O CH2CH3  HOH
butanoic acid ethanol ethyl butanoate water
acid alcohol ester

The functional group for an ester is a carboxyl group in which the H atom is substituted
by an alkyl group: COOR. The general structural formula for an ester is shown below.
O
(H or)R C O R
The general formula of an ester is written as RCOOR. When read from left to right,
RCO comes from the carboxylic acid, and OR comes from the alcohol. Hence,
CH3COOCH2CH2CH3 is propyl ethanoate. Note that, for an ester, the acid is the first part
of its formula as drawn, but is the second part of its name.

CH3CH2CH2COOH  CH3OH → CH3CH2CH2COOCH3  HOH

butanoic acid methanol methyl butanoate

Reactions Involving Carboxylic Acids and Esters SAMPLE problem

1. Draw a structural diagram and write the IUPAC name for the ester formed in
the reaction between propanol and benzoic acid.
To name the ester:
• the first part of the name comes from the alcohol—propyl, and
• the second part of the name comes from the acid—benzoate, so
• the IUPAC name of the ester is propyl benzoate.
To draw the structure:
• draw structural diagrams of the reactants and complete the condensation reaction.

NEL Organic Compounds 65

 O O
C OH C O CH2CH2 CH3
H2SO4
 HO CH2CH2CH3  H2O

benzoic acid 1-propanol propyl benzoate water

2. Write a condensed structural diagram equation for the esterification reaction

to produce the ester CH3CH2CH2COOCH2CH3 . Write IUPAC names for each
reactant and product.
First, identify the acid (four carbons—butanoic acid) and the alcohol (two carbons—
ethanol) that may be used in the synthesis of the ester. Then draw structures and include
the conditions in the chemical equation.
H2SO4
CH3CH2CH2COOH  HOCH2CH3 CH3CH2CH2COOCH2CH3  H2O
butanoic acid ethanol ethyl butanoate water

Example
Name the ester CH3COOCH3 and the acid and alcohol from which it can be prepared.

Solution
The ester is methyl ethanoate, and it can be prepared from methanol and ethanoic acid.

Practice
Understanding Concepts
11. Write complete structural diagram equations and word equations for the formation
of the following esters. Refer to Table 2 and identify the odour of each ester
formed.
(a) ethyl methanoate (c) methyl butanoate
(b) ethyl benzoate (d) 3-methylbutyl ethanoate
12. Name the following esters, and the acids and alcohols from which they could be
prepared.
(a) CH3CH2COOCH2CH3 (c) HCOOCH2CH2CH2CH3
(b) CH3CH2CH2COOCH3 (d) CH3COOCH2CH2CH3

Properties of Esters
The functional group of an ester is similar to the carboxyl group of an acid. What it
lacks in comparison to an acid is its OH group; the hydroxyl group is replaced by an
OR group. With the loss of the polar OH group, esters are less polar, and therefore
are less soluble in water, and have lower melting and boiling points than their parent
acids. Moreover, the acidity of the carboxylic acids is due to the H atom on their OH
group, and so esters, having no OH groups, are not acidic.
O O
RC OH RC OR
carboxylic acid ester

It is the low-molecular-mass esters that we can detect by scent, because they are gases
at room temperature. The larger, heavier esters more commonly occur as waxy solids.

66 Chapter 1 NEL
 Section 1.7

Reactions of Esters: Hydrolysis

When esters are treated with an acid or a base, a reversal of esterification occurs; that is,
the ester is split into its acid and alcohol components. This type of reaction is called
hydrolysis. In the general example shown below, the reaction is carried out in a basic solu-
tion, and the products are the sodium salt of the carboxylic acid and the alcohol.
O O
RC O R  Na  OH RC O Na  ROH
ester acid alcohol

As we shall see in more detail in the next chapter, fats and oils are esters of long-chain
acids (Figure 6). When these esters are heated with a strong base such as sodium hydroxide
Figure 6
(NaOH), a hydrolysis reaction occurs. The sodium salts of the acids that result are what Edible oils such as vegetable oils are
we call soap. This soap-making reaction is called saponification, from the Latin word for liquid glycerol esters of unsaturated
soap, sapon. fatty acids. Fats such as shortening
When certain reactants are used, esters can be formed repeatedly and joined together are solid glycerol esters of saturated
to form long chains. These large molecules of repeating units are called polymers, and fatty acids. Adding hydrogen to the
double bonds of the unsaturated oil
when the repeating units are esters, the polymer is the familiar polyester. We will learn converts the oil to a saturated fat.
more about these and other polymers in the next chapter. Most saturated fats are solids at
room temperature.

SUMMARY Carboxylic Acids and Esters hydrolysis a reaction in which a

bond is broken by the addition of
the components of water, with the
Functional groups: formation of two or more products
• carboxylic acid: COOH carboxyl group saponification a reaction in which
O an ester is hydrolyzed

C OH
• ester: COOR alkylated carboxyl group ACTIVITY 1.7.2
O Synthesis of Esters (p. 89)
What do esters really smell like?
C OR
Make some from alcohols and car-
Preparation: boxylic acids, and find out for your-
self!
• alcohol  (O) → aldehyde  (O) → carboxylic acid
oxidation reaction; add (O)
• carboxylic acid  alcohol → ester  H2O
condensation reaction
Pathway to other compounds:
• ester  NaOH → sodium salt of acid  alcohol
hydrolysis; saponification

Practice
Understanding Concepts
13. In what way is the functional group of an ester different from that of a carboxylic
acid? How does this difference account for any differences in properties?
14. Describe the experimental conditions in the hydrolysis of ethyl formate. Write a bal-
anced equation for the reaction, and name the product(s).

NEL Organic Compounds 67

 Applying Inquiry Skills
15. Design an experimental procedure for the synthesis of an ester, given ethanol and
acetic acid. Describe the steps in the procedure, the safety equipment required, and
the precautions needed in the handling and disposal of the materials.

Making Connections
16. Esters are often referred to as organic salts, and the esterification reaction considered
a neutralization reaction. Use chemical formulas and equations to identify similarities
and differences between esters and inorganic salts.

Section 1.7 Questions

Understanding Concepts 6. In the laboratory synthesis of an ester, what procedure can
1. Write IUPAC names for the following compounds: be used to recover the ester from the other components in
(a) CH3CH2COOCH2CH2CH3 the reaction mixture? Explain the strategy behind this pro-
(b) O CH3 cedure.

CH3CH2COCH2CHCH2CH2CH3 Making Connections

(c) CH3CHCOH 7. From what you have learned about controlled oxidations in
chemical reactions, describe some controlled oxidation
Br O reactions that occur in our everyday lives. In what situations
(d) acetic acid are controlled oxidations ideal, and in what situations are
(e) benzoic acid “uncontrolled” oxidations ideal?
2. Draw structural diagrams for each of the following com- 8. Working with a partner or a small group, brainstorm and list
pounds: several occupations that require a knowledge of alcohols,
(a) methanoic acid carboxylic acids, or esters. Research one of these careers
(b) the product of controlled oxidation of propanal and write a brief report on the main strengths and qualities
(c) the acid formed from saponification of butyl ethanoate needed, academic training, and job opportunities in the field.
(d) the ester that is produced in the esterification of
1-propanol and formic acid GO www.science.nelson.com
(e) the ester that is produced in the esterification of
phenol and vinegar 9. Tannic acid, originally obtained from the wood and bark of
3. Draw the structures of the compounds formed by conden- certain trees, has for centuries been used to “tan” leather
sation reactions between the following reactants, and write (Figure 8).
IUPAC names for each product. (a) Give the chemical formula for tannic acid.
(a) formic acid and 2-butanol (b) What effect does tannic acid have on animal hides?
(b) acetic acid and 1-propanol Explain your answer with reference to the chemical
(c) benzoic acid and methanol reactions that take place.
4. Name the carboxylic acid and the alcohol that may be used GO www.science.nelson.com
to produce each of the following compounds:
(a) O
CH3CH2COCH2CH2CH2CH2CH3
(b) CH CH COCH CHCH CH CH
3 2 2 2 2 3

O CH2CH3
(c)
COOCH3

Applying Inquiry Skills Figure 8

5. Describe an experimental procedure to carry out the Tanneries are notorious for the bad smells they pro-
saponification of propyl butanoate. Explain the evidence duce, as a result of the chemical reactions between the
that will indicate that the reaction has been completed. animal hides and the chemicals used to process them.

68 Chapter 1 NEL