Chemistry for Level XI of Senior High School
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Chemistry for Level XI of Senior High School
GLOSSARY
Alkane
:
Alkene
:
Alkyne
:
Saturated bond
:
Unsaturated bond
:
Addition reaction
Subtitution reaction
:
:
Elimination reaction
:
Oxidation reaction
Isomer
:
:
Cis - trans
:
Hydrocarbon compounds are saturated with
chains of carbon atoms that have a single covalent
bond.
Unsaturated hydrocarbon compounds with chains
of carbon atoms that have double covalent bonds.
Unsaturated hydrocarbon compounds with chains
of carbon atoms that have triple covalent bonds
Bond between two carbon atoms with a single
covalent bond.
Bond between two carbon atoms with double
covalent bonds
Double bond breaking reaction.
A form of chemical reaction, in which an atom in a
chemical compound is replaced by another atom
A reaction that is usually characterized by the
transformation of a single bond into a double
bond by releasing small molecules.
Oxygen binding reaction by a compound.
Compounds that have the same molecular formula
but different build formulas
The isomers belonging to the alkene compound are
asymmetrical, when the same group is unilaterally
called cis, when they are opposite, it is called trans
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Chemistry for Level XI of Senior High School
HYDROCARBON CONCEPT MAP
C atom
Characteristics
Hydrocarbons
Characteristics
C atom
Structures
Alkane
(CnH2n+2)
HYDROCARBON
COMPOUNDS
Type of
Hydrocarbons
Alkene
(CnH2n)
Alkyne
(CnH2n-2)
Reaction
Hydrocarbons
Properties
Properties
QUR’ANIC BOX
as well as ˹olive˺ trees which grow at Mount Sinai, providing oil
and a condiment to eat.
(Al-Mu’minun : 20)
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Chemistry for Level XI of Senior High School
CHAPTER I
HYDROCARBON
Introduction to Organic Chemistry
Organic chemistry is the study of “living” things⎼not in the same way that
biology is the study of life. Rather, organic chemistry takes a look at what composes
the living things, and how they’re structured. Organic chemistry breaks down living
things not only into into organs seen in organism, but goes a step further to break
down those organs into atoms and molecules. It focuses mainly on carbon, which is
highly essential to maintain life, and particularly zeroes in on the hydrocarbon, which
is molecule composed of hydrogen and carbon. Hydrocarbon not only compose what
we’re made of, but also what we consume, including carbohydrates, proteins, steroids,
fats and more! As a matter of fact, you may be surprised to know that everyday things,
such as caffeine, plastic, and paint are all composed of hydrocarbons!
Figure 1.1 The Roles of Hydrocarbons
A. Characteristic of Carbon Compounds
Carbon compounds are defined as compounds that contain carbon atom (C)
and other atoms, such as H, N, O, S, P and several metal atoms. Until now, there
are approximately 9 million carbon compounds.
1. Characteristics of Carbon Atom
This C atom has distinctive characteristics compared to other atoms. That
characteristic is its ability to form long C chains. Based on its electron
configuration, the C atom has 4 valence electrons that allow it to be able
to bond covalently with other atoms.
Figure 1.2 Lewis Structure of C atom
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Chemistry for Level XI of Senior High School
Carbon atom can form 4 strong covalent bonds with other C
atoms, and at the same time with other non metal atoms.
2. Carbon Atom Structure
Based on the ability of carbon atoms to bind to other carbon atoms, the
types of carbon atoms are grouped into four, namely primary, secondary,
tertiary, and quaternary carbon atoms.
a. Primary carbon atom (1°), C atom that bonded with 1 other C atom
b. Secondary carbon atom (2°), C atom that bonded with 2 other C atom
c. Tertiary carbon atom (3°), C atom that bonded with 3 other C atom
d. Quarternary carbon atom (4°), C atom that bonded with 4 other C
atom
(primary carbon atom)
(secondary carbon atom)
(tertiary carbon atom)
(quartenary carbon atom)
Figure 1.3 Carbon atom structure
SELF EXERCISE!
Look at the structure below!
a. Determine the primary, secondary, tertiary and quarternary
carbon atom base on the structure above!
b. Calculate how many primary, secondary, tertiary and
quarternary carbon atom base on the structure above!
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Chemistry for Level XI of Senior High School
B. Hydrocarbons and Types of Hydrocarbons
Hydrocarbon is the simplest carbon compound that consist of carbon and
hydrogen atom. Based on the arrangement of carbon chain, hydrocarbon are
classified into aliphatic hydrocarbons, alicyclic hydrocarbons, and
aromatic hydrocarbons. In this chapter we’re going to focused on aliphatic
hydrocarbon which divided into alkanes, alkenes, and alkynes.
1. Alkanes
Alkane are saturated hydrocarbons because they only have single
covalent bond between carbon atoms, C – C.
a. General Formula
The general formula of alkanes are:
Example:
(a) methane
(b) ethane
(c) propane
b. Nomenclature of Alkanes
The nomenclature of alkane follows the IUPAC nomenclature. The first
ten homolog series of alkane shown at table 1.1 below.
Table 1.1
Molecular
Condensed Structure
Name
Formula
CH4
CH4
Methane
C2H6
CH3CH3
Ethane
C3H8
CH3CH2CH3
Propane
C4H10
CH3CH2CH2CH3
Butane
C5H12
CH3CH2CH2CH2CH3
Pentane
C6H14
CH3CH2CH2CH2CH2CH3
Hexane
C7H16
CH3CH2CH2CH2CH2CH2CH3
Heptane
C8H18
CH3CH2CH2CH2CH2CH2CH2CH3
Octane
C9H20
CH3CH2CH2CH2CH2CH2CH2CH2CH3
Nonane
C10H22
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3
Decane
1) Straight Chain Alkanes
Alkanes that have a straight chain without branches are named
with the prefix n⎼ (normal).
Example:
a) CH3⎼CH2⎼CH2⎼CH3 ➔ 4 carbon atom ➔ n⎼butane
b) CH3⎼CH2⎼CH2⎼CH2⎼CH2⎼CH3 ➔ 6 carbon atom ➔ n⎼hexane
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Chemistry for Level XI of Senior High School
2) Branched Chain Alkanes
Number of alkyl-name of alkyl+main chain (no space
between the name of alkyl and the main chain)
List of alkyl group shown at table 1.2 below.
Table 1.2
Number of C
Structure
1
CH3⎼
2
CH3⎼CH2⎼
3
CH3⎼CH2⎼CH2⎼
4
CH3⎼CH2⎼CH2⎼CH2⎼
Name
Methyl
Ethyl
Propyl
Butyl
STEPS
- Determine the longest chain as the main chain,
- Assign numbers in the main chain, so that the branches set at
the lowest number
- The branches are alkyl groups and named alkyl according to
the C atom in the branches
Example:
Main Chain (longest):
Butane (4 C atoms)
Alkyl:
CH3 ➔ Methyl
(located in C no. 2)
Name: 2⎼methylbutane
-
If there are more than one alkyl gorup:
➢ Write down the branch number of identical alkyls,
separated with comma (,). If there are 2 alkyls with the
same number, then repeat the number
➢ Assign Greek prefix (di⎼, tri⎼, tetra⎼, penta⎼, etc) based on
the number of the alkyl groups
➢ If there are two different type of alkyl group, name based
on alphabet.
c. Properties of Alkanes
1) Physical Properties
a) Boiling Points
Straight chain alkanes has higher boiling point tha the
branched chain alkanes. The more branched the chain, the
lower the boiling point tend to be.
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Chemistry for Level XI of Senior High School
b) Solubility
Alkanes (both alkanes and cycloalkanes) are virtually
insoluble in water, but dissolve in organic solvent.
2) Chemical Properties
a) Elimination Reaction
The Reaction breaks alkanes into smaller molecule like short
chain alkanes, alkenes, and hydrogen. In short, elimination
reaction will convert single bond into double bond.
Alkanes (CnH2n+2) ➔ Alkene (CnH2n) + Hydrogen (H2)
b) Subtitution Reaction
This reaction occurs between alkanes and halogens group (F2,
Cl2, Br2, I2) at high temperature or the help of light. In this
reaction, one or more H atom in alkanes are replaced by
halogen atoms.
Alkanes (CnH2n+2) + X2 ➔ Haloalkanes (CnHn-1X) + HX
Example:
Figure 1.4 Alkanes substitution reaction
c) Combustion Reaction
Combustion is reaction between alkanes and oxygen gas (O2).
Complete combustion reaction will produce carbon dioxide
gas (CO2) and water (H2O), meanwhile incomplete combustion
reaction will produce carbon monoxide (CO) or carbon (C) and
water (H2O) as a result.
Alkanes (CnH2n+2) + O2 ➔ CO2 + H2O (complete)
Alkanes (CnH2n+2) + O2 ➔ CO/C + H2O (incomplete)
Example:
Figure 1.5 Alkanes combustion reaction
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Chemistry for Level XI of Senior High School
2. Alkenes
Alkenes are unsaturated hydrocarbons because they have at least one
C=C double bond.
a. General Formula
The general formula of alkenes are:
Example:
b. Nomenclature of Alkenes
According to IUPAC name, the nomenclature of alkenes is similar to
the nomenclature of alkanes. The suffix ‘-ane’ replace by ‘-ene’. The
homolog series of alkenes shown at table 1.3 below.
Table 1.3
Molecular
Condensed Structure
Name
Formula
C2H4
CH2=CH2
Ethene
C3H6
CH2=CHCH3
Propene
C4H8
CH2=CHCH2CH3
1⎼Butene
C5H10
CH2=CHCH2CH2CH3
1⎼Pentene
C6H12
CH2=CHCH2CH2CH2CH3
1⎼Hexene
C7H14
CH2=CHCH2CH2CH2CH2CH3
1⎼Heptene
C8H16
CH2=CHCH2CH2CH2CH2CH2CH3
1⎼Octene
C9H18
CH2=CHCH2CH2CH2CH2CH2CH2CH3
1⎼Nonene
C10H20
CH2=CHCH2CH2CH2CH2CH2CH2CH2CH3 1⎼Decene
1) Straight Chain Alkene
Number where the double bond located⎼main chain
Step:
- Determine the longest straight chain as the main chain
- Assign the numbering and set C=C at the lowest number
Example:
a) CH3⎼CH=CH⎼CH3 ➔ C=C located at C number 2 and there are
4 C atom as the longest chain ➔ 2⎼butene
b) CH3⎼CH2⎼CH=CH⎼CH3 ➔ C=C located at C number 2 and there
are 5 C atom as the longest chain ➔ 2⎼pentene
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Chemistry for Level XI of Senior High School
2) Branched Chain Alkene
Number of alkyl-alkyl-number of double bond-main chain
STEPS
- Determine the longest chain as the main chain,
- Assign numbers in the main chain, start from C=C bond.
- The branches are alkyl groups and named alkyl according to
the C atom in the branches
- Other rules follow the nomenclature of alkanes.
Example:
Main chain (longest):
4 C atom ➔ butene
C=C at C number 1
Alkyl:
CH3 ➔ methyl
Located at C number 2
Name: 2-methyl-1-butene
-
If there are more than one C=C bond, then the suffix ‘ene’
replaced by ‘-diene’, ‘-triene’ and so on based on the number
of C=C.
c. Properties of Alkenes
1) Physical Properties
Alkene have similar boiling properties with alkanes. The longer
the chain, the higher boiling point it has. The more branched the
lower boiling point it has. In other terms, boiling point increase
along with the Mr value.
2) Chemical Properties
a) Addition Reaction
In this reaction, 2 atoms or groups of atom are added to the
C=C bond to obtain C–C. In short, this reaction occurs to
change C=C (double bond) to C–C (single bond).
Figure 1.6 Alkene addition
b) Halogenation Reaction
This reaction happen between alkene and halogen groups (F2,
Cl2, Br2, I2). The reactivity of alkenes toward halogen decrease
along with the increasing atomic number of halogen.
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Chemistry for Level XI of Senior High School
Figure 1.7 Alkene Halogenation Reaction
c) Hydrohalogenation Reaction
Alkenes react with hydrogen halide (HX) to form haloalkanes
at room temperature.
Figure 1.8 Alkene hydrohalogenation reaction
In this reaction, when an unsymmetric alkene react
with hydrogen halide (HX), the hydrogen atom from
HX adds to hydrogen atom from C=C that has greater
number of hydrogen while the halogen atom add to
C=C with smaller number of hydrogen.
(Markovnikov’s Rules)
d) Hydrogenation Reaction
Alkenes react with hydrogen (H2) to form alkanes at a
temperature of 150 – 200°C with the help of a metal catalyst.
Figure 1.9 Alkene hydrogenation reaction
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Chemistry for Level XI of Senior High School
e) Hydration Reaction
Alkenes react with water (H2O) to form alcohol
Figure 1.10 Alkene hydration reaction
f) Combustion Reaction
Combustion reaction occurs when alkenes react with oxygen
(O2). Complete combustion reaction will form CO2 and H2O,
while incomplete combustion reaction will produce CO/C and
H2O.
3. Alkynes
Alkynes are unsaturated hydrocarbons because they have at least one
C≡C triple bond.
a. General Formula
The general formula of alkynes can be stated as follows:
Example:
CH≡CH
Ethyne
CH≡C⎼CH
Propyne
CH≡C⎼CH⎼CH3
Butyne
b. Nomeclature of Alkynes
According to IUPAC name, the nomenclature of alkynes is similar to
the nomenclature of alkanes. The suffix ‘-ane’ is replaced with ‘-yne’.
The homolog alkynes chain shown at tabel 1.4 below.
Table 1.4
Molecular
Condensed Structure
Name
Formula
C2H2
CH≡CH
Ethyne
C3H4
CH≡CCH3
Propyne
C4H6
CH≡CCH2CH3
1⎼Butyne
C5H8
CH≡CCH2CH2CH3
1⎼Pentyne
C6H10
CH≡CCH2CH2CH2CH3
1⎼Hexyne
C7H12
CH≡CCH2CH2CH2CH2CH3
1⎼Heptyne
C8H14
CH≡CCH2CH2CH2CH2CH2CH3
1⎼Octyne
C9H16
CH≡CCH2CH2CH2CH2CH2CH2CH3
1⎼Nonyne
C10H18
CH≡CCH2CH2CH2CH2CH2CH2CH2CH3
1⎼Decyne
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Chemistry for Level XI of Senior High School
1) Straight Chain Alkynes
Number where the triple bond located⎼main chain
Step:
- Determine the longest straight chain as the main chain
- Assign the numbering and set C≡C at the lowest number
Example:
a) CH3⎼CH≡CH⎼CH3 ➔ C=C located at C number 2 and there are
4 C atom as the longest chain ➔ 2⎼butyne
b) CH3⎼CH2⎼CH≡CH⎼CH3 ➔ C=C located at C number 2 and there
are 5 C atom as the longest chain ➔ 2⎼pentyne
2) Branched Chain Alkynes
Number of alkyl-alkyl-number of triple bond-main chain
STEPS
- Determine the longest chain as the main chain,
- Assign numbers in the main chain, start from C≡C bond as the
lowest number.
- The branches are alkyl groups and named alkyl according to
the C atom in the branches
- Other rules follow the nomenclature of alkanes.
Main Chain (longest):
4 C atom ➔ butyne
C≡C at C number 1
Alkyl:
CH3 ➔ Methyl
Located at C number 2
Name: 2-methyl-1-butyne
-
If there are more than one C≡C bond, then the suffix ‘yne’
replaced by ‘-diyne’, ‘-triyne’ and so on based on the number
of C≡C.
c. Properties of Alkynes
1) Physical Properties
a) Insoluble in water
b) Soluble in organic solvent
c) Less dense than water
d) Boiling point increase along with the increasing or Mr
e) Have higher boiling point than alkenes
f) They are very nearly the same as the boiling points of alkanes
or alkenes with the same carbon skeleton
g) Up to four carbons, gas at room temperature
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Chemistry for Level XI of Senior High School
2) Chemical Properties
a) Halogenation Reaction
The reaction takes place in 2 stages because of the C≡C bond.
The first stage occurs to break the triple bond into double
bond and the next stage happen to break the double bond into
single bond. In short, this reaction will breaks triple bond
into single bond.
Figure 1.11 Alkynes halogenation reaction
b) Hydrohalogenation Reaction
This reaction happened when alkynes react with hydrogen
halide (HX) and also takes 2 steps.
Figure 1.12 Alkynes hydrohalogenation reaction
c) Hydrogenation Reaction
Reaction between alkynes and hydrogen to produces alkane.
This reaction takes 2 steps, first step of the reaction will break
alkynes into alkane then for the second step it will form alkane.
Figure 1.13 Alkynes hydrogenation reaction
d) Hydration Reaction
This reaction occurs between alkynes and water (H2O) and it
will produce ketone as a result.
Figure 1.14 Alkyne hydration reaction
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Chemistry for Level XI of Senior High School
SELF EXERCISE!
1. Give the name of the structure below!
a.
b.
c.
2. Draw the structure of hydrocarbons compound below!
a. 4-ethyl-2,4-dimethyloctane
b. 4,4-diethyl-2,5-dimethyl-2-hexene
c. 5-ethyl-2,2-dimethyl-3-heptyne
3. Complete the reaction below!
a. C3H8 + O2 ➔
b. C2H6 + Cl2 ➔
c. CH2=CH–CH2–CH3 + Cl2 ➔
d. CH2=CH–CH2–CH3 + HCl ➔
e. CH≡C–CH2–CH3 + 2 H2 ➔
C. Isomerism
1) Definition of Isomerism
Isomerism defined as the occurrence of 2 or more compounds that have
the same chemical formula, in different structure (how atoms are bonded)
or configuration (the spatial arrangement of atoms).
The types of isomerism in hydrocarbons are structural isomerism
(position isomerism and chain isomerism) and strereo isomerism
(geometric isomerism).
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Chemistry for Level XI of Senior High School
2) The Classification of Isomerism
Chain Isomerism
Structural
Isomerism
Position
Isomerism
Isomerism
Strereo
Isomerism
Geometric
Isomerism
a) Chain Isomerism
In chain isomerism, isomerism have the same chemical formula but
different carbon chain/skeleton. This type of isomerism is found in
alkanes, alkenes, and alkynes.
Example:
b) Position Isomerism
In Position isomerism, isomerismhave the same functional groups, but
in different position. Position isomerism can be found in compounds
of functional groups. The functional groups in hydrocarbons are
multiple bonds of C=C or C≡C and branches. This type of isomerism is
found in an alkenes and alkynes.
Example:
c) Geometric Isomerism
Geometric isomersm is formed due to the absence of free rotation in
the bond. In the other words, geometric isomerism happened because
of the arrangement/geometry of atomsin the C=C bonds. This types of
isomerism only found in alkenes.
- If the same groups are on the same side of the double bond, it is cis
arrangement.
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Chemistry for Level XI of Senior High School
- If the same groups are on the different side of the double bond, it is
trans arrangement.
DID YOU KNOW?
PETROLEUM REFINING
Petroleum is one of the types of hydrocarbon which we can find
in our daily life. Petroleum is a complex mixture of organic liquids called
crude oil and natural gas, which occurs naturally in the ground and was
formed millions of years ago.
As crude oil comes from the well it contains a mixture of
hydrocarbon compounds and relatively small quantities of the
materials such as oxygen, nitrogen, sulphur, salt and water. In the
refinery, most of these non-hydrocarbon substances are removed and
the oil is broken down into its various components, and blended into
useful product.
In order to obtain the final product, some of the fractions are
passed through conversion process, removing impurities, and blending.
All of thes mechanism called Fractional Distilation with certain range of
boiling point.
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Chemistry for Level XI of Senior High School
CHAPTER ASSESSEMENT
A. MULTIPLE CHOICE
1. Carbon atoms possess characteristics, the exact statement regarding the
characteristic of carbon atoms is.....
a. Carbon has 4 valence electrons that are able to form covalent bonds with
carbon atoms and other atoms
b. Carbon has a relatively large size so that it is able to bind all elements
c. Carbon has 6 valence electrons so it can bind 6 other atoms
d. Carbon can be made by humans
e. Carbon can form ionic bonds from its four outermost electrons
2. Look at an alkane structure below!
Tertiary carbon atom shown by number … .
a. (1)
b. (2)
c. (3)
d. (4)
e. (5)
3. Given the list of hydrocarbons compound:
1) C4H8
2) C4H10
3) C6H12
4) C5H8
5) C5H12
Compound that came from the same type of hydrocarbon shown by number
….
a. (1) and (2)
b. (2) and (3)
c. (3) and (4)
d. (1) and (5)
e. (2) and (5)
4. The correct name for these structure is …. .
a. 2-methyl-3-ethylpentane
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Chemistry for Level XI of Senior High School
b. 2-ethyl-2-methylpentane
c. Isopropylpentane
d. 3-ethyl-2-methylpentane
e. 3-ethyl-4-methylpentane
5. The name of CH3CH(CH3)C(CH3)2CH2CH3 is … .
a. 2,2-dimethylpentane
b. 2,2,3-trimethylpentane
c. 2,3,3-trimethylpentane
d. 1,1,1,2-tetramethylbuatne
e. Isopentane
6. Look at the picture!
The correct name for the structure is … .
a. 2,5-dimethyl-5-ethyl-2-pentene
b. 2-methyl-5-ethyl-2-hexene
c. 2-ethyl-4-methyl-2-hexene
d. 4-ethyl-2-methyl-2-hexene
e. 2,5-dimethyl-2-heptene
7. The correct structure of 3-ethyl-1-pentyne is … .
a.
b.
c.
d.
e.
8. Look at the reaction below!
The name of the reaction is … .
a. Condentation
b. Elimination
c. Oxidation
d. Addition
e. Substitution
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Chemistry for Level XI of Senior High School
9. Given the reaction:
The types of the reaction repectively are … .
a. Addition, substitution, and elimination
b. Substitution, addition, and elimination
c. Addition, elimination, and substitution
d. Substitution, elimination, and addition
e. Elimination, substitution, and addition
10. Hydrocarbons compound below that has the highest boiling point is … .
a. CH3CH2CH3
b. CH3CH2CH2CH3
c. CH3CH(CH3)CH3
d. CH3CH(CH3)CH2CH3
e. CH3CH2CH2CH2CH3
B. ESSAY
1. Draw the structure of the following alkanes
a. 3-ethyl-2-methylpentane
b. 1,3-dibromopropane
c. 5-ethyl-2-methylheptane
2. Draw the structure of the following alkenes
a. 2-ethyl-1-butene
b. 3-propyl-1-heptene
c. 1,3-dichloro-2-butene
3. Draw the structure of the follow alkynes
a. 3-methyl-1-butyne
b. 2,5-dimethyl-3-hexyne
c. 4-chloro-2-pentyne
4. Give the name of the following structures!
a. Alkynes
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Chemistry for Level XI of Senior High School
b. Alkenes
c. Alkane
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