CARBON COMPOUND

2,1 Understanding carbon compound

A) WHAT A CARBON COMPOUND IS

 Carbon compounds are compounds that contain ____________ as one of their
constituent elements.
 These compounds usually contain
- C & ____ atoms only or
- C & H atoms in combination with other elements such as O, S, N, P and halogen.

CARBON COMPOUNDS
 Carbon compounds can be classified into two groups, _____________ compounds and
______________ compounds.
 Organic compounds – carbon-containing compounds
 - All carbon-containing compounds qualify as organic compounds except oxides of
carbon, _____________, cyanides and metallic carbides.
 Oxides of carbon, carbonates, cyanides and metallic carbides – can be obtained from
non-living things.
 Inorganic compounds – all non-carbon-containing compounds and few
carbon- containing compounds.

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Classify into organic and inorganic compounds

Organic Inorganic

Potassium cyanide

Copper (II) carbonate

Cellulose

Starch

Natural rubber

Calcium carbide

Carbon dioxide

Protein

Ethanol

Urea

Glucose

Carbon monoxide

HYDROCARBON (HC)
 Hydrocarbon are the simplest of all organic compounds, containing only 2 elements – C
&H
 Natural sources HC – petroleum, coal, natural gas and certain trees such as the rubber
tree.
 Non-hydrocarbon – organic compounds in which some or all the H atom have been
replaced by other atoms.
 Non-hydrocarbon contain C & H together with a few other elements such as O, N, P or
halogens. Eg: sugar (Containing C, H & O)

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 Carbon compound

Hydrocarbon Non-hydrocarbon

C&H C, H and
O, N, P, S, F, Cl, Br, I

Saturated HC Unsaturated HC

-C-C- C=C -C = C-

Single bond Double bond Triple bond

2 atoms sharing:
 ____ pair of electrons - single covalent bond
 ____ pairs of electrons - double covalent bond
 3 pairs of electrons - ________ covalent bond

Combustion products of organic compounds

- organic compounds are _______________ substance, burnt in excess oxygen to form
carbon dioxide and water
Examples :
1. C6H12O6(s) + 6O2(g) 6CO2(g) + 6H2O(l)
2. C2H4 + O2(g) _________ + __________
3. C3H8 + _________ ________ + __________
4. C2H5OH + ________ ________ + __________

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2.2 Analysing alkanes

B) ALKANES

1: Classification of Hydrocarbons
Alkanes are saturated hydrocarbons:
· _______________ (only single C-C bonds)
· hydrocarbon (only C and H)

H H H H

H C H H C C C H

H H H H
2: Bondings in hydrocarbon
Carbon atoms has _________ valence electrons
- need 4 electrons to reach octet ________________ arrangement.
- 4 bonds to each carbon atom
Hydrogen atoms has _______ valence electron
- need 1 electron to reach _______________ electron arrangement.
- 1 bond to each hydrogen atom
Carbon and hydrogen atoms can bond to each other to form very extensive and molecular
systems.

3: Formulae for organic molecules:

Molecular formula :
- shows the actual numbers and types of atom present in a molecule
Structural formula :
- shows how the atoms in a molecule are bonded together and by what types of bonds.

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 Write the molecular formula for each of the alkanes below.

H H H H H H

H C C H H C C C C H

H H H H H H

What is the general molecular formula for alkanes?

Alkanes have the general formula :- ____________ n=1, 2, 3,…..
n = no. of carbon atoms in the molecule

4 : Nomenclature of Alkanes
1. The name of alkanes consist of 2 parts : the root & ending.
2. Root - tells the number of carbon atoms in the longest continuous carbon chain.
3. Ending - tells the family of the compound.

No. of 1 4 6 8 9
carbon
atoms
Root Eth Prop Pent Hept Oct Dec
name

The root names for the first ten straight-chain alkanes

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Naming Alkanes
Example : Butane

Name of alkane Root Ending

Butane But (no. of carbon atoms -ane (the family is

= 4) alkane)

No. of C atoms Nomenclature / Molecular formula Structural Formula

1 C H
Methane CH4
H C H

2 C Ethane C 2H 6

3 C Propane C 3H 8

4 C Butane C4H10

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 5 C Pentane C5H12

6 C Hexane C6H14

5: Physical Properties
Alkanes- _______________ compounds

a) Melting and Boiling Point

Low melting and boiling points because these molecules are held together by
___________________________ forces.

• The boiling point ____________ between 20-30 °C per -CH2 group.

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• Boiling points and melting points increase as _______________________per molecule
increases.
• Then, __________ of molecules increases (molecular mass increases)
• Forces between molecules (Van Der Waals forces) are ___________
• More heat energy is needed to overcome the forces

b) Physical State at Room Temperature

CH4 - C4H10 : ___________ C5H12 - C17H38: ___________ C18H38 : ___________

c) Solubility
• ____________ in non polar solvents (organic solvents),
• Insoluble in water.

d) Density
 The density of the alkanes increases with increasing number of carbon atoms, BUT
is________________ than that of water.
 Hence, alkanes form the upper layer in an alkane - water mixture.

e) Electrical Conductivity
• ____________ conduct electricity
• because : alkanes are covalent compounds, do not have free ions but are made up of
_________________.

6.Chemical Properties of alkanes

• _________________ compounds
• Saturated compounds.
• The strong C-C and C-H bonds must be broken for the alkanes to react.
• Although alkanes do not react with most chemicals, they do react with oxygen and
halogens.

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a) Combustion
• The reaction with oxygen
• ______________ combustion of methane / in the presence of sufficient oxygen :
CH4(g) + 2O2(g) CO2(g) + 2H2O(l)
• _______________ combustion / insufficient oxygen available :
2CH4(g) + 3O2(g) CO(g) + 4H2O(l)
CH4(g) + O2(g) C(s) + 2H2O(l)
b) SUBSTITUTION
• Reaction with _______________
• Takes place readily in sunlight.
• C-H bonds-broken, formed C-halogens bonds
• Halogenation - example of a _______________ reaction
• Substitution reaction – when one atom or a group of atoms in a molecule is replaced by
another atom or group of atoms.
• Example - Mixture of methane and chlorine is exposed to _____________-varying
amounts of four different products are formed.

Main Product

UV
1. CH4 + Cl2 CH3Cl + HCl ______chloromethane

2. CH3Cl + Cl2  CH2Cl2 + HCl ______chloromethane

3. CH2Cl2 + Cl2  CHCl3 + HCl ______chloromethane

4. CHCl3 + Cl2  CCl2 + HCl ______chloromethane

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WORKSHEET 1
Figure 1 shows the electron arrangement of carbon atom.
x

x
x C x
x

x
Figure 1
a) Write the electron arrangement of carbon atom
_____________________________________________________________
b) Carbon atom forms a chemical bond with a hydrogen atoms
i) What type of bond is formed in the compound
______________________________________________________

ii) Draw the electron arrangement of the molecule formed

WORKSHEET 2
Answer all the questions.
1. What is the general formula for an alkanes?
_____________________________________________________________

2. Give the molecular formula for alkanes with

i) one C’s : _____________________
ii) four C’s : _____________________
iii) eight C’s : _____________________

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3. Give the name for the alkanes having
i) two carbon atoms : _____________________
ii) five carbon atoms : _____________________
iii) seven carbon atoms : _____________________

4. Draw structural formulas for

i) Propane (ii) Heptane

5. State 3 physical properties of alkane

i) ___________________________________________________________
ii) ___________________________________________________________
iii) ___________________________________________________________

2.3 Analysing Alkenes

C) ALKENES
 Are members of a family of hydrocarbons containing at least one carbon-carbon
_______________/ C=C
 ______________ hydrocarbons

GENERAL FORMULA OF ALKENES

CnH2n , n = 2, 3, 4,….
 n=1 as CH2 does not exist. Why?….

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NAMING ALKENES
 Example :-

1. Identify the longest

carbon chain containing the
double bond.

5. Number the carbon

atoms
from the end 2. Count the
nearest to the
H H H H H H number of
double bond. Give the carbon atoms
double bond the in the longest
smaller number.
H-C=
1
C-2 C-3 C-4 C-5 C-6 H chain.
[Position of double [6 carbon atoms]
bond is H H H H
1-ene]

3. Give the root name.

4. Identify the molecule’s
[Root name is hex-]
family
[Alkene family : ending
is –ene]

STRUCTURAL FORMULA
H H
 H-C=C-H ethene

H HH
 H-C=C-C-H propene
H

PHYSICAL PROPERTIES OF ALKENES

 Similar to those of alkanes.
 ___________ melting and boiling points.
 Soluble in organic solvents, insoluble in water.
 Less dense than water
 ______________ conduct electricity in any state.

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The physical properties of the first nine straight-chain alkenes

Name Numbers of Melting Boiling Density /

carbon point / 0C point /0C gcm-3
atoms
Ethene -169 -103 0.0011
Propene -185 -48 0.0018
But-1-ene -185 -6 0.0023
Pent-1-ene -165 30 0.6430

6 -140 64 0.6750
Hept-1ene 7 -119 93 0.6980

8 -104 122 0.7160

9 -94 146 0.7310

Dec-1-ene 10 -87 171 0.7430

CHEMICAL REACTIONS OF ALKENES

 _________ reactive than alkanes due to the presence of the C=C
a) Combustion reaction
b) Addition reactions
• Addition of hydrogen
• Addition of halogens
• Addition of _________________
• Addition of water
• Addition of hydroxyl groups
c) _______________ reaction

COMBUSTION REACTION
 C2H4(g) + 3O2 (g) 2CO2(g) + 2H2O(l)
 Alkenes burn with sootier flames as compared to alkenes.
 Because alkenes have a higher percentage of _____________ in their molecules than
alkanes.

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 ADDITION REACTIONS
Almost all reaction of alkenes occur at the _________________

 C=C + A-B -C - C-
A B

I ) Addition of hydrogen
H H HH
 H-C=C-H(g) + H-H(g) Ni H-C-C-H(g)
1800C
HH

- At 1800C , catalyst – ____________

- Called ________________________
- Hydrogenation is used in the manufacture of margarine from natural vegetable oils
which contain many double bonds in their molecules.

II) Addition of Halogens

 Addition with ______ such as chlorine and bromine- no catalyst or UV is needed
 Also known as ____________________
H H H H
 H-C=C-H(g) + Br-Br(aq) H-C- C-H(l)
Br Br

III) Addition of hydrogen halides

Takes place rapidly at room temperature and requires _______ catalyst.
Hydrogen halides- HCl, HBr, HI

 CH2=CH2(g) + HCl(g) CH2-CH2(l)

H Cl

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IV) Addition of water
 Is called hydration
 CH2=CH2(g) + H-OH(g) CH2-CH2(l)
H OH

V) Addition of hydroxyl groups

 Alkene + dilute acidified solution of ________________________, KMnO4
______________

[O]
 CH2=CH2(g) + H2O(l) CH2 – CH2 (l)
OH OH

Polimerization reaction
 Hundred/thousands of the alkene molecules link together to form long chains called
polymers.
 To form a polymer from alkene monomers – addition polymerization.
 Polimerization of ethane - Heating ethene to about __________ and a pressure of 1200
atm in the presence of trace of oxygen.

- Polymerization of ethene
H H H H H H H H
C=C + C=C + C=C or n C=C
H H H H H H H H

HHHHHH HH
-C-C-C-C-C-C- or C-C
HHHHHH HH n

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Comparing properties of alkanes and alkenes.
 C=C more ______________than C-C
 The soot test –alkenes burn to produce a more ____________ flame.
 Alkenes have higher C content than alkanes.
 Soot - unburned carbon

ALKANE ALKENE ALKYNE

General CnH2n+2 CnH2n CnH2n-2
Formula n=1,2,3,…. n=2,3,4,.. n=2,3,4,..

Functional C-C C=C C C

Group Single bond Double bond
Triple bond
Physical -Low melting and -Low melting and boiling -Low melting and
Properties boiling points points boiling points
-Less dense than -Less dense than water -Less dense than water
water -Cannot conduct -Cannot conduct
-Cannot conduct electricity electricity
electricity -Insoluble in water -Insoluble in water
-Insoluble in water -Soluble in organic solvent -Soluble in organic
-Soluble in organic solvent
solvent

Chemical -Combustion -Combustion (not cover in our

Properties -Halogenation -Addition of hydrogen syllabus)
-Addition of halogens
-Addition of hydrogen
halides
-Addition of water
-Addition of hydroxyl
group
-Polymerization

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Homologue Series
 Is a group or family of organic compounds that has the following:-
o Members of the series can be represented by a general formula.
o Successive members differ from each other by -CH2
o Members can be prepared by similar methods.
o Physical properties change regularly with increasing number of carbon atoms.
o Members have similar chemical properties because they have the same functional
group.
Functional group
 Is a special group of atoms attached to an organic molecule.
 This group-determine the chemical properties of the molecule.
 Alkanes - do not have any specific functional group.
 Alkenes - ___________ is the functional group

2.4 Synthesising ideas on isomerism

H Side
D) ISOMERISME chain :
H-C-H 1 C
atom

H-C-H

H-C-H Side
straight chain alkane
molecule chain :
H 2 C
atom
Branched-chain alkane molecule (2 branches)

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ISOMERISME
 Isomerisme – The ability of carbon atoms to form branched chains forming molecules
(isomers) with the same molecular formula but different structural formulae.
ISOMERS
 Isomers – are molecules with the same _____________ formula but with different
_______________ formulae.

ISOMERS OF ALKANES

HHHH H
H-C-H
H-C-C-C-C-H H H

HHHH H-C-C-C-H

Straight-chain HHH
Branched-chain
molecule molecule
C4H10 has 2 isomers

ISOMERS OF ALKENES

H
HHHH HHHH H-C-H
H H
H-C=C-C-C-H H-C-C=C-C-H
H-C=C-C-H
HH H H
H

Straight-chain molecule – Different positioning Branched-chain

of double bond molecule

C4H8 has 3 isomers

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HOW TO NAME ISOMERS
1.Find the ______________ continuous carbon chain in the molecule.
2.Give the name for this longest chain.
3.Identify the ______________ (alkyl group) in the molecule.
4.Locate and name the attached alkyl group.
5.Combine the name for the longest C chain with the name of branch chain.

ALKYL GROUP
 Branch / alkyl group – is an alkane from which one hydrogen atom has been removed.
 Alkyl group are named by dropping –ane from the name of the corresponding alkane
and replacing it with –yl.
H H
-H
H-C-H H-C-H
H
Methane ______________

NAMING ALKYL GROUP

Alkane Alkyl group

Name Molecular Name Molecular
formula formula
Methane CH4 CH3
Ethane C2H6 C2H5
Propane C3H8 C3H7

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NAMING ISOMERS OF ALKANE

H Step 1 :

H-C-H Find the longest

continuous
H H H carbon chain
in the molecule
H- C- C- C- C- H

H H H H

H Step 2 :

H-C-H Give the name

for this
H H H longest chain.
H- C- C- C- C- H
_____________
H H H H

Step 3 :
H
Number the C atoms
H-C-H in this longest chain
beginning at the
H H H end nearest to the
first branch
H- C- C- C- C- H
4 3 2 1 (alkyl group)
H H H H 20
 Alkyl group

Step 4 :
H
Locate and name the
H-C-H attached alkyl groups.
The position of each
H H H alkyl group is given
the number of the
H- C-4 C-3 C-2 C-1 H
C atom to which it is
H H H H attached on the chain.
_____________________
methyl _______________

Step 5 :
H
Complete the name for the molecule by
H-C-H combining the 3 component parts together.
Write the name as a single word.
H H H Use hyphens to separate numbers and
words & commas to separate numbers.
H- C- C- C- C- H
4 3 2 1
H H H H _________________________

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NAMING ISOMERS OF ALKENE

H Step 1 :

H-C-H Find the longest

continuous
H H H carbon chain
in the molecule
H- C- C= C- C- H
including double
H H bond.

Step 2 :
H
Number the C atoms in
H-C-H this longest chain
beginning at the
H H H end nearest to the
double bond.
H- C-
4 C=
3 C-
2 C-
1 H (not nearest to the
H H first branch/
alkyl group)

H
Step 3 :
H-C-H
Give the name
H H H for this
longest chain.
H- C-
4 C=
3 C-
2 C-
1 H

H H ____________

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 Methyl
Step 4 :
H
Locate and name the attached
H-C-H alkyl groups. The position of each
alkyl group is given
H H H the number of the
C atom to which it is
H- C-
4 C=
3 C-
2 C-
1 H attached on the chain.
H H
_________________

Methyl
Step 5 :
H
Complete the name
H-C-H for the molecule by
combining the name
H H H longest chain
and the name
H- C-
4 C=
3 C-
2 C-
1 H branch chain.
H H
_____________________

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WORKSHEET 3

1 Write the names of the following hydrocarbons.

HH H H H H H
H
H- C- C= C- C- H H- C= C- C- C- H
H-C-H
H H-C-H H H H H H
H-C-H H- C- C= C- C- H
H H H H

a) …………………………. b)………………………… c)………………………….

2. Draw the structural formula of the following isomers.

a) 2-methylbutane

b) 3-methylbut-1-ene

c) 2,3-dimethylhept-3-ene

d) 1,2-dibromobutane

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3. An alkane molecule, X has the molecular formula C5H12. A student suggested its name
as 2,2-dimethylpropane.

a) Draw the structure of this molecule.

b) How many isomers have the same molecular formula C5H12?

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2.5 Analysing alcohols

E) ALCOHOLS
 Example : wine is made from grape juice and rice wine is from fermented rice
 Familiar alcohol : ethanol, C2H5OH

THE ALCOHOL FAMILY

 Contain C, H and _____
 Organic compounds
 Contain hydroxyl group, ________ as the functional group
– This group is covalently bonded to a carbon atom as shown below

- C-O-H

 No _________ in an alcohol molecule. Alcohols do not show alkaline properties.

 Neutral compounds
 One H atom in an alkane is replaced by the hydroxyl group, an alcohol is formed
 R-H R-OH
 CnH2n+1H CnH2n+1OH
 General formula = CnH2n+1OH , n = 1, 2, 3, ……
NAMING ALCOHOLS
 The names of straight chain alcohols can be derived from those of the alkanes.
 Replacing the ending -e from the name of the alkane with –ol.
 A number in front of the –ol to indicate which carbon atom the hydroxyl group is
attached to.
HHH
H- C-C-C-H
OHH H
 Name of alkane : propane
 Name of alcohol : propanol
 Position of hydroxyl group : carbon 1
 Full name of alcohol : __________________

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ISOMERS OF ALCOHOLS
Example: C4H9OH
H HHH H H H H
 H-C- C-C-C-H H-C -C- C- C-H
OHH H H H OHH H
____________ _______________
H CH3H H CH3 H
H-C-C - C-H H-C-C - C-H
H OH H H H OH

______________ _____________

INDUSTRIAL PRODUCTION OF ETHANOL

 Ethanol – most important alcohols
 Its manufactured on a large scale by 2 main processes
– From sugars and starch by __________________
– From petroleum fractions by __________________

MAKING EHANOL BY FERMENTATION

 ________ is added to sugar or starch.
 Left in a warm place for several days in the absence of air.
 The fermentation process in ______________ which means it takes place in the absence
of oxygen.
 Yeast releases biological ______________.
 These enzymes break down the sugars and starches into glucose, C6H12O6.
 In the fermentation process, the enzyme (____________) slowly decomposes the
glucose to form ethanol and carbon dioxide.

 C6H12O6(aq) 2CH3CH2OH(aq) + 2CO2(g)

 Temperature : 18-200C
 Catalyst : yeast (zymase)

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  Other condition : absence of oxygen
 When the concentration of ethanol formed reaches about 15%, the yeast __________
and the fermentation stops.
 It is impossible to produce pure ethanol by natural fermentation.
 The ethanol is then purified by fractional distillation.

MAKING ETHANOL BY HYDRATION

 An addition reaction combines ethene with water to produce ethanol in the presence of
phosphoric acid as catalyst.
 Ethene is obtained from the cracking of petroleum fractions.
 CH2=CH2(g) + H2O(g) CH3CH2OH(g)
 Temperature : 3000C
 Pressure : 60 atm
 Catalyst : phosphoric acid, H3PO4
 The ethanol produced is condensed to form a _________ and the unreacted ethene is
recycled.

LABORATORY PREPARATION OF ETHANOL

 All you need is some ripen fruits or starchy foods and yeast.
 The yeast will convert the glucose to ethanol.
 Laboratory work

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 PHYSICAL PROPERTIES OF ALCOHOLS

Name Structural formula Boiling Solubility (g per 100cm3

point (0C) water)

Methanol 65 Miscible in all proportions

Ethanol 78 Miscible in all proportions

Propanol 97 Miscible in all proportions

Butanol 118 8.0

Pentanol 138 2.7

 Notice that none of the alcohols exists as a __________ at room temperature and
pressure.
 Unlike alkanes or alkenes, simple alcohols are __________________ in water.
 They have infinite solubility in water.

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 Physical state at
room conditions
LIQUID Smell
Boiling point SHARP
LOW BOILING
POINT
(780C)
ETHANOL Colour
Volatility
COLOURLESS
VOLATILE

Solubility in water
VERY SOLUBLE IN WATER.
MISCIBLE WITH WATER IN
ALL PROPORTIONS

CHEMICAL PROPERTIES OF ETHANOL

 Combustion
 Oxidation
 Dehydration

I) COMBUSTION
 Alcohols- very ________________ substances
 Readily undergo combustion
 Ethanol burns with ______________ blue flame
 Complete combustion of ethanol produces ______________ and water.
 C2H5OH(l) + 3O2(g) 2CO2(g) + 3H2O(l)
 Also releases lots of ___________ – suitable for use as a fuel. Clean fuel because it does not
release pollutants into the atmosphere.

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II) OXIDATION
 When a substance combines with oxygen
 Oxidizing agents are needed.
– Example :
• acidified potassium dichromate (VI), ____________ solution and
• acidified potassium manganate (VII), _____________ solution

 Form _____________________ – COOH group.

 When K2Cr2O7 solution is added to ethanol and the mixture is warmed, it turns form
_____________ to green.
 CH3CH2OH + 2[O] CH3COOH + H2O
 If KMnO4 solution is used instead, it changes colour from _______ to colourless.

III) DEHYDRATION
 The removal of water from a compound.
 In the dehydration of alcohols, a molecule of water is eliminated from each alcohol molecule.
 The alcohol molecule becomes an ______________ molecule.
 The dehydration of ethanol produces ethene.
HH H H
 H-C-C-H H-C=C-H + H-OH
H OH
 The ethene produced can be detected by the following tests:

– Decolourizes reddish-brown ___________ water

– Decolourizes purple acidified KMnO4 solution

 2 methods to carry out the dehydration of ethanol in school laboratory.

– Ethanol ____________ is passed over a heated catalyst such as unglazed porcelain chips,
porous pot, pumice stone or aluminium oxide.
– Ethanol is heated under reflux at 1700C with excess concentrated ___________________.

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Chemical properties of alcohols

Name Product
Combustion Oxidation Dehydration
Ethanol Carbon dioxide and water Ethanoic acid and water Ethene and water
Methanol

Propanol

Butanol

Chemical reactions of alcohols

Reactions Name Formula Chemical equation

Combustion Ethanol C2H5OH C2H5OH + 3O2 2CO2 + 3H2O
Methanol
Propanol
Butanol
Oxidation Ethanol
Methanol
Propanol
Butanol
Dehydration Ethanol
Propanol
Butanol

USES OF ALCOHOLS
 As a __________ in perfumes, cosmetics and toiletries.
 As a ___________ in lacquer, varnish, shellac and ink.
 As a ___________ for a compac disc and video cassette recorder head.
 As a __________ – clean fuel, biofuel, gasohol
 As a raw material in the _____________ of vinegar, fibre, explosive and plastic.

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  As a raw material to make _______________ products- tincture, antiseptic, cough syrup,
rubbing alcohol.

ALCOHOL-MISUSE AND ABUSE

 Ethanol – toxic
– Found in alcoholic drinks
– Act as depressant on the central nervous system. It slows down both physical and
mental activity.Causes the person to feel high and to lose all shyness.
 _______________.
 Cause chronic liver disease and brain damage.
WORKSHEET 4
The flow chart in the figure shows the reactions of alcohol P with a few substances.

Acidified
HH Reaction W KMnO4 H H H
Alcohol P Dehydration
H-C-C-C-OH Q H-C –C –C –H
C3H8O Substance Y
Substance X
HHO H OH OH
a. Name and write the structural formula for alcohol P.

b. Name substance X, substance Y, substance Q and reaction W.

X:_______________________________ Y:____________________________
Q:_______________________________ W:____________________________

c. Write the chemical equations for all the reactions involved.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

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2.6 Analysing carboxylic acids
F) CARBOXYLIC ACID
 EXAMPLES ORGANIC ACIDS:

–Acetic acid - Sour taste in vinegar

–Lactic acid – in sour milk
–Citric acid – present in citrus fruits
–Ascorbic acid – vitamin C
–Salicylic acid – make aspirin

The carboxylic acid family

 Organic compound
 Containing C, H, O
 The general formula CnH2n+1 COOH , n= 0, 1, 2, 3,…,
 The functional group ___________________ (carboxyl group)
 Structure functional group :
O
 -C
O-H
Naming carboxylic acids
 Straight chain carboxylic acids are named by dropping the –e from the name of the
corresponding alkane and replacing it with –oic acid
 The root name such as methane, ethane and propane indicates the number of C atoms in the
longest chain including the ________ in the carboxyl group
O
 -C-C- C Carboxyl group
O-H

Carbon no. 1
 In carboxylic acids, the carboxyl C atom is always the start of the longest C chain.
 Carboxyl C is the number 1 C and ____________ is needed to locate the carboxyl group.
 Example : CH3-CH2-COOH

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 propanoic acid

Making ethanoic acid

 Oxidation of _______________
 By refluxing ethanol with ________________ such as K2Cr2O7 solution or KMnO4 solution.
HH H O
K2Cr2O7
 H-C-C-OH + 2[O] H-C-C + H2 O
HH reflux H OH
Ethanol Ethanoic acid

Laboratory preparation of ethanoic acid

Water out The reaction is

carried out using the
apparatus as shown.
Liebig
The flask is fitted
condenser
Water in with an upright condenser
to prevent the loss of a
volatile liquid by
Absolute vaporization.This method of
ethanol retaining a volatile liquid
+ K2Cr2O7 during heating is
called refluxing.

heat

Physical Properties

 Carboxylic acid with

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 – low molecular mass
» colourless liquids at room temperature and have sharp or unpleasant odours.
– high molecular mass / larger molecule (ten or more C atoms)
» wax-like solids and have little odour
 Boiling points are ___________ than that of alkanes with the same number of carbon atoms.
 More energy is required to overcome the stronger force of attraction between the larger
carboxylic acid molecules.
 Within the carboxylic acid family, the boiling points increase with increasing number of
________________________________.

Physical properties

Name Condensed Structural formula Boiling point (0C)

Methanoic acid 101

Ethanoic acid C H 3CO O H 118

Propanoic acid 141

Butanoic acid 164

Physical Properties
 Like simple alcohol, the smaller carboxylic acid molecules with 4 C atoms or fewer are
_________________ in water.
 The high solubility is due to water molecules being strongly attracted to the carboxyl group.

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 The solubility _______________ with increasing number of C atoms per molecule.
 The longer carboxylic acid molecules tends to be alkane-like and becomes insoluble in water.

Chemical properties
Acid properties
 Ethanoic acid – __________monoprotic acid
 Only __________ atom in the –COOH can ionize in water to produce H+.
 CH3COOH CH3COO- + H+
Ethanoic acid ____________ hydrogen ion

 Partial dissociation occurs.

 The presence of H+ causes ethanoic acid to turn moist blue litmus paper red and react just like
any typical acid.
 Reacts slowly with _______________________________________.

Reactions with metal

 Reacts with _____________ metals to produce salt and hydrogen.
 2CH3COOH(aq) + Zn Zn(CH3COO)2(aq) + H2(g)
_______________

Reactions with bases

 Neutralizes alkalis to give an organic salt and water.
CH3COOH(aq) + NaOH(aq) CH3COONa(aq) + H2O(l)
______________
 Copper(II) oxide powder dissolves in dilute ethanoic acid to form Copper(II) ethanoate
and water.
 2CH3COOH(aq) + CuO(s) Cu(CH3COO)2(aq) + H2O
___________________

Reactions with carbonates

 React with metal carbonate to produce a salt, carbon dioxide and water.
 2CH3COOH(aq) + CaCO3(s) Ca(CH3COO)2(aq) +CO2(g) +H2O(l)

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 ________________

Reactions with alcohols

 Reacts with alcohol to form _____________ and water – Esterification
 Carboxylic acid + alcohol ester + water.
O O
 CH3-C-O-H + H-O-C4H9 CH3-C-O-C4H9 + H-O-H
Ethanoic Butan-1-ol _______________
acid
 CH3COOH + C4H9OH CH3COOC4H9 + H2O
 Concentrated __________________ - catalyst

 Butyl ethanoate is a colourless sweet smelling liquid.

 It forms an oily layer which floats on water.

Chemical reactions of carboxylic acid

 Carboxylic acid + reactive metal carboxylate salt + hydrogen
 Carboxylic acid + base carboxylate salt + water
 Carboxylic acid + metal carbonate carboxylate salt + carbon dioxide + water
 Carboxylic acid + alcohol ester + water.

Uses of carboxylic acids

 Ethanoic acid
 Major industrial chemical
 Large quantities of it – manufactured for its use in food as flavouring and as
preservative.
 Vinegar – solution containing 5% ethanoic acid
 Used with other chemicals to make drugs, dyes, paints, insectisides and plastics.
 It can be converted into esters for use as solvents.
 Methanoic acid (formic acid) is used to coagulate latex.
 Fatty acids are long chain carboxylic acids used in making soaps.
 Carboxylic acids are used in the manufacture of polyesters and polyamides which are fibres
used in the textile industry.

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 _________________ is a preservative in foods.

WORKSHEET 5
1.a) Name the elements found in carboxylic acids.____________________________

b) What is the general formula for the carboxylic acid family?__________________

c) Name the functional group of this homologous series._______________________

2. One mole of carboxylic acid X has a mass of 74g.

a) Name a compound X. _____________________

b) Draw a structure of X.

3. Figure shows a reaction scheme involving compound P. Compound P and Q have the same
number of carbon atoms. Compound P is neutral, whereas compound Q is acidic.

Compound P Compound Q

Ethyl ethanoate

a) Compound P is converted into compound Q by process I. Name process I.

___________________________________________________________

b) What type of compound is ethyl ethanoate?

___________________________________________________________
c) Compound P reacts with compound Q to form ethyl ethanoate. Name process II.
___________________________________________________________

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 2.7 Analysing esters

G) ESTERS

• ______________ compound

• Most esters are found in fruits and are responsible for the distinctive and pleasant fruity aromas.

• Example : ester isoamyl acetate is the main chemical that produces the smell of bananas.

THE ESTER FAMILY

• Containing ______________

• Esterification – ______________ reacts with an _____________to form an ester. A molecule of

_____________ is elliminated.

• General formula : CnH2n+1COOCmH2m+1

• m and n indicate the numbers of carbon atoms in the ester molecule.

• n= 0, 1,2,3, ... and m = 1, 2, 3,..

• The general formula contains the group _____________. This is known as the
_______________ group (functional group).
O
-C
O-

NAMING ESTERS

• The structure of an ester may be regarded as consisting of two parts, one deriving from an
____________and the other from a _____________________.
O

• CnH2n+1-C
O-CmH2m+1

Derived from Derived from

carboxylic acid alcohol

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• The name of an ester consists of 2 parts.

• The name of the alcohol part of the ester is given first and is followed by a separate word giving
the name of the acid part of the ester.

• The name of alcohol part of the ester is the name of the __________ group
(-CmH2m+1) in the alcohol.

• The name of the acid part of the ester is the name of the carboxylate anion derived from the acid;
the __________ acid in the name of the parent acid is replaced by ____________.

• Eg : CH3COOCH2CH2CH3

Derived from alcohol.

HO HHH
Alkyl group contains
H-C-C-O-C-C-C-H 3 C atoms.
H HHH Name of alcohol
part : propyl

Derived from acid. Name of ester :

Acid has 2C atoms –ethanoic acid.
Change –oic acid to –oate _____________
Name of acid part : ethanoate

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FORMATION OF ESTERS

• Esterification

• Carboxylic acid + alcohol (in the presence of a strong acid catalyst – concentrated H2SO4)
ester + water.
O O
H2SO4
• R-C-O-H + H-O-R ’ R-C-O-R’ + H2O
Carboxylic Alcohol Ester
acid

Example :

• Methanoic acid + ______________ methyl methanoate and water.

• HCOOH + CH3OH HCOOCH3 + H2O

Try This !!!

• Predict the ester produce from an esterification between propanoic acid and ethanol and write an
equation for the esterification reaction.

PHYSICAL PROPERTIES OF ESTERS

• Simple esters are neutral compounds – sweet pleasant smell.

• ________________liquids

• boiling points much ____________ than those of carboxylic acids of similar molecular masses.

• _______________ compounds.

• Slightly soluble in water but readily dissolve in organic solvents.

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NATURAL SOURCES OF ESTERS
Simple esters

• Most are found in fruits and flowers.

• Are responsible for the fruity smells and pleasant fragrances associated with most fruits and
flowers.

• Jasmine owes – benzyl ethanoate , Pineapple – ethyl butanoate.

The higher and more complex esters

• Higher boiling points and thus are less volatile.

• Not produce the familiar pleasant smells of the simple esters.

• Animal fats such as milk fat –___________ esters

• Vegetable oils eg: palm oil – _____________ esters

USES OF ESTERS IN EVERYDAY LIFE

Esters with low molecular mass

• Volatile liquid

• Have ___________ smells

• Pleasant aromas- cosmetics and perfumes

• Food additives to enhance the _____________ and smell of processed foods.

• Listed as artificial flavours on labels of processed foods, snacks and confectionery.

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USES OF ESTERS IN EVERYDAY LIFE

Ester Formula Flavour

n-penthyl ethanoate CH3COOC5H11 Bananas

Ethyl butanoate Pineapples

Octyl ethanoate Oranges

Isoamyl isovalerate C4H9COOC5H11 Apples

Methyl salicylate C6H4(OH)(COOCH3) Oil of

wintergreen

USES OF ESTERS IN EVERYDAY LIFE

• Simple esters - ethyl ethanoate are excellent solvents for organic compound.

• Sunburn lotions, nail polish removers and glues use esters as solvents. Example, polystyrene
cement is a mixture of polystyrene dissolved in ethyl ethanoate.When the ester evaporates, a
solid plastic is left behind to bind together the surfaces.

• Large esters are used in the production of ____________ and detergents.

• Fats and oils are hydrolyzed to produce soaps.

• Esters are also used in the production of polyester.

• The long chain polyester molecules are ____________and have great tensile strength. Hence
they are used to make polyester threads in the production of synthetic fabrics.

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