HALOALKENES ​& ​H​ALO ​ARENES ​GReplacement ​of

hydrogen ​atoms ​in ​a hydrocarbon aliphatic

(​ory ​aromatic ​by ​halogen ​atoms​, ​reits ​in ​formath ​of
alkyle ​hallide ​or ​areyl ​hallude​.
Haloalkynes ​contain ​halogen ​atoms attached ​to ​the
spo ​. ​hibridised ​carbon ​atom ​where ​as ​halo ​aren ​attached
to ​sp2 ​hibridised ​carbon a
​ tom​,

e ​classification ​of ​Halo ​ackenes ​& ​Haloarens​. ​1​)

On ​basis ​of ​no ​of halogen ​atoms ​: ​These ​may ​be
dassified ​as ​mono​, ​di​, ​tri ​ary ​poly ​halogen ​compound
• ​Poly ​halogen ​compound ​depend ​on whether ​they ​contain​,
​ f ​halogen ​atoms ​contain ​i ​i​n
one ​or ​two ​(​or ​more ​no o
t​h​e ​structur​e​.
Alt ​Eqë ​mo​no ​h​alo a​ lka​ne ​s​oy ​moushalma​nent
B ​C2HGA ​of c​ ompounds
containing ​sp3 ​hibridisation
• ​Allylic ​halides ​: ​These ​are ​the ​compounds ​in ​which ​the ​.​.​. ​Il
halogen ​atom ​is ​bonded ​to ​an ​sp3 hibridised ​hij ​drogen
carton ​next ​to ​carbon ​carbon ​double ​bound

• ​Benzyltic halides​. ​These a

​ re ​th​e
compoundsvaltached ​to ​ani ​Isp3 ​hibidization next ​to ​an
aromatic ring
cr ​2​:​.
 tad
.
as andma ​yor​'​s
React​?
when ​primary ​aromatic ​arene ​dissolved ​I
suspendended ​on ​il ​cold ​water ​cord ​aqueous ​mineral ​and ​is
treated ​a
with ​sodium ​nitrite ​a ​diagonium ​salt ​å ​formed ​mixing
soln ​of ​freshly ​prepared ​diagonium ​salt ​with ​I c​ upress
chloride ​bro ​bromide ​results in f​ ormation ​of
diagonium ​group ​by ​chloride ​cord
bromide
NaNoz​-​Her
O​rs​o
NA

C​HL​O

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N2 +​6X ​-
willa
Hel
+ ​N2
N

) ​s​w​artz ​React
T ​synthesis of ​alkyl ​flouride ​is ​best ​accomplished ​by ​heating
 an ​alkyl ​chloride ​Er bromide ​in ​presence ​of ​a m ​ etallic
Howrials ​such ​as A ​ gr​, ​Hg2Fz​, ​Cor ​e ​SB ​F3
R​-​*​* Aql ​.​.​. ​ngxVI​P ​CHg ​Br ​+ ​Agif ​- ​Ag ​Br
+ ​CH3E ​From ​alcohols ​: ​- ​CPreparation ​of
Haloalkenes​) ​R​-​OH ​THU ​znala ​Ratho ​R​-​OH​+
Na ​By ​+ ​H​, ​504 ​- ​R​-​BY ​+ ​NaHSO4 ​+ ​H2O
В ​он ​+ ​PX ​—​p​-​3 ​+H ​ ​Розм ROH ​+ ​polo
→ ​R​-​I ​& ​Pollz ​trilla
р-​он ​Сад ​P​[​+​» ​— ​-​х​+​н​, ​о ​co​, R​-​OH ​& ​Soll ​- ​Rice ​t ​o ​than
(​parzen​'​s ​) ​.

chile ​+ ​celat ​eta

from
hydrocarbons ​| ​1 ​from
alkanes ​a
- ​Chat​. ​U ​ho ​Fr​om
al​kenes​: ​-
et2​=​CH ​2 ​- ​le
CH2 ​= ​CH ​– ​CH2 ​H ​By
and

2
 CH2 ​- ​CH​, C
​ l ​+
HU
CH3 ​-​CH​-​CH2
​ ​14​.1
(​2 ​bromo​-​penten = ​ ​063 ​+ UBY
S

(​2​=​Cu​-​CH2 ​+
CLBY​.

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Electrophili
c
substitution ​reaction
:
. ​Cria ​a ​CH ​3
o ​l ​tela ​Anny​.
Alely
(​Toulene
)
1​2 ​t​o

Culla ​lhe
of ​N ​2
Z

Cubra
 mer
Z
N2
/
Sandmay
or​'​s
KI
· ​R​eactn
point​ ​s
IN

WAN​.

Halogen ​exchange
reacth
swart ​z ​Reaceno
:

CHEMICAL ​PROPERTIES ​- ​ALKLYL

HALLIDES​..
Nucleophilic ​substitution
Reacts ​& ​Elimination
Reaction ​& ​Reaction ​with
metals
& ​Reduction ​reactions ​1 ​©
 Friedal ​craft ​re​actions​.
lo ​Nucleophilic
substitution
i
SN​"​.
Doceur ​in ​2 ​- ​steps
I ​step ​Roxy
Rotxo
Rax ​TNO ​[​Nu ​-​--​R
Ne
-​-​-​-​x​] ​R ​+ ​x ​REINO
R-NU ​w ​YxTRX​)
sro ​[​Rx​] ​.
a​.​ox​[​Nuo ​i
Race ​mic ​mixture ​is ​formed ​i ​Inversion ​walden
67A) ​3°​/​2°​>​P​'s​ ​ctg ​i ​s ​CHg​? ​1​) ​> ​Ž​> ​A​>​B
n​ner
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a
as ​weak
Nucleophiles
Nucleophiles
prefer
prefe
 r ​SM ​reaction​! ​Polar
solvent ​prefer ​Sn​'
s
strong ​Nucleophiles
prefer
SN2 ​reaction​. ​Non ​idar ​Prefer ​sne
Eq​: ​Benzene​.
Eg​: ​Ho
&
Rearrangements
(​ie ​hidrides
are ​possible ​shift​"​.
Rearrangements ​are ​not
I
possibl
e
& ​Replacement ​by ​hydroxyl
group
• ​when ​alkyl ​hallides ​are ​made ​to ​react ​with ​boiling
aq son ​of ​NaOH ​Coro ​Koh ​corresponding ​alkchols ​are
produced
Rax tkoH ​R-​ ​OH ​+ ​KX
CGH ​BU ​+ ​KOH C​ HEON ​&
He ​*Replacement ​by ​Cyano group ​.
 • ​When ​alkyl ​halides ​are ​reacted with alcoholic​.
Pottasium ​| ​Cyanide ​corresponding a ​ lkyl ​nitrite ​are
produced
Rax ​+ ​KCN ​alichol ​RocN​'​T
kx
CHgd ​+ ​KCN ​- ​CH ​3 ​CN Tech

e ​Replacement ​by ​iso ​cyanide ​group

- ​Alleyl ​halides ​when ​treated ​with ​alcoholic ​silver
cyanide ​corresponding ​carbyl ​amine ​are ​formed
CN ​alwhol ​Rone​'​t ​Agx
R​-​X
​ ot​:
F​ag
.
.
e ​& ​Replacement ​by ​Nitrite ​group ​.. ​alohnic ​silver ​nitrite ​!
When ​alkyl ​halides ​are ​treated ​with ​walk ​Nitrite ​alky
nitrites ​are ​formed
R​-​x ​+ ​KNO​, ​Le​on ​R​-​O​-​N​-​O​+ ​Kx

alcoholi
c
silver
ton ​Replacement ​by Nitro
group
 When ​alkyl ​halides ​are ​treated ​with ​I
nitrite ​san ​nitro ​alkanes ​are ​formed
olie ​Ron​?
R​-​X ​+ ​Agno
Alcohol
ic
+ ​Aux ​!
o ​tag ​*

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-
-

-
-
-​-

R​ent
B​o​x
(​2 ​am​)
e ​Replacement ​by ​Alkoxy ​group ​- ​Williamson
Sy​nt​hesis
when ​halo ​alkanes ​are treated w​ ith ​alcoholic
sodium ​or ​Pottasium ​alkoxide ​eythers ​are ​formed
R​-​X ​+ ​NOOR​' ​alcohol ​R​-​o​-​r​' ​thay ​- ​CH2 C
​
+ ​NaO6​; ​He ​alcohol ​CH20​-​C​, ​H ​6 ​+ ​Nall ​&
Replacement ​by ​Amino ​group
when ​alkyl ​halides ​are ​heated ​with ​alcoholle
solution ​of ​Ammonia ​at ​100°c mixture ​of ​amines
are ​formed​. ​.​.. ​Rx​+
 NH3 ​-
CH​, ​> ​8 -​ ​ĐH​,​Cano ​cao​) ​r​in​z
R​-​NH​-​R ​- R-​NR ​» ​Replacement
by ​alky ​nyl ​group
When
sodium ​acetylide ​3 ​alkyl
halides ​are ​treated ​with ​higher ​alteynes ​fare f​ ormed​.
- ​Rax ​& ​Nac ​ECH ​R​-​CECH & Nax ​.
Replacement ​by ​Halides
' ​Alkyl ​chlorides ​are ​treated w
​ ith ​sodium ​/
Potassium ​bromide ​/ I​ odide ​corresponding ​alkyl
bromides ​& ​Iodides
are ​formed​.
Roll ​& ​Na Br ​I ​R​-​Brit ​Nall ​,
R​-​Ut ​ki ​M ​R​-​it ​kl​.
*​Replacement ​by ​carboxylate ​group
When ​alkyl ​halides a ​ re ​treated ​with ​alcoholic ​silver
carboxylate ​soin ​esters ​are ​formed
R​-​x ​+​. ​R​' ​Coong ​R ​coors ​+ ​Agx
A
 itin

and ​Elmination
Reactions​.​" ​4​> ​De ​hy​dro
halogenation
puring ​elmination ​Reacts ​t​' ​i ​preferentially ​removed
frons ​carbon ​containing ​less ​no ​of ​hydrogen ​& R ​ eaction
with metals
• ​Reaction ​with ​sodium ​- ​wurtz reaction ​:
1. ​R​-​x+ ​Na txor ​dry ​ther ​R​-​R ​T ​263 ​H​, ​4 ​+ ​ana
dry ​ether ​GH ​+ gnad

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• ​Reacts ​with ​magnesium
When ​alkyl ​halides a​ re ​treated ​with magnesium ​alkyl
imagnesium ​halide ​is ​formed which ​is ​known ​as
grighard ​reagent​. T
​ his ​upon ​protonation ​even ​in
 presence ​of ​weak ​acids ​produce ​alkanes​.
R​-​x ​+​Ma ​r ​-​Mg​-​x ​H ​RaH + Mg​(​OH​)​x
. ​Grignardh ​H2O​/​HC​/ ​CH2 ​100H ​- ​alkane ​React
with ​head ​Alkyl halid forms ​TELL ​Tetra ethyl ​lead) ​on ​react
with ​leado ​sodium ​alloy​. ​T​EL ​wa​s ​u​sed ​a​s ​an
an​tiknocking​, ​agent ​in ​petrol
'​4cy ​Hac ​+ ​+ ​Nas ​P​b​) ​+​(246​)​, ​Pb​+ ​4 ​Nall +​3
Pb

3​. ​Reduction
Reactions
Alkanes ​are ​formed ​when ​alleyl ​halides ​are ​reduced ​with
nascent ​hydrogen​. T ​ his ​naskent ​hydrogen ​can ​be
produced ​by ​zn ​& ​Hd ​for ​LEARHA ​(​or ​by ​catalytic
reduction ​in ​presence
of ​Nickle ​(​or​) ​Pd​: ​znthel
Rayt ​2 ​H​] ​LALHA
​ ​tHx ​. ​"​La
R​-H ​Nilpd​. ​.

to ​Friedal Craft ​Reacth

alkylation
| ​Alkyl ​halides ​when ​react ​with ​benzene ​in ​presence ​of
Canhydrous ​Allus ​l ​Fells ​Clouis ​acid​) ​as ​catalyst ​to ​form
alkyl ​benzene
- ​Roxt ​a ​an​. ​A143
 :

:
To ​FH

CHEMICAL ​PROPERTIES ​OF ​-

A​REY​'L ​HALIDES ​Nucleophille ​Realth
• ​Replacement ​by O​ H ​group ​- ​Dow​'s ​process ​to ​-
chloro ​benzene ​when ​heated ​with ​ag​.​soin ​Of ​NaOH
forms ​sodium ​phenoxide ​which ​when
probonated/​acidified
produce ​phena ​'a
​ s ​main
product
To ​+ ​Naot ​tho 3500
h ​300 a​ tm ​.
OH

+​*​+​☺
R​x​+ ​(​)
—
thx

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• ​Replacement ​by ​methoxy
group
 . ​When ​chlorobenzene ​is ​treated
​ t ​2002 ​anisol is ​formed
with a
sodium ​methoxide

-
ol ​Aniso​)
(​+ ​NaOCH2
200°c
1 ​CH2

• ​Replacement ​by A
​ mino
group
When ​chlorobenzene ​is ​heated ​under ​pressure ​with​:
aq​. ​son ​of ​ammonia
na ​in
in
presen
ce
presen
ce
of
of
cuprous ​oxide
anelene
cup
 ro ​is ​formed
a​roj ​+ ​2 ​NHą ​+​24​,​0 ​2​006> ​202 ​+ ​2 ​cull ​+ ​HjO
Willz
-
-​--
-​-
--

2​) ​Reaction ​wit ​metals

Fitig​'​s ​Reaction
- ​biphenyl ​Tox​?​Natxo
dry ​ethy ​oto ​tanax
1. ​Na
• ​Waltz ​F​o​l​i​g​'​s
Reaction
R​-​X ​Na ​to ​dry ​ether ​R ​J ​+ ​2Nax)
. ​Na ​Electrophilic
Substitutions​'​-
-​* ​tn
Friedal ​Craft ​Reaction
• ​FCR ​alkylation
fur

+
R
-
X

on
 o​l​e
Olt

Io​.​C​R
-
-
-

N​O​.

on​-​Нюз ​conc​.
H2SO4 ​Conc​ .
teses
1

O​S​O​OH
a ​choloroben ​zo ​sulphonic
a​ud​i
BH
Clz ​only
Alda
ORTE

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Reduction ​Chloro ​benzene i​ s ​reduced ​to ​benzene i​ n
presence ​of ​LALHE
♡ ​the ​li ​Alto ​thu

Pelyhalogen
compounds
Meth​elene ​chloride
CCH​C​12
• ​Chioroform (​CH3​)
• ​Todo ​form ​(​CHI​) ​o f​ reons ​-
chiotoroflouro ​Carbons ​(​LFCs​) ​1​. ​DDT
-​Dichloro ​brphenol ​Trichloro ​ethane ​1​.
Carbon ​Tetra ​Chloride ​(​Cela​)
a ​Methelene
Chloride
* ​Prepared b​y ​dir​ect ​c​hlor​ina​tion ​of ​m​ethane ​în p​ resence
of
sunlight​. ​This ​fellovas ​free ​radice ​substitution
mechanism ​* ​CHA ​ACL ​CH2a ​then ​* ​CHg ​i ta​, ​ho ​ch​.
22 ​til ​&
Methelene ​chloride ​is ​harmfull ​to ​CNs​. ​Exposure ​to ​even
lower
I ​levels ​may ​cause ​imparement ​in ​vision ​& ​hearing
Expsoure ​to ​higher ​levels c​ an ​cause dizziness​, ​nasia ​and
numbness ​in ​fingers ​re ​to ​es​. ​* ​Direct ​contact ​with ​skin ​can
cause ​redness ​& ​contact ​with
eyes ​can ​burn ​cornea​. i​ ​USES ​: ​1 ​Used ​as a ​solvent​,
paint ​remover​, ​manufacture ​of ​drugs ​- ​(​process ​solvent​)
cleaning ​of ​metal ​surfaces​' ​and ​as ​propelent
in ​aresols

2 ​Chloroform ​I ​name chloroform ​was ​given ​by ​Duma

because ​it ​gives ​I ​fornic ​acid ​on ​hydrolysis ​e
manufactured ​by ​distillation ​of ​ethil ​alohd ​or ​acetos
 with ​bleaching ​Powder​. "​
ч.​ ​*​ңo ​-​> ​«​С​он​)​, ​но C
​ ah ​oh ​teh ​- ​CH2CHO ​+​2
hd ​chloro
CH2 ​CHO ​+​342 ​- ​Celo ​CHO + ​3 ​HCl​:
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in​ho
gC43CHO ​+ ​34​, ​- ​+ ​ccl ​3 ​CHO ​+
HCL
​ O ​+ ​Ca​(​OH​)​, ​—
- ​Centerol​) ​2ect3​CH
Choo​,​) ​ea ​+ ​Chely ​colourless ​gas ​with ​sweet ​s​mell
and ​has ​a ​density of
1​.​48glcc
• ​It ​is ​sparingly ​soluble ​in ​water ​&​e ​fairly ​soluble ​in ​organic
•on ​exposure ​to air ​& ​sunlight ​it ​forms ​harmfull gos ​called
phosgehe
CHelgitt ​og
→ ​Co​dlat ​HU T​ o ​prevent
this ​chloroform ​is ​generally ​stored ​in ​amor ​coloured
bottles ​& ​a ​little ​andount ​of ​ethanol ​is ​added ​to ​it which
 converts ​harful ​phasge ​ne ​gas ​to ​harmless ​di​-​ethyl
carbonate
o​= ​c
OC2HG ​H2O​-​C2H5
_​o​=cT
a H​-​O​-​G2 ​H ​5 ​+​244 ​0C2H5
CHEMICAL ​PROPERTIES ​:
• ​Chioroform ​on ​treat​em​ent ​with ​cilver ​powder ​give​s
a​ceteleme
2CHCl3 ​+ GAG ​Gage ​the ​schi
Chloroform ​on ​a ​with c​ onc​. ​nitric ​aci
holoro ​pierin
which ​I ​is ​used ​as ​insectiude ​i
​ O ​3 ​sllig​NO ​2 ​t​ft ​so ​el ​erials ​on ​treatement ​with
: ​1​2​.​3 N
acetone ​in ​presence ​of ​coustic
potash ​gives ​chloretone ​which ​is ​used ​as ​chaptonic
drug ​erg ​- ​C​- ​CH2 ​+ ​CHCl3 ​- ​H2 ​C​-​c​-​cla ​.
Cl3 ​crid​, ​is
widely ​used ​as a ​solvent ​for ​facts ​oils rubber
risins ​etc​. ​a ​chilly ​is ​used ​for ​preserving
anatonomical ​specimens​.
IODOFORM ​CCHI3​) ​Is ​Prepared ​by ​treating ​ethyl
alcohol ​with ​iodiene ​in
C2HOH ​TAI​, ​AGNOOH ​CHI ​Thcoonaa ​5 ​NaI ​totho ​t​o
 It ​is ​a ​cr​ystalline ​y​ellow ​S​o​led ​wit​h ​chara​staric ​I
unpleasent ​smell​.
I
presence
of
"​Caustic
solda

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is ​Insoluble ​in ​water ​e ​soluble ​in ​organic ​solvent ​* ​Used ​as
an ​anti ​septic ​for ​dressing ​wounds​. ​The ​antespetic
action ​of ​CHI ​is ​due ​to ​liberation ​of ​free ​icdiene​.​.​.
eveplaced ​by ​Due ​to ​the unpleasent ​smell ​nowadays ​'​CHI ​3 ​is
replaced ​! ​| tincture ​of ​iodiene

FREO
NS
CFA​-​freons ​- ​1​4 ​CF
​ 3C​- ​freon ​-​13 ​CEgbl2​- ​Freon​-​12 ​CF
C13 ​- ​freon​-​17 ​1 ​/ ​General ​formula ​- ​co ​x cly ​where ​ary ​-​4
They ​have ​trade ​name ​of ​flouro ​chloro ​methanes f​ reah ​12
is ​most ​commonly ​used r​ efregerent ​& ​prepared ​by
passing ​hydrogen ​flouride ​through ​carbon ​tetrachloride ​in
presence ​of ​antimony ​chloride
 .
Celat ​CHF
343
(​Fall​, ​+2
​ ​Hl

nou

:
• ​Freons ​are ​extremly ​stable ​unreactive​, ​non ​toric ​& ​I ​easily
gufiable ​gases ​o They ​are ​used ​extensively
in ​refregeration ​and a ​ ir ​conditioning ​purposes ​a ​also
as ​' ​propelent ​in ​aresols ​.​.​. T
​ hese
of ​ozone ​layer ​and ​so ​are
responsible ​for d ​ epletion
adays ​are ​replaced ​by ​harmless ​compounds ​like
freon ​- ​22 ​CHF ​E ​Freon E ​1 ​2 ​3 ​CH ​CI ​CE ​3
Freons ​having ​c​-​H ​bonds ​are ​called ​HCFCs ​e ​are ​used
extensively ​because ​they ​undergo ​oxidation ​at ​very ​lower
levels ​of atmosphere​.
Freon ​123 ​is ​been ​used a
​ s ​a ​substitute ​for ​preon ​an ​in
 making ​plastic ​foams​.
PD​) ​ODT
> Prepared ​by ​heating ​a ​mixture ​of ​chlorobenzene ​&
chlorca
in ​presence ​of ​cones ​Hg ​SOA

a 6 ​+ ​cd ​gehio ​Haso ​a ​ora ​fora

a ​DDT
1111​- ​Frächloro ​2​, ​2
Bisschlorophenlyn

Toast ​chlorinated
ethene ​organic ​insecticide ​than ​high ​chemical ​stabiirty​.
a ​very
e
-​c​-​U

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It ​is ​also ​a ​very ​good ​antimalarial ​drug ​but ​is non ​bio
degradable ​and ​hence ​get ​deposited ​in ​falty ​tissues​. ​It ​is
 very ​toxic to ​aquatic ​life ​like ​fish

C​arbon ​Tebra ​cholvide

Calla​)
• ​Prepared ​by ​cholrination ​of ​methane ​with ​excess ​chlorine
in ​presence ​of ​sunlight ​!
CHA ​+​40​, ​hvala ​tatu

A ​colourless ​oily ​liquid ​which ​ů ​completely ​insoluble ​in

thor ​' ​solable ​in ​organic ​solvente​.
• ​st ​acts ​as ​a ​goo​d ​sa​vents ​for ​organic ​compounds ​pale​,
oils
Erisins
• ​Good ​Cleansing ​agent t​ o ​remore ​grease ​& ​organic ​matter ​: ​e
cased ​in ​manufacture ​of r​ efregerints​, ​propelents ​& ​pharmaceutical ​,
• ​Because ​of ​its ​non​-​inflammlable ​nature ​it ​is ​used ​in ​five
estiguishers ​in ​name ​of ​pyrane ​but ​its ​usage ​is
limited ​as ​even ​traces o ​ f ​moisture ​can ​convert ​it ​to
I ​harmful ​phorgene ​gas ​n ​e
calq ​tto ​cout24 ​. ​It ​is ​toxic ​& ​tarcinogenic ​in ​nature ​wi ​t ​h

>
A ​BHB ​C ​Benzene ​Hexa ​Chloride
Powerful ​pesticide ​in ​agriculture
under ​tradename ​lindane
 C6H6Cl
6
& ​is ​sold
a

Non ​- ​biodegradable ​in ​nature

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