ORGANIC CHEMISTRY 1

CONCEPT OF ALKANE

UNIVERSITY OF SUMAIT
CHUKWA
 ABDULRAHMAN AL-SUMAIT UNIVERSITY
BACHELOR OF SCIENCE WITH EDUCATION
DEPARTMENT OF SCIENCE, FIRST YEAR, FIRST SEMESTER
2019/2020

COURSE TITTLE: ORGANIC CHEMISTRY 1

COURSE CODE: CH 112
COURSE INSTRUCTOR: MR SAIM
TYPE OF ASSIGNMENT: GROUP NO.1 WORK
PARTICIPANTS
NAME REG.

1 ALI ISSA OTHMAN 19/PC/016

2 MARYAM KHAMIS MZEE 19/BC/056
3 MARYAM BAKARI RAMADHAN 19/BC/039
4 NARGIS SUEIMAN MKANGA 19/BG/014

TOPIC: THE CONCEPT OF ALKANE

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CONTENTS
CONCEPT OF ALKANE.......................................................................................3
PREPARATION OF ALKANE(They have four preparation of alkane) .........3
1. FROM UNSATURATED HYDROCARBONS:.........................................3
2. FROM ALKYL HALIDE.............................................................................4
i. Alkyl halides (except fluorides) on reduction with zinc and dilute
hydrochloric acid give alkanes............................................................................4
ii. Wurtz reaction...........................................................................................4
3. HYDROLYSIS OF GRIDNARD REAGENT.............................................4
4. FROM CARBOXYLIC ACIDS....................................................................5
NOMENCLATURE OF ALKANE (Six step of naming alkane)........................5
i. Identify the longest chain (parental name):......................................................5
ii. Identify the substituents group.........................................................................5
iii. Identify the position of the substituents group..............................................6
iv. Use the prefixes di, tri, etc.:..........................................................................6
v. Alphabetical arrangement of prefix:................................................................6
vi. Naming the complex alkyl substituent:.........................................................6
PHYSICAL PROPERTIES OF ALKANES (Four physical properties)...........7
i. Physical State...................................................................................................7
ii. Density.............................................................................................................7
iii. Solubility.......................................................................................................7
iv. Boiling Point and Malting Point...................................................................7
GENERAL CHEMICAL PROPERTIES OF ALKANE (Eight chemical
properties of alkane)................................................................................................7
1. HALOGENATION:.......................................................................................8
a. With Fluorine.............................................................................................8

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 b. With Chlorine............................................................................................8
c. In the presence of diffused sunlight, heat or halogen carrier’s..................8
d. With Iodine................................................................................................9
Mechanism of halogenation....................................................................................9
a. Chain initiation step.........................................................................................9
b. Chain propagation step.....................................................................................9
c. Chain termination step.....................................................................................9
1. NITRATION:...............................................................................................10
2. SULPHONATION:......................................................................................10
3. OXIDATION REACTION:........................................................................11
i. Combustion..............................................................................................11
ii. Slow combustion.....................................................................................11
iii. Controlled oxidation or by catalyst..........................................................11
4. THERMAL DECOMPOSITION (OR HYDROLYSIS)..........................12
5. ISOMERIZATION......................................................................................12
6. AROMATIZATION:...................................................................................13
7. REACTION WITH STEAM:.....................................................................13
USES OF ALKANES:...........................................................................................13

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CONCEPT OF ALKANE.
Alkane is the saturated hydrocarbon which consist carbon-carbon single bond. It
has tetrahedral structure and can be described in terms of carbon atom using sp 3
hybrid set of orbitals to bond four. It general formula is C nH2n+2 where, n is integer
starting to 1,2,3,4, …
Examples
When n=1 when n=2 when n=3
C1H (2×1+2) C2H (2×2+2) C3H (2×3+2)
CH4 C2H6 C3H8

PREPARATION OF ALKANE
Alkane can be prepared in the four ways. The following:
 From hydrogenation of unsaturated hydrocarbon such as alkene and
alkyne
 From alkyl halide
 From carboxylic acid
 From reduction of carbonyl compound
1. FROM UNSATURATED HYDROCARBONS:
Dihydrogen gas adds to alkenes and alkynes in the presence of finely
divided catalysts like platinum, palladium or nickel to form alkanes. This
process is called hydrogenation. These metals adsorb dihydrogen gas on
their surfaces and activate the hydrogen – hydrogen bond. Platinum and
palladium catalyze the reaction at room temperature but relatively higher
temperature and pressure are required with nickel catalysts.
For alkene
C H 2=C H 2+ H 2 Pt ∖ Pd ∖∋ ¿ C H 3−C H 3 ¿
→

C H 3 CH =C H 2 + H 2 Pt ∖ Pd ∖∋ ¿ C H 3−C H 2 C H 3 ¿
→

For alkyne
1
CH ≡ CH + H 2 Pt ∖ Pd ∖∋ ¿ C H 3−C H 3 ¿
→

C H 3 C ≡CH + H 2 Pt ∖ Pd ∖∋¿ C H 3−C H 3 ¿

→

2. FROM ALKYL HALIDE

Alkyl halide can be converted into alkane by the following method:
i. ALKYL HALIDES (EXCEPT FLUORIDES) ON REDUCTION WITH ZINC AND
DILUTE HYDROCHLORIC ACID GIVE ALKANES.

C H 3−Cl+ H 2 Zn , H + ¿ C H 4 + HCl ¿
→

C H 3 C H 2 C H 2−Cl+ H 2 Zn , H +¿ C H 4 + HCl ¿
→

ii. WURTZ REACTION: is the organic reaction between haloakane and sodium
under presence of dry ether to form alkane. Alkyl halides on treatment with
sodium metal in dry ethereal (free from moisture) solution give higher
alkanes. Wurtz reaction is used for the preparation of higher alkanes
containing even number of carbon atoms.

C H 3 Br +2 Nadry ether C H 3 C H 3+ 2 NaBr

→

C H 3 C H 2 C H 2 Br+2 Na dry ether C H 3 C H 2 C H 2 C H 2 C H 2 C H 3 +2 NaBr

→

3. HYDROLYSIS OF GRIDNARD REAGENT

Grignard reagents are organic compounds with general formula of
RMgX (alkyl magnesium halide) where R represents any group of
hydrocarbon and X is halogen. It is prepared by mixing haloakane and
magnesium under presence of dry ether.
D ry e th e r
RX + Mg RMgX
If X is iodine, the Grignard reagent becomes most reactive and therefore alkyl or
aryl magnesium iodide is the most preferred Grignard reagent.
Generally;
RMgX + H2O 5RH+ Mg(OH)X
For example,
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 CH3CH2MgI + H2O CH3CH3 + Mg(OH)I
Grignard reagent always undergo double decomposition with water or with other
compounds having active hydrogen (the hydrogen attached on O, N, F or triple
bonded carbon atom are known as active hydrogen) to give alkane.
For example;
CH3CH2MgI + NH3 CH3CH3 + Mg(NH2)I
4. FROM CARBOXYLIC ACIDS
Sodium salts of carboxylic acids on heating with soda lime (mixture of sodium
hydroxide and calcium oxide) give alkanes containing one carbon atom less than
the carboxylic acid. This process of elimination of carbon dioxide from a
carboxylic acid is known as decarboxylation.

RCOONa + NaOH Soda¿ →¿ RH + Na2CO3

CH3CH2COONa + NaOH Soda¿ ¿ CH3CH3 + Na2CO3

→

NOMENCLATURE OF ALKANE
Is the system of naming organic compound following IUPAC system, IUPAC
means International Union of Pure and Applied Chemistry?
THE RULES OF NOMENCLATURE FOR ALKANE
The rule used to name alkane and their derivatives are the follow:
i. IDENTIFY THE LONGEST CHAIN (PARENTAL NAME): the
longest chain is the series of organic compound which contain the larger
number of carbon.
H3C 2 5 CH3
1 6
3 4

5 6

CH3
7

The longest chain contains seven carbon atom, and this compound is named as a
heptane.
ii. IDENTIFY THE SUBSTITUENTS GROUP: when alkane group
appear as a substituent, they are named by dropping the -ane and adding
3
 -yl. For example, -CH3 is obtained by removing a hydrogen from
methane and is called methyl. And halogen remove -ene add -o example
iodine named Iodo.
iii. IDENTIFY THE POSITION OF THE SUBSTITUENTS GROUP:
the position of substituent is number of carbon in the parental chain in
which substituent is attached and then numbering is stated from that end
will give less numerical value of the substituent group position. Also,
note that hyphen is written between the number and substituent name.
Substituent group at carbon number four known as ethyl group.
iv. USE THE PREFIXES DI, TRI, ETC.: if the compound contains more
than one similar alkyl groups, their positions is indicated separately by
comma and the name of substituent is not repeated but an approximate
numerical prefix di, tri is attached to the name of carbon.

CH3
H3C 2
1
3 4

H3C 5 6

H3C CH3
7

2,3,5-trimethylhexane
v. ALPHABETICAL ARRANGEMENT OF PREFIX: if are different
substituent group present in the compound, their named are written in the
alphabetical order. Di, tri not considered for the alphabetical order.

vi. NAMING THE COMPLEX ALKYL SUBSTITUENT: if the alkyl

substituent is father more branched, it is named as substituent alkyl
group. It proposes, the carbon atom group separated numbered in such a
way that carbon atom directly attached to the parent chain is given
number. Also the prefix/name of such substituent is enclosed in brackets.

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 CH3
CH3 Cl H3C 8
9
H3C 2 5 CH3 7 6 CH3
1 6
3 4
H3C 5 4 H3C CH3
Cl 5 6
3 2
CH3 CH3
7
1
3-chloro-4-(1-chloroethyl)-2-methylheptane 2,2,7-trimethyl-4-(propan-2-yl)nonane

PHYSICAL PROPERTIES OF ALKANES

i. PHYSICAL STATE: the first four members are in gaseous form, the next
four members are existing in a liquid form and the remaining in solid form.
ii. DENSITY: their density increases with increasing of the number carbon due
to increases the molecular weight of alkane.
iii. SOLUBILITY: alkane is non-polar molecule, so that they tend to dissolve
in a non-polar solvent such as benzene and toluene. But not dissolve in
water.
iv. BOILING POINT AND MALTING POINT: the branched isomer has
lower boiling point compared to the unbranched isomer of the same number
of carbon due to smaller surface area of the molecules with the result weak
intermolecular force of attraction and poor package of atom in a more
branched chain. The aim which is more branched has minimum area because
it is more spherical in shape, also boiling and melting point increases with
the increasing of number of carbon
Example: arrange the following compounds according to the increase in the
boiling points.
H3C CH3 H3C
H3C
CH3 H3C H3C H3C
H3C CH3
CH3
H3C CH3 CH3
H3C
CH3

A B C D E F
Answer
A˂D˂E˂G˂B˂C˂F

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GENERAL CHEMICAL PROPERTIES OF ALKANE
Under ordinary condition alkane do not react with many reagent this is because
i. They any reactive functional group
ii. C-Candy C-H sigma bond are strong and required large amount of
energy to break.
iii. C-C and C-H bond are essentially non polar and hence electrophilic or
nucleophilic substitution reactions do not take place
Substitution Reaction: Is the type in which one or more hydrogen atoms of alkane
molecule are replaced by an equal number of atoms or groups. Lower alkanes do
not undergo nitration and sulphonation reactions. The product so formed are
termed as substitution products
1. HALOGENATION:
Halogenation takes place either at higher temperature (573-773 K) or in the
presence of diffused sunlight or ultraviolet light.
R−H+ X 2 ∆ R− X+ HX
→

 It is found that the rate of reaction of alkanes with halogens is

F2 > Cl2 > Br2 > I2.
 Rate of replacement of hydrogens of alkanes is:
3° > 2° > 1°
The effect of halogen on the process of halogenation of alkanes
a. WITH FLUORINE: Fluorine react with alkanes violently and yield
hydrogenfloride and carbon .example
CH4+2F2→C+4HF

b. WITH CHLORINE: Chlorine in the presence of bright sun light reacts

with alkanes
→
C H 4 + 2Cl 2 bright light C +4 HCl
c. IN THE PRESENCE OF DIFFUSED SUNLIGHT, HEAT OR HALOGEN
CARRIER’S chlorine react with alkaline to given -chloro derivatives of
alkane.

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 C H 4 + Cl2 hv C H 3 Cl+ HCl
→
C H 3 Cl+Cl 2 hv C H 2 Cl+ HCl
→
C H 2 Cl2 +Cl 2 hv CH Cl 3+ HC
→
CH Cl 3 +Cl2 hv C Cl4 + HCl
→

d. WITH IODINE: Iodination is very slow and a reversible reaction. It can

be carried out in the presence of oxidizing agents like HIO3 or HNO3.
CH4+I2 CH3I+HI
5HI + HIO3 → 3I2 + 3H2O

MECHANISM OF HALOGENATION
a. CHAIN INITIATION STEP: The reaction is initiated by hemolysis of
chlorine molecule in the presence of light or heat. The Cl–Cl bond is
weaker than the C–C and C–H bond and hence, is easiest to break.
Cl−Cl hv 2 Ċl
→

b. CHAIN PROPAGATION STEP: Chlorine free radical attacks the

methane molecule and takes the reaction in the forward direction by
breaking the C-H bond to generate methyl free radical with the formation
of H-Cl.
H 3 C−H + Ċl hv C Ḣ 3+ HCl
→

The methyl radical thus obtained attacks the second molecule of chlorine
to form CH3 – Cl with the liberation of another chlorine free radical by
hemolysis of chlorine molecule.
Ċ H 3 +Cl−Cl hv C H 3−Cl + Ċl
→

C H 3−Cl+ Ċl hv Ċ H 2 + HCl

→

Ċ H 2 +Cl−Cl hv C H 2 Cl 2 + Ċl
→

C H 2 Cl2 + Ċl hv Ċ H Cl2 + Ċl

→

Ċ H Cl2 +Cl−Cl hv CH Cl 3 + Ċl

→

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 CH −Cl 3+ Ċl hv Ċ C l 3+ HCl
→

Ċ Cl 3+ Cl−Cl hv C Cl4 + Ċl

→

c. CHAIN TERMINATION STEP: the above mentioned chain reaction

do not continuous indefinitely. The chain come to an end either the free
radical gets deactivated or combine with each other to form a stable
molecule. The possible chain terminating steps are
i. Ċl+ Ċl →Cl−Cl
ii. Ċ H 3 + Ċl → C H 3 Cl
iii. Ċ H 3 + Ċ H 3 →C H 3 C H 3
Though in (ii), CH3 – Cl, the one of the products is formed but free radicals are
consumed and the chain is terminated. The above mechanism helps us to
understand the reason for the formation of ethane as a byproduct during
chlorination of methane.
1. NITRATION:
Under suitable condition give nitro alkane (-NO2) replace the H-atom in the
alkane molecule.
R−H+ HN O 3 ∆ R−N O 2+ H 2 O
→

Higher member is nitrated by heating concentration nitric acid and lower member
molecules are attached only by nitric acid vapor at higher temperature (150-475)
℃
C H 3 C H 2 C H 3+Conc HN O 3 420℃ C H 3 C H 2 C H 2 N O 2+ H 2 O
→

Mechanism (OH+-NO2-)

2. SULPHONATION:
Reaction with alkane even at elevated temperature but from hexane onward, react
with fuming sulphuric acid at high temperature to form alkane sulphuric acid.

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 R−H+ OHS O 3 H 400 ℃ R−S O 3 H + H 2 O
→
C H 3 C H 2 C H 3+OHS O 3 H 400 ℃ C H 3 C H 2 C H 2−S O 3 H + H 2 O
→

NOTE: sulphorication of n-alkane is show, but the brunched chain alkane

undergoes sulphorication readily the order is 3° > 2° > 1°
3. OXIDATION REACTION:
Include the following
i. COMBUSTION: Alkanes on heating in the presence of air or dioxygen are
completely oxidized to carbon dioxide and water with the evolution of large
amount of heat.
C H 4 +2O2 →C O2 + 2 H 2 O(l) ∆ c H θ=−1890 kJ mol−1
( g) (g ) ( g)

The general combustion equation for any alkane is:

3 n+1
C n H 2 n+ 2+2+ [ 2 ]
O 2 → nC O 2 + ( n+1 ) H 2 O

Due to the evolution of large amount of heat during combustion, alkanes are
used as fuels.
During incomplete combustion of alkanes with insufficient amount of air or
dioxygen, carbon black is formed which is used in the manufacture of ink, printer
ink, black pigments and as filters.
C H 4 (g )+ O 2(g) C(s) +2 H 2 O (l)

ii. SLOW COMBUSTION: lower alkanes such as methane and ethane +O2 at high
pressure and low temp undergo slow combustion yield alcohol, aldehyde,
acid finally C2O + H2O

→
C H 4 + O2 [O] C H 3 OH [O] [ CH ( OH )2 ]−H 2 O [ HCHO ][ O ] [ HCOOH ][ O ] C O2+ H 2 O
→ → → →

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iii. CONTROLLED OXIDATION OR BY CATALYST : Alkanes on heating with a
regulated supply of dioxygen or air at high pressure and in the presence of
suitable catalysts give a variety of oxidation products. Lower alkane on
oxidation in the presence of a catalyst give alcohols and aldehyde. Higher
alkanes give higher fatty acids

2 C H 4 +O 2 Cu ∕ 523 K ∕ 100 atm 2 C H 3 OH

→

C H 4 + O 2 HCHO+ H 2 O

C H 3 C H 3 +O2 ¿ ¿

NOTE: Ordinarily alkanes resist oxidation (KMnO4) but alkanes having tertiary H
atom can be oxidized to corresponding alcohols by potassium permanganate.

( C H 3 ) CH KMn O4 (C H 3)3 COH

→

4. THERMAL DECOMPOSITION (OR HYDROLYSIS)

Broken down of higher alkanes in to lower alkanes by heating is termed as
‘thermal decomposition’. Higher alkanes on heating to higher temperature
decompose into lower alkanes, alkenes etc. Such a decomposition reaction
into smaller fragments by the application of heat is called pyrolysis or
cracking.

C 6 H 14 ( 500−700 ) ℃ C6 H 12+ H 2
→

C 6 H 14 ( 500−700 ) ℃ C4 H 8 +C 2 H 6
→

C 6 H 14 ( 500−700 ) ℃ C3 H 6+ C2 H 4 +C H 4
→

This process is great in industrials importance.

5. ISOMERIZATION
The straight chain alkane on heating in the presence of Anhydrous
Aluminium chloride and hydrogen chloride gas isomerize to branched chain
alkanes.
C H 3 ( C H 2 )4 C H 3 Anhy AlC l 3 /HCl C H 3 ( C H 3 ) CH ( C H 2) 2 C H 3 +C H 3 C H 2 (C H 2 )CHC H 2 C H 3
→

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This reaction is Important in petroleum industries
6. AROMATIZATION:
Alkanes contains six or more carbon atoms when heated under the pressure
in presence of catalyst get cyclized to give aromatic compound
CH3 C r2O 3 o r M 2O 3

CH3 773K
1 0 -2 0 a t m

7. REACTION WITH STEAM:

Methane reacts with steam at 1273 K in the presence of nickel catalyst to
form carbon monoxide and dihydrogen. This method is used for industrial
preparation of dihydrogen gas.
C H 4 + H 2 O CO+3 H 2
USES OF ALKANES:
i. Lower alkane occur as natural gas and lighter petroleum fraction are
used as fuels
ii. Low boiling liquid alkanes e.g. hexane are used as solvents
iii. Heavy petroleum fractions are used as lubricants (grease) and for
obtain waxes and vaseline.
iv. The product of cracking process is generally used for producing
lower alkyl benzene used as row material for manufacturing
detergents.

REFERENCESITRY
Organic Chemistry Eight Edition by Francis A. Carey &Robert M. Giuliane
Organic Chemistry Fifth Edition by L.G. Wade Jr
Organic Chemistry by Ngaiza

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