CHEMISTRY GRADE 11

6.4 

At the end of this section, you will be able to:

) list common organic acids and name their sources
) write the general formula of saturated monocarboxylic acids
) write the molecular formulas and names of the first six members of the
saturated monocarboxylic acids
) give the structural formula for the first four members of the saturated
monocarboxylic acids
) give the examples of mono, di and tricarboxylic acids
) name some branched carboxylic acids]
) explain why “Tella” or “Tej” turns sour
) describe the physical and chemical properties of saturated
monocarboxylic acids
) explain the general methods of preparation of saturated monocarboxylic
acids
) explain the industrial and laboratory preparation of acetic acid
) conduct an experiment to prepare acetic acid in the laboratory
) name and write structural formulas of some fatty acids
) describe some uses of common carboxylic acids.

        

Activity 6.7
Discuss the following questions in groups, then present your response to
the whole class.
1. What are acids?
2. Name some common house-hold carboxylic acids.

294 UNIT 6
 Carboxylic Acids

   

Carboxylic acid is one of the class of organic compounds containing the carbonyl
functional group (C=O). A carboxyl group (COOH) is a functional group consisting
of a carbonyl group (C=O) with a hydroxyl group (O−H) attached to the same carbon
atom. It is usually written as —COOH or —CO2H.
O
C OH
Carboxyl group
A. Saturated monocarboxylic acids
The general formula for saturated monocarboxylic acids can be written as:
O
R C OH
where R is either hydrogen or an alkyl group for aliphatic carboxylic acids. When R is
phenyl (aryl) group, the structure represents aromatic carboxylic acids.

Example 6.29
1. The structure of the first three saturated monocarboxylic acids are
written as follows:
O
a. H C OH Methanoic acid
O
b. CH3 C OH Ethanoic acid

O
c. CH3 CH2 C OH Propanoic acid

2. The simplest aromatic acid is benzoic acid.

COOH

Benzene carboxylic acid (Benzoic acid)

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B. Di- and tricarboxylic acids

Carboxylic acids containing two carboxyl groups in their structure are called
dicarboxylic acids.

Example 6.30
1. The structure of the first three saturated dicarboxylic acids are shown below:
O O
a. HO C C OH Ethanedioic acid

O O
b. HO C CH2 C OH Propanedioic acid

O O
c. HO C CH2 CH2 C OH Butanedioic acid

2. The simplest aromatic dicarboxylic acid occurs in three isomeric forms.

One of these is phthalic acid; its structure and IUPAC name are shown
below.
COOH
COOH
1, 2- Benzenedicarboxylic acid (phthalic acid)

Give the structures, IUPAC and common names of the other two isomers.

Similarly, carboxylic acids that contain three carboxyl groups in their structure are
called tricarboxylic acids. Example: citric acid is a typical tricarboxylic acid.
Can you give the structure of citric acid?

Activity 6.8
Form a group and make a list of some fruits containing carboxylic acid.
Which acid is commonly present in most fruits? Which carboxylic acid is
present in wine fruits? Is this acid a monocarboxylic, a dicarboxylic or a
tricarboxylic acid?
Present your responses to the whole class.

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Exercise 6.7
1. Write the structure of the following monocarboxylic acids:
a. Butanoic acid b. Pentanoic acid
2. Write the structure of the following dicarboxylic acids:
a. Pentanedioic acid
b. Hexanedioic acid
c. 1,3-Benzenedicarboxylic acid
3. A great many carboxylic acids are encountered in nature. List some of
them and their respective sources.

      

i. Common names carboxylic acids

A. Straight chain monocarboxylic acids
A large number of carboxylic acids have widely used common names which need
to be learned. The common names of some basic carboxylic acids are derived from
Latin names that indicate the first original natural source of the carboxylic acid.
Table 6.3 lists common names of some of the most important monocarboxylic acids.

Table 6.3: Common names of some monocarboxylic acids.

Structure of Acid Natural Source Common Name

HCOOH Ants (Formica) Formic acid

CH3COOH Vinegar (Acetum) Acetic acid

CH3CH2COOH Basic Fat (Propio) Propionic acid

CH3CH2CH2COOH Rancid butter (Butyrum) Butyric acid

CH3CH2CH2CH2COOH Present in a Valerian herb Valeric acid

CH3CH2CH2CH2CH2COOH Goat (Caper) Caproic acid

Note that the common name of carboxylic acids end with the suffix –ic acid.

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B. Branched chain and substituted carboxylic acids

In common naming system, the branched chain and substituted acids are named as
derivatives of straight chain carboxylic acids. In this case, the position of the side
chain or substituents is indicated by Greek letters, α, β, γ, δ... for designating the 1st,
2nd, 3rd,… position of carbon atoms as shown below:
O
δ γ β α
C C C C C OH
5 4 3 2 1

Example 6.31

β α δ γ β α
a. CH3 CH COOH b. CH3 CH CH2 CH COOH
Cl CH3 CH3
α-chloropropionic acid α,γ-dimethyvaleric acid

C. Dicarboxylic acids
Dicarboxylic acids also possess common names which are based on their sources.
Table 6.4 lists common and IUPAC names of some of the most important dicarboxylic
acids.

Table 6.4: Common and IUPAC names of some dicarboxylic acids.

Structure Common Name IUPAC Name

HOOC−COOH Oxalic acid Ethanedioic acid

HOOC−CH2−COOH Malonic acid Propanedioic acid

HOOC−(CH2)2−COOH Succinic acid Butanedioic acid

HOOC−(CH2)3−COOH Glutaric acid Pentanedioic acid

HOOC−(CH2)4−COOH Adipic acid Hexanedioic acid

HOOC−(CH2)5−COOH Pimelic acid Heptanedioic acid

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D. Aromatic carboxylic acids

Aromatic carboxylic acids are compounds which have a carboxyl group directly
attached to an aromatic ring. The common name of the simplest aromatic
carboxylic acid is benzoic acid.
O
C OH

Benzoic acid
In common naming system, the position of the substituent is indicated by the prefixes
ortho (o-), meta (m-), para (p-) as it is shown in the structure below.
O
C OH
ortho ortho

meta meta

para

Example 6.32

COOH COOH
CH3
a. b.

Cl
CH3
m-chlorobenzoic acid o,p-dimethylbenzoic acid.

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Exercise 6.8
1. Write the common names for the following carboxylic acids:
a. CH3 CH CH2 CH COOH b. HOOC (CH2)2 CH2 COOH
Br Cl
2. Write the structures of carboxylic acids for the given common names:
a. β-Bromobutyric acid b. p-bromobenzoic acid c. glutaric acid

ii. IUPAC names of carboxylic acids

A. Straight chain monocarboxylic acid
In IPUAC system, monocarboxylic acids are named by replacing the terminal
“−e” of the corresponding alkane name with “−oic acid.” They are named as
alkanoic acids.

Example 6.33
1. Write the IPUAC names for:
a. H-COOH b. CH3-CH2-COOH c. CH3-CH2-CH2 CH2-COOH
methanoic acid propanoic acid pentanoic acid
2. Write the structure of the following carboxylic acids:
a. Ethanoic acid b. Butanoic acid c. Hexanoic acid
O O O

a. CH3 C OH b. CH3 CH2 CH2 C OH c. CH3 CH2 CH2 CH2 CH2 C OH

B. Branched chain and substituted monocarboxylic acids

The IUPAC name of a branched carboxylic acid is derived from that of the longest
carbon chain that contains the carboxyl group. The positions of the substitutes are
indicated by Arabic numerals as 1, 2, 3. The numbering of the chain starts from the
carboxyl carbon and it is always assigned C-1 position. Note that C-2 position in
the IUPAC system corresponds to the α-position in the common naming system.
O
δ γ β α Common System
C C C C C OH
5 4 3 2 1 IUPAC System

Example 6.34
a. CH3–CH(CH3)CH2–COOH b. CH3–CH2CH(Cl)–CH(CH3)–COOH
3-methylbutanoic acid 3-Chloro-2-methylpentanoic acid

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C. Dicarboxylic acids
In the IUPAC system, dicarboxylic acids are named as alkanedioic acids. These
names are obtained by replacing the suffix ‘‘–e’’ in the name of corresponding
alkane by ‘‘–dioic acid’’. Table 6.4 above gives the common and IUPAC names
of the first six dicarboxylic acids.

Example 6.35
HOOC–CH2–CH2–COOH
Butanedioic acid
Write the structure of hexaneanedioic acid.

D. Aromatic carboxylic acids

IUPAC name of the simplest aromatic carboxylic acid is benzenecarboxylic acids.
COOH

Benzenecarboxylic acid

Substituted aromatic acids with one carboxyl group are named as derivatives of
benzenecarboxylic acids. The position of substituents is indicated using the Arabic
numerals 2,3, etc according to their position on the benzene ring relative to the carboxyl
group. The carbon on which the carboxyl group is attached is by convention C-1.
COOH COOH
1 1
6 2 6 2
or
5 3 5 3
4 4

Example 6.36
COOH
1
6 2 Br

5 3
4
2-bromobenzenecarboxylic acid

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Exercise 6.9
1. Write the IUPAC names for the following carboxylic acids:
a. CH3 CH COOH b. CH3 CH CH2 CH COOH
CH2CH3 CH2 CH3
CH3
c. Cl CH2 CH2 CH2 COOH d. HO CH2 CH2 CH2 COOH
COOH NH2

e. Cl
f.

CH2CH3 COOH

2. Draw the structures of the following carboxylic acids:

a. 3-chloro-2,3-dimethylpentanoic acid
b. 4-bromo-2-hydroxybenzoic acid
c. p-Methylbenzoic acid
d. 2-ethyl-3-methylpentanedioic acid

      

Activity 6.9
Discuss the following questions in groups, then present your ideas to the
whole class.
1. The solubility of monocarboxylic acids in water decreases with
increase in molecular mass. Explain.
2. Higher members of monocarboxylic acids are almost odourless. Why?
3. Compare the boiling points of monocarboxylic acids with alcohols,
aldehydes and ketones of similar molar masses?
1. State
The lower aliphatic acids containing up to 9 carbon atoms are liquids, whereas
the higher members are colourless waxy solids. Benzoic acid and most of its
derivatives are also colourless solids.

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2. Odor
The odors of the lower aliphatic acids progress from a sharp, irritating odor
of methanoic acid and ethanoic acids to the distinctly unpleasant odor of the
butanoic, pentanoic and hexanoic acids.
3. Melting and Boiling Points
The melting points and boiling points of carboxylic acids are higher than those
of hydrocarbons and oxygen-containing organic compounds of comparable size
and shape and indicate strong intermolecular attractive forces. Figure 6.6 gives
boiling point comparison of carboxylic acid with alkene, ketone, and alcohol.
What is the molecular mass of each compound shown in Figure 6.6?

O OH O

OH
2-Methyl-1-butene 2-Butanone 2-Butanol Propanoic acid
bp (1 atm): 31 °C 80 °C 99 °C 141 °C

               
  
A unique hydrogen-bonding arrangement, shown in Figure 6.7, contributes to these
attractive forces. The hydroxyl group of one carboxylic acid molecule acts as a proton
donor toward the carbonyl oxygen of a second. In a reciprocal fashion, the hydroxyl
proton of the second carboxyl function interacts with the carbonyl oxygen of the first.
The result is that the two carboxylic acid molecules are held together by two hydrogen
bonds.
Hydrogen bonding

δ δ δ
O H O R
C Carboxylic acid
Carboxylic acid C
R O H O
δ δ δ

Hydrogen bonding

   

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 CHEMISTRY GRADE 11

4. Solubility
In aqueous solution intermolecular association between carboxylic acid molecules is
replaced by hydrogen bonding to water. The solubility properties of carboxylic acids
are similar to those of alcohols. Carboxylic acids of four carbon atoms or fewer are
miscible with water in all proportions. Figure 6.8 shows hydrogen bonding between
carboxylic acids and water molecules.
Water Hydrogen
bonding
δ
Ο
δ δ δ
O Η Η
δ
C Η Carboxylic acid
δ δ δ
R O H Ο Water R
δ
Carboxylic acid Ηδ O C
Hydrogen δ δ
bonding O H
                  
 

Does the solubility carboxylic acids in water decrease or increase with increasing
molecular mass? Why? Do you predict that carboxylic acids will be soluble in organic
solvents? Explain.

The boiling points, melting points and solubilities of some carboxylic acids are
given in Table 6.5.

Table 6.5: Physical constants of some carboxylic acids

Boiling point Solubility (g/100 mL)

Structure IUPAC Name
(°C) H2O at 25 °C

HCOOH Methanoic acid 100.5 ∞*

CH3COOH Ethanoic acid 118 ∞*
CH3CH2COOH Propanoic acid 141 ∞*
CH3(CH2)2COOH Butanoic acid 164 ∞*
CH3(CH2)3COOH Pentanoic acid 187 4.97
CH3(CH2)4COOH Hexanoic acid 205 1.08

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 Carboxylic Acids

Boiling point Solubility (g/100 mL)

Structure IUPAC Name
(°C) H2O at 25 °C

CH3(CH2)5COOH Heptanoic acid 223

CH3(CH2)6COOH Octanoic acid 239 0.07
CH3(CH2)7COOH Nonanoic acid 253 —
CH3(CH2)8COOH Decanoic acid 269 0.015

∞* means miscible in all proportions.

Exercise 6.10
1. Arrange the following aliphatic carboxylic acids in the decreasing order
of boiling point:
a. butanoic acid c. octanoic acid
b. decanoic acid d. propanoic acid
2. Which of these aliphatic carboxylic acids has the lowest boiling point?
a. pentanoic acid c. hexanoic acid
b. methanoic acid d. propanoic acid
3. Arrange the following compounds in increasing order of their boiling
points:
a. C5H 12 c. C4H 11OH
b. C2H 5COOH d. CH 3(CH 2) 4COOH

     

Activity 6.10
Form a group, discuss the following questions and present your responses to
the whole class.
1. Why does ‘Tella’ or ‘Tej’ turn sour when kept for a longer time but not
Katikalla?
2. Why does beer have a longer shell life than ‘Tella’?
3. What is the practical use of metal salts of carboxylic acids in your daily life?

UNIT 6 305
 CHEMISTRY GRADE 11

The carboxylic acids show reactions due to the alkyl or aryl group and the carboxyl
group. The carboxyl group is further considered to be made up of a carbonyl and a
hydroxyl group. All these groups modify the properties of each other due to their
interaction. Some of the common reactions of carboxylic acids are:

i. Reaction as an acid
In aqueous solution, the cleavage of O–H bond occurs leading to the formation
of carboxylate ion and hydronium ion. Carboxylic acids ionize partially and an
equilibrium exists between the ionized and un-ionized forms.

O O
R C O H + H2O R C O + H3O
Carboxylic acid Carboxylate ion Hydronium ion

Carboxylic acids are weak acids and dissociates slightly. The following are examples
of reactions of carboxylic acids as an acid.
a. Reaction with metals: Carboxylic acids react with active metals such as Na, K, Mg,
Ca, etc. to give metal carboxylate salts, RCO2−M+, and hydrogen gas.
O O
2 R C O H + 2 Na 2 R C O Na + H2
Carboxylic Sodium Hydrogen
acid carboxylate gas
The salts of carboxylic acids are named by writing the name of the metal first,
followed by the name of the acid replacing the ending -ic acid by -ate.
For example, sodium reacts with ethanoic acid to form sodium ethanoate and
hydrogen.
2 CH3 COOH + 2 Na 2 CH3 COO Na + H2

b. Reaction with Bases: Carboxylic acids react with strong bases like sodium
hydroxide or potassium hydroxide to form the corresponding metal carboxylate
salts and water.
O O
R C OH + NaOH R C O Na + H2O
Carboxylic acid Sodium carboxylate

306 UNIT 6
 Carboxylic Acids

Reaction with a base is a simple neutralization reaction. Carboxylic acids react with
weak bases like carbonates or bicarbonates to form salt, water and carbon dioxide.
O O
2 R C OH + Na2CO3 2 R C O Na + H2O + CO2
Carboxylic acid Sodium carboxylate

O O
R C OH + NaHCO3 R C O Na + H2O + CO2
Carboxylic acid Sodium carboxylate

They also react with ammonia to form ammonium salts of carboxylic acids.
O O
R C OH + NH3 R C O NH4
Carboxylic acid Ammonium carboxylate

ii. Formation of Esters

One of the important reactions of carboxylic acids involves the replacement of –OH
group by an alkoxy group to form esters as products. In this reaction, carboxylic acids
are heated with alcohols in the presence of concentrated sulphuric acid. The reaction
is called esterification.
O O
H2SO4
R C OH + H O R' R C O R' + H2O
Alcohol Ester
Carboxylic acid

Exercise 6.11
1. Write the chemical equations for the reaction between ethanoic acid
and each of the following reagents and write the names of the products
formed:
a. KOH b. Na 2CO 3 c. NH 3
2. Write the chemical equations for the reaction between methanoic acid
and ethanol and write the name of the product.

UNIT 6 307
 CHEMISTRY GRADE 11

    

One of the important methods for preparation of carboxylic acids is oxidation. Many
saturated monocarboxylic acids are obtained by the oxidation of the corresponding
primary alcohols, whereas aromatic acids are obtained from the corresponding
alkylbenzenes.

i. Oxidation of Primary Alcohols

The primary alcohols are readily oxidized to the corresponding carboxylic acids by
their reaction with common oxidizing agents like K2Cr2O7 or KMnO4.
O
KMnO4
R CH2 OH R C OH
1° Alcohol Carboxylic acid
For example, oxidation of ethanol yields acetic acid (ethanoic acid).
O
KMnO4
CH3 CH2 OH CH3 C OH
Ethanol Ethanoic acid
ii. Oxidation of Alkylbenzenes
Aromatic compounds containing alkyl group as substituent undergo oxidation to
form aromatic acids. The reaction involves oxidation with KMnO4 or K2CrO7 under
vigorous conditions. The alkyl group is oxidized to carboxyl group irrespective of its
size. For example, toluene and ethylbenzene, both give benzoic acid on refluxing with
KMnO4 in alkaline medium.

308 UNIT 6
 Carboxylic Acids

Example 6.37

O
CH3 C OH

KMnO4 / OH
heat
Toluene Benzoic acid

Write the chemical equations for the oxidation of ethylbenzene with KMnO4 in
alkaline medium.

iii. Preparation of acetic acid (Ethanoic acid)

Acetic acid is one of the important carboxylic acids which is used as food preservative. It
can be prepared in laboratory by the oxidation of ethanol with potassium permanganate.
It can also be obtained by passing the vapours of ethanol through copper oxide as
described in Experiment 6.3.

Experiment 6.3
Laboratory Preparation of Acetic Acid
Objective: To prepare acetic acid in the laboratory by oxidation of ethanol.
Apparatus: Goggles, test tubes, test tube rack, quickfit distillation apparatus,
250 mL beaker, pipettes, Bunsen burner, stand, clamp, tripod, wire gauze, digital
balance, blue litmus paper, boiling chips such as fine gravels, broken porcelain
pieces, etc.
Chemicals: Ethanol, sodium dichromate, 1M sulphuric acid, 0.5M sodium
carbonate solution.
Procedure:
Oxidation of ethanol to ethanoic acid
1. Set up the Quickfit distillation apparatus for refluxing as shown in

2. Place about 10 mL of 1M sulphuric acid into the 250 mL round-bottom
flask.

UNIT 6 309
 CHEMISTRY GRADE 11

3. Add 2-3 g of sodium dichromate (Na2Cr2O7) and a few pieces of boiling

chips. Swirl the contents of the flask until the solution is complete (warm
if necessary).
4. Cool the mixture under a running tap since the process is exothermic.
5. Add 1 mL of ethanol dropwise into the flask.
6. Boil under refluxfor 20 minutes
7. Arrange the distillation set up as shown in (Figure 6.9 b) and distil up to
2-3 mL
8. Notice the smell of the product (distilled liquid) and compare it with that
of ethanol.
9. Add a few drops of the distilled liquid to a small amount of solid sodium
carbonate.
10. Add a drop of the distilled liquid to moistened blue litmus paper.

 
Observation and analysis
1. What happened to the colour of the solution in the flask?
2. What is the role of sodium dichromate in the above reaction? Is it oxidized
or reduced?
3. Write the chemical equation for this reaction.
4. What do you conclude from this experiment?

310 UNIT 6
 Carboxylic Acids

       

Large quantities of acetic acid are obtained in industry from fermentation of ethanol.
The process is known as Quick Vinegar Fermentation Process. In the process large
wooden vats are used which have a perforated bottom. They are packed
with wood shavings moistened with old vinegar. Ethanol solution is poured from the
top and trickles down slowly to the perforated bottom. From the lower portion, air
is pumped in the vat. The bacteria present in old vinegar, ferment the ethanol into
acetic acid. The liquor obtained at the bottom is recirculated through the tower. The
maximum concentration of acetic acid obtained by this process is about 10%, which
can be fractionated to yield glacial acetic acid (anhydrous acetic acid).

UNIT 6 311
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Activity 6.11
Discuss the following questions in groups and present your answer to the class.
You have learned about the six foodstaffs in your lower grade biology lesson.
Which one of these foodstaffs produces fatty acid during digestion? Why
are they named fatty acids?

Fatty acids are carboxylic acids with long hydrocarbon chains. The fatty acids most
frequently found in nature are shown in Table 6.6. Most naturally occurring fatty
acids contain an even number of carbon atoms and are unbranched. Fatty acids can
be classified as saturated or unsaturated.
What is the main difference between saturated and unsaturated compounds?

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 Carboxylic Acids

Double bonds in naturally occurring unsaturated fatty acids are never conjugated.
How many methylene (−CH2−) group(s) usually separates the double bonds in
unsaturated fatty acids?(See Table 6.6).
Table 6.6: Some common naturally occurring fatty acids

Melting
Number
Common Name Structure / Formula Point
of carbons
( C )

12 Lauric acid CH3(CH2)10COOH 44

14 Myristic acid CH3(CH2)12COOH 58

16 Palmitic acid CH3(CH2)14COOH 63

18 Stearic acid CH3(CH2)16COOH 69

Arachidic
20 CH3(CH2)18COOH 77
acid

Palmitoleic
16 CH3(CH2)5 CH=CH(CH2)7 COOH 0
acid
18 Oleic acid CH3(CH2)7 CH=CH(CH2)7 COOH 13

18 Linoleic acid CH3(CH2)4 CH=CHCH2CH=CH(CH2)7 COOH -5

Linolen-ic CH3CH2CH=CHCH2CH=CHCH2
18 -11
acid CH=CH(CH2)7 COOH

The physical properties of a fatty acid depend on the length of the hydrocarbon chain
and the degree of unsaturation. The melting points of saturated fatty acids increase
with increasing molecular weight because of increased van der Waals interactions
between the molecules.
Why do unsaturated fatty acids have lower melting points than saturated fatty acids
with comparable molecular weights?

UNIT 6 313
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The melting points of the unsaturated fatty acids decrease as the number of double
bonds increases. For example, an 18-carbon fatty acid melts at 69 °C if it is saturated,
at 13 °C if it has one double bond, at -5 °C if it has two double bonds, and at -11 °C
if it has three double bonds (Table 6.6).

   
Acetic acid is used as a solvent and as a starting material in the preparation of acetates,
acetic anhydride, etc. It is also used to prepare the vinyl acetate polymer which is
used in paints and adhesives. Vinegar contains about 8-10% acetic acid which is
used in many food items. Perhaps one of the most important industrial applications
of long chain carboxylic acid is for making soaps, detergents, and shampoos.
Can you suggest some more examples of the use of carboxylic acids in daily life?

Exercise 6.12
1. Explain the difference in the melting points of the following fatty acids:
a. palmitic acid and stearic acid
b. palmitic acid and palmitoleic acid
c. oleic acid and linoleic acid
2. What are omega fatty acids? Give some examples of omega fatty acids.
3. What is the difference between omega-3-fatty acids and omega-6-fatty
acids?
4. List some essential fatty acids. Why are they called ‘essential’?

Project 6.3
Form a group of five and share information on some carboxylic derivatives
(anhydrides, amides, and acid chloride), then submit a written word and PDF
documents to your teacher. In your write-up, put the following key points into
consideration:
• structures and naming (both IUPAC and common systems) of
anhydrides, amides, and acid chloride
• physical properties of anhydrides, amides, and acid chloride
• common reactions and methods of preparations.

314 UNIT 6