Introduction
°
°
°
:
names
halogen 0h11mn1s
wmponnd
general
where
colourless
lii )
immiscible
1
more
hydrogens
halo alkanes
,
are
replaced
with
halogen
atoms
:
properties
bit
polar
one
hullide
alkyl
.
liquid
and
molecules
as
heavier
the
l
-
than
halogen
water
to - ✗ bonds )
bond
are
polarised
due
to
the
difference
n
h
tf
c
8
-1
>
-
a
↳ greater ability
H
polarity
attract
decreases
from
bonding
L
-
F
to
elutions
to
c-
I
.
as
electronegativity
decreases
down
the
group
.
in
elertnnegativity
ot
cand
halogen
atoms
.
Ot
Uassitilhtion
°
depends
halogenoalkanes
the
on
number
of
R
-
R
y
Naming
begin
e.
it
C
-
C
1
I
H
end
akyl
I
nanites
the
g.
R
X
-
H
two
at
to
the
carbon
nearer
cus
I
to
groups
the
Br
1
lhzllllllzluzlnctlz
I
3
4
5
b
2- bromo
2
-
5-
methyl hexane
bonded
to
the
halogen
tertiary
'
R
I
l
-
bonded
secondary
primary
R
directly
groups
'
1
-
X
that
R
-
C
-
X
1
R
are
substituent
equally
whose
distant
name
''
from
comes
the
first
end
of
the
main
alphabetically
.
.
Preparations
of
halogen unlkanes
his
electrophilic
audition
wit
nucleophilic
substitution
viii )
free
UH
elertwphilic
radical
of
hydrogen
of
substitution
addition
alkanes
I
to
5042
an
1
akene
phosphorus
hallide
.
.
alkenes
hydro halogenation
halogenation
Yz
+
halogens
HX
with
11×1×2
of
1
with
alcohols
of
( Xz )
( MX )
hnllides
-1
HX
1-
H
X
.
✗
=
U
n
"
413
✗
Br
,
✗
H
×
a. Bv ,I
:
Markovnikov
wit
substitution
117
reflux
of
alcohol
alcohol
with
R
1-
-
products
on
HX
HX
R
>
-
X
HW
+
↑
nucleophile
(2)
warm
with
alcohol
thionyl
1500127
chloride
formation
of
union alkanes
steamy white
R
-
OH
>
5042
-1
R
U
-
+
502cg)
+
.
tunes
.
HUCG )
both son and 1101 can
mixture
escape leaving pure
of
(3)
heating
reation
for
R
of
alcohol
and
hnlogenoalkcsne
.
hotline
phosphorus
U2
-
oh
PUS
+
R
>
-
U
+
POU 3117
+
MU ly )
r
tou
Iz
I
phosphorus
Bvz
containing
product
1-
3rd
-
On
separating
+
PX }
phosphorus
>
3k
-
✗
containing
1-
1131703 ( l )
product
with
hnioalkane
>
fractional
distillation
.
Viii )
free
substitution
radical
ot
reaction
not
+
alkanes
favoured
a
til
gives
lii )
multiple
alkanes
ot
.
it
as
reaction
mixture
a
"
Bra
1
Uz
of
_
halogen alkanes
substitution
often
occurs
ltnvther halogenation )
distillation
fractional
X
+
×
-
is
-
of
-
used
to
wlibht
n
✗
=
different
the
separate
heat
/
,
-
Brin
¢
-
products
×
+
mechanism
initiation
BFT3v
>
-
Br
Br
+
-
propagation
n
n
I
n
c
-
n
I
-
l
i
v
-
n
-
>
n'it
n
-
'
iii. ↑
n
-
-
n - Bv
+
¥
BV
'
iii.
M
c
-
c
-
c- n
-
/
iii
>
I
.
I
n
n
-
H
y
'
n'
run
c
-
c
-
-
n
+
Bv
-
ÉiÉBv
termination
Bv ?
"
-
Bu
>
Bv
-
Bv
n
n
I
n
Br
.
~
i
-
1-
.
-
I
n
C
-
-
H
>
e
Br
I
I
n
-
e
u
-
-
↑
i
-
n
↑
-
n
c- → 1 -
I
n
-
c-
1
n
_
i
-
n
n
c- n
-
o
-
I
n
↑
↑
n
l
u
-
In
11
u
n
c- n
-
n
-
-
1
I
n
e
-
n
n
>
n
_
-
c- n
n
-
I
c
c
n
-
e
-
n
I
I
n
o
I
-
b
n
n
-
gn
n
n
.
-
×
tree radical
carbon
has
substitution
an
electron
,
"
not
PMS
charge
.
Physical
1-
boiling
in
INCREASES
°
0
size
of
°
U
halogen
stronger
→
no
branched
.
Ot
stronger
R
-
Bv
atom
area
,
branches
hnlogcnoalkanc
exposed
to
→
R
,
-
increases
forces
London
as
surface
-
elections
move
,
becomes
R
increases
carbons
increases
forces
from
DECREASES
°
2.
molecular size
london
of
number
as
INCREASES
°
hiii )
hhlogenoalknnes
points
°
wit
of
Properties
more
needed
energy
to
number
,
move
energy
of
electrons
needed
to
increases
overcome
uii )
soluble
isoluble
°
in
in
polar
organic
spherical
more
intermolecular
forces
,
are
short and
reduced
compact
.
solvents
water
,
BUT
cannot
form
the
increases
are
bonds
L
solubility
lil
the
overcome
hydrogen
bonds
with
water
molecules
.
.
bonus
Use
1-
hnlogenoalkanes
of
solvent
As
in
in
dry cleaning
tvilhlowethane
bin
removing
Freon -113
2-
Flame
°
in
grease
raw
alkane
+
a
material
halogen
atom
CFCs
l
lpolyuhlowlthene)
LLBVF]
due
to
,
ozone
five
ciii>
tire
extinguisher
.
plastic
windows
Tenon
/
electrical
,
-
used
in
cable
non
-
insulation
stick
extinguishers
depletion
Properties
wit
in
.
plastics
for
Lpoiytetvathuwethene >
refrigerants
banned
is )
?
tihmmhbility
venules
greatly
chlorofluorocarbons )
in
°
manufacture
to
PTFE
.
.
retardant
PVL
4
circuit
electronic
LLFUZLFU ?
bwmotvitnow methane
3-
and
engineering equipment
chemically
non
low
-
uses
inert
flammable
toxicity
n'v7
Odour less
cut
volatile
.
ui)
uii)
hiii )
refrigerants
frame
Leaning ttnids )
retardant
cleaning agent
in
in
extinguisher
eletwniie industries
pans
.
CFCs
◦
°
Ozone
vs
inertness
makes
diffuses
into
C- 01
a
637
persist
them
stratosphere
the
bonds
atmosphere
the
by
the
catalyse
for
long
periods
.
where
,
down
broken
are
radicals
free
in
Uv
light
breaking
up
( fwm
of
sun ]
ozone
to
form
chlorine
free
radicals
.
layer
>
protective
shield that
absorbs most
sun 's
of the
radiation
UV
.
mechanism
U)
step
1
CU
✓✓
zFz
U
y
t
-
CCI
-
note
Fz
-
V7
step
2
chlorine
:
reacts
with
+
U
>
.
chlorine
UO
excessive
hi >
crop
lii )
skin
-
exposure
radicals
03
t
to
40
light
.
Wz
+
4-
:
damage
>
viii )
Oz
regenerated
are
>
UV
+
.
cancer
cataracts
and
manufacturing
at
the
immune
chlorine
own
ozone
-
03
:
clouding
of
the lens
of
system
your eyes
.
tree
radicals
molecules
homogenous
.
catalyst
can
destroy
thousands
at
Action
1.
2.
3.
taken
banned
protect
to
/reduce
the
use
water
find
substitutes
G)
no
-
lii )
for
chlorine
HCFCS
NFES
electronic
in
industries
.
atoms
with
chlorine
shorter
Viii )
CFCs
CFCs
HFCS
lefts
less
of
layer
cleaning system
based
e. g.
use
03
life
Lhydw fluorocarbons ]
least
at
atoms
in
the
one
=
H
03
atom 7
depletion
atmosphere
,
↓
potential
destroyed
in
the
atmosphere
chyduotksouoethers )
fluorine
replaces
chlorine
,
compound
move
stable
as
c-
F
bonds
are
stronger
.
1.
Nucleophilic
hi>
lii )
substitution
hydrolysis
c- 0h7
viii) formation
nitrites
ot
formation
of
general equation
involves
vii )
halogen
hiii > carbon is
6-1
n' v7
carbon
rate
reaction
of
-
I
-
is
go#
of
more
✗
g.
C
-
+
:Nu
]
1
-
y
-
c
-
X
attracts
,
attacked
of
by
a
halo alkane
F
nucleophile
-
-
electrons
bonding
8-
,
with
.
different
c- ×
U
going
:
bonds
explanation
G)
L
:X
+
bonds
electronegative
I
-
Nu
,
elerhopnitiu
,
is
c- MHz
I
:
breaking
CX )
amine
primary
_
bi )
c- CN )
:
down
the
Vii ) bond length ↑
atomic size
group ,
bonding electrons
,
increases
further
twin
1
INCREASES
-
t
-
Bv
hiii )
thus less
UV )
bond
attracted
strength
↓
to
,
the
nucleus
bond
.
energy
↓
I
UV)
I
-
c-
I
I
v
lesser
energy
needed
to
break
C- ×
bonds
.
nucleus
G)
hydrolysis
longest
togas
CkkYqqB•qpa•mgggEs-ñ
otsaT-o.hr#gpm
,
↓
:
reagents
conditions
:
under
heat
nucleophile
:
product
:
1
NaOH
aqueous
aqueous
contains
=
water
KOH
aqueous
reflux
i. OH
alcohol
^
equation
shaped
tiny , unevenly
of substance
pieces
:
added
R
e.
-
X
OH
+
-
Y
R
-
OH
×
+
'-
>
Naoh
+
lHzlHz0U
+
Nau
heat
the
mixture
ionic
(Mzuzu
exception
↳
R
:
PTFE
-
with
G)
☐ burrs
more
reason
:
°
°
Viii ) equation
F
:
hydrolysis
vii )
On
+
>
-
not
does
UMJCMZOU
undergo
-
in
hydrolysis
poly tetrafluoroethylene
:
non
-
stick
c- F
as
pan
slowly
than
with
hot
NaOh
fully negative
HW
partial negative
material
Naoh
aqueous
charge
on
on
oxygen
-
is
.
+
HW
?
cuz
£13
chloro dimethyl ethane
-
c-
on
+
In]
1,1
-
KOH
[° " ]
11ft
in }
y
1
'
iii.
oxygen
:
c
bond
the
water
in}
oh }
-
U
+
reaction
without
evaporating utt the
volatile organic compound
:
eq
make
move
calmly without bump
g.
0h3mn
to
liquid boil
-
dimethyl ethanol
HU
11ft
reaction
very
flush
strong
.
.
.
Vii ) formation
°
nitrite
ot
substituted
halogen
with
ON
-
to
I alkanonitn.ie/aky1
nitrile
tovm
cyanide
solvent
↑
reagents
conditions
i
nucleophile
:
products
R
UNAMI
cyanide
sodium
reflux
under
T.CN
nitrite
:
equation
heat
/
cyanide
potassium
ethanol:c
:
:
X
-
>
KUN
1-
R
-
CIN
KX
+
↓
contains
one
more carbon
than
lM3Yl2M3
bromo
Uh}
KBV
+
I
CN
2-
-
LU3lhzU
2-
X
Ulslllz
>
KIN
+
Br
1-
-
:
example
1.
R
2- methyl propane nitrite
methyl ethane
KON
+
M3UHzUN
>
+
KU
propane nitrile
ionic
equation
bllzbhzll
:
IBN
t
>
that's why it
with
✗
-
is
bonded
,
.
Mt
↑
reduction
reflux
-
in
carboxylic acid
to
and
R
charged
negative
carbon is
nitrite
+
MzMzcN
/\
in
R
>
-
:
→
Lint 114
reducing agent
.
11
dry ether
c. IN
>
ethamiii
n
I
R
-
e
-
1
n
-
primary
n
amine
I
KCN
11
hydrolysis
avid
alkali
>
t
reagents
:
dilute nvsoa
dilute
reagents
:
!
H
.
-
o
-
Nhon
P,
,
114
R
n
aqueous
-
C
n
-
O
-
acidification
V
r.io
-
n
,
naan
-1
hiii ) formation of
°
:
overall
heat
:
nucleophile
c-
-
NHI
MHz
Nhs
in
pressure
under
container
semen
a
T.NU
:
R
:
product
ethanol it
excess
wnditions
with
substituted
halogen
reagent
amine
primary
Nuz
-
:
equation
R
( amines
-
X
+
)
>
21443
R
-
Nnz
Nha
+
×
Fth
UH
? ??
if
what
R
r
×
-
-
×
Nhs
+
+
is
H
in
-
R
not
+
in
NY }
excess
?
can
←
-
>
n
R
-
I
l
n
iyi
-
R
n
✗
+
R
'
-
n
-
N
-
>
n
iy
-
-
-
n
N
-
R
X
+
R
'
-
ii
1
R
-
R
"
R
I
>
'
R
-
nx
+
reaction
"
amine
n×
+
630 )
R
-
prevent
nucleophilic
*
l
n
R
to
( 20 )
. .
R
nucleophile
nx
+
further
substitution
,
'
'
I
as
11° )
R
"
-
act
*
'
n
R
ni
n
-
NH4X
>
'''
NÉR
"
+
✗
-
'
R
[ quaternary
ammonium
salt ]
stops
stage
at
primary
2-
Elimination
reagents
conditions
H
neat
:
products
i. 0h
/
base
and
X
equation
s
KOU
requires
→
proton acceptor
eliminated
much
higher temperature
nucleophilic substitution
.
from
carbon
adjacent
2
¢ ¢
+
-
-
4=4
>
NaOh call )
n
-
atoms
Max
+
U
Lsalt
iii. i
-
than
:
✗
'
reflux
or
are
-
'
1
alkenes
:
as
NaOh
ethanol iu
:
o
-
o
-
e
o
-
-
1h ↓nsBv
e
1
n
-
+
NaOH Lalu )
,
HW
+
water )
and
u
-
c
-
c
-
c
-
( = ,
_
u
n
c
-
-
c
-
5- l
LL 'm, 'n
thins
n
i
if
↑↑↑↑↑
>
can
show
-
l
-
n
'
'^
cis-trans
isomers
Nau
+
°
substituted
highly
move
e.
g.
,Bv
Guzman
alkene
product
elimination
uh ]
reaction
>
predominates cmajov product
lHzCh= Chul }
2- bromo butane
but
Lmajov
mechanism
on
why
1
-
as
base
-2
-
+
hw
]
M30HzlU=Mz
+
but
one
-
l
-
ene
product )
?
i. OH
I
n
n
i
allow for the
formation of ohonble
↑ ⑤✓→
u
-
elimination
bond
.
↑ ↑
Y=c
"
uhhh
Htcpwton
c
-
c
-
c
-
"
Br
"
>
n
-
-
o
-
'
'
n
n
n
+
no -11
+
:B
↑
accepts
)
3.
Nucleophilic
information
general
bit
requires
Vii ) i. Nu
"
a
with
reacts
Liv )
hence
W)
order
→
U' 7
lii )
,
by
size ↑
:
,
LR
-
✗ 7
substitutes
and
L
at the
polarised
are
reactivity
atomic
group
substrate
attacked
of
"
leaving
Viii ) hnlogenoalkanes
two
ISN )
mechanism
substitution
-
X
bond
SN
mechanism
a
mechanism
:
:
C
atom
,
CX )
is
to
get
product
.
LR
electrophilic
nucleophiles
R
bond
-
U
→
R
length
-
↑
Bv
,
→
bond
R
-
2
strength
major pathways
5N ,
halogen
tertiary
primary
haiogenoalkane
haioycnonllcane
.
↓
,
bond
energy ↓
,
easier
to
break
.
-
Nu )
rate
sNZ
G)
determining
bit
takes
his
inversion
place
both
→
rate
mechanism
particles
2
.
a
single
reacting
the
process
t.no
step
carbon
intermediates >
.
.
:
nucleophile
hnlogenoalkane and
after
by
concentration
of
in
involved
are
R
both
-
and
×
rate
the
determining
hiii )
vespertine
'
the
/
leaving group
hi) chlorine l
away
.
C- a
bona
broken
with
C- OH
partially
LV)
b- U
Wi )
chloride
Wii)
configuration
,
bond formed
partially
more
electronegative
> moves
biv )
bona
fully
ion
broken
departs
,
b-
OH
bond
formed
.
carbon
inverts
completely
.
carbon
the
of
wntiyurationot
Lthe
atom
hydrogen
atom 's
arrangement )
bonding
electrons
.
begins
order of
↳
↳
to
invert
reactivity
more
.
}
2nd order
inn
chlorine
to
step
:
6) backside attack
Unions
in
at
bimolecular
→
ot
involves
information
general
Viii )
step
reaction
akyl groups
akyl groups
shield
connected
reacting
to
the
carbon
reacting
carbon
from
incoming
,
slower
the
nucleophile
reaction
.
.
completely
.
rxn
hi>
Snl
reaction
information
general
in
distinct
2
Vii )
takes
viii )
steps
→
rate
ot
intermediate
carbocation
.
.
:
nalogenoalkane
only
→
process
formation of
a
halogenoalkane
tertiary
place in
unimoleuulav
involves
,
in
involve
only affected
reaction
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halogen alkane
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c
-
c
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formation
of
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carbocation
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