1 Alkanes

Alkanes are saturated hydrocarbons because every carbon atom forms

four single covalent bonds with a hydrogen atom and no further bonds
can be added. Straight chain alkanes form a homologous series that
follows the general formula of CnH2n+2

Each carbon is sp3 hybridised and has an angle of 109.5˚, having a

tetrahedral shape.
2 Structure

c-
It H A It H H
I I I I I

c-
1
It -
C
-

C -
C - C -11
N
I I I I I 1

c- m
H It 't tl '+
H
H H H it A skeletal formula

11Cut
1
of othexane
c-c-
1 1
displayed formula displayed formula hexane
A- 't
of pentane

t H H It H

A It

|\H
structural formula

Hlc
CIA
CHZCHZCHZCHZCHZ , ,
qpentane

~
skeletal formula com
HYYCWH
It

F
|

-
y
M
of pentane
skeletal formula
It H
qcydohexane
displayed formula
ofcydohexane
3 Physical properties
All alkanes exhibit similar physical properties with gradation as we
move along the series to larger molecules. They are as follows:

1. Alkanes are non-polar in nature because carbon and hydrogen are

similar in their electronegativity and the C-H bond is almost
symmetrical.

2. As they are non-polar the only intermolecular force present is Van der
waal forces due to induced dipoles.
4 Physical properties
3. Being non-polar they do not dissolve in polar solvents, hence they
dissolve in, and form non polar solvents eg. Hexane.

4. The boiling point and melting point of molecules increases down the
series as there is increase in the number of electrons and thus stronger
van der waal forces.

5. Due to weak intermolecular forces, the molecules tend be volatile

and the initial few molecules are thus gases at rtp. With increasing
intermolecular forces down the series the state of the molecules shifts
to liquid and then solids at rtp.
 5 Physical properties
In summary, the melting and boiling points, density, and viscosity
increases, while volatility and vapour pressure decreases as we go
mistry
down the alkane series.
Number Physical state at
e Molecular of carbon Melting Boiling room temperature
a Alkane formula C nH2n+2 atoms point/K point/K and pressure
s– Methane* CH4 1 91 109 gas
Ethane C2H6 2 90 186 b.p. gas
increasing
Propane C3H8 3 83 231 gas
Butane C4H10 4 135 273 gas
Pentane C5H12 5 144 309 liquid
Hexane C6H14 6 178 342 liquid
*The naming of these compounds will be discussed shortly (page 334).
 boiling points of members of a recall from chapter 2 that the size of a non-polar molecule, such as an
homologous series. © IBO 2007 influences the strength of its intermolecular forces due to the increasin
van der Waals’ forces between the molecules. As the length of the mole

6 Physical properties
increases, melting and boiling points increase, viscosity and density in
and volatility and solubility in water decrease.

180

Note that increased boiling point 160

140

with increasing carbon atoms is only 120

100
true for unbranched molecules 80

60

40

boiling point (°C)

20

–20

–40

–60
Boiling points of organic compounds
–80

–100

–120

–140

–160

–180
0 1 2 3 4 5 6 7 8 9 10
number of carbon atoms
PRAC 11.1
 straight-chain isomer. The branching of a chain results in a more sp
to the molecule. This means there is less surface contact between m
7 Physicalstraight-chain
properties isomers, so these branched isomers will have weaker
hence lower boiling points (Figure 10.54).
In branched molecules, the boiling point and melting point decreases
with increased branching. This is because an unbranched molecule
packs more uniformly
a with other molecules, and hence has higher b
vander waal forces between them.

Elongated molecules have greater surface More oval or

area for attraction have less surfa

■ Figure 10.54 a Elongated straight-chain molecules will have greater surfac

lecular forces will evaporate less easily, and have higher boiling points. There are three factors
ontribute to the observed pattern for the different homologous series.
8 Physical properties
, volatility decreases and boiling point increases with increasing molecular size (chain
th). As we go up a series the chain length increases by the addition of a −CH2− unit. This
lts in a longer molecule, stronger London forces between the molecules and, therefore, an
Increased branching makes the molecule spherical
ease in the boiling point (see Figure 10.9). Thus, at room temperature, the early members and decreases it’s
series are generally gases or liquids, while the later members are more
surface area in space and the molecules pack less tightly with each likely to be solids.
ond, a branched isomer of a compound is likely to have a lower boiling point than its
other.
ght-chain isomer.The intermolecular
The branching forces
of a chain results are
in a more therefore
spherical weaker and the boiling
overall shape
he molecule. This means there is less surface contact between molecules other than for
and
ght-chain melting
isomers, so thesepoints are lower
branched isomers compared
will have to straight
weaker intermolecular forces andchain alkanes with
ce lower boiling points (Figure 10.54).
the same number of carbons.
b

Elongated molecules have greater surface More oval or spherical molecules

area for attraction have less surface area for attraction
9 Physical properties
The states at rtp also become more volatile with increased branching
due to weaker intermolecular forces.
 C containing carbon and hydr
show similarities to carbon, b
× × products,
If carbon
of
carbon
the C −compounds
dioxide
C bond compared are towan
10 Chemical propertiesFig 13.1 Electron
Table 13.1 Some sharing in methane
H average bond energies
H with oxygen
strength
conditions, of the exothermically
and C− H bond.
that meansA
Bond Bond energy /kJ mol–1 containing CH carbon4 (g) and
+ 2O hydr
2 (g)
If carbon compounds are to b
products, carbon dioxide an
Alkanes are generally considered
Fig
C—C 13.1 Electron
nonreactive
sharing in methane
346 as the C-H bond
conditions,
Now, is
although non
and that means
methane
with oxygen exothermically
is eni
Table
C=C 13.1 Some average bond energies
610 containing
products, itcarbon
does not and hydro
react w
polar and is thought of as a stable bond having –1a high bond energy.

products, carbon
CH dioxide
(g) + 2O and
Bond
≡
C C Bond energy
835 /kJ mol other words, it 4needs 2(g)
lightin
Table
C—C 13.1 Some average bond energies
346
with
methaneoxygenand exothermically,
oxygen has a hi
Si—Si 226 Now, although methane is en
the reactionCH will(g) proceed.
+ 2O So
2(g)
–1
==CSi
Bond
CSi Bond energy
318 610 /kJ mol
(estimated) products, it does 4 not react w
and hydrogen, is energetically
≡C
C—C
CS—S 346
835
272 other words, it needs
Now, although methane is en lightin
C=C
C—O
Si—Si 360
226
610
Compounds
methane and containing
oxygen
products, it does not react wi has silic
a h
relative
the to
reaction their
will combustion
proceed.
other words, it needs lighting So
C=
Si ≡C
Si—O Si 464
835
318 (estimated)
and hydrogen,
methane and is
oxygen energetically
has a hi
C—H
Si—Si
S—S 413
226
272 SiH 4(g) + 2O 2 (g)
the reaction will
Compounds proceed.silic
containing So
Si = Si
Si—H
C—O 318 (estimated)
318
360 Thishydrogen,
reaction is much more u
and is energetically
relative to their combustion
S—S
Si—O 272
464 methane, largely because of
C—O 360
Compounds
unlike methane, containing
silane
SiH4(g) + 2O2(g) silico
is no
C—H 413
relative
activation to energy
their combustion
of the abo
Si—O
Si—HKEY POINT 464
318 This reaction is much more
flame spontaneously
SiH (g) + in air.
2O (g) O
C—HOrganic compounds, though 413 methane, largely4 because 2 of
behave similarly, so silicon d
Si—H 318 unlike methane, silane is no
11 Chemical reactions
Generally the bonds being broken must be stronger than the new
bonds being formed, C-H bond being a strong bond, therefore, is not
broken as most resultant new bonds are not as strong. Alkanes,
however, do undergo three reactions as the resultant products have a
stronger bond than the bonds in alkanes. They are as follows:

1. Combustion 2. Cracking 3. Free radical substitution reaction

 displayed formula
ofcydohexane
12 Combustion
In air or oxygen, alkanes are completely oxidised to carbon dioxide and
Czltg
water, and the t 502 302
reaction is highly exothermic.
+
41+20

Czltg t 502 302 +

41+20
Czltg t 502 302 +
41+20
In a limited supply of air or oxygen, alkanes burn incompletely forming
highly toxic carbon monoxide, as well as carbon dioxide and water.

CZHS + 3.502 ->3CO + 4h20

CzH8
If the supply of air or + 202
oxygen is even more 3C + 4h20
restricted, the major
CZHS + 3.502 ->3CO + 4h20
products will
CZHSbe soot+ (carbon)
3.502 and ->3CO
water. + 4h20
CzH8 + 202 3C + 4h20
CzH8 + 202 3C + 4h20
13 Combustion
⇐ / tHz

methylwgdohexane

The greater the number of carbon atoms, the more energy produced
and the greater the amount of oxygen needed for complete
combustion. Hydrocarbons follow this general equation for their
complete combustion.

'

+24204 ) DHOI -890 KJMOT

CH4μ, t
202$) COqg,
KJMOTI
Czottkcyt 30.502cg, 2002$ +21429 BH= 13368
-

, ,
14 Combustion
In the following equation, ratio of moles of gas is the same as the
simplest ratio of their volume.

Catty
,g ,
+ (
n+% ) 02cg
, nC02(g, + 9124204 )

ZCO + ZNO ZCOZ + Nz

15 Pollution
Combustion of fuel in motor vehicles are generally the main source of air
pollutants. Engines that burn petrol or diesel fuels can pollute the air for
three main reasons:

• They do not burn the fuel completely

• The fuel contains impurities

• They run at such a high temperature that nitrogen and oxygen in the air
can react.

Carbo monoxide, oxides of nitrogen, and unburned hydrocarbons are the

main products of fuel combustion.
16 Pollution
Pollutant Problem

A toxic gas that combines strongly with haemoglobin, which

Carbon monoxide means that the blood can carry less oxygen. In low doses, this
can put a strain on the heart. In higher doses, it kills

Oxides of nitrogen: Reacts with moist air to make nitric acid in acid rain. Affects the
NO & NO2 lungs and can cause breathing problems

Unburned Some of the hydrocarbons, such as benzene, are carcinogenic.

hydrocarbons Others react with ozone to form harmful pollutants
17 Catalytic convertors
Catalytic converters are used to convert these harmful products into
Catty +
environmental
,g ,
(
n+% ) 02cg
friendly products.
, nC02(g
A catalyst is used got
,
+ 9124204
speed up )

reactions that do this.

The reactions convert oxides of nitrogen to nitrogen and oxygen,

carbon monoxide to carbon dioxide and unburned hydrocarbons to
carbon dioxide and steam.

ZCO + ZNO ZCOZ + Nz

NO Nz + Oz
18 Greenhouse effect
Most radiation from the sun reaching earth is reflected back into space
as infrared radiation.

Some of this infrared radiation is absorbed by molecules in the air

that warms up the atmosphere. The gases that do this are referred
to as greenhouse gases.
This phenomenon is normal and is responsible to keep earth warm
enough to sustain life by preventing it from becoming too cold.

atmosphere, about 30% is reflected into space, 20% is absorbed by gases in the
air and about 50% reaches the surface of the Earth.
19 Greenhouse effect
Visible and UV radiation from the Figure
Sun warms the surface of the Earth. Green

Some of the Sun’s

radiation is reflected.

The warm surface

of the Earth radiates
infrared radiation.
Greenhouse gases in the
atmosphere absorb some of the
outgoing infrared radiation.
20 Greenhouse effect due to greenhouse gases
One of the major greenhouse gas is CO2 which even the catalytic
convertor fails to break down into other safer products. Since
increased industrialisation and increased use of automobiles there
has been a marked increase in it’s production. This has disrupted the
existing natural balance resulting in more infrared radiation being
absorbed, causing global warming.

21 Distillation of crude oil

Crude oil is a natural resource which is a mixture of commercially useful
organic substances but is of no value in it’s original state. Useful
products are therefore obtained by fractionally distilling it.
22 Cracking
Hydrocarbons obtained from crude oil are usually large chain molecules
that are viscous in nature and are of little value commercially. However
they are available in abundance.

Shorter chain hydrocarbons are less viscous and more commercially

valued. However they’re relative scarce. This supply and demand gap
paves way for a process known as cracking.

Cracking is the decomposition of large chain alkanes into smaller more

useful alkanes and alkenes by using heat and pressure with or without a
catalyst.
 + C2H6 CzHg• t HBV

Bsi
23 Cracking
CzHg• + Brz CZHSBV +

The larger hydrocarbon molecules are fed into a steel chamber which
contains no oxygen, so combustion does not take place. The larger
Bf + Cuts CzHsB and are
hydrocarbon molecules are heated to a high temperature
passed over a catalyst.

When large alkane molecules are cracked they form smaller alkane and
alkene molecules. Possible examples of a cracking reaction are:

Goltz Cceltk + Cults

Ciottzz Czltg t Czltytcglho

24 Skill check
Explain what is meant by the term cracking.

Complete the equation to show the thermal cracking of decane

C10H22 ➞ C4Hx + ___ CyHx

25 Skill check
Butane is formed when hydrocarbon X is subjected to a cracking
process. One molecule of X produces a molecule of pent-1-ene, two
molecules of ethene and one molecule of butane.

Identify hydrocarbon X.

26 Homolytic and hetrolytic fission

There are two ways to spilt the shared paired of electrons in an
unsymmetrical covalent bond.

1. Equal splitting: this is known as homolytic fission and produces two

highly reactive radicals having unpaired electrons, without the
development of a charge. This makes it non-polar, and it thus reacts
with non-polar bonds.

2. Unequal splitting: this is known as heterolytic fission and produces

ions by giving e- to the more electronegative element making it the anion
and the other the cation.
 Reaction involves functional groups on both molecules
Initial step is often nucleophilic attack of one molecule on the other
27 Homolytic and heterolytic fission
Homolytic fission (homolysis) Heterolytic fission (heterolysis)
ing Is when a covalent bond breaks by splitting the shared Is when a covalent bond breaks with both the
pair of bonding electrons between the two products shared electrons going to one of the products
Produces two free radicals, each having an unpaired Produces two oppositely charged ions
electron
Depicting the movement of electrons
Uses a single-barbed arrow (fish-hook) to show the Uses a curly arrow to depict the movement of an
movement of a single electron electron pair

–
Cl Cl Cl + Cl HO C X
28 Free radical substitution
The term substitution in organic chemistry refers to a type of reaction in
which one atom or group of atoms is replaced by another atom or
group of atoms.

A free radical is a reactive species with an unpaired electron usually

formed due to homolysis.

A free radical substitution is the replacement of hydrogen atoms in a

molecule by halogen atoms in the presence of UV light. It is one of the
three reactions alkanes undergo.
 Cl Cl Clz
. •

29
CH ;
Free
Cl
radical
za
substitution
+
.
CH

Alkanes react with chlorine and bromine

dichloromethane to produce
Cl
halogenoalkanes
CHZCF in + HCI
.
t CHZCI
CHz•+ CH ; CH3cHz
the presence of UV light.
Hz t CHZCK U•
"
CHZCI +

Any or all of the

dichloromethane
hydrogen atoms in an alkane may be replaced
HCI
and the
Cl
trichloromemanl u• CHZCF
.
t CHZCI t CHIK
+
CHCIE + Ha
reaction can continue until allt ofCHZCI the hydrogenCHZCKatoms have been
Hz U•
"

Ckt CHAE + cl•

•

Clz 29 initiation CHCIG +

substituted by halogen atoms.
ne trichloromemanl
Cl t CHZCI
.
tutrachloro
u• CHZCF
t CHIK
Methane
+ HCI CP CHCIE
+ CHCIZ
+ Ha Caz• + HCI
a CH4 CHF HCI
.
+
}
+

propagation
CHF Ck
Hz CHZCI + Cf
t CHZCI
"
CktCHZCK
CHAE U•
Ckt cl•
cay
+ .
+ CHCIG cafe
+ + a

Cl Clz Ct
.

+
anl tutrachloro
u• CHIK
tMethane CP CHCIE CHCIZ Ha Caz• HCI
}
+ + +
CHI + Cl CHZA termination
.

CH ; CHCkt
; CHAE CktCHCIG cl•
cay
.
+ Chsatg cafe+ + a
30 Free radical substitution
Free radical substitution reaction has three stages:

Initiation: this step involves production of free radicals in the presence

of sunlight, the free radicals are produced by homolysis and are
responsible for the continuation of this reaction.

Propagation: here the free radical reacts with an alkane to form

halogenoalkane and another free radical. This is a chain reaction stage
which will continue to happen unless stopped at the termination stage.

Termination: when two free radicals react and form a final product and
no resultant free radical is formed.
31 Free radical substitution
Chemical bonds are usually strong and do not break easily. In order for
the bond to break, the new bond being formed must be stronger than
the bond being broken.

During initiation, out of all the possible bonds that can break, the
weakest/relatively least stable bond having a higher is broken as it
requires the least energy. In a mixture of alkane and halogen the
following bonds are present; C-C, C-H, X-X, where X represents a
halogen.
32 Initiation
The bond present between halogens is the weakest bond in a mixture
of alkanes and halogen as represented here via bond energies

C—H C—C Cl — Cl
410 350 242
Therefore, in such a mixture, chlorine undergoes homolysis to give Cl
free radicals.

'x¥u÷
:& : EEIY
 t.E.io
33 Propagation
Because the free radical has an unpaired electron, it acts as a highly
reactive species in an attempt to complete it’s outermost
city
+ shellHaby at ;
-> +

bonding with another atom.

t.CI
ANAIC
H H
I

it H a
The free radicals then attack the
- -

methane molecules abstracting H H

a hydrogen atom to form

Ci city -> HCI + CHZ
hydrogen chloride and a methyl +

CH3● free radical.

H H
 Ci + city -> HCI
34 Propagation

~~
H
Reaction with methane could occur in one of two ways. The could Cl●
a C .
H H - - -

bond with H atom in an exothermic reaction forming an H-Cl~ bond.

~~1
H I

Exothermic reaction suggests that the new bond formed is more Hstable .

a C H Cl
.
H H - - -
+
than the old one broken as it has less energy.
~ '
I C -
It =
413 KJMOT
H a KJMOH
It - =
431
'
C It 413 KJMOT
IF Cl● were to combine with the C atom instead, a C—H bond would be
-
=

It -
a 431 KJMOH
=
AH 413 =

broken for a C—Cl bond in an endothermic reaction.Ctl This suggests

338 KJMOHthat =

the new bond formed now has more energy than the original bond and
is less stable compared to it. Ctl 338 KJMOH
= AH 413 = -
 C It KJMOT
413 KJM
-
=

It a 431 KJMOH
AH =
413-431=-18
35 Propagation
- =

Therefore only the H-Cl bond is formed and a free radical is CH3●
Ctl 338 KJMOH = AH 413 338=+75 = -
KJM
generated. The CH3● free radical is equally as reactive as a chlorine
radical.

It is likely to react with the first molecule it collides with. If it collides with
a chlorine molecule, the following reaction occurs and a chlorine free

Eu
radical is regenerated. H H

# •u#a - A -

ta
.

I I

H It
'
CI -

Cl = 242 DH= 242-338=-96 KJMOT

C -

a = 338
 C a 338

36 Propagation
Thus in propagation, the reaction starts with a free radical and proceeds
to produce another free radical.

Q•+CH4 CHE +44

+42 a
.

CHZ -> CHI +

Therefore, it’s a chain reaction that will Cl + Cl

. •

Clz
continue to proceed until all the reactants
CH ; + Cl CH za
.

are used up, or two free radicals combine

together to form a molecule in termination
CHz•+
+ HCI
CH ; CH3cHz
step. Cltytclz CHZCI
37 Termination
This is the highly exothermic stage of the reaction which marks the end
of the free radical substitution reaction. When two highly reactive
species such as free radicals combine, they become stable by giving
off energy as heat.

Cl Cl Clz
. •

CH ; Cl CH za
.
+

CHz•+ CH ; CH3cHz
38 Overall reaction
Once the chain reaction has
•

stopped it would require another Cl2 Clz 29 initiation

to split to restart the reaction.

Overall, the alkane molecule has a CH4 CHF HCI

.
+
}
+

propagation
been chlorinated.
CHF + Ck CHZCI + Cf

Each step in free radical substitution Cl + Ct

.

Clz
is exothermic in nature. CHI + Cl CHZA } termination
.

CH ; + CH ; Chsatg
39 Chlorination of methane: energy changes
^
J

± ^ Note that this is a

¥ two-step reaction

~⇐Et*
'

#CltHC1
±¥e÷÷μI
PROGRESS
-
- .

OF Reaction
)
40 Further substitution
a CH4
.
+
CHF + HCI
} propagation
CHF + Ck CHZCI + Cf
The reaction doesn’t have to stop once chloromethane is formed. The
chlorine free radicals can
Cl also
+ Ct react
.
with
Clz chloromethane and substitute
the remaining hydrogens CHIin+ the
Cl molecule.

CHZA } termination
.

CH ; + CH ; Chsatg
As the reaction proceeds, the concentration of methane decreases and
chloromethane increases. The chlorine free radical is more likely to
react with chloromethane and form dichloromethane.

Ct CH 34 HCI CHZCI
•

+ +

CHZCI Clz CHZCIZ Cf

•
t +
41 Further substitution
Further substitution gives dichloromethane, trichloromethane and
eventually tetrachloromethane. A mixture is formed.
dichloromethane Cl CHZCF HCI
.
t CHZCI +

Hz t CHZCK U•
"
CHZCI +

trichloromemanl u• t CHIK CHCIE + Ha

Ckt CHAE CHCIG + cl•

tutrachloro Methane CP + CHCIZ Caz• + HCI

Ckt cay
.

cafe + a
 •

Clz 29 initiation

42 Various propagations during the same time

It’s important to note that all four a CH4 CHF HCI
.
+
}
+

propagation
CHF + Ck CHZCI Cf
of these reactions are
+

happening simultaneously.
dichloromethane Cl CHZCF HCI
.
t Cl CHZCI
+ Ct Clz
.
+

Eventually, one reactant will start CHI + Cl CHZACHZCK } termination

.

Hz t CHZCI U•
"
+
to decrease and one product CH ; + CH ; Chsatg
will increase, which will result in
trichloromemanl u• t CHIK CHCIE + Ha
one propagation reaction
Ckt CHAE CHCIG + cl•
happening more vigorously than
the others. Ct CH 34 HCI CHZCI
•

+ +

tutrachloro Methane CP + CHCIZ t Caz• + HCI

CHZCI Clz CHZCIZ Cf
•
+

Ckt cay
.

cafe + a
43 Termination products
The termination stage can also produce Utz .
t Cl .
→ Cltzcl

the same products that are being

CHS . +
City
.
→
CHzCHz
produced during propagation. Free radical
substitution reaction can therefore CHAI • t Cl .
→ CHzU2

produce a mixture of products. These are

CHAI • t Utz . → Utz CHA
the examples of the various products that
can be formed: CHIH t CUz• → CHZU Cuz

Clo t Cloe → U2

Cugat cuz → Crab

44 By-products
A set of by-products are chlorinated ethanes.

These arise from the ethane produced in termination undergoing a

similar set of substitution reactions, or chloromethyl radicals combining
at termination stages.
 Ck
H• Ci Ck free radicals removed
Cl•tCAz•
+
H• Ci CHI free radicals removed
45 Bromination of ethane
+
CHCl•tCAz•
; City +
Ck
CHI
Cttzatz
Cl•tCAz• CHI
CH ; City + Cttzatz
Bromine reacts CHwith
; ethane
+ City to
produce bromoethane,
Cttzatz C2H5Br. The
reaction is a free radical substitution reaction.

Initiation: Bromine splits byBvzcg

homolytic
) fission
-7 using
2Br° UV light.

Bvzcg ) -7 2Br°

Bvzcg ) -7 2Br°

Propagation: The
Bro Br• radical
C2H6 removes a hydrogen
+ CzHg• atom
t from ethane.

HBV
Bro + C2H6 CzHg• t HBV
Bro
CzHg•+ + Brz
C2H6 CZHSBVt
CzHg• + Bsi
HBV
CzHg• + Brz CZHSBV + Bsi
CzHg• + Brz CZHSBV + Bsi
Termination: Two radicals join to form a molecule.
Bf + Cuts CzHsB
Bf + Cuts CzHsB
Bf + Cuts CzHsB
 )I
46 Isomeric free radicals
H .

Alkanes having 3 or more carbons have the ability to form free radicals
involving different carbons. The resultant free radicals are isomers of
each other, which will result in in isomeric final products.
•

CH3CHzCHz t HCl
19
CHgCHzCHz t CI .

I.
.

CHZCH Utz t HH
47 Halogenation of higher alkanes
There are two monochloropropane isomers: 1-chloropropane,
CH3CH2CH2Cl, and 2-chloropropane, CH3CHClCH3.

When propane reacts with chlorine, a mixture of the two monochloro-

compounds is produced.

This is because the chlorine atom can abstract either one of the end-
carbon hydrogens or one of the middle-carbon hydrogens, the former
resulting in CH3CH2CH2Cl and the latter CH3CHClCH3.
CHZ CHZ CH3-CHz-CH2• H
•
a + CHZ -> + Cl
- -
-

C1• + CHZ -

CHZ
-

CHZ CHZ -
EH -

CH3 + H -