I CHEMIST

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BASED ON
SETS
M
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T Structure, nomenclature,
E properties and uses of
R
I ALKANOATE ACID AND
A
L ALKYL ALKANOATE

for
XII
grade
 Carboxylic acid and ester
1

Chemistry Instructional Materials Class XII

Material Structure, Nomenclature,
characteristics
and usess based SETS(Science,
Environtment,
Technology, and Society)

Copyright 2016
Compiled by: Eti Ofriani

It is strictly forbidden to quote, plagiarizing, copying part or all of the

contents of this
book and retrieval system, without permission.
 Carboxylic acid and ester
2

WHAT IS SETS APPROACH ?

SETS approach (Science, Environment, Technology, and Society)
in
Indonesian known as mutual temas which is science, environment,
technology, and
society. Asyari (in Tristanti, 2011: 12) defines SETS approach as an approach
to
learning science associate with the environment, technology, and society.
SETS
approach is intended to help learners to know the science, development and
application of scientific concepts in everyday life. The approach is about
things that
are real, that can be understood, it can be discussed, and it can be seen.
According podjiaji (in Tistanti) Learning Environmental Science
Technology and Society basically provides an understanding of the links between
science and technology and society is the vehicle to train students' sensitivity to
the
environment as a result of the development of science and technology. Based on
these students are expected to apply their science lessons by exploiting the
environment to create technologies that benefit society.
Carboxylic acid and ester
3

CONTENTS
Cover..................................................................... 1

Introduction.......................................................... 2

Content................................................................. 3

Core Competences................................................ 4

Basic Competences............................................... 4

Indicators and Learning Objectives..................... 4

Alkanoate Acid
1.1 Structure of alkanoate acid............................. 6

1.2 Nomenclature of alkanoate acid..................... 9

1.3 Properties of alkanoate acid............................ 10

1.4 Uses of alkanoate acid.................................... 11

Alkyl Alkanoate
2.1 Structure of alkyl alkanoate............................. 13

2.2 Nomenclature of alkyl alkanoate.................... 13

2.3 Properties of alkyl alkanoate........................... 15

2.4 Uses of alkyl alkanoate................................... 21

Lest Have Fun....................................................... 25

Glosarium............................................................. 26

References............................................................. 27
 Carboxylic acid and ester
4

CORE COMPETENCES
CC1
To internalize and practice the teachings of individual religion.

CC 2
To internalize and practice honest behavior, discipline, responsibility, caring
(gotong
royong, cooperation, tolerance, peace), polite, responsive and pro-active and
displayed as part of the solution to various problems in interacting effectively
with
the social environment and nature and put them selves as a reflection of the
nation
in the association world.

CC 3
To understand, implement, analyze and evaluate factual knowledge,
conceptual,
procedural, and metacognitive by curiosity about science, technology, art,
culture,
and humanities with the insight of humanity, national, state, and civilization-
related
causes of phenomena and events and applying procedural knowledge in
specific
areas of study that suit their talents and interests to solve the problem.

CC 4
To process, reason, present, and creat in the realm of the concrete and the
abstract
realm associated with the development of learned at school independently
and to
act effectively and creatively, and are able to use the method according to
the rules
of science.
 Carboxylic acid and ester
5
Basic Competences, indicators,
and Learning Objectives
BASIC COMPETENCES
1.1 To recognize the order in colligative properties, redox reactions, the
diversity of
nature elements, macromolecular compounds as a manifestation of the
greatness of Almighty God and the knowledge of the existence of such
regularity
as a result of human creative thinking that truth is tentative.
2.2 To demonstrate cooperative behavior, polite, tolerant, peace-loving and
caring
environment and saving in the use of natural resources.
3.1 To analyze the structure, nomenclature, properties and usefulness
carboxylic acid
compound and ester
INDICATORS
1.1.1 Be aware that the carboxylic acid and ester is a gift of God Almighty
2.2.1 To demonstrate cooperative behavior, polite, tolerant, peace-loving and
caring
environment and saving in the use of carboxylic acid and esters.
3.1.1 To write the structure of product that contain the carboxylic acid and
ester
3.1.2 To identify the nomenclature of carboxylic acid and ester the compound
3.1.3 To describe the properties of the carboxylic acid and ester
3.1.4 To analyze the products (uses, technology that use, impact for
environtment)
containing carboxylic acid and ester in daily life
LEARNING OBJECTIVES
 Students can realize that carboxylic acid (carboxylic acid) and esters is a gift
of
God Almighty
Students can demonstrate cooperative behavior, polite, tolerant, peace-loving
and caring environment and saving in the use of carboxylic acid and esters.
Students can write the structure of product that contain carboxylic acids and
esters
Students can identify the nomenclature of carboxylic acid and ester
compound
Students can explain the properties of the carboxylic acid and ester
Students can analyze (uses, technology that use, impact for environtment)
product containing carboxylic acid and ester in their daily life
 Carboxylic acid and ester
6
STRUCTURE OF CARBOXYLIC ACID
Objectives : Students can write the structure of product that contain
carboxylic acids.
Students can give name some structure of carboxylic
acids.

Do you like to eat meatballs? What are the

material that you add to make the
meatballs more delicious?
Have you ever add the vinegar ? The
vinegar is added to the meatballs to make
it more delicious. What the chemical
formula of vinegar ? Whats it belong to?

The formula of vinegar is CH3COOH. CH3COOH is belong to acid, exactly

carboxylic acid. Why ?
Is it because the structure of the vinegar? What is the structure of carboxylic
acid
look like?

What are carboxylic acids?

The carboxyic acids are a homologous series of organic compounds with the
carboxyl functional group as shown in fig 1.1

For simplicity, the functional group is often written as COOH. Carboxylic

acids
are waek acids. They are a class of organic acids.

All carboxylic acids have this

functional group

Fig 1.1
Carboxylic acid and ester
7
Naming Carboxylic Acids
The name of carboxylic acid ends with -oic acid. Most of us are familiar with
vinegar.
Vinegar contains ethanoic acid, which is a carboxylic acid with two carbon atoms.

Table 1.1 the formula of some product that contain carboxylic acid.
Carboxylic acid and ester
8
Product The carboxylic Molecular formula
What is the general formula thatfor carboxylic
acids? Vinegarcontain
Acid
From the structural formula of the carboxylic acids
given (CH3COOH)
in Table 1.1, we can conclude that the general
formula of
carboxylic acids is written as CnH2n-1COOH. Using the
general formula, we can therefore predict that a
carboxylic acid with six carbon atoms has the
molecular Tartrat Acid
formula C5H(2x5)+1COOH, that(Cis
4HC6O6)
5H 11COOH.

Oxalate acid
(H2C2O4)

Palmitate Acid
(C16H32O2)
To name a carboxylic acids by the IUPAC system, first
identify the longest carbon chain, including the carboxyl
group. Then form the acid name by dropping the e- from
the corresponding parent hydrocarbon name and adding
oic acid. Thus, the names corresponding to the C-1, C-
2, and C-3 acids are methnoic acid, ethanoic acid, and
propanoic acid. These names are, of course, derivated Some ants spray
from methane, ethane, and propane: methanoic acid
(commonly callod
formic acid) to
string their
attackers.
CH4 methane HCOOH methanoic acid
CH3CH3 ethane CH3COOH ethanoic acid
CH3CH2CH3 propane CH3CH2COOH propanoic acid
The IUPAC system is neither the only not the most generally used method of
naming
acids. Organic acids are usually known by common names. Methanoic, ethanoic,
and propanoic acids are commonly called formic., acetiic, and propinoic acids,
respectively. These names usually refer to a natural source of the acid and are not
really systematic. Formic acid was named from Latin word formicia, meaning
ant.
This acid Contributes to the stinging sensation of ant bites. Acetic acid is found in
vinegar and is so named from the Latin word vinegar. The name of butyric acid is
derived from the Latin term for butter, since it is a constituent of butterfat. Many
of
the carboxylic acid, pricipally these even numbers of carbon atoms ranging from 4
to
about 20., exist in combined from in plant and animal fats.

A dog can be trained to track people because its

sensitive nose can recognise the characteristic
smell of human sweat. Each persons sweat
contains a unique blend of carboxylic acids
Carboxylic acid and ester
9
PROPERTIES OF CARBOXYLIC ACIDS
Objectives : Students can explain the properties of the carboxylic acid

Properties of Ethanoic Acid

Ethanoic acid (CH3COOH) is colourless liquid at room temperature. It has a
characteristic vinegar smell.
Like ethanol, ethanoic acid is completely miscible with (soluble in) water. An
aqueous solution of ethanoic acid is a weak acid.

Physical Properties of Carboxylic Acids

Table 1.2 the boiling points and solubilities of some carboxylic acids.

Chemical Properties of Carboxylic Acid

The functional group of carboxylic acid is the carboxyl group. It is carboxyl
group
that is reactive.
1. Reactions with metals
Ethanoic acid reacts with reactive metals such as sodium, potassium and
magnesium to give a salt and hydrogen. The salts of ethanoic are known
ethanoates.

Ethanoic acid + magnesium magnesium ethanoate +

hydrogen

2. Reactions with carbonates

Ethanoic acid reacts with carbonates to give a salt, carbon dioxide and
water.
 Ethanoic acid + sodium carbonate sodium ethanoate +
carbon dioxide + water

Acid o Soubility in water

Boiling Point ( C)
Methanoic acid 101 Very soluble
Ethanoic Acid 118 Very soluble
Propanoic Acid 141 Very soluble
Butanoic Acid 164 Very soluble
Carboxylic acid and ester
10
3. Reactions with bases
Ethanoic acid reacts with bases to form a salts and water.
Ethanoic acid + copper (II) oxide copper (II) ethanoate
+ water
 USES OF CARBOXYLIC ACIDS ACIDS
Objectives : Students can analyze (uses, technology that use, impact for
environtment) products containing carboxylic acid and in their
daily life

Some of the carboxylic acid compound is important

as follows:
1) The formic acid
Formic acid is a colorless liquid, pungent, easily
soluble in water, alcohol, and ether. In small
amounts are also present in sweat.
In the industry, formic acid is made of carbon
monoxide with water vapor is passed through a
Formic acid is used to
catalyst (metal oxide) at a temperature of around agglomerate the latex
200oC and high pressure. (rubber tree sap)
 CO + H2O HCOOH

Formic acid is used in a small industry, tanning skin, and rubber plantations to
agglomerate the latex (rubber tree sap).

2) Acetic Acid
Acetic acid is the acid in vinegar eat. Pure acetic acid, the so-called glacial
acetic
acid is a clear liquid colorless, odorless very sharp, freezes at 16,6oC, forming
crystals resembling ice or glass.
Carboxylic acid and ester

Acetic acid can be made from the oxidation of ethanol because of the B
effect of m
various types of bacteria such as acetobacter. This method is still used to u
B
make p
vinegar dilute acetic acid to eat. Materials used are grape or other fruit a
juice.
6
Most of the acetic acid is made by passing ethanol vapor mixed with air P
through a catalyst. m
i
a
d
a
d
s
a
c
Acetic acid is the vinegar that usually we use a
d
3) Adipic acid is used to make nylon.
u
e
i
t
p
c
s
g
Nilon that we use contains adipic acid. o
t
4) Oxalic acid to remove rust and manufacture of dyes. s
5) Tartaric acid, an acid is used as an astringent drinks, candy, and baking a

powder.
11
 Carboxylic acid and ester
12
STRUCTURE OF ESTERS
Objectives : Students can write the structure of product that contain
esters
Students can identify the nomenclature of ester compound

Do you know it? What is it?

The fruits esters is often we use. We
use it when we wnat give the essens
to our food. Whats it belong to?
Fruit esters is belong to alkyl
 alkanoate or ester.

What is an esters?
A carboxylic acid reacts with an alcohol to form an organic compound called an
ester. This reaction is known as esterification.

During the formation of an ester, the OH group of the carboxylic acid is

replaced by the CH3 O- (or C2H5-O- , etc.) group of the alcohol.

Esters are alcohol derivatives of carboxylic

acids. They are named in much the same way
as salts. The alcohol part (R in OR) is named
firs, followed by the name of the acid modified
to end in-ate. The ic ending of the organic
Functional group of an acid name is replaced by ending ate.
ester
 Carboxylic acid and ester
13

How do we name on ester?

The name of an ester consist of two part. For

example.
Ethyl Ethaboate
group group
Table 2.1 shows the names of some common esters, together with the alcohol and
carboxylic acid used to prepare them.

Name of ester Structural Alcohol used Acid used

In IUPAC system, ethanoic formula
became ethanoate. In the common names, acetic acid
Ethyl ethanoate
becomes acetate. ToCH 3COOC
name Ethanol
2H5be sure
ester, Ethanonoic
to recognize the portion of theacid
ester
molecule that comes from the acid and the portion that comes from the alcohol. In
Methyl CH3COOCH3 Methanol Ethanoic acid
general formula for an ester, the RCO comes from the acid the RO comes from the
ethanoate
alcohol.
Carboxylic acid and ester
Ethyl ethanoate HCOOC2H5 Ethanol Methanoic acid
14
PROPERTIES OF ESTERS
Objectives : Students can explain the properties of the ester

How do we prepare esters?

If ethanoic is warmed with ethanol in the presence of a few drops of
concentrated
sulphuric acid, an ester called ethyl ethanote is formed. Concentrated
sulphure acid
acts as a catalyst to speed up the reaction.
Esterification is the reaction to make esters from alcohols.
 Carboxylic acid and ester
15

The procedure for preparing an ester is illustrated in the diagrams below

and
a detailed description of the method for preparing ethyl ethanoate is
described.
 Ethyl ethanoate and water are both colourless, but to help in following
the procedure via the diagrams, coloured the ester yellow and the
reaction mixture and aqueous solutions a pale grey.

STAGE 1 Making the ester: In the round-bottomed flask the alcohol

(ethanol) is mixed with the carboxylic acid (ethanoic acid) and a small
amount of concentrated sulfuric acid (catalyst) is added too. Anti-bumping
granules are added to ensure a smooth boiling action. The mixture is
carefully heated to get the mixture gently boiling and refluxing.
Stage 1 is a technique called 'heating under reflux', and ensures the
reaction occurs the fastest at highest possible reaction temperature, the
boiling point of the mixture. However, to prevent vapour loss by
boiling/evaporation, particularly of the desired product - the ester, the
vapourised liquids are condensed back into the reaction flask recycling
everything.
The diagram shows a bunsen burner being used to supply the heat ('my
days'), these days its more likely, and safer, to use an electrical heater that
the round bottomed flask fits in snugly.
Carboxylic acid and ester
16
 STAGE 2 Fractional distillation: The colourless ester liquid is separated from
the reaction mixture by fractional distillation which is fully explained on the
elements, compounds, mixture notes (the example described is separating an
ethanol/water mixture, but the same principal applies in separating the ester
from some of the water, unreacted alcohol and acid and the sulphuric acid
catalyst. Again the mixture gently heated and boiled, but this time you want
the vapour of the lowest boiling component (ester) to separate out in the
fractionating column and pass through into the condenser. This happens when
the temperature at the top of the column reaches the boiling point of the
ester. The ester and small quantities of carboxylic acid, sulfuric acid and
alcohol can be collected from the condenser in a suitable glass vessel.
Preferably a quick-fit one that connects to the condenser, but it must not be a
completely sealed system otherwise pressure would build up, hence the vent
to the sink. You should realise at this point in the preparation that the ester
(ethyl ethanoate) is very impure.
Carboxylic acid and ester
17
 STAGE 3 Removing acidic impurities: The rest of the procedure is all about
purifying the initial ester distillate from the fractional distillation. The
condensate (liquid distillate) from the fractional distillation apparatus is
transferred to a separating funnel (tap funnel). Sodium carbonate solution
is added to neutralise any acids and the stopper replaced. The separating
funnel is shaken to ensure complete removal of the acid, but carbon
dioxide is formed, so every so often you invert the funnel, open the tap
and allow the gas to escape. When there doesn't seem to be any more
effervescence or gas pressure, the mixture is allowed to settle. When the
two layers have fully separated, the stopper is removed, and the lower
aqueous layer is careful run off, don't lose any of the ester in the process!
When doing the run-off the stopper must be removed. The acidic
impurities and any salts formed have now been removed in the aqueous
sodium carbonate solution, therefore there should be no carboxylic acid or
sulfuric acid catalyst left in the ester layer.

STAGE 4 Removing the ethanol impurity: However, despite removing some

impurities there will still be some traces of the alcohol left in the ester
layer. Concentrated calcium chloride solution is added to the still impure
ester in the separating funnel and the mixture shaken again. The aqueous
calcium chloride will remove any remaining unreacted alcohol (ethanol).
Again, the lower aqueous layer is tapped off to leave only the ester layer
which will still contain some water.
 Carboxylic acid and ester
18

STAGE 5 Drying the product: By now the only impurity left is water. So, to dry
the
ester, it is run off (tapped off) from the separating funnel into a small conical
flask
and some granules of anhydrous calcium chloride added. The conical flask is
stoppered and the mixture shaken, and the calcium chloride absorbs any
remaining
moisture in the ester. The pure ester can than be filtered off.
 Carboxylic acid and ester
19

A nice experiment.
LETS DO EXPERIMENT WITH YOUR FRIEND

A very simple method of making an ester

 You can mix equal volumes of small quantities of a carboxylic acid and an
alcohol
with an even smaller volume of concentrated sulfuric acid.
The mixture gently warmed in beaker of warm water for 5-10 minutes.
The mixture is then poured into a beaker of sodium carbonate solution.
The sodium carbonate neutralises the acid catalyst and any unreacted
carboxylic
acid.
You should get some drops of ester left on the surface which can be carefully
smelled to appreciate the aroma of the ester.
You can do this is as a nice class experiment with ethanoic acid and a variety of
alcohols and noting what they think the esters smells like (likely to be 'fruity')
alongside appreciating its molecular structure too!

After you and your group do the experiment, please

make a report of experiment.
Before experiment, ask your teacher about your
experiment planning!
 Carboxylic acid and ester
20
USES OF ESTERS
Objectives : Students can analyze (uses, technology that use, impact
for
environtment) products containing ester in their daily life

Uses of esters occur widely in nature and are usually sweet/pleasant smelling
liquids
and widely used as fragrances (components in perfumes) and food
flavourings.
Perfumes can natural, obtained from plant sources, or artificial, since
esters are
readily synthesised in the laboratory.

Parfume is one of
essens that belong
to esters
 Natural substances are used in many cosmetics but many mixtures contain
synthetic organic compounds.

Cosmetics are one

of example esters

Many esters have pleasant sweet or fruity smells and the colourless liquids are
quite volatile, that's why fruits have strong pleasing odours or aromas.

Fruits are usually

made for aromas
Carboxylic acid and ester
21
 Wax are esters of long chain carboxylic acids.

Wax is one of esters

Fats are esters of glycerol with carboxylic acids high rate. For example, the
animal fat, fish oil and coconut oil.
The major use is as a food fat (cooking oil and margarine) and to make
soap.

Fat is a cooking oil including

ester.

Rancid butter has a foul smell because of

the presence of butanoic cid. Howefer, the
esters of butanoic acid have the fragnant
smell of fruits. For example, methyl
 butanoate smells like apples and ethyl
butanoate smells like pineapples.
Carboxylic acid and ester
22

ONE OF IMPORTANT CARBOXYLIC ACID

AND ESTERS

Did you ever eat bread cake? What do you feel when you eat the bread
cake? The
cake that we eat is very closely related to carboxylic acids and esters.
In the process of making bread cake, we often use baking powder and
essesns to
add to the taste of the bread that we will make. Apparently, baking powder
and
essens is one of the carboxylic acids and esters applications in daily life.

Baking powder is a developer material

(leavening agent), which consists of a
mixture
of sodium bicarbonate, sodium aluminum
phosphate, and monocalcium phosphate.
The nature of these substances if it met
with
fluid / water and exposed to heat to form
carbon dioxide. Carbon dioxide is what
makes the dough so fluffy. Baking powder
also contains inert such as starch.
 Carboxylic acid and ester
23

The materials contain inert fat is intentionally mixed to keep the components
of
baking powder material remains in good condition.
Baking powder is usually used as a developer (leavening agent)
cake, a
cake baked, steamed cakes, cup cake and pancanke. Baking Powder contains
the
substance to be neutralizing, usually used on materials that dough recipe has
been
neutral milk samples. Baking powder produces a neutral flavor and texture of
a
small pore.
Aroma essences are extracts of food
ingredients such as vanilla, chocolate,
mocha, orange, strawberry and others.
Essences used to augment or reinforce the
aroma of the ingredients of cake, bread,
cakes, puddings and drinks. Liquid form. Its
use is enough 1 teaspoon per 1 liter of
Food Essens
liquids or 1 kg of powdery material usage.
 In society, baking powder and essens
are very helpful. Because without the
baking powder and essens, when they
would make the bread, the bread that
they make become less fluffy and has a
Pict. Baking powder is used to
pleasant aroma, so less add flavor.
make bread swell
Undeniably, the community relies
 heavily on essesn when baking powder
and baking cake.
Carboxylic acid and ester
24

One of the manufacture of baking powder is to use yeast. For the first process
you
need a bowl, sieve, whisk, a box with a lid, baking soda, cream of tartar, and
corn
starch. Use cup baking soda, cup corn starch or arorut, and cup cream
of
tartar. Sift ingredients. This will avoid any premature clots from forming in
your mix,
and will help to further mix the entire ingredients. Stir the mixture. Use made
of wire
beaters to whisk all the ingredients together. Keep your yeast. Yeast must be
stored
in an airtight box to prevent moisture and will remain good quality for 7 to 10
weeks.

As had been explained that the baking powder is an example of a carboxylic

acid
and ester essens an example of. Carboxylic acid contained in the baking
powder is
tartaric acid, while that of the essens ester is an ester.

Tartaric acid is an organic compound

derivative
of ascorbic acid, such as oxalic acid and acid
treonat. Tartaric acid had 4 hydroxyl groups
and
 is one of the primary acid that is found in
Pict. structure
carboxylic acid grapes other than malic acid and citric acid. The
 chemical formula of tartaric acid is C4H6O6
structure

Pict. structure ester

Carboxylic acid and ester

25

LETS
HAVE FUN
 Write down the using of vinegar which is an aspect of SETS (science,
environment, technology, society)!

Society

Sains
Technology Environtment
 Write down the positive effects and the negative impact of the use of baking
powder and food essens in everyday life that you encounter after reading this
material.
What can you conclude about the carboxylic acid and ester? What is the
structure and properties of the carboxylic acid ester?
Write some other existing products in your everyday life which is the
application
of carboxylic acid and esters.
 Carboxylic acid and ester
26

GLOSARIUM

Alkyl alkanoate / Ester

Alkanes derived compounds with functional groups -CO-.
Carboxylic acid / Carboxylic Acid
Alkane derivatives with -COOH functional groups.
Ester Fruits
Esther is ten or less carbon atoms (ie carboxylic acid esters of low rates with
lower alcohols) which at room temperature in the form of volatile liquid and
has a rich aroma.
Esterification
Reaction formation of esters from alcohols and carboxylic acids.
Isomer of functional groups
Isomer that occur because of differences in functional group but with similar
molecular formula.
Isomer of position
Isomer that occurs because of the difference lies in common functional
groups but with molecular formula, functional group, and skeleton.
 Carboxylic acid and ester
27

REFERENCES

http://www.docbrown.info/page04/OilProducts10b.htm

Michael, Purba. 2007. KIMIA untuk SMA Kelas XII. Jakarta:Erlangga

Toon, Tan Yin, dkk. 2010. Chemistry Matters. Singapore: Marshall Cavendish
Education