-..-~•y ·•--~y·p~------,..._-- - ----:-:"'"',.,. ~ -- ,.., ... - .. __ ... :- •· •....,._•.,_..,.,.-":"'" !:'."':~·- ~-_,... .. --.

- -, -- ;◄
_..., - -.;•·-·~=--'""· ~- - - ... -·. .,_,..._..._.. _____ ___ __,___...,._ _.,.. . . . .- -..· -

Alkyl iodides are often prepared by the reaction of alkyl chlorides/

bromides with Nal in dry acetone. 1his reaction is known as Finkelstein
l_;;. ,- ! r
. • ,._ -~. t ---- •
reaction. ti ( i f · ..
R-X + Na!
1 1
~ R- 1 + NaX
- I
·1 I
#-

X - CJ, B r "' , . j.,,..

~-".,~, ;~,- ~
~ - ,/,, '1
c,~

J\J!>t:'ll- nr I\T~ ~... ~h .. w C'.'t r""__,, -A- .:-~- - ~.:.-~-1,,_ .;.s-_-:.,;,_ I:! As Z-L. c - - .... ....... ..L. -
 t:>2 F 2 , CoF2 or SbF 3 . [he
AgF, Ho- reactipllis-~et~~~
.....,____ __ _ ~ -~
"---t_ _ _ _ ~·-
a&:.~~ a:n.-~
s !~q
• , . ..., , _ _ .. .. ...... ... . ,. ..

H 3 C-Br + Ag}! ) H3C-F + Ag\3t' .

 (ii) From amines by Sandmeyer's ~e~ction
When a priinary aro1natic amine,' .dissolved or suspended in 1

· =1s
aqueous mineral acid, · t reat e d WI·.th. so d 1um
· 111·t rite,
· a diazon·cold
salt is formed (Unit J3, Class XII}. Mixing the solution of fre~~~
prepared diazonium salt _ w itµ cuprous chloride or cuprou~~
bron1 ide results in the repl_a cement of the .diazonium grou1
by -Cl or -Br. ., ,
' ' '

_,,' . ' . ., .
.'~' '

' ,., '

Benzene' diazonium
' . ! 'I

,, '. .r,,· halide 1

+ ·- ,,
N2X . · o,·: . X

O · .

'
Cu:){,_/
I

_· L
'
', ) ' '
.,
•.
1·,: ~
•

'

. Aryl p.alide
~
,

• I
.· +

x: = Cl, Br

Replacement of the diazonium group _. iodine ~oes not require 1 by

presence of cuprous halide and is doQe sfuiply hY,. ~haking the diazont,
salt with potassium iodide. · · ·

,.
. I +

' 1
 Wurtz reaction
Alkyl halides react with sodium in dry ether to . give hydrocarbom
containing double the number ()f carbon atoms present in the halicl~
This reaction is known as Wurtz reaction (Unit 13, Class Xl) .
_ _ ____.> RR +2NaX
2RX. + 2Na
(.1v) Fnt:~(fe:~J -Cra.f ts reactfcln
(; I

Anhyd. AlCl~ CH-~ ,J

+ CH:1CI . I . +

l-Chloro-2-methylbenzene
(Minor)
1-C·h loro-4-methvllY:nztW::
¥'

(Major)

( ~1 Cl o
\
Anhyd. AlC13 CH'.)., +
➔

2-C.h loroacetophenone o ~ CH _;
(Minor) 4-Chloroacetophe~10·.
lMajor)
 3 . Reaction with metals .
-
Wurtz~Fi.ttig reaction .
A mixtur: of an ~kyl_halide and ·aryl ~alide gives an .alkylare . 'f.
treated with sodmrn m dry ether and 1s called Wurtz-Fut ne \1:
.. . , ·; ig react\r . ~
X . ·, . . .· ' .. . R ,, r
. +.·. . . a·.· +:· ,RX
··. ·.' ' Diyethe; ~ -1
~
N· . .

--~ -- ~ -N~
~ .·

:Fi,ttig reaction .
. .

Atyl halides-also ,give an·a logous compounds when ·treated With sodium
fr~ dJy eth~r, in ~hich t~o .aryl groups_are joined togethef. calleu\ uis
F1t tig reaction. , ·
I
,. .,
. i
'

X Dry ether
2 + 2Na > I. . + 2NaX

Diphenyl ._