1 8

Y D Ro O
39 6 5 7
H c
28 8
hydrogen yttrium xyg en carbon
Arn B O N
argo boron oxygen
nitrogen

DERIVATIVES

ALCOHOLS
PHENOLS
ALDEHYDES
kETONES
CARBOXYLIC ACIDS
AMINES
AMINO ACIDS
 Hydrocarbon derivatives 3
33 Hydroxy derivatives. A lcohols. p henols 5
34
Methanol. Ethanol. Ethane-1,2-diol. 13
Propane-1,2,3-triol
35 Phenol 26
36 Aldehydes. Methanal. Ethanal 34
37 Ketones. Propanone 44
38 Carboxylic acids. Ethanoic acid 53
39 Benzoic acid. 2-hydroxyBenzoic acid 63
40 Amines. Amino acids 75
PROJECTS 85
Click on a topic to jump to the page
 HYDROCARBON DERIVATIVES −
compounds of carbon, hydrogeN and something else
Many organic compounds may be considered as derivatives of hydrocarbons in whose molecules one
or more H atoms have been replaced by other atoms, or atomic groups, called substituents. Such
compounds are called hydrocarbon derivatives. Their molecules are built up of carbon atoms,
hydrogen atoms and atoms of at least one other element – most often halogen, oxygen, nitrogen.
The properties of these compounds are highly dependent on the nature of the substituent (an atom,
other than hydrogen, or a group of atoms).
The simplest hydrocarbon derivatives are their halogen derivatives (for example chloromethane
CH3Cl, tetrachloromethane CCl4, bromoethene C2H5Br, chlorobenzene C6H5Cl etc.). If the substituent
is a specific atomic group, called functional group, molecules are more complex. The chemical
reactivity of these compounds is highly dependent on the functional groups. The major classes of
hydrocarbon derivatives correspond to the major types of functional groups:

О H
=
–

–С–О–Н С=О С=О – С– N

functional О –Н
–

Н H
group
hydroxy aldehyde ketone carboxyl amino

HYDROCARBON carboxylic
alcohols aldehydes ketones acids amines
DERIVATIVES
In the molecules of many organic compounds there are two or more functional groups (same or
different). For example:

O
Н Н Н H С
OH

‒
–
–
– H O

‒
Н – С – С – С –Н N‒ C‒С
H OH ‒ ОН
–
–
–

‒
НО ОН ОН H
glycerol glycine
three hydroxy groups −OH salicilic acid
one amino group −NH2
one carboxyl group −COOH one hydroxy group −OH
one carboxyl group −COOH

Hydrocarbon derivatives are widely used – in the pharmaceutical industry and medicine, as
components of perfumes compositions, in the food industry, the textile industry, for the production
of plastics, dyes, varnishes etc.
 H ydroxy derivatives
33 Alcohols. phenols 6
c 1
CARBO
N
H
hydrogen
8
key TOPICS O
oxygen
1. What are alcohols?
2. What are phenols?
3. Why are alcohols and phenols hydrocarbon derivatives?
4. How to name alcohols?
key words
●● Substituent
НO ●● Functional group
●● Alcohol
‒

H ‒ ‒C ‒ ‒ H oH ●● Phenol
C C
‒
●● Monohydric alcohols
H‒C‒H
‒

C ‒ C‒ ●● Polyhydric alcohols
H‒
‒
C H Primary, Secondary,
‒

●●
H Tertiary alcohols
‒

H
Hydroxy derivatives of hydrocarbons are composed of carbon, hydrogen and oxygen. In hydro-
carbons molecules one or more hydrogen atoms have been replaced by hydroxy groups –OH. This is
the functional group of this class of organic compounds.
The hydroxy derivatives of the aliphatic hydrocarbons are known as alcohols (in Arabian language
means something fine), while those of the aromatic hydrocarbons in whose molecules the –OH group
is bonded directly to the aromatic ring are called phenols:

OH

‒
Н НO
OH

‒
H oH Н ‒ ‒C Н Н ‒ ‒C Н
‒

‒ ‒ ‒ ‒
C C C C
‒

H‒C‒H H‒C‒H

‒
C ‒C‒ C ‒C‒
Н‒ Н‒
‒

‒ ‒
H H C Н C Н

‒
Н Н
hydrocarbon alcohol
(methane) (methanol) Hydrocarbon phenol
(Benzene) (hydroxybenzene)

6
 Alcohols are organic compounds with one or more –OH groups
bonded to carbon atoms of hydrocarbon chains.

The simplest alcohol is CH3OH (methanol). The general formula of the straight chain monohydric
(contain only one ‒ OH group) saturated alcohol is CnH2n+1OH (CnH2n+2O).

Express the molecular formulae of the hydroxy derivatives of ethane and pentane
PROBLEM! with one ‒ OH group.

Solution: 1. The hydroxy derivative of ethane C2H6 has 2 C atoms in its molecules and n = 2. From the general
formula we calculate the number of hydrogen atoms bonded to these 2 C atoms:
2n + 1 = 2.2 + 1 = 5 H atoms.
2. The hydroxy derivative of pentane C5H12 has a five carbon atoms chain and one –OH group in
its molecules. So n = 5 and the number of H atoms in its molecule (except the H atom of the
–OH group) is 5.2 + 1 = 11 H atoms.

Answer: The molecular formula of the hydroxy derivative of ethane is C2H5OH.

The molecular formula of the hydroxy derivative of pentane is C5H11OH.

7
Depending on the number of the hydroxy groups in their molecules alcohols are classified as monohydric
(with one –OH group) and polyhydric (with two or more –OH groups):

monohydric alcohols

H H H

‒ ‒
‒ ‒
‒ ‒
H ‒ C ‒ OH H ‒ C ‒ C ‒ OH
H H H
methanol ethanol

polyhydric alcohols

H H H H H
‒ ‒
‒ ‒

‒ ‒
‒ ‒
‒ ‒
HO ‒ C ‒ C ‒ OH H‒ C ‒ С ‒ C ‒H
H H HO OH OH
ethane-1,2-diol propane-1,2,3-triol

8
Alcohols are classified also as primary (the –OH group is bonded to a primary C atom), secondary
(the –OH group is bonded to a secondary C atom) and tertiary (the –OH group is bonded to a tertiary
C atom). For example:

H H H H H H H H H3C

‒ ‒
‒ ‒
‒ ‒
‒ ‒
‒ ‒

‒ ‒
‒ ‒
‒ ‒
‒ ‒
H‒ C ‒ C ‒ C ‒ C ‒H H‒ C ‒ C ‒ C ‒ C ‒H H3C ‒ C ‒ OH
HO H H H H H OH H H3C
butan-1-ol Butan-2-ol Methylpropan-2-ol
primary alcohol secondary alcohol tertiary alcohol

Note down that these alcohols are isomers because their molecular formulae are identical ‒ C4H10O.

It is interesting to know:
Molecules with two −OH groups attached to the same carbon atom, as well as molecules with
one −OH group attached to double bonded carbon atom, are unstable. They transform easily
into more stable compounds:
O‒H О О
H О‒Н
‒

=
=

H‒C‒О‒H H2O + ‒C ‒ ‒C ‒

‒
‒
H H HC = CH H 3C H
‒

H methanal ethanal

9
How to Name alcohols?
Alcohols are named according to some rules:
1. The parent hydrocarbon gives the name of the alcohol (the longest chain always includes the –OH
group). The final „e“ is dropped and the suffix „–ol“ is added:

X → methan + ol = methanol
methane H3C − OH

X → ethan + ol = ethanol
ethane H3C − H2C − OH

2. The place of the –OH group is indicated by the number of the carbon atom to which it is bonded,
written after the parent hydrocarbon name and separated by dashes. The numbering of the carbon
atoms always starts from the chain end nearest to the hydroxy group:
HO
X → propan + -1-ol = propan-1-ol
propane

‒
H2C ‒ CH2 ‒ СH3
1 2 3

OH
X → propan + -2-ol = propan-2-ol
propane

‒
H3C ‒ CH ‒ СH3
1 2 3

10
 CH3 HO CH3

‒
‒
H3C ‒ C = СH2 H2C ‒ C = СH2
3 2 1 1 2 3
-2-
methylpropene → 2-methylprop en + -1-ol = 2-methylprop-2-en-1-ol

Note that the numbering of the C atoms in the hydrocarbon molecule and the alcohol molecule is
not the same.

3. If there are two or more –OH groups this suffix „–ol “is preceded by the prefixes „di–“ (if there are
two –OH groups), „tri–“ (for three –OH groups) etc. For example:

HO OH HO OH OH
‒
‒

‒
‒

‒
H2C ‒ CH ‒ CH2 ‒ СH2 H2C ‒ CH ‒ C = СH2
1 2   3 4 1 2 3 4
butane-1,2-diol but-3-ene-1,2,3-triol

11
 CAN YOU ANSWER THESE QUESTIONS
1. What are alcohols?
2. Why are alcohols and phenols different classes of hydroxy derivatives of hydrocarbons?
3. How is the alcohol C4H9OH named?
4. Why is the alcohol name propan-3-ol wrong? What is the correct name?
5. How many hydroxy groups are there in the molecules of butanediol?
6. What types of isomers do alcohols with three or more carbon atoms have? Why?
7. Do you expect that alcohols are reactive compounds? Why?

12
34 M ethanol. Ethanol
Ethane-1,2-diol. Propane-1,2,3-triol
key TOPICS
1. Why do methanol and ethanol display similar properties?
2. Why are methanol and ethanol perspective fuels?
3. What are the health hazards of the alcohol abuse?
4. Why is glycerol so important for the human metabolism?

key words
С3H5(ОН)3 СH3ОН ●● Methanol
●● Ethanol
●● Ethane-1,2-diol
●● Propane-1,2,3-triol
●● Esterification
С2H5ОН С2H4(ОН)2 ●● Nitroglycerine
●● Triglycerides
●● Biofuel
 The simplest alcohols are METHANOL Ch3oh and Ethanol C2h5oh. Ethanol is the most widely
used alcohol. It is known from ancient times but pure ethanol was first prepared in the late XVIIth
century. Its common names are simply alcohol, drinking alcohol, ethyl alcohol and is found in all
alcoholic beverages. Methanol is also known as wood alcohol.
Methanol and ethanol are monohydric alcohols − they have only one −OH group in their molecules.
Ethane-1,2-diol and propane-1,2,3-triol are one of the simplest polyhydric alcohols. They are
commonly called glycol (or ethylene glycol) and glycerol (or glycerine). In both compounds the −OH
groups are bonded to different carbon atoms.

PHYSICAL PROPERTIES

ga
s
Methanol CH3OH and ethanol C2H5OH are 100
colourless, volatile, flammable liquids. Ethanol C2H5OH B. P. 78,5 oC
CH3OH B. P. 64,7 oC
has a pungent taste and a characteristic vinous 50

Temperature oC
H H H odour, while methanol has a distinctive odour 0
‒

‒
‒

d
H ‒ C ‒ OH H ‒ C ‒ C ‒ OH and is sweeter than ethanol.

ui
q
li
‒

‒
‒

-50
H H H Both methanol and ethanol are lighter than
water and dissolve in it. The content of ethanol, CH3OH M. P. - 97,6 oC
CH3OH C2H5OH -100

Methanol Ethanol
expressed in volume percentages, is called C2H5OH M. P. - 114 oC

alcoholic strength by volume. For example there

are 12 ml of pure ethanol in 100 ml of wine with alcoholic strength by volume

so
li
d
12 % vol. Methanol and ethanol are good solvents of many compounds.
M. P. - melting point
Methanol is toxic. If ingested it can cause blindness. B. P. - boiling point
14
 Ethane-1,2-diol and propane-1,2,3-triol are
colourless, odourless liquids, look like syrups, sweet
(their common
300 290 names originate
H H H H H
Boiling point oC

from the Greek

‒
‒

‒ ‒
‒ ‒
‒ ‒
200 197,3 word „glyceros“ HO ‒ C ‒ C ‒ OH H‒ C ‒ C ‒ C ‒H

‒
‒
meaning sweetish) H H HO OH OH
100
and dissolve easily
78,5 OH
in water. But it OH
0 is dangerous to HO HO OH
confuse them as
C3H5(OH)3
C2H4(OH)2

glycerol is a food
C2H5OH

sweetener while C2h4(OH)2 C3h5(OH)3

Ethane-1,2-diol Propane-1,2,3-triol
18 glycol is a poison.
Melting point oC

0
-12,9 Both alcohols are heavier than water (unlike methanol and ethanol
-100 which are lighter). Because of the presence of two or three –OH
-114 groups their melting and boiling points are relatively high. At 18 oC or
less glycerol is solid. It is highly hygroscopic and can burn the skin.

Methanol, ethanol, etane-1,2-diol and propane-1,2,3-triol display some similar properties as all four
alcohols have the same functional group –OH in their molecules. But there are some differences in
their chemical properties resulting from the different number of hydroxy groups in their molecules.
15
CHEMICAL PROPERTIES

The chemical activity of alcohols is strongly affected by the presence of the –OH functional group.
Both O – H and C – O bonds are covalent polar bonds and can be broken down.

disruption of the O – H bond

Interaction with active metals. As the O – H bond is polar active metals easily substitute the hydrogen
atom in the hydroxy group. For example in the reaction of ethanol with sodium the products are
sodium ethoxide and hydrogen:

2C2H5О‒Н + 2Na → 2C2H5О‒Na + H2↑

sodium ethoxide

Ethanol and methanol slightly dissociate in water (even less than water). The concentration of H+
(H3O)+ ions is very low and they cannot be considered as acids – the blue litmus does not turn red.

16
interaction with oxy-acids. In these reactions the hydrogen of the hydroxy group is replaced by a
positive acidic ion. For example NO2+ if nitric acid HNO3 is used.
For instance the reaction of the concentrated nitric HNO3 acid with ethanol:

Н+
→ C2H5О‒NO2 + H2O
C2H5О‒Н + HO‒NO2 ←
nitric acid ethyl ester
(ethyl nitrate)

This reaction is catalysed* by H+ ions. The process is molecular, slow and reversible. This is a reaction
of esterification. The products are an ester and water:

The reaction of an alcohol with an oxy-acid,

yielding an ester and water,
is called esterification.

*Catalysts are substances that accelerate chemical reactions without themselves being consumed. 17
PROBLEM! How many molecules of nitric acid HNO3 react with 1 molecule of propane-1,2,3-triol?

Solution: There are three hydroxy groups in the propane-1,2,3-triol molecule. Each of them reacts with 1
nitric acid molecule. The chemical equation of the reaction (it would be more clear if structural
formulae are used) is:
Н Н
− − − −

− − − −
Н − С − ОН НОNO2 Н − С − ОNO2
Н − С − ОН + НОNO2 → Н − С − ОNO
← + 3Н2О
2

Н − С − ОН НОNO2 Н − С − ОNO2
Н Н

Answer: 1 propane-1,2,3-triol molecule reacts with 3 molecules of HNO3.

This reaction was discovered by Ascanio Sobrero in the mid XIXth century. The nitric acid ester of
propane-1,2,3-triol (glycerine) is commonly known as nitroglycerine – a colourless viscous liquid that
explodes on impact and is an active ingredient of the dynamite. Nitroglycerine (tablets, ointments,
solutions, sprays) is used as a medicine for some heart diseases.
Blue litmus does not turn red in aqueous solutions of ethane-1,2-diol and propane-1,2,3-triol (as for
ethanol).
18
DISRUPTION of the C – O bond
Interaction with hydrogen halides. The products are halogen derivatives of the corresponding
hydrocarbons and water. For example:
to, conc. Н2SO4
→ H C ‒ H C ‒ Br + H O
H3C ‒ H2C ‒ ОН + H‒Br ← 3 2 2
bromoethane

The water is formed by the ethanol – OH group and the hydrogen of the hydrogen halide

dehydration (loss of a water molecule). The reaction is catalytic and undergoes at high temperature.
Ethanol is converted into ethene and water is liberated:

Н Н Н Н
‒
‒

‒
‒
t о , conc. H2SO4
Н ‒ С ‒ С ‒Н Н ‒ С=С ‒Н + H2O
‒
‒

Н ОН

19
TEST REACTIONS FOR ALCOHOLS
If a iodine solution is added to ethanol, followed, under heating, by a solution of NaOH, after a
few minutes an yellow precipitate of triiodomethane CHI3 (iodoform), smelling as an „antiseptic“,
appears.
The reaction with iodine I2 in the presence of sodium hydroxide NaOH
is a test reaction for ethanol.
If methanol CH3OH is used instead of ethanol no reaction occurs. This could be a test to distinguish
between methanol and ethanol. That might be very important as methanol looks like ethanol, but it
is a poison and can cause blindness or even may be fatal if ingested.

Polyhydric alcohols as ethane-1,2-diol and propane-1,2,3-triol react with Cu(OH)2. The solution turns
ink-blue:

С3Н5(ОН)3 + Cu(OH)2 an ink blue solution

The interaction with copper dihydroxide Cu(OH)2 (freshly precipitated)

is a test reaction for all polyhydric alcohols.

20
Combustion

The products of the complete combustion of alcohols are CO2 and water vapours. For example:

C2H5OH + 3O2 → 2CO2 (gas) + 3H2O (gas) + energy

Energy is in the form of light (pale not smoky flame) and a considerable amount of heat. Ethanol is
a renewable biofuel (it is produced from plant biomass in a short period of time). To burn efficiently
ethanol must be aerosolized.

The use of methanol and ethanol as fuels contribute to the reduction of greenhouse gases emissions
as from 1 mole of methanol is produced only 1 mole of CO2 and from 1 mole of ethanol − 2 moles of
CO2. Ethanol and biodisel are the two most widely used biofuels.

In the laboratory ethanol is used as a fuel in the alcohol burners. This ethanol and the ethanol
for domestic uses is denaturated – it is made undrinkable by the addition of some compounds
(denaturants), which usually have an unpleasant odour.

21
PRODUCTION
On an industrial scale methanol CH3OH is produced using natural gas as a feedstock. But CH3OH can
be synthesised also from carbon monoxide or carbon dioxide (even from air) and hydrogen:

CO + 2H2 cat. CH3OH CO2 + 3H2 cat. CH3OH + H2O

A well known method to produce ethanol is the ethanol (or alcoholic) fermentation. This is a
biochemical process in which glucose C6H12O6 is transformed into ethanol and carbon dioxide. The
process is catalyzed by the enzyme zymase:

C6H12О6 zimaze 2C2H5ОН + 2СО2

The raw material are fruits, cereals (barley, rice, wheat, corn etc.), sugar beet.
On an industrial scale ethanol is produced from ethene (the most important petrochemical product).
(hydration of ethene, see p. 48 chap. V. Hydrocarbons).
In the laboratory a small amount of ethanol may be prepared in the reaction of an ethyl halide (for
example C2H5Cl) with a strong base (for example NaOH):

C2H5Cl + NaOH → C2H5OH + NaCl

Carl Wilhelm Scheele first isolated propane-1,2,3-triol (glycerol) in the second half of XVIIIth century
‒ in a reaction of fats with NaOH (a process called saponification) he produced glycerol and soaps.
On an industrial scale ethane-1,2-diol (glycol) and propane-1,2,3-triol (glycerol) are petrochemical
products. Glycerol is produced from propene (see the problem in your Study book). Glycol is produced
from ethene. 22
 chemical
USES
Methanol CH3OH is one of the most widely used industrial
chemicals. It is a key chemical to manufacture formaldehyde and
fuel
СН3ОН
acetic acid in chemical synthesis. It is used as an antifreeze and methanol
as a solvent. Methanol is also a fuel and is used for wastewater
treatment. The worldwide production of methanol exceeds
130 billions litres annually.
wastewater
treatment
Solvent disinfectant Ethanol C2H5OH is a widely used organic compound. It is a raw
material to synthesize ethanoic (acetic) acid, esters, amines
etc. Ethanol is a very good solvent of many compounds and
С2Н5ОН is used to prepare tinctures (the Iodine bought in a pharmacy
biofuel is in fact a solution of the crystal I2 in ethanol), perfume
ethanol
compositions, varnishes. Ethanol is also a disinfectant as the
proteins structure dramatically changes under its action – if
you put the egg white in a bowl and add a few ml of ethanol,
alcohol raw materiaL
beverages you will see soon that the egg white darkens.
Ethanol is a biofuel.
All alcoholic beverages contain ethanol. It becomes an intoxicating agent if a person consumes more
alcohol than the organism can metabolise. Cardiovascular diseases, cancer, irreversible damage of the
nervous system, depression, antisocial personality disorder are inevitable after a long-term alcohol
misuse. Drinking alcohol and driving is absolutely irresponsible and is prosecuted by the law. 23
Ethane-1,2-diol (glycol) is miscible with water in any proportions. The 50 % solution freezes at – 34 oC
and is widely used in the cars engine cooling systems (antifreeze) to lower the freezing point of the
water. It also increases the coolant boiling point thus preventing it from overheating. Glycol is also
used for the production of polymers – for example polyethylene terephthalate (basic component of
polyester fibres and plastics used worldwide to package foods).

Propame-1,2,3-triol (glycerol) is widely used in the food industry, the cosmetic industry (it is added
to tooth pastes, ointments, soaps to prevent them from drying as it does not irritate the skin and is
a good humectant), the production of plastics, explosives, fibres, also sometimes as an antifreeze, in
the tobacco industry, the leather industry.

Propame-1,2,3-triol play an important role for the body functioning because fats are esters of propane-
1,2,3-triol and high molecular weight carboxylic acids. The content of fats (called triglycerides) in
the blood is an indicator of the risk of heart attack and stroke. So it is very important to maintain an
optimum level of triglycerides in the blood.

24
 CAN YOU ANSWER THESE QUESTIONS
1. Why is ethanol highly soluble in water, while ethane is insoluble?
2. Why does ethane-1,2-diol boil at a higher temperature than ethanol?
3. Can you propose three methods to prepare ethanol?
4. In a test tube containing 5 ml of water are added carefully 5 ml of ethanol. Two layers are
formed as ethanol is lighter than water. They disappear after gently shaking the test tube.
The liquid temperature slightly increases and the volume shrinks. Why?
5. Why does not the blue litmus turn red in aqueous solutions of ethane-1,2-diol and propane-
1,2,3-triol?
6. How to prepare the Cu(OH)2 used in the test reaction for polyhydric alcohols?
7. How to distinguish between ethane-1,2-diol and propane-1,2,3-triol?
8. What is common between propane-1,2,3-triol and dynamite?
9. Why is it very dangerous to taste the antifreeze?
10. What does propane-1,2,3-triol have to do with human health?
11 Why is short term and long term alcohol abuse a health disaster?

25
35 Phenol (Benzenol)
key TOPICS С6H5ОН
1. Why is phenol the simplest aromatic alcohol?
2. Why is phenol an acid?
3. Why is phenol more reactive than benzene?

Н
О‒

Н‒ ‒C
‒
Н ‒ ‒
C C key words
‒

C
‒ ‒C‒ ‒ ●● Benzenol
Н Н
‒
C ●● Phenol
‒

Н
●● Carbolic acid
●● Picric acid
 phenol C6H5OH, also known as benzenol (also hydroxybenzene
‒.. or carbolic acid) is a monohydric derivative of benzene C6H6 – one
.. O← H hydrogen atom bonded to a carbon atom of the aromatic ring has
been replaced by a hydroxy group –OH. Owing to the interaction of
one of the lone electron pairs of the oxygen of the hydroxy group with
Polarity of the −OH bond in
the phenol molecule the delocalized electrons of the aromatic ring the O – H bond is more
polarized than the O – H bond in the alcohol molecules.

PHYSICAL PROPERTIES

ga
s
200
Phenol is a colourless crystalline solid with a specific odour. It is easily Boiling point 182 C
o

oxidized by the oxygen in the air and its colour turns pink. It melts at 150
43 oC and boils at 182 oC. Phenol is completely miscible with hot water.

Temperature oC
ui
In cool water it is only slightly soluble. The diluted aqueous solution of

q
100

li
phenol is used as disinfectant.
Melting point 43 oC 50

Phenol is poisonous. May cause severe skin burns and is

so
0

li
toxic (its vapours must not be inhaled).

d
-50

27
It is interesting to know:

CHEMICAL PROPERTIES
Typical for phenol are reactions involving the functional hydroxy group –OH or the aromatic
ring:

reactions of the –OH group:

As the O – H bond in the hydroxy group of phenol is more polarized than the O – H bond in
the alcohols molecules, phenol partially dissociates in water into positive hydrogen ions H+ and
negative phenolate ions C6H5O–:
C6H5OH ← → C H O− + Н+
6 5
phenol phenolate ion

Thus blue litmus turns red in aqueous solutions of phenol – phenol is a weak acid. Its aqueous
solution (carbolic acid) has been one of the first antiseptics used in surgery.

Dissolved in water phenol reacts with active metals and their bases, yielding salts (called
phenolates) and gaseous hydrogen:
2C6H5O‒H + 2Na → 2C6H5ONa + H2↑
sodium phenolate
28
 How many moles of water are formed in the reaction of 5 moles of phenol C6H5OH with
PROBLEM! 5 moles of sodium hydroxide NaOH?

Solution: The balanced chemical equation of the reaction is:

C6H5ОН + NaOH →
← C6H5ОNa + Н2О

From the incomplete molar ratio n(C6H5OH) : n(NaOH) : n(H2O) = 1 : 1 : 1

we have n(H2O) = n(C6H5OH) = n(NaOH).
So for n(C6H5OH) = n(NaOH) = 5 moles we obtain n(H2O) = 5 moles.

Answer: In the reaction of 5 moles of phenol C6H5OH with 5 moles of sodium hydroxide NaOH
5 moles of water are formed.

29
 reactions of the aromatic ring
Phenol reacts with halogens and strong acids (for example HNO3). The reactions are easy as
compared to benzene because the hydroxy group makes the aromatic ring more reactive than it
is in the benzene molecule. As a result the reaction with bromine water undergoes without any
catalyst and heating, yielding a white precipitate of crystalline 2,4,6-tribromophenol (the –OH
group directs the substituents to ortho- and para- positions*):

ОН ОН

‒
‒

Br
‒ ‒
Br

+ 3Br2 → + 3HBr

‒
Phenol Br
2,4,6-tribromophenol

ОН
*The place of the substituents is indicated by the symbols: o- (abbreviation of „ortho“),

‒
m-(abbreviation of „meta“) and p-(abbreviation of „para“): o- o-
m- m- 30
p-
In the reaction with dilute nitric acid (it is not necessary to use concentrated acid or to mix it
with concentrated H2SO4 as it is for benzene) hydrogen atoms on orto- and para- positions are
substituted by NO2+ ions and water is released:

HO HO

Н‒ ‒C ‒ NO2 ‒ ‒ C

‒
Н NO2
‒ ‒ ‒ ‒
C C C C
‒

‒
‒C ‒C‒ C ‒ ‒C‒
Н Н + 3HONO2 → Н Н
‒ ‒
C C + 3H2O
‒

‒
Н
NO2

phenol 2,4,6-trinitrophenol
(picric acid)

The product of the reaction 2,4,6-trinitrophenol (TNP) is commonly called picric acid. It is a
crystalline substance easily exploding on impact or friction.
The interaction with aqueous solution of FeCl3 is a test reaction for phenol.
The solution turns violet:

С6Н5ОН + FeCl3 violet solution

31
 PRODUCTION
A common industrial method to produce phenol is the oxidation of
‒ ‒СН
Н 3С 3

СН
2-phenylpropane (or isopropylbenzene commonly called cumene). Propanone

‒
(known as acetone is a by-product). In the laboratory phenol may be prepared
in a substitution reaction involving chlorobenzene and sodium hydroxide –
look at your Study book. 2-phenylpropane

USES
CН3
The annual world production of phenol is about 10 millions of
‒ C‒

‒ ‒
tonnes. It is mainly used as a start material to produce bisphenol A
(BPA used in the production of plastics and epoxy resins), phenolic OН ‒
CН3 ‒ OН
resins, cyclohexanol also synthetic fibres, drugs and others. Bisphenol A (BPA)

polymers herbicides

Phenol is a common water and soil pollutant. It and others phenols

may be released to the environment (in industrial processes, use of
drugs
С6Н5ОН
products such as disinfectants, from cigarettes, vehicle emissions
phenol
and many others) and may affect the brain, the heart, the skin etc.
Thus the development of the so called green phenol technologies is
synthetic disinfectant a key factor for safeguarding the environment.
fibres
32
 CAN YOU ANSWER THESE QUESTIONS
1. What names of the compound C6H5OH do you know?
2. The melting and boiling points of methylbenzene C6H5CH3 (‒ 95 oC and 111 oC respectively)
are lower than those of phenol. Why?
3. Why is phenol a weak acid while ethanol displays acid-base properties?
4. How to distinguish between ethanol and an aqueous solution of phenol?
5. Why is phenol harmful for man and for the environment?

33
36 Aldehydes. m ethanal. E thanal
key TOPICS С O
1. What is a carbonyl group?
2. What are aldehydes?
3. How to name aldehydes? С=О
4. Are aldehydes reactive compounds?

key words
6
c HСHО ●● Carbonyl group
CARBO
N ●● Aldehyde
1
H ●● Aldehyde group
hydrogen ●● Methanal
8 СH3CHO ●● Ethanal
O ●● Silver mirror test
oxygen ●● Polyformaldehyde
(Polyoxymethylene POM)
The atomic group С = О (double bonded carbon and oxygen atoms) is a major functional group
in the molecules of organic compounds as it is essential to their chemical activity. It is called carbo-
nyl group. organic compounds considered as derivatives of hydrocarbons in whose molecules two
H atoms, bonded to the same C atom, have been substituted by a double bonded oxygen atom are
called carbonyl derivatives of hydrocarbons. They always have at least one carbonyl group in their
molecules.
The carbon atom of the carbonyl group can be an „end“ atom − two hydrogen atoms bonded to a
primary carbon atom have been replaced by a double bonded oxygen atom. The carbonyl group is at
the end of the carbon chain and its carbon atom is always covalently bonded to a hydrogen atom.
This „end“ carbonyl group О=С is called aldehyde group. In condensed structural formulae
H
it is always expressed as –CHO (not –COH to not be confused with alcohols and phenols). Organic

compounds with aldehydes groups in their molecules are called ALDEHYDES:

H H H H H
O
‒
‒
‒

‒
‒
H‒ C ‒ C ‒ C ‒ H =
H ‒ C ‒ C ‒ C‒ H
‒
‒
‒

‒
‒
H H H H H
hydrocarbon aldehyde

ALDEHYDES ARE ORGANIC COMPOUNDS WITH

ALDEHYDES GROUPS О = С IN THEIR MOLECULES.
H 35
HOW TO NAME ALDEHYDES?
Aldehydes systematic names are formed following
the same rules as for alcohols, but the added suffix is
ALDEHYDES
condensed formula name
„-al“(the final „e“ of the alkane name is dropped):
O
H ‒ C ‒= methanal
X → methan + al = methanal
methane HCHO Н

X → ethan + al = ethanal
ethane H3C − CHO
H3С ‒ C ‒=
O
Н
ethanal

Remember that to the carbon atom of the aldehyde O

H3С ‒ H2С ‒ C ‒= propanal
Н
group always is assigned the number 1.

H3C ‒ СH2
PROBLEM! O

‒
Name the aldehyde: H3С ‒ H2С ‒ C ‒=
Н

4 3
Solution: 1. Determine the longest carbon chain that contains the aldehyde H3C ‒ СH2
O

‒
group and number the carbon atoms: H3С ‒ H2С ‒ C ‒=
2 1 Н
2. The main chain gives the name of the aldehyde − this is a branched
butanal.
3. Name the branch chain: 2-methyl

Answer: The name of the compound is 2-methylbutanal.

36
 Methanal HCHO and ethanal CH3CHO are the simplest aldehydes.
They are better known with their common names − formaldehyde
and acetaldehyde.
O
H ‒ С ‒= H
H
METHANAL HCHO. ETHANAL CH3CHO

‒
H ‒ C ‒ C ‒=O
Methanal H

‒
CHO H
PHYSICAL PROPERTIES
O
Methanal HCHO is one of the few organic compounds with only one C atom in its
molecules. At standard conditions it is a colourless gas while ethanal CH3CHO is a
colourless liquid. As the
Condensed Relative Boiling Melting C = O bond is polar their H
Compound formula molecular point point melting points (- 92 o
C
mass o
C o
C Ethanal
for methanal and - 121 C o CH3CHO
propane CH3CH2CH3 44 ‒ 42 ‒ 188 ethanal) and boiling
points (- 21 oC for methanal and 21 oC for
ethanal CH3CHO 44 21 ‒ 121 ethanal) tend to be high compared to that
of alkanes with a similar molecular mass.
ethanol CH3CH2OH 46 78,5 ‒ 114
But they are low compared to the alcohols
with the same number of carbon atoms.
Methanal is a poison with a specific sharp, irritating odour. It is soluble in water. Its 37 % aqueous
solution is known as formalin. It is used as a disinfectant, a preservative for biological specimens, etc.
Ethanal is also soluble in water and has a sharp odour too.
37
CHEMICAL PROPERTIES

Typical for methanal and ethanal are reactions involving the aldehyde group –CHO.
Addition of hydrogen H2. Under heating and in the presence of a catalyst (nickel Ni) one of the bonds
of the double C = O bond breaks down and two H atoms are added to each molecule. The product is
the alcohol with the same number of carbon atoms (for example methanol if methanal reacts):

Н
t o, Ni
+ Н Н
Н

HCHO + Н2 → CH3ОН
Methanal Methanol

H H OH
‒

‒
‒
H ‒ C ‒ C ‒=O + H2 → H‒ C ‒ C ‒ H
H
‒

‒
‒
H H H
Ethanal Ethanol
38
Reaction with Ag2O and Cu(OH)2. The hydrogen of the aldehyde group is very mobile and the aldehydes
easily transform into compounds known as carboxylic acids − an oxygen atom is „inserted“ between
the carbon and the hydrogen atoms of the aldehyde group. If methanal reacts methanoic acid HCOOH
is produced and if ethanal reacts ‒ ethanoic acid CH3COOH.
Typical are the reaction with Ag2O and Cu(OH)2 but aldehydes transform into carboxylic acids even
reacting with oxygen in the air.
In the reaction with Ag2O (ammonia solution of Ag2O known as Tollens' reagent) metallic silver is also
produced. It is disposed on the test tube walls:
O to O
H ‒ С ‒= + Ag2O H ‒ С ‒= + 2Ag
H OH
methanal methanoic acid
This reaction is known as silver mirror test.
In the reaction with Cu(OH)2 (freshly precipitated, known as Fehling's solution)) a brick-red precipitate
of Cu2O is produced:
O to O
H3C ‒ С ‒= + 2Cu(OH)2 H3C ‒ С ‒= + Cu2O↓ + 2H2O
H OH
ethanal ethanoic acid
Both reactions take place under heating.
The reactions with Ag2O (an ammonia solution) and freshly precipitated Cu(OH)2
are test reactions for aldehydes.
39
polymerization. Owing to the disruption of one of the C = O bonds methanal easily polymerizes:

Н Н Н
O

‒
n H ‒ С ‒=
H
polymerization ... ‒ О ‒ С ‒ О ‒ С ‒ О ‒ C ‒ ...

‒
Н Н Н
polyformaldehyde

This polymer is a crystalline substance and has oxygen atoms along with carbon atoms in the main
chain. Polyformaldehyde plastics are rigid and with a high mechanical strength. They are commonly
known as POM (polyoxymethylene) plastics.

Aldehydes burn, yielding carbon dioxide and water. For example:

HCHO + O2 → CO2 + H2O

40
PRODUCTION
Aldehydes can be prepared from primary alcohols (the –OH group is attached to a primary C atom)
with the same number of C atoms in their molecules. Alcohols are oxidized under heating and in the
presence of catalysts (for example a mixture of iron oxide, molybdenum and vanadium). Dihydric
alcohols are produced. They are very unstable – one water molecule is released and an aldehyde is
formed (in Latin language alcohol dehydrogenatus means dehydrogenated alcohol). If methanol is
oxidized the intermediate is methanediol:

Н Н
O

‒
‒

Н ‒ С ‒ ОН t o, Cu Н ‒ С ‒ ОН t o, Cu H ‒ С ‒=
+ 1/2O2 H + H2O

‒
‒

Н OН methanal
methanol methanediol

If the alcohol is heated in the presence of effective Н

catalysts undergoes a process of dehydrogenation t o, cat. O

‒
Н‒ С ‒О H ‒ С ‒= + H2↑
of the alcohol. For example methanol looses two H

‒
‒
hydrogen atoms and transforms into methanal: Н Н

Ethanal can be prepared also by hydrating ethyne (adding water to ethyne) − see chapter
„Hydrocarbons“, p. 58.
On an industrial scale ethanal is produced in a process of catalytic oxidation of ethene C2H4 (see your
Study book). 41
USES

Methanal (formaldehyde) is a major industrial chemical. It is mainly used in the production of

NН2
O

‒
C

=
‒
C
polymers. If it polymerizes with phenol, urea , melamine N N
hard resins are produced.

‒
H 2N NH2 ‒ C ‒C‒
Н 2N N NН2

They are used in adhesives to make insulations and moulded products. More than the half of the
produced methanal is transformed into formaldehyde resins. Aqueous solutions of formaldehyde
are disinfectants as it kills many bacteria, fungi, moulds.
Ethanal is a start material in the preparation of organic compounds such as ethanoic (acetic) acid, its
ester with ethanol and others. Ethanal is found in coffee, tea, alcohol beverages, tobacco smoke. In
the organism ethanol is oxidized to ethanal by the action of a specific enzyme. Ethanal is much more
toxic than ethanol and is responsible for many of the negative effects of the alcohol consumption
including hangover.

42
 CAN YOU ANSWER THESE QUESTIONS
1. What is a carbonyl group?
2. What are aldehydes?
3. Why are aldehydes reactive compounds?
4. Why are aldehydes prepared from primary alcohols?
5. How is the 5-carbon atoms aldehyde called?
6. At standard conditions ethanal is in liquid state while ethane is gaseous. Why?
7. How to distinguish between ethanol and ethanal?
7. Why is methanal used as disinfectant?
8. Can you enumerate three POM (polyformaldehyde) products?

43
37 Ketones. Propanone С O

С= О
key TOPICS
1. What are ketones?
2. How to name ketones?
3. What is the simplest ketone?
4. Why is propanone less reactive than methanal and ethanal?
5. Why is propanone a key material for many industrial processes?

6
c
1
CARBO
N H3СCОCH3 key words
H H O H ●● Ketone
hydrogen
Ketone group
=
‒ ‒

‒ ‒

●●
8 H‒ C ‒ C ‒ C ‒ H ●● Propanone
O
oxygen H H ●● Acetone
●● Dimethyl ketone
KETONES are a major class of organic compounds. They always have a carbonyl group С = О in their
molecule but unlike aldehydes it is always „inside“ the main chain – the carbon atom of the carbonyl
group is bonded to two radicals (two, usually different, carbon chains). This functional group is called
CH
ketone group. For example: О= С 2 5
CH3
Ketones, like aldehydes, are considered as derivative of hydrocarbons − two hydrogen atoms bonded
to the same carbon atom inside the hydrocarbon chain have been replaced by a double bonded
oxygen atom:

H H H H O H

=
‒

‒
‒
‒
‒
H‒ C ‒ C ‒ C ‒ H H‒ C ‒ C ‒ C ‒H

‒
‒
‒
H H ‒
H H H
hydrocarbon ketone

KETONES ARE ORGANIC COMPOUNDS WITH KETONE

R1
GROUPS О= С IN THEIR MOLECULES.
R12

45
HOW TO NAME KETONES? KETONES
condensed formula name
Ketones systematic names are formed following the
H3C ‒ C ‒ CH3 propanone
same rules as for aldehydess, but the added suffix is

=
„-one“(the final „e“ of the alkane name is dropped): O (acetone)
H3C ‒ C ‒ CH2 ‒ CH3
Remember that the carbon atom of the ketone group butanone

=
O
is never and end atom. The place of the ketone group
is identified by the number of its carbon atom always H3C ‒ C ‒ CH2 ‒ CH2 ‒ CH3
pentan-2-one

=
starting the numbering from the nearest to the ketone O
group end of the carbon chain. For example: H3C ‒ CH2 ‒ C ‒ CH2 ‒ CH3
pentan-3-one

=
O

C3H7
PROBLEM! Name the ketone: CH3 ‒
‒
C ‒ CH2 ‒ CH3
=

O
3 4 5
CH2‒ CH2 ‒ CH3
Solution: 1. Determine the longest carbon chain that contains the ketone 1 2

‒
CH3 ‒ C ‒ CH3
group and number the carbon atoms:

=
O
2. The main chain gives the name of the ketone − this is a branched
pentan-2-one.
3. Name the branch chain: 2-methyl

Answer: The name of the compound is 2-methylpentan-2-one.

46
Propanone, commonly known as acetone or dimethyl ketone, is the simplest ketone as the carbonyl
group С = О is bonded to two methyl groups (−СН3).

H O H
Propanone O

=
‒ ‒

‒ ‒
H‒ C ‒ C ‒ C ‒H
H H

H3C
С=О
H3C
PHYSICAL PROPERTIES
Propanone is a colourless, volatile, flammable liquid with a specific

ga
sharp odour. It is lighter than water (its density is 790 kg/m3). At

s
100

standard pressure it boils at 56 oC and at temperatures lower than Boiling point 56 oC 50

Temperature oC
- 94 oC it is solid. It is completely miscible with water. Propanone is a
very good solvent of many organic compounds. 0

d
ui
q
li
Propanone is found in small amounts in the urine and the blood. Its -50

quantity is greater in people with diabetes. Melting point - 94 oC -100

A long exposure to concentrated propanone vapours may cause

so
irritation of eyes and mucous and may affect the brain.

li
d
47
CHEMICAL PROPERTIES
Similarly to aldehydes propanone takes part in a reaction of hydrogenation − one of the bonds of the
double C = O bond breaks down and two hydrogen atoms are added to the propanone molecule. The
product is a secondary alcohol (propan-2-ol). The reaction is catalytic and undergoes under heating:

t o , Ni
+ Н Н

H3CСOСH3 + Н2 → H3CСНОНCH3

H O H H OH H
=
‒ ‒

‒ ‒

‒ ‒
‒ ‒
‒ ‒
H‒ C ‒ C ‒ C ‒H + H2 → H‒ C ‒ C ‒ C ‒H
H H H H H
Propanone Propane-2-ol

This addition reaction is much difficult than the hydrogenation of aldehydes.

48
It is interesting to know:
Aldehydes and ketones display common properties owing to the functional carbonyl group in their
molecules. However they exhibit some specific properties as the carbon atom of the aldehyde
group is always a primary C atom while the ketone group contains always a secondary C atom.
Propanone is less reactive than methanal and ethanal. It does not react with Ag2O (ammonia
solution) or freshly precipitated Cu(OH)2 and does not polymerize. But it discolours the purple
water solution of KMnO4 (in the presence of H2SO4) yielding ethanoic acid and carbonic acid −
one of the C − C bonds breaks down:
O O
KMnO4
=

=
H3C ‒ C ‒ CH3 H2SO4 H3C ‒ C ‒ ОH + CO2 + H2О
propanone ethanoic acid carbonic acid
Propanone can take part in reactions involving the methyl radicals −CH3. Typical is the catalytic
reaction of halogenation − hydrogen atom is substituted to produce halogenopropanone (or
halogenoacetone). For instance:
O O
=

=
catalyst
H3C ‒ C ‒ CH3 + Cl2 H3C ‒ C ‒ CH2Cl + HCl
Chloropropanone
Chloropropanone and bromopropanone are lachrymatory agents.
49
Combustion
Propanone burns – the products are carbon dioxide CO2 and water:

H3CCOCH3 + 4O2 → 3CO2 + 3H2O

A mixtures of propanone vapours and air can explode.

PRODUCTION
‒ ‒СН
Н 3С 3
OH
СН
On an industrial scale propanone

‒
O
is mainly produced in the O2

=
cumene process – oxidation of + H3C ‒ C ‒ CH3
isopropylbenzene (cumene) to
produce phenol and propanone: Cumene

Another way is the catalytic reaction with oxygen or dehydrogenation under heating of propan-2-ol:

CH3 CH3 CH3 CH3

t , cat. t , cat.
o
−

−
o
H  − C − OH + 1/2O2 C=O + H 2O H  − C − OH C=O + H2
−

−
CH3 CH3 CH3 CH3

50
USES
polymers solvent
Annually in the world are produced millions
of tonnes of propanone. It is mainly used as a
solvent and in the production of polymers (for
example bisphenol A (see p. 32), produced from varnishes СН3СОСН3
propanone and phenol, is an essential component propanone
of many plastics). As propanone is volatile (easily
evaporates) and is readily miscible with water, it is
used as a drying agent. DYeS drying
agents

51
 CAN YOU ANSWER THESE QUESTIONS
1. What is the difference between an aldehyde group and a ketone group?
2. Why is propanone the simplest ketone?
3. Why is propanone less reactive than methanal and ethanal?
4. How to distinguish between ethanol, ethanal and propanone?
5. Why must safety precautions for flammable liquids be respected when working with
propanone?
6. Why is propanone used to produce dyes and varnishes?
7. Propanone is a very good solvent of many organic compounds but is not used to prepare
herbal extracts. Why?

52
38 Carboxylic acids. Ethanoic acid
key TOPICS O
‒ С ‒=
ОH
1. What are carboxylic acids?
2. How to name carboxylic acids? O
3. Why is ethanoic acid a weak acid? С
4. How do organic acids react with alcohols? O H
5. What would happen to wine if exposed to air for a
long time?
key words
6
c ●● Carboxyl group
CARBO
Carboxylic acid
1
N
СH3COOH ●●
●● Methanoic acid (Formic acid)
H
hydrogen H ●● Ethanoic acid (Acetic acid)
O
‒ ‒

●● Glacial acetic acid

8 ‒ ‒
H C С‒ =
O оH ●● Ethanoate ions
oxygen Esterification
H ●●
●● Esters
The atomic group ‒ С ‒=O (a carbonyl group С = О bonded to a ●● δ−
ОH δ+ O
hydroxy group – OH) is another major functional group essential to the R С
●●

●●
δ− δ+
chemical activity of organic compounds. It is called carboxyl group. In О
●●
H
condensed structural formulae it is expressed as −COOH.
R‒ COOH
Owing to the effect of the carbonyl group the O – H covalent bond of the
hydroxy group is strongly polarized. In aqueous solutions the hydrogen
carboxylic acid
atom is easily liberated as a positive hydrogen ion H+ (H3O+). So these
compounds are organic acids. They are called carboxylic acids.

CArBOXYLIC ACIDS ARE ORGANIC COMPOUNDS WITH

O
CARBOXYL GROUPS ‒ С ‒= IN THEIR MOLECULES.
ОH

The general formula of the monovalent (with one carboxyl group) saturated carboxylic acids is
CnH2n+1COOH. The simplest carboxylic acids are the methanoic acid HCOOH and the ethanoic
acid CH3COOH. Methanoic acid was first isolated from red ants and was named formic acid (in Latin
„formica“ means „ant“). It is an antibacterial agent and a preservative.

54
HOW TO NAME carboxylic acids?
Aliphatic acids with one –COOH group in their molecules are named (according to the IUPAC
nomenclature) after the name of the aliphatic hydrocarbon with the same number of C atoms,
dropping the final „e“, adding the suffix „-oic“ and the word acid. For instance:

X → methan + oic + acid = methanoic acid

methane H‒COOH

X → ethan + oic + acid = ethanoic acid

ethane H3C‒COOH

Express the molecular formula and name the saturated monovalent carboxylic acid with
PROBLEM! three C atoms in its molecules.

Solution: From the general formula of this class of organic acids it follows that n = 2.
So there are 2n + 1 = 5 H atoms in the hydrocarbon chain ‒C2H5 and the molecular formula of this
acid is C2H5COOH.
The name of the acid, according to the IUPAC recommendations, is:
propaneX → propan + oic + acid = propanoic acid

Answer: The saturated aliphatic monovalent carboxylic acid with 3 C atom is propanoic acid C2H5COOH.

55
One of the most used carboxylic acid is the ethanoic acid commonly known as acetic acid.
H O
ETHANOIC ACID O

‒ ‒
H ‒ C ‒ С ‒=
Ethanoic acid is known from ancient times – since оH
people have been producing wine. Alcoholic H OH
beverages can by oxidized by the oxygen in the air under the action of acetic acid bacteria to produce
ethanoic acid. Vinegar is an aqueous solution (3 ‒ 9 %, some times more concentrated) of ethanoic acid.

PHYSICAL PROPERTIES

ga
s
120
Ethanoic acid as a colourless liquid with a specific pungent smell and sour Boiling point 119 oC

taste. It is completely miscible with water. At standard pressure it freezes at

Temperature oC
90

16,5 oC, forming crystals which look like glace crystals and is called glacial acetic

d
ui
60

q
acid. Ethanoic acid boils at a relatively high temperature (119 oC) because

li
of the strong interactions between its molecules − more energy (compared 30

Melting point 16,5 oC

to ethanol) is needed to overcome the electrostatic attraction between 0

molecules as the O−H bond in the carboxyl group is much polar.

so
li
d
Owing to the strong polarization of the O – H bond, ethanoic acid dissociates in water, yielding a
negative ethanoate (acetate) ion CH3COO– and a positive hydrogen ion H+ (H3O+):
→ СН СОО− + Н+
СН3СООН ← 3
ethanoic acid ethanoate ion
Because of the presence of hydrogen ions H+ the blue litmus turns red in aqueous solutions of ethanoic
acid. But not all molecules dissociate in water and acetic acid is considered as a weak acid. 56
CHEMICAL PROPERTIES

Ethanoic acid displays the common for all acids chemical properties − it reacts with active metals,
basic oxides and bases.

In the reactions with active metals hydrogen is liberated and salts are produced:

2CH3COOH + 2Na → 2CH3COONa + H2↑

sodium ethanoate
(sodium acetate)

In the reactions with basic oxides and bases the products are salts and water:

2CH3COOH + MgO → (CH3COO)2Mg + H2O

magnesium diethanoate

CH3COOH + KOH → CH3COOK + H2O

potassium ethanoate
This is a reaction of neutralization and the temperature raises as heat is evolved.
The reactions are slow compared to the reactions of the inorganic acids (for example HCl, H2SO4,
HNO3).

57
Carboxylic acids are oxygen-containing acids and similarly to HNO3 they react with alcohols (see p. 17).
The products are an ester and water. The reaction is molecular, reversible and slow and is called a
reaction of esterification:

cat.
carboxylic acid + alcohol →
← ester + H2O

For example ethanoic acid reacts with ethanol to produce ethyl ethanoate (ethyl ester of ethanoic
acid) and water. The esterification reaction undergoes in the preseance of a catalyst* (conc. H2SO4):

O to, conc. Н2SO4 O

H3C ‒ С ‒= + HO ‒ С2H5 →
← H3C ‒ С ‒= + H2O
ОH О ‒ C2H5
Ethanoic acid Ethyl ethanoate
(ethyl acetate)

The ester (ethyl ethanoate) is a colourless liquid with a fruity odour and is used as an artificial food
flavour and as a solvent.

*Catalysts are substances that accelerate chemical reactions without themselves being consumed. 58
It is interesting to know:

Ethanoic acid reacts with halogens. Hydrogen atoms in the methyl group –CH3 are substituted
by halogen atoms. For instance in the reaction of chlorination the product is chloroethanoic acid
(commonly known as chloroacetic acid):

Н catalyst
+ Cl Cl Cl
+ Н Cl

CH3COOH + Cl2 → CH2ClСООН + HCl

Ethanoic acid Chloroethanoic acid

Chloroethanoic acid is more reactive than ethanoic acid. If there is enough chlorine all three
hydrogen atoms of the methyl group are substituted by chlorine atoms.

59
PRODUCTION

The oxidation of ethanol by the oxygen in the air under the action of specific bacteria is a well known
biochemical process. The products are ethanoic acid and water:

C2H5OH + О2 acetobacters CH3COOH + H2O

That would happen if wine has been exposed to air for a long time.
The oxidation of ethanal is a common reaction, yielding ethanoic acid:

O 1/2O2 O
H3C ‒ С ‒= + H3C ‒ С ‒=
H ОH

On an industrial scale ethanoic acid is prodouced in a reaction of methanol with carbon monoxide
(process of catalytic carbonylation of methanol):

CH3OH + CO cat., to, p

CH3COOH

60
USES

Vinegar (dilute water solutions of ethanoic acid) is a seasoning and a preservative. But it is also a
cleaner (for example to remove spots of wet cups from the wood furniture, carpet stains, etc.). The
mixture of vinegar and baking soda can be effective to unclog drains.
O

In the industry ethanoic acid is a start material for the production of ethenyl O
ethanoate (vinyl acetate) used in the production of plastics, resins, textile,c etc. O
H2C = CH

=
and also cellulose acetate ‒ a key material for the production of synthetic fibres C
and plastics. O CH3
Ethenyl ethanoate
(vinyl acetate)
pharmaceuticals varnishes
plastics plant protection
chemicals Ethanoic acid is also an intermediate for the pro-
solvents СН3СООН duction of dyes, pharmaceuticals, plant protection
ethanoic chemicals, varnishes. The odour of some esters of
perfumery
acid the ethanoic acid is very pleasant and they are used
preservatives synthetic to prepare perfume compositions. Ethyl ethanoate
fibres
seasoning dyes is a good solvent of varnishes.
61
 CAN YOU ANSWER THESE QUESTIONS
1. Why are organic compounds with carboxyl groups in their molecules acids?
2. Carboxylic acids are stronger acid than phenol. Why?
3. Why does ethanoic acid boil at a relatively high temperature?
4. Methanoic acid HCOOH reacts with Ag2O (silver mirror test), while ethanoic acid does not
react. Why?
5. How to produce ethanoic acid?
6. Is it good to leave an open bottle of wine?
7. Why is a mixture of vinegar and baking soda used to unclog drains?
8. What is ethanoic acid used for in everyday life?

62
39 Benzoic acid. 2-Hydroxybenzoic acid
O
key TOPICS ‒ С ‒=
ОH
1. What is the simplest aromatic carboxylic acid?
2. What is E210, E211?
3. What is 2-hydroxybenzoic acid used for? ‒ ОH
4. What is aspirin?
key words
●● Benzoic acid
HOС6H4COОН С6H5COОН ●● Benzoate ion
●● 2-hydroxybenzoic acid
●● Salicylic acid
●● Acetylsalicylic acid
●● Aspirin
●● Phenylsalicylic acid
●● Salol
Benzoic acid C6H5COOH is the simplest aromatic carboxylic
acid. In its molecules one carboxyl group is directly bonded to an
O ‒ C ‒OH
aromatic ring thus substituting one H atom if compared to the

‒
benzene molecule. The name „benzoic“ originates from „gum
benzoin“ – a natural gum from which it has been extracted.
O= OH
C ‒

‒
O= OH
C ‒
Н

Н‒ ‒ C Н‒ ‒ C
‒

‒
Н‒ ‒ Н‒ ‒
C C C C
‒

‒
‒C ‒C ‒ ‒C ‒C ‒
Н Н Н Н
‒ ‒
C C
‒

‒
Н Н

ga
s
Hydrocarbon Aromatic carboxylic acid Boiling point 249 oC 240
Benzene Benzoic acid

Temperature oC
200

PHYSICAL PROPERTIES

d
ui
180

q
li
Benzoic acid is a crystalline colourless substance with a peculiar smell. It
140
is heavier than water (its density is 1 279 kg/m3). Under strong heating it Melting point 122 C
o

sublimates. It melts at 122 oC and boils at 249 oC. Benzoic acid is slightly 100

soluble in water but its solubility increases if the temperature rises.

so
li
It is soluble in many organic solvents (methanol, ethanol, propanol,

d
propanone, benzene, tetrachloromethane, etc.).
64
It is interesting to know:
As all weak acids benzoic acid dissociates partially in water, yielding negative benzoate ions and
positive hydrogen ions:
→ С Н СОО‒ + Н+
С6Н5СООН ← 6 5
benzoic acid benzoate ion

In aqueous solutions of benzoic acid the blue litmus turns red.

CHEMICAL PROPERTIES

Both the functional carboxyl group –COOH and the aromatic ring might be involved in chemical
interactions.
Reactions of the –COOH group
These reactions undergo easy as compared to the saturated carboxylic acids (like ethanoic acid
for example) as the O – H bond is more polarized. All reactions for the ethanoic acid are possible
– with active metals, basic oxides, bases, salts of weak acids and esterification.

65
 How many moles of hydrogen H2 are evolved in the reaction of 4 moles of
PROBLEM! benzoic acid with sodium Na?

Solution: The chemical equation of the reaction is:

2 ‒ СООН + 2Na → 2 ‒ СООNa + H2↑

sodium benzoate

The incomplete molar ratio for benzoic acid and hydrogen is:

n(C6H5COOH) : n(H2) = 2 : 1.
So n(H2) = (1/2)n(C6H5COOH) = (1/2).4 = 2 moles

Answer: In the reaction of 4 moles of benzoic acid with sodium 2 moles of H2 are evolved.

66
 How many moles of benzoic acid do react with ethanol to produce 10
PROBLEM! moles of water? What type of reaction is that?

Solution: The chemical equation of the reaction is:

to, cat..
‒ СООН + НОС2Н5 →
← ‒ СООС2Н5 + H 2О
ethyl benzoate

The incomplete molar ratio for benzoic acid and water is:

n(C6H5COOH) : n(H2O) = 1 : 1.
So n(H2O) = n(C6H5COOH) = 10 moles

Answer: To produce 10 moles of water, 10 moles of benzoic acid have to react with ethanol. This is
a reaction of esterification.

67
Chemical reactions of the aromatic ring
Substitution reactions of the aromatic ring can take place but the carboxyl group deters the
substitution of the H atoms. So these reactions are slow compared to the substitution reactions
of benzene. The substituents are first directed to the 3rd (or meta) C atom relative to the carbon
atom bonded to the –COOH group. Typical reactions are the chlorination and the nitration of
benzoic acid:

FeCl3 ‒ СООН
‒ СООН + Cl2 + HCl

‒
Сl
3-chlorobenzoic acid

3-chlorobenzoic acid is a start material of many organic synthesis.

‒ СООН + НОNО2 ‒ СООН + H 2O

‒
NO2
3-nitrobenzoic acid

3-nitrobenzoic acid is stronger than benzoic acid.

68
PRODUCTION
In the industry benzoic acid is produced in a catalytic process of oxidation of methylbenzene:

‒ СН3 (O)
‒ СООН

Methylbenzene Benzoic acid

USES
Benzoic acid is used in many organic synthesis. plasticizers raw materials
Some of its salts and esters are active components
of ointments. They are also used as components
(plasticizers) of some plastics. Benzoic acid and its
sodium salt are used as food preservatives. E210 pharmaceuticals
С6Н5СООН
(benzoic acid), E211 (sodium benzoate), E212 Benzoic acid
(potassium benzoate), E213 (calcium benzoate),
E214 – E219 (derivatives of the benzoic acid)
preServatives dyes
are food additives, permitted in the EU, used as
antibacterial and antifungal food preservatives.

physiological action
The concentration of benzoic acid and sodium benzoate in plants and foods is low and these compounds
are not harmful for man. But if swallowed benzoic acid can cause serious damages to organs. Prolonged
or repeated exposures to benzoic acid vapours can cause skin irritation, serious eye damage and can
damage organs too. 69
2-HYDROXYBENZOIC ACID
The molecule of 2-hydroxybenzoic acid contains two functional
groups – a carboxyl group –COOH and a hydroxy group –OH.
They are bonded to two adjacent C atoms of the aromatic ring,
O‒ C ‒OH
i.e. this is benzoic acid with one hydroxy group on o-position

‒
(o-hydroxybenzoic acid). ‒OH
O= OH O= OH
C ‒ ‒ OH C ‒
Н‒ ‒ C Н‒ ‒ C
‒

‒
Н‒ ‒ OH
‒ ‒
C C C C
‒

‒
‒C ‒C ‒ ‒C ‒C ‒
Н Н Н Н
‒ ‒
C C
‒

‒
Н Н

Benzoic acid 2-Hydroxybenzoic acid

The common name of this organic acid is salicylic acid (the acid was first isolated from the bark of a
white willow – Salix alba).
2-hydroxybenzoic acid is a colourless and odourless crystal solid. It is soluble in hot water. Under
moderate heating it sublimates. It dissolves to different extents in many organic solvents –
tetrachloromethane, benzene, methanol, ethanol, propanol, propanone, methylbenzene, etc.
2-hydroxybenzoic acid is an antiseptic and an antibacterial agent. It is also used as a preservative.
2-hydroxybenzoic acid is stronger than benzoic acid. As all acids it reacts with active metals, basic
oxides, bases and salts of weak acids, yielding salts – salicylates.
70
 How many moles of sodium hydroxide NaOH are needed to neutralize
PROBLEM! 5 moles of 2-hydroxybenzoic acid?

Solution: Both functional groups are involved in this interaction:

‒ СООН ‒ СООNa
‒ ОН + 2NaOH → ‒ ОNa + 2H2O
sodium salicylate

The incomplete molar ratio for 2-hydroxybenzoic acid and sodium hydroxide is:

n(HO ‒C6H4 ‒COOH) : n(NaOH) = 1 : 2.

So n(NaOH) = 2n(HO ‒C6H4 ‒COOH) = 2.5 = 10 moles

Answer: 10 moles of NaOH are required to neutralize 5 moles of HO–C6H4–COOH.

71
Owing to the presence of two different functional groups 2-hydroxybenzoic acid can react with
acids as well as with alcohols and phenols. Both are reactions of esterification. The esters with
ethanoic acid and phenol are commonly known as aspirin and salol:

‒ СООН t , catalyst.
o ‒ СООН
‒ ОН + HOOCCH3 →
← ‒ ОOCCH3 + H 2O

acetylsalicylic acid (aspirin)

O O
С ‒= С ‒=
‒ ОH to, catalyst.
‒ О−С6Н5
‒ ОН + HOC6H5 →
← ‒ ОН + H 2O

phenylsalicylate (salol)

Both esters are drugs. Aspirin is a widely used anti-inflammatory, analgesic (relieves pains) and
antipyretic (reduces fever) drug. It is also used to prevent blood clot formation and thus prevents
heart attacks and strokes. Salol is an antiseptic. 2-hydroxybenzoic acid itself is also an antiseptic
with strong bactericidal action and is used as a food preservative.
72
Other well known carboxylic acids with two functional groups in their molecules are the ethandioic
acid, better known as oxalic acid, and 2-hydroxypropanoic acid known as lactic (milk) acid.

Oxalic acid (COOH)2 removes rust spots. The calcium salt of oxalic acid is insoluble HOOC − COOH
in water. If the content of calcium oxalates in the urine is high, kidney stones of Oxalic acid
calcium oxalate can form.

Lactic acid CH3OHCHCOOH is a product of the lactic acid fermentation of glucose CH3 − CH − COOH
or other saccharides (for example lactose) by the action of some microorganisms

−
OH
(for example Lactobacillus bulgaricus used in the yogurt production). During
physical training lactic acid is accumulated in the muscles. Lactic acid

73
 CAN YOU ANSWER THESE QUESTIONS
1. Why is the compound C6H5COOH an acid?
2. Under standard conditions benzene Is a volatile liquid while benzoic acid is a crystalline
substance. Why?
3. Benzoic acid can be harmful for man but in spite of that it and some of its salts are used as
food preservatives. Why?
4. Is 2-hydroxybenzoic acid stronger than benzoic acid? Why?
5. How to distinguish between benzoic and salicylic acid?
6. Why does 2-hydroxybenzoic acid take part in esterification reactions both with carboxylic
acids and alcohols?
7. What is the product of the esterification of 2-hydroxybenzoic acid and ethanoic acid? What
is its common name and what it is used for?
8. Why is aspirin used as a food preservative?

74
40 Amines. Amino acids ‒ ‒H
N‒
H

key TOPICS O
‒ С‒=
1. What are amines and amino acids? ОH
2. What are α-amino acids?
3. What is the simplest amine and the simplest amino acid?
4. What is a peptide bond? Why is it important for all living
organisms?
key words
6
c СH3NH2 ●● Amines
CARBO
N
1 ●● Methylamine
H NH2СH2COOH ●● Aminobenzene
hydrogen
(Phenylamine, Aniline)
8 ●● Amino acid
O ●● α-amino acid
oxygen 7
N gen ●● Peptide bond
o
nitr
●● Polypeptide
Amines and amino acids are nitrogen containing organic compounds. Amines are H
the simplest nitrogen-containing organic compounds and amino acids play an N H
important biological role.
Amino group
●●
AMINES −NH2
Amines are organic compounds composed of carbon (as all organic compounds), hydrogen and
nitrogen. In organic compounds nitrogen is mainly trivalent and forms polar covalent bonds.
The simplest amine is metylamine CH3NH2. It is considered as derived from ammonia (for this reason
these organic compounds are named amines) by substituting one H atom with a methyl group –CH3.
But in the same time it can be a derivative of methane in whose molecules one H atom has been
replaced by an amino group –NH2. Both are correct:

‒H ‒H
H3С ‒ H N‒ H3С N‒
‒ ‒
H H

H H
H

‒
‒

‒
H2N ‒ H‒ C ‒ H N‒ C ‒ H
H ‒
‒
‒

H H
Methylamine
or Aminomethane 76
It is interesting to know:
Generally, one, two or all three atoms in the ammonia molecule can be
substituted by hydrocarbon groups (– C2H5, – C3H7, – C4H5, etc.) They are named
amines and the name of the radicals are added as prefixes. For example
C2H5NH2 – ethylamine; C6H5NH2 – phenylamine (the simplest aromatic amine,
commonly known as aniline).
Similarly to hydrocarbons amines are primary (one H atom in the NH3 molecule
has been substituted by a hydrocarbon group), secondary (two H atoms have
been substituted by hydrocarbon groups) and tertiary (all three H atoms have
been substituted by hydrocarbon groups: H ‒H‒
H3C ‒ N ‒ CH3 H5C2 ‒ N ‒ CH3 H3C ‒ N ‒ CH3 H2C5 ‒ N ‒ CH3 N
Н‒ ‒ C

‒
Н
‒

‒
‒ ‒
H H СH3 СH3 C C

‒
Dimethylamine Ethylmethylamine Trimethylamine Ethyldimethylamine ‒C ‒C‒
Н Н
‒
C

‒
Н
Some times it is more convenient to name an amine using the name of the
Phenylamine
hydrocarbon with the same carbon chain, adding the prefix „amino-“. For (Aniline)

example phenylamine C6H5NH2 is also named aminobenzene, H3C ‒ CH ‒ CH ‒ CH3

‒
‒
NH2 NH2
is named 2,3- diaminobutane, etc.

77
PHYSICAL PROPERTIES

H3C ‒ N ‒ H
●●
:
The nitrogen atom of the amino group has a lone electron pair ( −NH2).

‒
It attracts the hydrogen atom of the amino group of another molecule,

H
H3
thus forming an intermolecular bond (called hydrogen bond). It is ‒

C‒
●●
N
weak as compared to the hydrogen bonds between alcohol molecules

‒ H
H
because the nitrogen atom is less electronegative than the oxygen
atom. As consequence, the melting and boiling points of the saturated ●● ‒H
amines are higher than that of alkanes, but are low if compared to the H3C ‒ N ‒ Hydrogen
H bonds
saturated alcohols with the same molecular mass.

Alkanes amines alcohols

Melting and boiling points increase

Methylamine CH3NH2 is a gas at STP. The other low molecular weight primary amines are liquids,
while the high molecular weight amines are solid substances. Aminobenzene is a very slightly
soluble in water, oily, flammable liquid with an unpleasant odour.

78
CHEMICAL PROPERTIES
   H
●●
   +
The soluble in water amines form positively charged ions in their aqueous H3C−NH2
solutions as hydrogen ions are attached to the lone electron pair of the Methylammonium
nitrogen atom. ion

Similarly to ammonium hydroxide (NH4OH), in aqueous solutions of methylamine CH3NH2

methylammonium hydroxide CH3NH3OH is formed:
   H   +
→ H C−NH
●●
:
H3C−NH2 + H−OH ← + OH‒
3 2

Methylammonium
hydroxide
Dissolved in water amines react as bases (generally, they are stronger than ammonium hydroxide).
In reactions with soluble inorganic acids soluble salts are formed:
  H    +
→ H C−NH
●●
:

H3C−NH2 + H−Cl ← 3 2
+ Cl‒
methylammonium
chloride

79
Aminobenzene (phenylamine or aniline) is a weak base – weaker than NН2

●●
‒
saturated amines and ammonia. The lone electron pair of the nitrogen atom
is attracted by the 6 delocalized electrons of the aromatic ring. The lone pair
is not anymore „lone“ and the partial negative charge of the nitrogen atom is
lower. Thus it is more difficult for a hydrogen ion to bond to the nitrogen atom.
Aminobenzene
But the substitution reactions for the aromatic ring are facilitated. For example
bromine water discolours if aminobenzene is added to the solution. The –NH2 group directs the
substituents to o- and p-positions. A white precipitate of 2,4,6-tribromoaminobenzene forms:
Br

‒
‒ NН2 + 3Br2 → Br ‒ ‒ NН2 + 3HBr

‒
Br
2,4,6-tribromoaminobenzene

The discoloration of bromine water is a test reaction for double or triple carbon – carbon bonds. But
in a substitution reaction aminobenzene also discolours bromine water (similarly to phenol).
A common test reaction for aminobenzene is its
interaction with chlorinated lime – the solution turns violet.
Aminobenzene is a strong poison.
Many amines are basic components (chemical building blocks) for organic synthesis. They are used
in the production of drugs, dyes, explosives, synthetic (polyamide) fibres, corrosion inhibitors, etc.
80
AMINO ACIDS amino acids
condensed formula name
Amino acids may be considered as derived
from carboxylic acids in whose molecules H2C ‒ СOOH Aminoethanoic acid
one or more H atoms have been substituted

‒
NH2 (glycine)
by amino groups. They are named simply
by adding the prefix „-amino“ to the name H3C ‒ CH ‒ СOOH 2-aminopropanoic acid
of the carboxylic acid (see the table). The

‒
NH2 (alanine)
place of the –NH2 group is indicated by
the number of the C-atom to which it is H3C 2-amino-3-

‒
attached. As a rule to the C atom of the HC ‒ CH ‒ СOOH methylbutanoic acid
–COOH is assigned number 1. Many amino

‒
‒
H3C NH2 (valine)
acids (especially the biologically important)
2-amino-3-
are known also by their common names. ‒ CH2 ‒ CH ‒ СOOH
phenylpropanoic acid

‒
NH2 (phenylalanine)

amino ACIDS ARE ORGANIC COMPOUNDS WITH two functional groups in their
molecules − a CARBOXYL GROUP −COOH and an amino group −NH2.

81
 If the –NH2 group is neighbour to the –COOH
3 2 1 group the amino acids are designated as α-amino 3 2 1
H3C ‒ CH ‒ СOOH acids (all acids listed in the table). If the –NH2 H2C ‒ CH2 ‒ СOOH
‒

‒
NH2 group is bonded to the third C atom the acids are NH2
2-aminopropanoic acid β-amino acids. If the amino group is bonded to 3-aminopropanoic acid
(α-aminopropanoic acid) the fourth C atom – γ-amino acids, etc. For living (β -aminopropanoic acid)
organisms the most important are the α-amino
acids as they are building blocks of proteins.

PHYSICAL PROPERTIES
Amino acids are colourless crystalline solids. They melt at relatively high temperatures (above 230 oC).
They are soluble in water but are insoluble in nonpolar solvents (for example benzene and other
hydrocarbons).

82
CHEMICAL PROPERTIES OF α-AMINO ACIDS
α-amino acids react with acids (the –NH2 group is involved) as well as with bases (the –COOH group is
involved). But for the living world the most important chemical property of α-amino acids is the ability
of their molecules to bond to each other, thus forming long chains. It is not obligatory to link identical
molecules. One H atom of the amino group of one molecule and the –OH group of the carboxyl group
of another molecule form a water molecule. The two molecules residues link to each other by the
so called peptide bond, thus forming a dipeptide. For example the formation of a dipeptide of two
molecules of aminoethanoic (glycine) acid may be expressed as follows:

+ N + O
H H
O N
H H

O O
H2N ‒ CH2 ‒ С ‒= + HNH ‒ CH2‒ COOH → H2N ‒ CH2 ‒ С ‒= CH ‒ COOH + H2O
ОH NH ‒ 2
Peptide bond
This dipeptide may react with another molecule of aminoethanoic (or another α-amino acid) and so
on. The long polypeptides build proteins.
The most important for human organism α-amino acids are a little bit more than 20. Some of them
(the so called essential amino acids) can not be synthesized by the human body. They must come
with food. Therefore the nutritional balance is essential to the body health. 83
 CAN YOU ANSWER THESE QUESTIONS
1. What is the functional group of amines?
2. What is the valence of nitrogen in amines and amino acids?
3. Why do amines react with acids?
4. What are the functional groups of amino acids?
5. Why are α–aminopropanoic acid and β–aminopropanoic acid different compounds?
6. What is a peptide bond?
7. What are polypeptides?
8. What are essential amino acids?

84
 PROjECTS
1. Use of alcohols and phenols in the everyday life
Learn about some interesting uses of alcohols and phenols in household. What are alcohols
used for? (See for example www.methanol.org)

2. Physiological effect of ethanol

Ethanol is a drug (narcotic). Learn what happens in the organism when drinking beer, wine,
vodka, whiskey. Why is alcohol abuse destructive?

3. Triglycerides
Learn about the physiological role of triglycerides. Why is the level of triglycerides in the blood
an important health indicator?

4. Phenol - a serious pollutant of soil and water

Learn about the impact of phenol pollution on the environment. What is the effect of
contaminated with phenol water on the vital functions of human and animal organisms? What
are the major industrial processes that might contaminate soil and water with phenol? How
is phenol removed from wasted water? Is there near your town or village an enterprise that
might be a potential source of phenol contamination?
5. Aldehydes odour
Many aldehydes have a very pleasant odour. They are components of perfumes and some of
them (for example vanilla, cinnamon) are used in confectionery. Learn about them.

6. Propanone in nature
Is propanone found in nature? What may happen if propanone contaminates water, soil or air?
Why should not be thrown out varnishes and dyes in the sewage?

7. Carboxylic acids in the everyday life

Citric acid, malic acid and tartaric acid are used in cookery. What are their chemical formulae
and structures? In which fruits do they naturally occur? In which food products do we use
them and why?

8. Aspirin
Learn about the „history“ of aspirin. How is aspirin synthesized? What are the beneficial effects
of aspirin? What are the possible side effects?

9. Essential amino acids

Which are the essential amino acids? Which foods do contain them? What is the daily need of
the organism of these acids? Propose a healthy week menu for your family.