~ e d as Lhe parent compounds of general formula R-X wh,..re R rcpresenr~ an nlk-yl group .

:iod
- unds. Different classes of organic X a halogen arom (F, a. Br or f)
'i,Ji' ~brainedby replacing one or more
- t,e t in hydrocarbons by different atoms Class,fication of Alkyf Halides
~ ex,ample, replacemenr of a hydrogen Depending upon the narure of cnrbon mom ro which tltc
__.aliphatic hydrocarbons by a halogen mom halogen atom is atrached, the alkyl hahd••s (monohnlogcn
~ e s and replacement of a hydrogen derivatives) are funher cfossafied a,; foUow~

...
I

_.-
group fonns alcohols. Other families of
can be obramed u, Lhe same way
~aves of hydrocarbons consonne an
« organic compounds and find se\ eral
(a) Pnmary (1-, alkyl halides : The h,lloalk:mes in which
the halogen atom is attached co n pnmarJ carbon mom ore
called primary or 1° allcyf halides.
For example,
me laboratory and in industry. In the H
IEIDllialU, we shall discuss this important class I
CH3-Cl Of3 -C-Br Ol3-CH2-CH2-I
Olloromc&h.aoe I I iodopro~
(propyl wd :k
(mahyf chl11t11U) H
· n of Halogen Derivatives of Btomodlunc
Ctthyl bromide)

m:n~ of alkanes, al.kenes~ alkynes and The carbon atom bearing the halogen atom is linked wnh
classified as follows. 2 or 3 H-acoms.
(b) Secondary (2") alkyl halide.,. : The haJoalkanes in which
the halogen atom is linked to a secondary carbon atom arc
• · of aliphatic hydrocarbons are called secondary or 2" alkyl halides. For e:umple.
halogm. compounds. They are obtained H Cl
more hydrogen atoms present in alkanes, I I
halogen acoms. They may be classified
CH3 -y-Br Oi3-CH-CH,2-0i3

CH3
halogen derivatives of alkanes are called 2.bromopcop,inc 2-chlombumnc
g upon the number of hydrogen (uopn,p1fbromidt) C:i.« bu,yldllondt:)
en atoms, they are termed as mono-, The carbon atom bearing the halogl!n atom is linked wirh
es. For exampJe, one H-atom.
H (c) nrrlary (3•) all(yl halides : The haloalk.ane:. comninins
I
1-
8
halogen atom auach_ed ton ternary carbon atom nre callecJ
H- Cl reruary or:, al/o'l ~~•:es. For example, CH
3
Dlchloro~ethane I I
(dihalogen dtri110riw) CH3-C-CJ CH3-C-Br
Cl I I
CH3 CU3
I 2 -chloro-l•~thyl~M 2 •bromo-2, mc:th)'lpn,l"11\C
Cl- C-Cl (etn,bci(>fc:ltloridl) (1c-n.buo,lbrumtUL")

J,
Tetrachloromethane
The carbon atom bearing the h1llog~n atom comnlns no
H-atom.
) (tttrahaloge-n de-m-otiw) I
• (II) Halt1lk1n11 : Tht ha ogtn dtrivuriv~ of alk
es are wually referred co as haloalk.tnes or alktnyl halides. For example enes are called
a, Alkyl halides. They have the •
509
11 0 I No ota n SSC Ch em ~X ll
04 2 - Q t-c t Ot:z - 01 - CU i0
A. compounds Con\ainlng C ll,-xBonci
~
(X F, Cl, Br. I)
(1' .1\~
'{~ l 3 < ~ '"" "
(tlb 4c~ nltl In th\s l)'JlC or monohnlo ~mpound$, •he
Ol l- al - Ol- 012l\r dlrtetl)' bonded 10 nn sp ,hylJrl dl~ cu
--~,l,nw compounds mil )' runhcr l>e s11btJlvlde11rtr.in ~
(~th 'll!l! IIIJ t)
categories.
~
1'h e sn, up 01 :-a \-i sa .U cd ,in ll
SfOUP· l-.:o •
(\11} 111\oa..,... : Tht ha l~ dnnvnws (-/ 1• Haloalun11 or alkyl halldoa : In hnloalka
~ art rolltd atom b bonded ,o nn
~ or alt ),u i halica R nlkyl group (R) . n,cyrO:•~
x~. scriC$ hl\\ ing the gcncrnl fonnult1 <;II 1
H- C- c- & 01 3-C -0 -0
~
may further be clns.sincd ns primnry (1')~•1X
\~:2,-
(~ ~l to v) teeth\')' (3') hnlldc.s ns dlsc:uucd earlier. '
~
H If
2. Aromatic Halogen Compounds I I
Tht hcloSffl dac n:m a cf mm a art mU R- G- X R -C -X
"1
td Gl'CNIIGtk haJoiffl I l I I
mm pou nda . Tb ac art af rou o-in g Rr--C..l
(ll hclear Ml 1I• ,. _h lllw s: \\'ht:n a tt,~
GtbX.hft! mc mc :nn crx Ml u npl ocr d ~a
n\'O C)-p &

ascn atof fl diffltty

H
1•ha)Nll.anc
~
rha1oaib.nc 3~
!
da uan w. ciiccinrd u mli td a nucuar ha
halo Sffl arom . tht lf R is nliq 'tlic. R- X ls tcnncd ns hafoc)
los • Jeriwrfvc or C]doolky'f halide. Such
hal o ara w o, ar, t Wi de. n comp~rnnd ls dlhc
tcnl&U)~
For•nmplit.

~
X

on
~&

a
6
C)'dohc:ryt halide
2. Altyllc 11111•11: In lhls t)'PC of 11:ilides. tht
C' = I. ::..at I ~ti I I s .,.
l ( 3 ~
buu ac is bon ded to an .sp -hy bri d~ carb on
_ ,._ atom ncxuu
lbe bal opn am mb dir ttd) 'Un ked 101 carbon double bond. Such :i cnrbon ls term
hec mt, aaa 1C 11D of for c:nmplc, td ucII)&
All)'tkcu bo:I
(I) . . . ... _ 11111111 Nr lfll lftl ; WIi ...I
m • Jo,d,oaos aram
p.. -& uli tad tdl afn ana dtt dro aam a 012- CH - CH2 -X
.., Cl . , , . . . . . . . . . . IM dtm
:& rin lfu qkc ef
cw ff o!waiMd & mlW G . . 3,~ 1- <n e
dlafn W pz: daf wa riw . The sid ccb airh

..... aJo pad aha dw es CH3

1ft np rde d a die arJI dc ma I
tha alhe'neDr• 21 ud are CH3 --o -t- Ot-O i-X
... ., lltia ad - and aUol ha. Iida
. Som,>.,.,, pies 1ft • 4-halop::nt·l ~
X

p
~ ~· ©
...!..... .... .:_, n etc s: rt EN "-J tr sr
~
6 •l<o
a. 11 -.., UII NI: •~ this type of hnlledcs, th e~
-. .= -- o.-a ldd llri dct l 1
0.- -:t n,. ...,
fl bonded to an JP -hybritlised cnrbon
1be lla lo pa --• pu rm IA die side lnNDadc ring. Suc h I carbon u tenned acorn 1k
as t,tff t)
chain.
...,.
Por eum ple ,

-o
C1assfflcallon of Manohelo Co mp oun ds on the
of lhe Hy b(. dill lfon $late of lhe Carbon BaSIS

....,.wa. c6
of C-X Bo nd
. . . . . . . . cla twd ,u "' 11, dao c:at aw
er tfled 11C1CD1111ns10dle wo llaJ b,M ked an.old. , llllo be
--l ~o ud ed IO die,..._ .....
mefa1 .. die ad Jo ldl llrd Na lcl l propad
ie m t.
11111 dw lhk la It 'ftl J
ei. AcconUlta 10
t ,halo-1 1 2, 3, '4•
&acnJi)'dlonlrh''"ldlt
dll l-1 dfl. ... . a»a dl lop .a . . . . .
clllv J I If d ... .d
.,. dz :n.s • All yll e~ bcmyUc halides may be P ~ ,
~
 cc,otelnlng Cs,;-X Bond
2 Ha!oaDcanes anc1 HaJoarenes f s 11
:.:....nahnlo compounds, 1he halogen atom b •A/ii ~llfdei • Th
,..,.. ,pl-hyl>rldlscJ cnrbon morn These nnked to aQ;boncsc halides ha\-e the halogen lllOffl dtrectJ)
co"' . may atom t>( the :uonuuc ring. for anmple.
15 follows.
: In rhls type or compounds, the halogen ~ ~x
CO one 0 ( 1he cnrbon ntonu or a cnrbon. _,_.JV
... ux .'
lu!(t,-...:0: J~
, l.t., 10 n vl11yllc carbon, for C.Umple, p~
C.Compauo<fs Contain ng C -X Bond
In thh '>"PC of lulldts_ die sr,
to one or the bons b~en ltom lS dtlffll} bandtd
mmpt'-, cu o{ ~ c:ubc,n-oubon mplt bun&!. for
I halocydoha •~
H-ta::c-o
Qh,~ CHJ-taC-CJ
abapop,tc:

JREVIEW EXERCISE~
lkanes and how a,e tht')" cl H1tr~,
undc,~t.,nd by il 3' .'liq I halide/ GI\~ ~ ~. Wr t • !he ~.ire of~ foll<M~ u V'imi chloride.
b All}lddo,~

aafn ~rucrural difference b;~""~ 1' and r i. \\ nte the $t1UtturtS oi,1 di'OJW -'ffl! .rnd ll ch!oro.lll) nc.

or Alkyl Halides (aJ T1tt Pritfiz n- : Tbt prdu r..- sundJ for r.anr.al. h is
::sai ro clClcribe m Ilk)1pocp which C'Of'ltuns a conunuou:s
claimril'f!S of alkanes arc wuaI1y mltd malg1u cha.In ofartxm atoms. For cump!c.
halide£; The)' nre obrruntd by rq,J.icing

-
CHl-otl-Otl- Of3-012-CH:-Br
t In an olbne b)•a hal~ inom. c~lptc;, a-~lb:t:cik
-H Oil-Of2-0l1-0l:-
-x R-X c•IM)t~
tl4~Clf
Al\}1~e Oi3-0t:-CH.:-Ol:-O
ii• bu:) I chbiJc
ofhnloalknnes is CnH2n, 1X, "btttXzn
fb) ~ prefrz uo-: 'Tbc pr,fix £so- is USC'd ro llcsaibc DA
can also lie rtpr~med nsR~t. r.hatR a!hi gr,,up "-hlch cont1fns II methyl (-Of,i) brnnch :u I.he
cypical h11lo:ilknnes arcOIJO. OiJBr. roJ of die dl:i.n. For wmplt.
etc. The dnssifiaidon af h:ll~ OIJ-CH- 013 -0l-Br
!lltUllled earlier (sec§ I), 1 I
Oil or,
CJ,..,_~S'UIIP ao-~1btoa:JJc
(,,i11.:fftf'Jf~l
in ttic: followins two ,,-:1)-,;;
• ; In the ni\'inl S)'MCffl. ~
~aa. The nnmc is den,-cd b)· oddill$
o( the rormponJ{ns~)igt®P.
wrinenM t\\'O$tp.VDltWOois. R,r

013-012-I
Elh)l~

ofallcjl group$: Jn rmi.11 ))'St~

.__ ocncrall)' used to ilt.StJ' CH3
-" " --ru;d ls ftlO• pa:11)1 lroc:ldir
ups. The u,e 0£ these tw~·
au I N■ ,_ 'SC Oen' ~ Q~
311 t ~
enl ~ 2
l
I l
i -~~ a,J
,t•-..Q>- J 3
Oil 013 • ~
.s " ll 12 1 Br

~3 l~J
l. ;.o,
1
01.,~l-a1-<rC1l2C1 01 12 I l
j
. ~ 1.2.1-trimuhylpcnw.c .....-'?'

TIie c:oaunaa :md IUPAC names of

~ Iii tabl~ 1. SOtnc ~

Con11u,,... IUP~na.,-
ChltJTOmc~

-..,.,,... ,.
-• IJr
Brom oc:lh:inc
b,S..,C cMa ill l-chloroproP-1Jsc
2<hlol'OJ1TOJ),.'lne

l •brorn obut.lDC.
2·bromobumne

1-daloropmranc
 Hatoalkanes
folla\\ins; cwo l)po of bomnhm,
V1ad' ,,,-o or mart haloaUana hal1f\l rht

in
dijftr in tht stU of rhr l~u• dtcln
thtlft, rhry arr $aid to c•hihlr ch"ln
a,,
1 J tb J ~~
ilDrnensm ls .$hown b), lhc ia1o.1Jbnc1
_,,c aarbOn u10,ru. lllt hlllln bcmtrt&rs I \\'7trn nm .,, 1!10t1 "~'""'''"-~-
lht1.imt fMifflJI tj, lffltl :J .f'_l'lJtU , ~ ~ ~---•"'
anc (C,.H.90) h:u the followfns ihrtt fO rh/lrttlll ffl!Mtt WMU tf tit., t 1', I ~ ~
:.u.it1D11d...
po111l,m lwmtrlJm, l\nulon lvi:r,;,n ~
013 hato.tlinno nmu nlna 11utt ct mott c:.uoon ••
I For c:umpk. thlompr~nt (C,H,<!1) h:11 lhi-
CJ Iy-CH~lr-CI P{)Sf1lon luimcn
1-chltJl'O•l•mnb)~ a
Oli-01:-01)-C
l•ch.l-np~

11111
IREVlttW E~ER(ISESI
Of1

hill Ct IJ--{-a
CHJ

[n1 01J-f'-Oii(J

IU~ \ C Nm~ •I 1-chloropropJne

G/IJ
2 mc.1h, Ip op.1 t' 11 2<h'~nc OtJ
l-<.hl()f~•l•mtffi)lbuUnt:
Ii\')
l'- 1-(h1oro-2. 2-dimdh\lJWOf)Jntl !..J
ol the follO\, 1ng ~
0
M c»1=CHJH-y=CHJ
Cl

MJ (CH1l.,C • CHJ • CH,P

Of1 of
f\,iJ OfJ+Of 1--0fiC)
01,
 514 I Nootan lSC ~
" 1-<:hbt> 2. 2-dam(.'df\lproJHrw
0-f , chloml---tha~
l.l\n I
('Witt Of1--ot~t-{-0t1
'I Wn•c ..11 the f>O'-"hlf!' d~m, nd ~
01, Ot1 "aw,,poun<i, h.Mng formul.'I (: 1t 1 \\r ~ I ,a
la)
Br
Oir-C'O-CH-Qi,r--01,P
Nmt"'t and uk.---ntlf) lN.-m .n 1 2 ~ I h !:.
10_ ""1mt' ,h(-. tollO\,,ng etxnpuund\ Ira I p~ ,
Qi ,t o-t,-Ol-CHz-CH.z(h

~ CH --co-yt-CH.:--CHP b
C:K. I 01·1:-CHi-CI
-~1
i....c-n• • •

~~~
1-dooro-
,~ iim ?I1'=1
..._1'1m>,J
o:1p
~ "i
I\ CH1CHCi
-""'-l'uur;~,...........~ -

• , , CHCIJ
a.~ die ~ a ~ ~ ~ and \I) ca..
.da-,lhlm~t l a l haLde..
1~2~--... H 1-ct,loroprop.1n-2-o , I 2
11.'J 1. 1-dlchlorocLh.u"K• ~ 1,
1-btuctol~ propme,

3. General Methods of Preparation of

Haloalkanes
Hak-Dr::enes ~ ~ p;epaaed m 1hr labcawcy from
cilller bjdaoc:ubam or aknball rallowins mrmods are URd
•mm~ Ol.3CH2 CH2CI
1-chlorop,op:tn,. .... --
A. From Hydrocart>ons (4S'-)

80lb •lbnrs aact •lkrna an be med for die p;epwari&,a of 1ft such a case, the case of rcplru:t.'fflcm of \"illlOUl ~
lpJoefhnes hydrogen atoms in the given nlknne follow, the ordd
(I) fnlll s0:1111: Alhna raa widl ""-iw and --.l,w ~ H -atom > 2• I l•Dtom > 1• H-a-.m..
la die pn:xnce ~ sunllpr or heal to pie• ec ■4Aa lllimn J ~ ol alJuincs Is rC\etJiblc because III ron:tdi
c l ~ ad poly subldnad blHths wbidl 1ft 4ifflcuk 10 reaaion Is a .ruong reiiuc:ing agent ond rcdu~ ~
be l!panlled. for eample, dabtn■•k• o/. ...,,.._ ia rhe iodide formed (n the re.,cdon b.Jck Into nllalne. 1w.
JftiN!lklt ./JIIUDHpr or heat pva a lDimfto{faar pradua,_ eqwllbrium is sec up between the alk:nnc ond tht a!k)i
a, ~ lhe equilibrium can be shlrteJ In the
01, h•s»-6,_ dncdon by uslng an o:ddlsing ngcm llkc cone. IL\
or HI04 whlc:h oxldbcs HI Into I2,
Of,C • OIA • atCIJ • c:a..
a..
d
....,_
a.ii..
TrliclibD
_, Id
T• Hew
..... 014 -t J2 !§ 0~3I • H1

II a proper rado oldie halopn IO

,-Ible ID IIIPPI• die pn,c:ea be)uld ~
die..._
II used, JI II
. . .__.___
SHI + mo3 - , 312 1 311i0
..IMl\'t I
•~Ion ol alkancs takes plnoc with ~...-Jhcf
However. die pnall fl DOI o/ ad pracdal me fa die aad nsuka In the rup1ure or C-<? bond In hl bf
~ , , . fflllbod JI 1111d ladmatallJ co Nn:c&ca,n
c:lalodDlud ......., ~ eUcyl Ouorldcs are generally prepattd
maW..roraamp1e,
la a. of hlsber, •Pr•na. u n:mpt of ainy(n, GU&
. . . . . ." . . . . , , . . 1111111ft of •-11omer1c
p;odsra,, u., 1 admn of 1•. 7 111d 7 lllcyl halldll, 11
~-01r-O
W.1 1 ••
-+

....
~182~

. . .wl.Par--,le. 20l3Cl12F
Pluororthfflr
 :i
ofnh~n;log;cn~n~ti;on~of~n~lt.a;no~....
::- .. :._": --'.:-----H"''--" -
_,, u-.: ~ ~~==.:::.;:arxl~tia!!!='n<~m~ena~l5~
1 5~
tfft:J b Gpplicab
~ ~ of henr or Ught halozcn:nJon o! noi to the atldition ... onJ U> ihe lddwon of HBt
1 .,nud' vi:t/rcc radical mtchanl.sm. He 01 lU amd
~ 8 From Altol-uJ...
~ Pwtth nl~.ane:. v.ith cxplosr.e ._,otenc:c. uui:,
~
-.-Jd
rc:tdilY but rh reaaion ..._,th bro,....,..,. ~ ll lhc rnou <nm aucn1
odi i ....., ,er Lhe "'-- • a:11h.he cx,,.t ~ ' -•.,._.. C
p--,e4cuon wuh I nc s re-.mib!c. 'Thus ~-,.uan o r ~ The--~, ~method
111'o( tinlogcns fol lows lhc order haJor- '!%11 of ~-OU graup or rncthcd lm'Oh1:.\ ~
,,,..-~ f .. ... Cl2 .,. Br2 12 !:II atntn., 1bn c.n be aduc L i ~ b-1 the ttqwed
, .-- ., ,, as &wen b-Jo,~ ~ ln any of the mcihods
._,...,ll)' gh:cs a complex mix1ure of mono 0) ew lb! 1...:_
~ ..a.d~~,ut_.1 L"V
h3hdcs. Ho-~C\et the p-..,•-•
,uy..._ "-'ttatbalom~
WUh :a halogm acid • .1..._ . . _ ~ 3n a1mbo\ u ~
.J:..W::-mt ....., (rna.ion:11 dlsttlladon unn;) Ion.,
,,..._,..-:=-.-. "J o o
the -0 m Ult P l ~ of II d......_..._
H group xeu ~ .._ ....,u.~i agent
,!...co,aumns ~tsolnai."led. .., \hc~a:o:n and a
~sut,stuudon of different C}J>CS of hydrogen
--=:~ foUows aJ,e order
,,,
,,,..J1,4110ffl .:> s~ndary II-atom -, Pt111tary
P.--on w; --...;;.
l'Jmbc
1bc dc.'r,'dmmg ag,::u n:mo-.b HtJ fun:icd
"

~ : Ha)o.'lllcnnes cm be prepared b, Lie and thus p1c.ems lru! mCDIC n:aaion to~~~
i
-::'r tcids CW:, X -= O. Br or() to alur.c The
balogen adds, alkenes undergo add1u
rc:!.CtMty of alcrihoh t ~ dm
b.a!ozm acid fo\ic,,,.., the order l'CXlio:l ~ 1 P'tn
.. i)jak,alknnes For example. ra:nary (3, alcahot

i. ,...,.
•.
'
- ; Ot3-CH2 -Br
8n.n:wdh
, .A..:L pruuw-,
... ~ lh!! re.:tal\1ty of ~en aam w-m U'lC rt.XUon
m th•ordtt
u,
1«.0ndar)' (r) a1r.ohol
almhol
~
-► CH3-CH2-I HI > HBr :> Ha
' '
&pl.anatian lh:s ~ ts am az::,;tt of ~
lodocsb-1ne
es, the addauon of h3Iogm submnmon rmma:u. )met the orde of mbi1itJ' of
nee to Markoumilcoffs ruh.. The cutoariims follows the ~ 3 > 2" > t tht ordff
~ af n:aan1Il of a1mho!s also follows me mne ~ tL.
I/ an unsymmancal nagmr of tht 'JJTt :r > Z' > l Fun.her. the bond dm«Ytm ~ ol K-1
alkoit.. the negam~ pan (X) o' dtt bond is m~ on1er R-0 > H-Br > H-1. me ~ a! ■
.T -, cm:bon atom of the double bond b-ltfd: h:J.logm :icids follows Utt orda lU > HBr > HQ.
ofhjdrogcn atoms, whu:rC1S the pasuirt (aJ Prim,uy and mondary chlorncO:cnt, m be pitp.!led
gm orrachcd ro that carbon cuom ofrr.t b) treaang alcohols with HO m the PflXDtt of anh)"C1rou)
n.s larger number ofhJ~ c:tonu; mu: chloride (Gro\-e·s pn,ces,).
CH30ilOH • HO A::..~ Zi:0:
Br Eduid
l ttl:tf d::o1'.d)
+ HBr - , O l3-0t-CH3
2 ~

cc of orgnnk peroxides such as Oil

sC0-0-COG,Hs), the nd.diuon I ~ZdJl
nlkencs uikes plncc contnuy to 0 13___
-01-011
.,,d • HO
as known us ptroxidc t/f«r or ~~.
a
I
Bmroyl penuidc
-------•
cH3-cu1-
1- b t ~
0t2Br ~=
Gtl-Ot-CHJ • H~

In lhest rcxitons. anh)'drvm 7.n02 no, onl} am us 3

dfh llr.itlng 1gtnl but ;ma hdps ln the w,iige or C-0
0

:11dds to nlkcnc:s usuiUy tnkcs plxt ~ of lbt olcohoL II is :a Jn,s add und cocmilnatcs wtth
(clearophtllc addition) but [n and thus "ukcm tht C-0 bonct Thb
Dlam
or the OX)JCll
pefo11dcs, the oddhlon HBr co results in die (~UOP or uaibocunan wtttch COnwu~ ...;\.:...... 'th
W\
a free mdlcn1 mechanism m we Cl ion co ronn the c:hk,ro31bnt.
dass XJ It is to be noted that tbe
 1tromnalkart('j and lodoalkoi,~ arc ~
a)C'ahols wr.h a mixture of red ph~~l'J! bi
iadbe- Thts ts bt<ausc PRr, nnd ()11 ar, ~ ~
a!t o.'ffnned by the ncuon of red ~ ~ ~ , ,
iodint dunn..~ ,he course of the rc-\C't,an ~ ~ ~""<I
• 1'4 • 6Br2 ' '1Jli\rl ,~,."\
30t3Glt20H • r-nrl • lC11101 ti•
~
~ r, •
I!, \.2 I

\ t
silnn.,fy. 612 , 4r1, , ~
1
JQt1a t20t201l ~ Pl3 ~ 30t1a1 0i ~t
~ '~
2
• H..0
• l ~40;::•J;ll:·/ ' li.-- !
(00 If ,,_ action ~• thionyl chlo~12e : Otlo 'I\
~ byrtOuxutg_nl_coho~ ,,,th thion; ~ ~
1
,n the pn:scntt or p.)ndmr. For c:cnrnptc_ -~
at~ou .. soa2 ~

CH30l2Cl '+ so2 Cg} • ~

The wt o/rluo:o-f chloride/or. rhc PrtPGrarfcn oftt•
u prrjrrrrd O\W the wt of HO or phaspho.,u ~,.••s
04pt-GI • ~ Gt Oi:9' • H:0 dcscn'bcd e:micrl beciusc the other Produas o!; ;~
.._. tll,
~ { , , •• ~ .-ind HCl) being gaseous escape oUt ~
~ CIIMi
w dUMD d HIii' am allo bt med the diloro.:iUcnnc in almost pure lUHe•
an,-• ..4ft al
~
10

c. By Ha' de Exchange Method

re: 'h C C an. p;,...,a1 t-, rdhmrc almhoo With Kl

...... ,,,...
-, ,.. ,fwk il0d li'OJ This fflClhod is \'Ct)' useful for the prc~r.1tion of
A If PO, - . Dl:JO• • HI
"iuch att diflkuh to be prepared b)· the di~
of albncs. Th, method involves an exchange of
1111
.....
OIPf:OH • ta --. Oipi:J • Hp
bromine ~nt tn n chloro or briomo.ilbnc "Q
,.,,
When a chloro:lllcane or a bromoalknnc ls heated~
iodide in acetone or methanol, the oorre:sP9nding
n." a ca 111D lat caned• wn a mi+a11illtd isobwncd.
~ I ••HL
... ., .. _11181 ,·1•111M11:1wn1'he,;tabt -,~,r-;11-•
,\cct~

IFS ■ 4LI . . . Jlltdllfn:f'ue. . . . . waph'4•m

...... " 2 Fl a
Clht C ■ aae.p ;z:mlli!Jcbtaam"ph'4•tuna
12 111a 00.., • pt 11 aw Cridiladde (JIQ,) •
pa
..... re.- ,Is.
.....
<HJGtpn • Nls -...
at,atp • POCls • Ha
cc a o Tbis IUCtlon ls known as finktlsr~ln reaction. R>r
Oft
Attconc
-~-►
XHJ-A.t-at, • Fa.1 --. tk:n
" C U CH3CI 121 -+ NaBr
rooocchanc:
?
3CH,-Gl-at 1 I\POj
fluoradanes can be prep,uedby Swarts Hcnction A
Mod ror lhe prepnra1lon of fluoro•llmnu bb
Jets U5 a l1'lnl Pncti6n. In lhis method, u chloroalkD":
• 11o_11,z
. 1r l◄
r,~ ..........
,....... iM••i
.._..__,._• :1 If..
.Nldmony1r1nuoridoln1hepres•nreofan
an••---.,
-•
1r- n r- -
uu,a, r .............._. ■ t • 11111U11 In +s stntc (e.g., SbCI-'
;y when
byRuortne.
 ~nesanc1~
for Onntplc. I s1 1
ltnfoalkcn, •
sbd~
__ n_ • Ot,F
_., ~H sC f:t • Sb (l ug{Un,g pofnr (IQ • 01 C1 QI ll 01 1
Sbf.J l l r
• l An •
hicrt:1sc ln lhc iizc
194 6
24 276.6
l
31S 4
of Fatly Ac ds m.,grutudc of Yan du \\' of ~
halogen atom increases ~
fnllY ncld ts hentcd _whh bro P<>ints lncrc.is.c. ants for ru. Con1equcntly, the boilin
brornonlknnc comnimng on mtnc ln (b) forrftcsa h g
y nd d ts olnnmed. e carbo t
nacasc wtt me alogcn arfffl, th L.....~
n Cl.lrnplc. h l1la -··- . "uuui.ni polnu ofha
loa lka na
ca,. ms.t en rhc Jt:. c of tht
aflo'I group. For
• Br2 H •
lfalooll:ant
R- 01 2 -B r OIJ0 Boilini po inr (1\1
n:o mo :itk.;tnt:
ettia1:0 248.8

0' ,0 '2 0¼ 0
2855
C0 4 319A
He 2t
~ '1 0 lt 0 lSl .S
This is also due to an Ina .
CH 2- Br ... CO2 ... Wac1s• fort . C3"C tn the m:lgnltudc
"&Br cs wnh llla we in the slz. of van dt r
nc c of , he ulky\ gro
(c) for isomD1C ha '-' L up
ns Hunsdi tck u reaction -and brunch· """1Wncs ·
is • tng. f.or examp?e, . tht boiling pcnnts dtc mu c with
prcparotion of higher bromo
alk
adds. The reaction is sunabt .incs Haloalkant
c only Bolling po inr (11.1
omOillkanes because the yie Oi 3- 0i 2- Gl 1- ot 2B r
ld of
y this method ls '--ert ~ lbo . •ti ;n~
r and 37 2.6
ned -at nll in the react10n.

rties of Ha\oa\kanes
of Physical Properties)
ic:al pr op en ies of halo:ilka
nes are as
CH3
and odour : The lower hJlo:ilhn 1111
Q l38r, CH3CH2F and CH
Gt 0 '
es
ture. Al\ oth er h:i\o:ilk:ines3 1 lltc
up to c
'
0\ 3- C- Bt
34 5
highe r onl!.S nre sohds. ln the 15
pure
up to c, 8 nre colourless a n
d~
Th e highe r ones :ire odourle
ss. Thebranchingoh he dw n aw:es
'4alllng po\nls : The melting point lhc molecule more com
l)3CI.
s anJ :lNl dl'CRases its SiJmCt an
anes ore much higher than a. Due to dec:rus.e in surfac
thast of uu . a brancbcd dw n e
is be tmise the molta1la molttule h3.s lesser contact
r ~ adjJctnt molttule. ..-.;th an
Thls deaustS the magn1rude
or
r th an tho5e the correspon
dm& Waals' forcr:s or \'QO du
exisnns M \\t tn the two, and e<>nsequc
re: hn\oa\knnes possess ntly the
&~ater boiling point of lht h.m1]unc
ls fo rte s nnd cons~uentl~· ~s de er ~. This is why, the
htr
to pa re\ \\ a\b nes. th e t.~te.n boil,n o f ' ~ decn:ise with bra
c-e g pouns nching.
on s du e to slight po\aril)' . .
in tht1r \\I\\ Solllbility :i\ltbougb ~
the ir me \un g points and nrt sllghll)' po br (dlJIOle
boiling moment. 20 5- 2.l S 0), )'tt . ili q·
are insoluble in \\,U er. Th1s
is b«ausc they can nathff form
trends in their boiling points hydrogm bonJs with "'V t?r '
. molccu!ts nor can bmlk rhc hydrogen
bolling points nrc significant. bonds olmid;,v cxurinl in
"'Cltr, n 'e\- U. they are soluble in organic soh~nts su
u~
, the boiling points of hatoalkan a}cohols, ~ clilorofonn. car , ch ns
cs bon tta.ichlona e, Clt :.
sile and the m<lS'S of tht halOg(ff N} o..sllY : C h ~ are
~ group R. their boiling poi liJhte.r than
nlS \ and iodc,.,lbneS .m heil\'icr tha nw:itcr., whUe
wa tet . Th eir
~ t i e s fuUow the onlcr
< RBr < Rl. ttla ll\' e l,KI Y< Rl '> RBr > RO.
 511 \ Na .... ISC O e ~ .a die('OGipOunds can be S)nthes1sed ,.,,1h the he.1
!r, 4 ) W (mmr,1 liodlk) D C t ~
_____ ,-.a
► 1 & 1 ID ,acnl tht dcllrf cil bl
..::Ct-1 pc
T1us lS ,\'h)': hatoalknnes are regarded P <lf
~tile reagents for the Pf'eJ)arauan of a<l
,.. laaw In tbt w rl dat - .-.. P_...,. .....Jlt
cirpnic compounds. The rcaruons \hfl\,. b, lar7e.
11
.Q\4'iiP. b e ~ mto follomng fne ,y~ ' ha!tc..::'
Nd D
\ ~•udtDPhil,c subsmvnon rtac:rroru ~
a..,, B f1unmanon rma1oru
(&,11111)
c F.t.duman rramoru
IIJ P 1 C I 1 PR • llar maM mliiil1 d ~ o Rro:mm ",rh maals
.._,dRClld!ris IQ P> 11 TIii~ > Ee Rtam:tr~anmi rmmo,u_
bad tai£i4da vi C-l tmd . . . , dlt ~ "aD
C-0 > C-lr C-l Tk t-1 bmd • dlr 1rd mbk A brief dtsrusslon of these reactions. and 1
diir G-1' ..... n. • .., al:11 mdiid8 lff do J?Phclnons are gt\"Cll belo,\ .hetr
"1IIIS ar lnlls1I ca ii ■ Ml•
ad at.P he 10
,_ & - •61.puaadiprlDl"'iadint- ._ NiJdeoph c SubstJtuuon Reacttons
As ~ e d earlier. lhe carbon atom of lhe
aD.)1 halides pos.sesscs a parual pos, u, e cha C-x t,q
dcaronegath-c nature of the h_aJogen a%~u,
Co
5. Nalln d C-X Bond dearon nch species, Lt... nucleoph1les c:an au.:id:
M, snc of the c.arl>on atom. If the attatkin
11 tht
15 monger than the halide ion, nucleophili:
mes platt and the halide 10n gets ~plaC't(f by the

. .,,
mxxaphile..,-,,--... _
,.__
-..',
R-X • l\'u- - R- Nu • X
~ A:udmg Produa ~
~ ~c::
ha.103.lkanes undergo nucleophllic
11m,
ar laaiom. \\~ have already scuclied that the
salminnion reactions are of two (}'PeS s._ l and s~2.

-
ll'IBlll!II! ol ...... - - - ct.Jr• - . . . . . . al:JI halides (l haloalkane.s) nannall) unduio ruam~
O

---1111 ....... _ ~--· -dlfl ¥ nttdaanum whuea.s tertiary alkyl halides (3' h
.awl ;SF -.-.n. ■ -,M• +.n1m111t I, S,.1 muhallwn. Stt.0ndary alkyl halides (2' ha!
adcmlll aad••'-lr lu-ol-1 ++whm llldop, subsricurion by both Ss 1 and SN2 mtchanlSll.
...... , 1 ·~
a.r II mc1lvlty of haloalkanes : The order of r
llraoldtrWp--lm ••--.dawtdlepaap Aaaat fYPeS of haloalkanes is disctl.ssed below.
■ daepa1adlcaMr.. - , ............
.._--.dill ..... s * :
aa-1111111. die c-,r ,., 11t ordu of rtactivity for cht samt alk)l f1'0IIP •
11111
......... laa -c-,·~•...---. IIICliwy of a h.alo3lkane depend upon I.he bond
laadanJ11,Laad . . . _ _ lf'6 de+• dieC-Xbond. Lowu die bond encrgyof C-Xbond.
....... 'Dlllt2. • ~ of the haloallcant. The bond dissooJOOo
r•zc-x...,
Mor
Le• ..,
thl111I n■
111 •
4lec:n.s With the inaease in the size of halogen 111
darhm lhe following dnm.
°"
C,.;lbaad: C-F C-CI C-D•
,__ dwodatlon
.... OiJmor'J: 439,3 330.S 276,1

ifie cleavage of C-1 bond is the ea5ie.si wht~

bond ls most difficult. r-or the ~me olkyle~.
oCfacdvlcy of alkyl holldes follows the 0rd •
~J > R-Br :> R-CI > /? -F
halogen
..,_ of reactivity for tire same •11,,i
., · of an .w-,
halogen atom the rcocuYl[)' _......,.
' att~
a, the number o( olkyl groups of 0~i
e,...,,y bond. Hightr tht numW iJ rht
mrbon of 1he C-X bond, gmJ'''ps nrt' e
This Is bea1Usc: ulkyl grou
1
number
_,.,. shared
_of alk;i &roups_~--:~==-~
pau rcr.-,-arc1s_ Ult. fu t- -
------i--.--._.J~
~2 ~
..,,. ~
and HaJoarenes

.U:.Iy un'Oh-.
the, 1he
In - o:,stq
I 51 9
~
~
"tl zd o! t h ~~
Pe
:-"& On I
u~ D'i ,yo flh eal kji ha! id. _ Tbu :,ll, o
,e:,<
foUows !he order
°"'1ztiou , a a - , ,.... and
~ af tht halide urn.
0

H R
R -c ..._._x /
Nu6-- c- -~
I
H
T~ SW c

H
--r -

halide depends upon

> R-c-x In this rtacoon. tht rcaan,ty of aU.,1 tk on at
~~,..,th \\lUch the ~ g nudeophile can anz
~
[Q form transiUOll state. Ob-.ioum. lt Would
depend upo n

H ~~ huu1rczna of the all.·yt ~p . Higha-

dt.e n1'771bc
on atom of rhe C- X bond.
of alJcyt VOUps atta dtt d ro carb
morr u ~ JUric hindrancr and WIU
?ri ::u :,1 ('(JUatdy lessa- is
m1mr,:z:.e ards ~2 rmaions.
CM r=an-uy of the a1kyf luuid.t <aw
(11 alkyl halides., lhe or de ro i~ m JS aik}i halides contain thrte allc}1
gr-ou~ ~ttached to che
c:a:rhon of C- X bond and ~o re ~
the maxunum
, Of; P- i~ > CH3CH2C H~ etc. stenc mnd.r.mce. This as "'it } 3 alkyl
halides are least reacave
1• alkvl hal tde s
rm ctM l:y row ard s Ss l an.cf
~2 to.,-;uus ~2 re:?aJons. On lhe Olber hand,
1y
r ruc tivity of primary (Ji . seconda~2 ~ tile least stenc ~ and a~ mOSt reaa:ive
reacn,it)· of 1•. 2°
haloal.kancs to,·,'ards S~l :ind towards 5x2 reactions. This is wh } the
ns follow~ the ord er
Jnd J9 b:iloCalb.ne:s towards Sx2 reacno
1= >~ >J
Sr-ll : 3c > 2 > 1°
~2 : l > 2° > 3~ Examples of Nudeoph1hc Sulls!Jtution
Reactions and allli
_
their Synthebc Applications
ol reacti\-icy can ~ explained as follows
.
, nudeopbilic substiruco~ reacn.o ns
?t
tak e pla ce in two ste ps. In the rust seep Some important nons (gi..-eo lD
ionises to fonn a planar carboanon. bal oalbnes and Iha . S]11c.hak appUca
follows.
step, che amu:king nucl'°phile aaacks brachtS) are as
yl gro up ~ o/
c:arbocarion and gives lhe produa. The (i) Substitution by hydrox ,-.,th aqueous) KOthe .H
alc,w While che St.>cond one lS fasL h ls) • When ..,1...,1 hal ide s~ lre3 ted
• ..._ .,;--
....,.
alco o . tn ..........~ wa ttt •
R2 R1 or moist sih u oxide (AgzO sus pen ded rmmoof n
~~ffl~ • ~~ ~ the nudeophile OFr The
1.::.-:tuted 1,,,.,
"{
c + I\ ~-- (str p l,Jlo w) )itlds an almhol and rhus may bt ustd
for the J)t'l'pG. ra.non

alcohols.
I RIX ... 1'l0 H (aq ) - R ~H • t.::.'\
R3
H,J
Plana, cubomuon
R1 KB
R1 for example. r
! + ! (stt pl.J mt) ~
Of B .. KOH (aq) - + CH30H ...
~ledwJDI

/I " /I '
Nu R3 R?
- Ag{)H
Ol 30 f:i-8r . (mos sih'ff o.lidr)
--+
A2 Rl Nu AgBr
Bn,m oc1tm,c 3 2
rn ot OH T

rea • n. Hen
coo ce.
bill[)' Elhmol
decide s the rate of
'1ky( halide depends up on ~.stDtt, w . . by alkoxy gro up (Pr-q,anui
on of «h as) :
fo._-... in the reaction. ~>
San
r> Cul s~ °: a with mem1 alltoxide to form etben. The
is in the. ord u ., u used for
sa:.own cu Wi)liammn's syalbesis and
•UK U
• Alk yl hai:
~lQvityras o/differmlcypa~a lky l
rmm onaranon oft dlm .
Jftp
tht
ru follows th samr
110 I Nootaa lSC QK!m1J1l'Y'Jlll tftMfu••ff·;I C>11nldc ion ls nn nmbfdt'lu
nudrop.htllc sites~ 1hown below, if.,m ,~
·c N.
• is:. :c::::::r~,.-.
• ,_ '• ,

I II •
ThtJS. t)'lnfdc fon c::in :miick 1hc clcnron d
tfuou'&'"'• corbon (form IJ co form nu~ C)'II\I.I.
tficitrh... 'l' ~
nJrrogtn (Corm II) ,o form nlkyl u«yanld ·w.it ti: ~
comp<>und nnd Joni~ to gi\'c m:afnly fo-rmti. •:o.: h
• NaBr
,.u __.. t•• .. - ll],L . t ,
l(y , I - " " .. c-.u, ..q--lfti~
Tbc.rcfarc:, 11 solution or HCN comatn: ·
l.'llong "'Uh o :,mnll amount of form n. lhb ~'Jy li
• •• ~ua tn the nbo,c rc11cdon I$ nlky1 q~i:j ~<.J
._......,
OIJObr • Na0Cffi0t1 __. c-C bond ls ,nongt r shun C-N boncJ, i\U. t. .V.,;.
obmincd onl)' ln smnll nmounc. Yi~ ~

=
a.pt2-0-0JPI.; • ~•I
~ion is_largt#y •~d / 01 rhc Prq~
11i( abcn-t
m,nida.. 'Thts rrcnron provr tJ 011 fm/>ON
MIii ca a be obalt«d ~ htatiAJ alk)1 halides with dr,· fnmcuin., ,ht tcwl, of tht carbon clwfo tr_~ r,,:::
The re.1Clion can :1lso be used for the S}luhcm r~
lih'tfcmddt.AlrON...,
cubiox)'lic addi .ind primary nmint,\ bca,u1eci ~
Caffjlr +- AI/J • CiHsBr --+
c,Jls--0-CJHs • 2Ag8r
an t.3Sil1 be com,:.ncd Imo lhe\t•COmP.Qunds M
~ Jldor O
'!!: •
(Ill) W.dllMI• by..,,_,.~ (Pnpanlrioft ofltijhir
~ t Wbte halotlbPCS are aeaml with sodium
1?,--C N •
Alam': ruulk
1120 - - -,
AU. II~.:.
(l\m1a1
#\n!~J
llllyaldts. dat bllolm &di subaau-d by aa ilk)'Tl)l group
llld1W..,..,_lsotuintd.77k•mcrionN.Ybtwaf/or R-C-N ~ 2H20 Dll ua
(Cotnpln,~~,'
lkpapa,mioil,/M,-cal.Jna.
0
n
R-C--OH
Aluit•nn~ • 1'
R-C-N • 4H N(IC:11~011
f A.l,m! rrcmon) ROf:-,;~l
.-
I

In 1
Awmcnple.

I
•
01,-1r·
t
•
..............
,rllOl-0i ~

Ql:,-6-G-H ♦ Hdr
(v) Subldtudon by isocyunlde Jn>t:lfl (l'rtpa,u
IJ«yanido) : When haloalktlnC) arc ttt.1tcil "-WI
so1udon or silver cynnfde (AgCN), alkyl is{,q~
obcaJMd as thf major product nlong whti ri nna!.I

(M S.a..d-- ~c,wsr-,~. .adonof.qmi/Jllij

•,.,,,..,, : When b1loa!bne • aared wtdl alcDbolJc
loludae ol pacallla (Jllllde. tbe CDndfPedlq aDcyJ
~~
R-(D::A&JCil'I
(clm.~1:)
- • R-N • C: •
AJ\)1 UQC)'l~
-
(llt'{iO"l''"·f;tll)
..
1
c,-iilde Car alatle) II olicalned • & _ . prac1act aJoaa lwuampte.
wtda•...a-otalltyl&ocyuldi. Ol3012Br + AgCN ---t GI l3CH2NG "
l:.lhrlGll~
c,,fu-t~rjy)
i-Lf+ tc'lor -. a,a,,s • H .. xx Mi!FHI Cyanldc ls nn ambfdent lon :rruJ Oil\
cete,a crlt?r\ lhe eltdron defldent she through both (cum I 11.1!1
n as described above. Silver cy,mide b P.
awilmt. Only N•ntom hos elecuon p:air ror t,ond
CAI-C-N:). TlitfC!forc, product 1s RNC
♦. m, ---+ ~ + II
ldiiii • - .a...X
R-X + Aa- C•N: - , R-NcO! .. ~
S.tm q-illide
the rna).,r product in this re.,cdon ls al
not cyanide. Alkyl C)'1'nfde ls otmsineJ
 ' r •J he-O'flth ou ofo1kJf ~er~
~yl he lb:i~ tlJ
jj.()C')"olnide$ ain ~naand~ 521
·
,sst>O"'"
bdow
u .. .. .. .. ..
r;~H~ I I r; can ~ the i.___
--
4tl - - - - : • R-;°"-<li1 o: th,~ ~""""1n ~d"10en: sue diht,t t!uough oxygen
..

dta.r rutrogen (due co a}M: prr;scnec of a lone ~u- o(

tf' • in0 .,-cup (Prrpar at fon ofamines): has tbc~~ i-~wm nhri:c b Ctn Conk mmpoun d .:and
"1~,r:d ,-nth nkoholtc .immnrua SOrut1on -;---u13 Stt\Kn:rr.
~ K. ,he halo-ten b sutnrhut td by 1'1t.2 ..' ,. ....
,111"' 8111Joe ts obu11ned,
,,~ - • R-NH2 • HX
..
~~J ~~Oz .the bond ~Ka nd nnme lon ls Nmic in
an 1 Thcrc{orc, UlC llCplnc di.-ugc o:i oiygcn sens u
~ __. Of3Cll2Nlf2. ~ flBr lladlng Site. Hma:_ an alkyl nuntc lJ obwncd ~n an
♦ r••J Ethllna~. e alqi fiaUdc b trwa) \liah •:s°-2 o: Na.-.:Oz.
(okl (tr¼mi::t -J
('_iii)
11
S u ~ by nltro group (~rq,aru tlon of
ii in e,:CCS:S, n mlxrurc or " l"OCIDcano) : Whci, l.\ lwa.dbn c {i lmltcd wuh Sllffr
er>
pfimary (I')
amfne, 1cn~ry (3'] amine and ihc ~~
r ~ is obtalned.
~
gm repba:d by a nnro poup nnd a
"'"$.llr is oblllinl-d. h'>r Cl.Dmple,,
HH ~ Oi3Nll2 ... HBr •
.._. + :3 Mnlu~m tn: P.X • 4~~ -• R X 0
...--' CokJ (l"amir.r) u 0
:.+ CH,Br - t CH3-1 -11 H)f Cll!mp?t_
• lmr
Oi30i2B , ,. 4,'\0i --+
013
S medrytmeiha:.-~:::::ne. .. 0
(,., lfflW".t) CH3 -Gl2 -N
:,.~O

-
CH3-1 -0t1 - lfSt
11'-.t ra:ntcn u lU(J far rht: prrpa,uuo:1 of ninoolkonc:s.
OiJ
N, N-ill:ndhytmcthaiu::ime (?m · ftftjj S0\-ez nilntc ls a cmialcnt a>mpound nnd b:is the

.
(T a:clM)
.. ..
mutrurt Ag-0-N =O:. Al the Ag-() bond is cm,'ll!e.m.
1 I ' r Qi3 Br -
• I.he lo~ p;J.Ir o!clecuvm Pfddll on nitrogen ac:u as .inacking
r· .. [(Ol3 ) 4 N]Br- sitt fo1 nudfOP.hllic wbsti:utio."l. Hcncr. \\ hen nn nlk)i ~
I Tt ' 1 r ~ ~
(~~)
as ""ated with .s1ku nitnte, the nltritc group nttacks the
maron dtfltian site through nbrogcn :ind a nim,3llmne is
as Hoffin11nn ammonol,ru, of clqi funned pffdomirumtl}
dtt prtparahon oJ am1nr.s. (lt) SubstiNuon b} hJdl'OTillphldc group (Prrpara rion
. , nltrire grou~ (Pr~paration of alk)l of thlol1lmhots 01'. tnn"aJpran.sJ : When a h.ilO.tlknnc is
nes nre uca1~ whh 50dlum nu.nu! uurrd wuh potm1um hyd~ns ulphidc, the halogen gees
the halogen gea substituted br nitrite substinr.td b)· hydrosutphlde (-SH) group nnd n 1h10ilkohcil

F
~ alkyl mmrcs ;ire oliuuned. (mtturpwt) is obwnid.
R-jl ~ K, SH (al:..) - ' ADRSH • RX
- ; R-0-N =O,. Kl:"
lltmt Alkyl clucc ~
¥~~ (a:~
O! ~l1 ~rr.A,an

filroamp l~
02 ot1CHl8r -t- KSH -it Ol3CH2 SH • KX m
(alcnbolic) f.dwtcth10l
CH3CH 2-0-N ~O 'T KBr (ctltr lc~
Ethyl rutntc or ttfot
m., a:ptwa) n of
Prtparation of alJ:yl nimres; u wed for: iM p,:rpatt1rlon of thloaltahob or
11tt lffltion
Ion, nitrite ion is al.so nn aml,Uin,
,ntrtaptr uu. ~ftom
shes, O and N. It exists in the rwo substirutioa by alkyl merapd dc group (Prrpar arion o/
~]odhm) : \'1im a hal0,11bnc b ue1t~ wuh hot tllcohollc
 522 l Nooten lSC CJ,em:istry-Xll
.dvtian of.odium alk}i n.aCDpcidt".. ,h e ~ d subsdnucd 111 al ~
by alkyl maupidt (SR-) poupand a ~ h c,buli~. I l "6
CH3-d'-t'- H f,
__. 1\-S-R• • Sa.': I I
R-~ .. N~fr lb,~
~ll!lt H H d
e,ei::a;:.Ar. l~
t«aample.
01~:Br •
·-
Na...~: OiJ
<!11.:,- CU -
l'rof,:l-c'ne
cu2
. ~q1.waear;'Cidc
... 2......
QJl C J , 1
~tbioctlx:r'
~ :Ot · l

TIit naax,n is u.xdfo,r dtit s,mhtsis of chiatthas.

• ,s•-n.--

013-
.au,

Ot2-d-C
H 11
- II • ~OH (ak.}
I I - ,
(IQ s-llsdlucioa by cad,_oxyla~ ~ {Pl ,~non. oJ H H
~ : \\'bm a twoalbnr is heated \li1th '3kobolic'50luoon \~:ll:fte
olsllftr:sahol a carboX)ik acid. w
twogui S'U subslirutl-d
by a cmtmytm (RCQO-:) group and an ester u formed.
0 0
Cff1-t.H2-
l\vt-1 -cnc
GH = Ol:. -r- Kar • H,fl
n Sa)udf"s rule : \Vh~ \.he ~tt'UClUrt'. c;af aJk)i ~ t
-~~ - K-C-0-R • As,X
that it pennits the formation of t w o ~ tht

~a- !pfo
Sltfl . . u•
a&cq1icilc:SIS pn:dominates.. can tie known \\ith the hdp or 1:1
Nle known ;,s Sa~ s rule. ~:ncff's ru!, Q:iti
.a,s. follO\'•'S : I

\\'hm a hafoafkant am undcrso dth,-dnm~..~ ~

diffamt \\'CJ)'S co Jonn n,-o diJJmnt all:mcs. U"-! 6n:
0
. II prrdominati:s is the most subsrituitd ane. I,(., li!t~ , •
at1 -C--O-O!pl3 • "8,Br aun~ a grttJltr number ofcUo•l groups c.:ad-..td r., ~..
~'1' bonded cmbon acorn.<

- • rmaion u mm/or dit:papa,mwn ofatG"S.

8. BimanaClon ReadiOnS (Preparation of alkenes)
For ~ e . when 2-cliloroWmm. ~ I i ~ "i:h mill~.
KOH. 80% or tiut•2~ ne 311d 20% of but-1-otm
Wbm heloetbna arc hcal2d wilh alcobolic ~ w n lblsis because tiut-2-ene (e.urying two meih)-t~
h)'dsaxlde. lmJ undergo cbe diminMioadbydn,pn halide to 1M doubl~• bonded mroon :stotn$) ~ more
(HI) ID bJD alkcncs. comparison to. but-1--enc (\~hich rnrria ON}' ocie

~ group 1n:ached to lhe doubly bond~ aubon ~

CH3-0l s::10\
R-y-y- 11 • ICOH(ak.l _,.
H H
Cl
I l«tUP
t~~
=:"f~
Dct~.CC

R- at - 01.z • Q • Hi() Oil -GH1-C-Cll3 i(()U (ll~)

Siacc ll1Cla raaiofls inwolYc die: 1~11 of- I bydrogtn I
and a haJosm arrm &om die ti-Joetkene, dlese are known H
2 <tooroti1.11.1M:
a s ~ racdam. The hydrogen atom ~ ctt3-0t:-O
remaved In such remb11 II ■ ,.hJdiolen (hyc1ropn at.om ll..2•1-W
praem at II polidoa. i.e.. ar die cmbon aiom nm u, lhar Ctn!ni'llf".'~
(\N J\l,."!il~
~
~l .
canying die. halosea --1. 'lberelore. sud) laalona ae
abo refened to as lkfladlllidaa reacdom. These reactions Eau 11••~1to11n1Uon:Th~en.se.ofdeh)'\1.....,..,,..-
are used for • pcepa.adon ol 1Drraes Some aamples of of different """-
·ir-
or hntonlknnts Collows the ol\itf '11\J.ll
sudt racdom are sl¥en below. les1lary (3') > scconilnf')' c2•J > rn
H 1bb be aphilned with thi! help of ~~
~-r-H ♦
(an
Acmnllilg to the Sayaeff's rule, durins Jeh)\I~
mM(ak.) - .
the alkene whh lfflltcr number of tt\k)·\ gl1>Ufd
H
Irr
H
, .... bonded cattion atoms ls tl\e preferred prodU~•
~"l.qre._tituttd afkme u mo~ scable andust3
Therifo~ the alkyl tiallde wbich gh'd tt ntort
 Oi
Oi;aJ . .. Oi1I ~~
~
~
- ·
°'>---Oi.J
~
- 2,.\:~

of dehydroba l ~ c( cet Oi10i:3: .. :..~ . OlJOt:~

On-~
me order ~

·~--tpro:pJ.nt! > 24uamcp: p;m~ ~

-
Reactions (Preparat on o· a ~
l!tCOIH:ffiOnding albn~ upon te!di.~ nit
&carried OU[ br anroflhc tollow~ ~
Hi In the prttence of a m?tll ~ ~ er,~ CHJ\.. OIJ ■
~11.c:c:-..c~...... h}~~ in the p ~ «a o«i! ---; /~ Di( .. '!N~
ilkRI, p.-ilbdium or P.btint1mr h!'o."I\:cts
albne.$. for d:lmplt:.
Ol3
:~'"""'-~
CH1 ~
H, ~, ·r.:i ~ ua:IW "uni IQCOOQ cf u 11\W.~· t..-w ior·
,. 52.SK Oi30iJ ,. HS:
~
d:t ~ ~ &:!1=a l\ ~ - '-"' (\'ffl :.:i~\a of ~'\:'t
OlX:1$;
Na
525K CH30i20fJ - t-~ Th,e ~'Sm) ol tm.»lbncs &:t."O ~nei m\ it.1so be
ProfU:ic QtiicJ out ~- ZI\ HO. H~~ ~ ?\-1. li'\ltt... ttc.
-.COpper ~uple ind rur,t 1Ja;bcl : (ii.} Rs-ctiaa ~ ~ (PfrpmJolJ t1 Gri;u,tl
I .1kohol (95%), nQl.~ o.,uplc ru;t::.ts.}: \\'bfcl lw,wbnes ~..-c trtllN "'th nu.ttncsiwn 1n
to co~ndins nlk:mo. F v r ~ di)• ttbtr.:d)1 ~ h.ilijom ~Md
s()H - \ Zn (0Cif4h • .'!H
~~ ~-X • ~~~ ~ °'r, R
'1l._,1~~~
2H --+ C..!Ho -t HBr
ctlu'1t'
11 the presence ot rn pr.os,tto11Sa..: CCllt

rtduti.'d to c:umspond,n.g ,illlines "J

roiodlc- ncid in th~ pn~ntt of ~ >n 01
For cxnmptc,
tit Ital P ,.u MJ -t 11
.QI --. '-"'3"-' 13
430 ..:
;>

.n~.nc
"ed out ,,,th
C3t\ Li~~
nlso be c:im
SUCH ;is Zn/HCI. Sn 1-1c1. • .
• ~in.scJ
de), etc. The mlui~1... ts.
th~ prtparution ofWJW~
 ~~Cl;; ,~.,~Ii.'~ e<'
' f ~ ~~~ ~~~,~
"WK ◄l!lt _, ~IICGQ c:rn ~ ...t, ~~
~~'-cql!!IN'!~~~~Mllt~'"'~

--■ . . - - - .... ,... • "'

~ ) ~ '"'"t ~'tt
--..~~~~rt-..
.. ,=~
----- ...... :

~ ac:... ~ aa cq
~~
.sq< • it !b-a Mf«

~~-~
...
~ac

,.,,
...
«:11:,0t,:lr'. 41b ~ ~ m. OMH_ }.?t,
.... ":l
~
flial!

-~-~ Ci3 CH1

'lma:did .1111111 t'lBJ a ~ a C OH i w i-. ~ a
I I ! ---•aed•a~m 11 w;w, -
0:3--e -OH
- I
-Oi~-c-oa
E. Rea••-JIS e:- q '.IQ,s -z I
SWne,e I Of p M IWWN ( ~ pmc:aa & ah-4
CIW-i ■, o/ 4llr -■a' - - - - adlB a11D11 r&4
rd~ ·hr ne a J . _ baaa:I • s:"3 E • • • Sbw ae I s.,
ilft::, of 1 rmction.s : Them~
Dlll!l'Di 4aa •••PlcwJ t;dma > •
1111\c:.".-ed m Ss l l"C3alOnS a~ rnbot-ations which m

•
dalra:ide-. Fare i ' t.
a J?'['is Smee.a carboc:::::uion as planar. th~ nmu:kins •
CID c:ack on ii ·wich equal ease from lhe either m
Ol,--ot--m, eaer_from fn>m~r from~). Therefore, if,heall:)\
Wt I 9 aan-e ,
ii ClpX:aJJ_}• tHeorericaDy a I : 1 mi'c::rurt of tit
ffl l&IVDCJs should be obtnined. Hence, 1he prodm
be a na:mit mixture. ror example,

Jll:uur nt1boaUIIC

01,-
--,--~.
(FrOflll'll
•
IIIIICkl
 ,,,, 11111 111,111111, ,,,,.,
ti ltW\11 ll i I lllll1 III\ I !fin\ ,t 11111
I tnk1111h11Hi 1 I If
•111 ti h, ~1111I,, i!11lr11111y
I
I'll I
111 111t h~llil,
t "' ' ~, 11,.,, J t,ih
11\1' ~N;,.\ l!iUll'llhull1111 01 dt1i,,,fil/i "ill 11111 111 11 t "'' ••111J11y ,: 111 h ,,,,, ii 1111,11,,, 111 :t,
• __.,, 01 ,, th11w lllll I• n11h1t1r l\t lt•il 11 t hy 111 , , hy I I I >11 ~11 I 111, ,, ,,,, ,, JI,,.,,,,
1 ... 1ttll ul lt. ,lU I1111 tlr pt till
1"":'""-•cl1'"' 1 •, U111 I•h fJ., .. '"'!II( It,,11,11111111!' ,,,,I,,,,,, , _ ,,,
I I ,,, I ,,,,,,, ,,,,
h hh1 1 1II 11 l
, ~ 1111e1 '"' \Y\ tl 1111 I 1t'111,1c,,
111 I II I ll'
111 11111 ~· Unon or f loloo1kom,
'"',~1lhll<" Ihm II sNa lt\11 """ ,, 1 -~·"'
'"' lht• lnll' Ih\V
11(M~ '\ ht11, ~I() JI~ llh I llfl 11
-1 ~ IHuh~11n111 I I1u1,•h•ophll~I 1/IIJ lilt W1J11!y h "ti
11 1 1
~,:flt
h111;;m I • Ill ' 'JI. II If µ !J I
J(:tt1rmlnln11 "ih'J' luvul\'o~ thll 11,11 1, 1r , (1 I ' M• nlc t'(Ju t" I It,,.
~11111, ' ti• div I
'Y11111 t s fit • Ill, ., rl ,,.,, iA
J I
1 111 11 II "'HI'" 'Ylllh11 I I . , , , ~ JF '"' ill~ ll~ 1
tr nnJ I h~ ,,uolcophll1.1 ;A I
(\JJ1111r1,.. I lh)l ll;111',' •ry ltr ,, , '"' ,,. ,,,,,,' ,,~,,, I '.fl ,,,,
--;\Ir tluc,u,-ih n r,nn,.hlon ~' "l' IN ~lumn I r,frlki•r1tnf f ,' ,'1" Ii It tJ H I J,,- 1) II • ti f'llt 11(1 \
b.11blr11r If~ d,u;,1yl itorrtJdr h II ,I for ii' I,, f flulrm ,,r

m.,,•• Ac I

10 d otnPOund :A «lnt.,ln; C41bon end lr/drog,m

II
on Y 4" h,ts rnotoculn, rnou of72 Ila ohotoct11or1nntk>n

'\ ¥..y•e,•· -
110.....
I
l • 11<>-cE~ . a,
\1r1ti.,no1
QI.es flll"tu,, containing onlt ono m.onoi:h10,c, and only
lwo dlchlorohyd,OC&boni Dcduto tho mucturo 01 th.ti'
9
tat1l"g compc,unc, A And u,e chl0ttr>Df.td Pto.Juct,
•rn.. Titc given et11npouruJ h II hydrr,c;arbt,m wlt}1 tntJltUil.ir
fflilis '2f n. Since 11 undcrgO!:, 11utnuiu11on reanfon whc:n
H CtubuitutJun Sl~llaJ 1r~1cd with dtlonne, It should be a 1.111.1r11ttd l11uroc::arbf-1n
IKleOfl:llile (OH 1n the nbo,"t ca~) aunds nnd.should hne rhe g<nmil formul:i C,,Hz.,. Thus,
2
(CH3 Br in the above t.lse) .n the face most (12 • n) • 1 # (2n • 2) 12
existing nucleophilc (Br in the nbo\"t or 11 5

llbd: of the nucleophTic omu-1 trom the Hcnct., the compound" ts ptnt.lnc wirh molttUL.r formula
molecule. ln the rransition st.ace. both Csff12
phile (OHl and the alrt..idy existing The &Jhouxhlonnilncn oi t\ p,.es only one m()nod,Jmo
are partially bondeil 10 the arbon acorn :>.nJ lWD dkhloro deih-adves ThetcfOR. aU rht hydrogffl
t'CUle (shown b,) doned lines). As t1-.t Jroms present In A ,houlil be !dcntlm1, tt., A must ha~-c "
e (Off) is a stronger o~~ lhe elttll'On symmemc:al :muawe. Hence, AJhould b e ~ and
.ihou!d h.:i,c !he following ffl'UCIUrc.
it and c1 pennn.nent G--OH bond is
time. the C- - - Br bond is brokm ilnd Of3
don state from ,be fronr side. The ett'©' I
0(3 T013
ge of C- - - Br bonJ '5 p:ird)' pro~ided
ed in the tormation of C-OH bantl CH3
l. ~-dimedlJt."C~
Sjy2 reactions ~ As menn~u:u
• .,.__,I 31,o\rC'
• (Ml>--~J

the attacking nucleophile tnt::1cks ~ ochlonn.1non it will gi\-e onl) one monosubstin.ited
On phot ::JJld o,uy
_1 (WO disub:stirut~ derh':ltiv~ ill shown
from th~ rear side and th~ ah1'1Jd) deffi"31l\'C
1,aves tJ,e molecule from the front b,eloW: Qtl
-...ch.on as• afwQ)'S Jollowtd
...... ntl b) an
raoon Oil Oi3 I
I CHJ- ..-...02
tfon.. The invtr.,,i on of co su ·,
Walden inversion. I11 • he subsm1eult
1l
OI -(-Ot2ct
J I.
Y
Oi a
ru Cl
37013
Oi -Qfal

OI
- edQS'3re5
bstiturion producl obtrun ,_,tt J
•~~
l
I J '1dlloro.2. l, l ~ l .

I~~
l di!nnhyf~
opticaUy ncnve and has lhe op,,-- ,. • ~• ~
• (dldlforvdtmu:ncJ
ris'<I light. For e,-mmple.
~3 hef of ctiemlcal equation .show how
With ' ~ n • to t-bromoprop4n1 In two
.... / ,.. Br- will)'OU rt2
Oli-.HO-~H s(lps.
C6H13
 .
Wi-bt-013 ~:1 Qtl-OfasOf2
>I p s• ~

-
~
••
fG

What mus 01 prooene {CHr-CH-CH:> is

·~
CH3- 0f-, - OtlBr
Cl f3 -GHJ-CI
Br
•~- Atr'""'-0IJ
2 hmmo,lt'fli..nr

olalnld f,o,n 61.S g of 1 ~on 1reating with

lhnalcKOti.dttMt,..Sb.,.7
11:ra tllit ft9lt'lbl m•OMQJ drh~arion o(
1.a.
t1f,atP¥r IIDll'*i
H
llil.-
...m,..r
o C
11

at,-af-Of,2 .. HBr
~ : ·,..
.,...,..... ~
Clllll--u,-,"*J
CH3-Cl 12 -Cli=CH--OfJ
ma GI I O CI • - · pa PftlPC,ik • 42 I N-nr •2 fflt'
Cmujor fl'NUct a ~ IOtht ~t:.d',
61.51.r1"-r: IJfioSW .rill sfYr P1'1pC!De'
Br
42
-1161.S. 21,.
ID
I
CH3-ot2:-0I-CH2-CH1
.........,....,. . rmabaisonly ....
J«>H (ak.)
,.___,_.,,'41\fiG•ckllawd --->,
-HBr
CH3-<!ll=CII-CH7-0ll
Pal!·1--cPC
21 •40 • .... Am. (tht-ont,~)
100 _,"
Si~ lhe gI,·cn alkyl haJfdr gi1,•cs only 1ienc•!~•
- - - - , . . . _ ~118r OMi _.., Plflt-1--.e l-b~ntnne nnd .shoutd hnvc 1he rollowu,s
.._ rs, rt , • a:iotta1c KOH. Wttte the lltructuraJ CHr-Ofz-CHz-CH2-CHzBr.
fonnuladllllt-t1IIIL

!REVIEW EXERCISESj
lilt•-.... ~ IS. £:llf)brn 1t1t, following bt1l'lly:
(IJ Al~, h.1lo.1lk.111~ lUt! por;ir In (hJf .
.l(td
n
"-•~
.,11..2'.cM
- . . .....,~ ate fMOlublc, fn W,llN, ht;,ttf
~ - o l ti.o C'II) The bo.lins pofnl o( broml'k-th.1nl' ls
ailbciil .... eada al dtlorocth,rno. --1n1 #'
fftll ttbucyl lNomloo h,u a fowc, 1,<illh•Ht....
b , ~. , on~1
1J. av, ~ lodlck't uJually ot.'<'0111(' bUII\-I lfl<
11. Why do alky.l halfdes !tho,.. nucl,"~
on taalonsl
11. ~ lhe lc>Uowlng in tho ore"-"
ol lnCtl'~
,noc,dlfflt"
~ ~ U o n, Ctl.1CCh(tlp
1.f. Howwifl CHJ0t1CJ, ett1CJ ICICHJ uod O
a, Q\'ift!iSOM.
~ a 11c11,c;• cu ,ct ,u~Hi , ~ ~
"c,tl-
(IDhallOP"~
mo
\L n. ~ , : j / alkyl chlodtlc ;;J:
h~~
to ihit ~on of alcohol,. w rot r'.....-
OYJ
OA tlJcCfJft arc the m.>,
~=--.:r
 ng rn the ntdc, o( 11tci,
......,¥1fllfk sutxuruuon fCcltilons 'll<1t.1drig
GH,Or, CH,CI h
IAns. Ctl1f cH,a CH,e, CH11 ~

1.
),
(bromommhanc) to ac~Ic actd lS

IO 1.h,omoprop.lnc
ID 1-bfomQJ>r~p.1n,..
Ide 10 f~>ropyl hrnm1dt=
ro ethoxyci.h,me.
ao 2-bre>m0f>rop,1nc-1
h.ilo.1lknnc:s g,w ,1IJ...yl cv~nlib "tie,
but give ~•llq;J lsotyJnldes \vfrh s lvt1

e«ectl fJCpl:tln \'Wllh a "u1c.1bl ''l°d,np;e.

wuh hydrobrom,c add

w11h thronyf cl,foode;
w 11h phosphOrils rnbromit.k-;
'tlp,ln\
:ued ,, ith :ikchot,c itl\-cr C"(,,nide-; I t.lnt-
,d,~
he.'llt.-d ;it 573 kl
2'. ldt,it1~•1hetompound,. W:} .andlrne.xhcilht-l'ol~1~
9cl wlll h.we the lowest boil rtgpgint
11\ns. 2 t.h!oro-2-meth11p,op,w
~ °' K'J(tiOrtS.

1ng re.1cr,ons. (iJ CJ\lw 41c rot• X ~ ) ~ .z

~:de ~ :.c,, tt,O
l + HBr - -• I• CH:-oi1-• X -, > ' ~• Z

----~
Alcoholic:: KOH

Bromoethane, e2HsBr
-
lmponnnr monwlogm J c,i\,:,lhtt
le synthesis.

moethane
by nnyofthe~ n,ethods
d~aibed e.irliet lcs bbbRICM)'
are discussed ticlow,
Bah I bromide con (Oll,~oitntly bt
f
by headng ethyl
~ 1with•
e and concentrated
~-
-
, of
 l
528 Nootan isc Chttrn1suy-Xll
Th~ mtuure or elhyl bromldc and water thus ob1111.ned •~ e. Physical Propenies of B"(\rnoeth
5-Cp'1.nntd ,,ith the hdp of II sqt.1r,tting funnel. Ethyl bromidt
(t) Ethyl bromide is n colour1C&..\, 1'-~ tl
thus Obtalnl-d is ,,.ubtJ ,,i\h Miler followl!CI by sodt~
Uquld, •~• l!t,~
C:Ubon:ne solution .tml finalh· \\ith water. It ls then dn
(ll) lt boll~ :u 312.J I<. ~
O\'cr anhydrous mkium c:hloridt' i1nd 'Ina}' funh,r be purified
b)· dbt.Illiltion. (illl II is lnsolubt(' in wmcr but llfsl0lv'3
such M nlco'hol. ether, cue. L'\t>,11.,,
2. Manutactun : On conunttdal .5Cllc. ethyl bromide is (t\'} It ,~ mfl,lrn111nbtc.
P~~ by uu~ cthyk~ with hyd~cn bromide in thc
Presence of anhydntt.is .ilumlnlum bromide. c. Chemlcol P.rope,tles and SynuietiO
Brornoe\hane APr!.t>
..
Ql,.-==:QI~ - • tmr Al!li) Ol3CH2Br lith}'l bromldc~lbhs nU thcchcrnlc.,t rea
Ethylffle: rt'qUiffl! fot: the process is obtained by cr.icki~ or or haloolknncs dcsmbed carlfct A sumll)~1OJb~
petroleum pn,duc:u. chcmknl rcoc:tions nnd S)'nthetic nPllHcini!~~~;
lroH(aqJ ~
orJl.l()H (Preparation of etl1yl alcohol)
01..0.-...
CH3cn 2-0-CH3 (P.repamrion o/ methyl c,hyl rrher)
C:ff~a
c2Hs-O-~Hs (Prepamnon of diethyl ethcr)
~
..
c~_H2--:e-cH (Preparo.tion of but J.ync)
,:cs {
CHlfill~ (Prtparation ofethyl C)'Onide)
~(uc.)
CH;i<:H2NC (Preparatton of ethyl isocyanide)
Mll(ak.J
Jm CR3CHiNH 2 (Preparation ofethyl amine)
ICNOi
GH3CH ,r-0-N =O (Prepcrrocion of cthyLni1rit¢)
~ •,/0
Ol3CH2 -N '- (Prtpanulon of nicroetha.ne)
mt(alc. "o-

CH1CH2Br
.-
HaSat,Pl,
01301i5t1 (~pan.uion of ecl1yl mcrroptan)

CHJCH2 -5-CH~H3 (Pieparadon of diethyl thioethu)

OIJCOOA&
Of1COOCH20f3 (Preparation of clhylttc:etalt)
ICDtt<ak.)
CH2-=CH2 (Preparah·on of ethylene)
Hj/NJ
.52SK CHr-Cff3

Z.VCU♦ (Preparation ofttl1ane)

CAQII

......."'
Na
Ol,-cH3

CHPJ:zCH~)
CH3:--Clf2-M1-Br
CJ>i'tpararlan ofburane)

(Pitparatio,1 of C-ri8t1Qrd:i n-llft'llt)

--u
1"'
A
0f1CH21J

(CH,CUa)2Zn
(Prtpararion of etflyl llcla(um)

CPrtparar1an ofdietl(yl :inc)

(ctfaCHJ)4Pti cPrrparg1i0n of tcmittloil ft(ld)

,
 ne _____ ~~-h

·d Is us~d ns ,,n cthylating.,1, 111 In r -~ ...~

...., °""°" -----.;,;;;;;;;:~::::.J....;::::_
fbJ r,-. ~a n d ~ ~ I s29
.....,, e °'ll-lnlc ,,....,. , .._ .... 1"'1on,i, a....,..,_ CUI
., ........ "" '"° ..
~- n,pnring b•rbn •••<e d"'g,. ~ """""- n,,
~ ~
• • ""-·•.
........,, -., o,, "'"')
~•:. annes1he1ic und r,fng,r, 0L
~ ~--• ns a solvent.
lho f,/~
(i) 8'eac-.an
"""°"
f/loJof..., "°'"••l Qi,,, p1.,a,
;,:f:,
2
,/IP _, <aldu,, Jii~. tatu "hi, - "' !Iv. <hloria, 1od
rogen Compounds c.oa, • H.,o -. a, . c.,oHJ,
unrl< tonrain,ng mon, rhao .,,, ,.,,.,,. II) Oil rw,,..,.., ofdt/o,/n,)
':ur" ar< <01ful pal;,hol"X<n "'"'""••ds. <hlori,,7" llu, °"""""•"".,a""'""''""°''"' ,,.,
0es "<t!Ol'lt tn forni u1d1~onc.
d
Cff2 ~ ..
CH3-CHC12
I ......,,...""' Ot -l II
0

, dllorid<I (""1lldn,,......, ~Cl, • Jo, ~• CC,-c-o,, • lflO

CHCl3
Br Tridllorormrhanc CCI,
TtnldiJc~ 1-., 11,1i~2.,.
) ( • ~•...,,._r, ,n' (Cllrboq~,LL.,·;')

~-. ......, IC!llo,...rion)

subsccdons we >hall d:.a., ..,.~ (ii;) Tdr~.., lb,. r....,i h h i ~ b; caJdum
ogen compounds. h;"d.TJtidr to il\'t chlorofonn. •
r frichloromelhane, CHCJ CaCOfih • .....,._
2COlCOO(J - · .......,, -.._,,
20-lal • (Oi3COO~ea
3
die nam.,15mcl11oMmethane Is lhe ln<hJa111 lie us, o/ ..,,.,. • ....uy - ., o,,.,. ,r
....,i.,ne. 11 rommonl) kn01,n archl.,.fe,,,,_ ah~ ~"'biol i.e.,.. i• ,;.Id h binoc r.,01 lhc bbor.,10,y

""''°"of..:,,..by""""'-..
,J ,~pa,,,;,, of d,fon,f...,,., o!bLa, ..i.... of l<ldium
of Chloroform "-"""' (oblain.s 1n, O>ld ond
_.dS :
f Chlorofonn ;, pn:p.u,d In the dJlu, "rdmfd,) OIJJ' oho bo ""'1
dng ethanol (ethyl alcohoO or ptQp,cono mp1aoo ol hlr,chiog ,._dtt In thk ""'· "" lutJofo,,,,
bicnchlng powder. The reacnon is cal!al 1'CailJn Proceeds u fol 0\\1
,iilloa. This method may also bo U,.S r,, thi Iii.OH • a, ~ s,oo , N,a , H,O
~ • ofalcohol)
tliiiiil (ethyl chlorofonn.
: Whena past, o f ~. r,,,.,.,,.,;,. "'°""'"' h1J'O<hlorir,J I
It lb h,.t<.-d with ethyl alcvbol dilono~ O II
0
·on (haloform rtacnonJ tam pm 111 -ell CH 3SJOC - • COl-C-ot1 • JNaOH
reacts with w111er to ~,-e WI\IOnt
ruJ - 1•' T~
. Lt.. ai:d (C'1JO~

0D •••···--...
••• •
Ofl ..;(-Ct"&.
.•--;; [+ ~Jl -
(Libtratio11 ofdtloriMJ ~
•ned nets both 11S 311 O.uw.13bbol inro
..-J:;;..4' as well
OC!J + CHJCOO.'o
c. h first oxidlsc.s elhyl ~" C1bdarm ~aaaic
•
ihen cnlonnatcs u ..ln:de
nreta~• 1
to V,
Qlyilrofyru)
(chloral) as ~hown bel0\~C1 . or chlorof0n:1 in the IAborarory. 3 thin
-. ett3GHO + ., r« lhc P"p:ir:1~'1 ~er Is made b)' miting about 100 8 of
F.lluml p.tSlt o( bk.ldlir.); ~200 ofwattf.. The pa.sa~ u transfemd
(OMJhldt]dt)
..:A..1 ..IJICA"-
( .... ..,.1•
, •..;1.r~~tler~1th
tom,r.ied ~J and '25 mL of .xrmnc ls •~ded
UXJ-'1111....., iruoa round . fi td to :l a:mderueund a receiver ns
,.. 3H0 1be tl.uk fs now m iv heated when chlorol'onn
CC13CHO to 11. • Fi -, 'The 11:isk is gent,, •..., ~•·ncr wuh
2, :z. 2,Uldl /tj.Jt .,..,,,,a
lian,edi.WI
~••
sh(J\\n Ill" '•~·.utd
0
-
st• "'Uc«Ni
. , tn lb1!! r,tt1t
mlxt= ..r wu.-o
of chlotll(onn :tnt1
/lrfdl1-14, a,Jori,tadDnl dow> 11.t dl,ttllit< willdt u fuMd. Oilotofonn 1hu,
t
h);!Jol),td """.
•hydthus Conn~ dlloroixlll-
od /Jr' 1<J>,Ulllllll noo fa11-,d by
.-,HJ • ~-,,t,<,I with dilute aJIIIIU ..i,c,ldwtt chlorld~
roxide lO gl\'e nan"li)t.r!l ~ IS " dritd oru wi)'Cirws
2CHOJ ~ ~
,~v-n- It is 1ben .
widl"-atet _...RM bydisolboon.
_ . Qi]orO(onD fd# ~abtt-.....-
~ llmJ)'
 530 I Nootan ISC Chemt~XII
(,·I) fts vnpour1 wlic" inhnlcd
unconsdousnc.ss TI,erefor<: fi ' t:lu~
nn nnocsthct fc, B~.iuse of'horrn~r1,. Ii ~
tonger In use. s 10lic ~, ~ ~ '1
u,. '".;
"tt\
c. Chemrcal Properties of Chloroform
Sorne lmpononr chemlcnl propcn ,c~ of
(oltow~. chJoroft,:
(0 OddaUon : When CJCposcd to nit and l:l \o.
gets oxidised to fom, n highly J'l91~onou .tuni,tht ,
d1toridc or pl1osgene. ' RM ~,~ ~
Sunlight ~
.... ZLlbot1tcxy PttP,lflOOft of chl0f0fonn1 2CI 1€13 l 0 2 11fr • 2coc11
2. M1n11J1clurlng ol chloralo"" : on tnrgc m,tr. chloroform is Cllrhor11l Clllor!Jc • 2#tJ
uaunlly prcpattd by lhc following ml!rhocb. lph01rui-)
(a) F'Joom methane : The chlorin.:nlol\ or meihnnc In Since pl1osgr11c i.t htgl1ly poisouous, flt
the prescn~ of sunlight gi\~ n miJtturc of nil rhc four cl1loroform unfit for me as an anac.uhwr flrtJ<tq ~
chloromethnncs. Stora.gt of clalt,rofol'm : In ordt?r to prevent the .
0,2 c:hlorofonn, following precnm1011!i should be obi0~ . ;1
CH_. Of3CI -t CH2Cl2 s.,fc .storage. ~~,
Mdhiuw hw- °' 67S IC CJ\lotQ 01dlbo
mrtho1nt ITl('Ihanc- (") Chloroform should be stored ln dtirkcot
CHCl3 ➔• Celt to protect it from sunllght Dnrl< colour~u~-~
Ttkblo«> Tl'tnldlloro off light and protect chloroform from bci --....qta
mnhlnt mel,Nn(' ,
( b) The bottles containing chloroform s-ho;~o~
(dlhl,tfon,t) (cctflon rrmidlkridt)
up LO 1he brim and stoppered tlgh1ly 10 'l'rriiJC;
However. by adjusting the mrlo of chlorine co melhAne :tnd presence of nir lns1de the bottle. ~
ualng a suitable catalyst. chloroform can be obuuncd as the (r) A smnll quantity of ethanol (0.6-1%) should be~
main product. O\Jorofonn ls M?pnrnrrd from the mixtun? by to chloroform tn the time or pncknging Ellwiol1n:1
(racdonal dlstilLtdon. •
with phosgcne (ff formed) nnd c:onvcns ii r:orm
Cb) Prom cubon ~lnlehloridc : Chloroform can also be poisonous diethyl carbonate.
prcpo.red on a ~ S0llc by the p:snfal reduction of carbon 2C:tHs0H + C0Cl2 - ,
rctrnchloridc with iron filings and stcAJn. £,h;inol PhOJgcoo
11111 ff•Stcui
(porsOl!oui)
CCI◄ + 2H - - - - - . CHC3 ~ HO (Cil t5 )aC~ • 2!ll
Dkth)'I wbonalt
3. Pnparallot1 of ..,. dlloraform : Pu~ chlorofonn can be (nCln•~)
obtained ~ heating chloral hydrate (CCJJ0~0-H2') or
0l3CH(OH)2J '!'_~~fum hydroxide. (II) ReducUon : When treated wf th zinc nnd hydroc.hbiao!.
-·.... .
: :-...
•~ptC>;Hz() + NIO H,- . a-ta,
chloroform ls reduced to methylene chloride
Qlofal ~ a.Joniorm CHCl3 + 2H Zn ~HCJ CH2Cl2 ~ lid
Dlcbloromcdi;1oc
+ HC00Na + H~ I (mrtlo-/tMchlon.!tJ
Sodium ~
When reducLlon rs cnrried out with zinc dusl 3nd ~
8. Physical Properties of Chloroform methnnc Is obrnlned.
Some lmponanl physical propcnles of chloro(onn are u CH€l3 ot- 6H Zn duH. wa1cr• CH4 • 3Jl(l
follows.
ota~J
(I) Ir Is a colourless and heavy Uquld with a peculiar (111) H~drolysls : When bolled with nQueous follllJ
slcJcly smell and a sweetish burnJna '-'· potassium hydroxide, II geLS hydrolysed , s~;~,!1t.
10
(Ji) It Is heavier than warcr (sp. ~ 1.485). which combines with KOi i lo give poross,um
(ill) Ir Is pracdcaUy insoluble In warer bur JOluble In most
ofOl'1Janlc solwncs. It can dissolve IUbnanca llke oils
fats. waxes, ere. 'Jbus, It II a good solvent ror many
organfc substances.
H-r/.~CII
~
+ 3K0H -_"ifci•
Oilofofonn
Ul\l(~Nt
j[u-~I 0
(h) rr bolls ar 334 ~anti rreczes at 210 k. o II rJ
(, ) It ts not rnflilMmlbte bur when a Bunsen b(riiier Ii II ~ H~~
--► H-C- OH -H1o
1
pla)'ed on It, Ir vaporises and bums with I Ptelt Nl·p....
edgedfJnme. - H20 Fonnic llCfd
 • ylhen (l'eaced wi~ ch!orine m the PrescnQ!
;~r. ~~dO~ · undef8oe5 chlonnanon to Zive
1t
t':1..4.--
-:uuun
~ K, 2,tJ)· d r~kao~
~ and Haloamnes I 531
as the rnajor Pl'Odua. 1nttll)de _bal.lcylaldch}'de) u obtn.incd
~ ~~e- suntiitht ca rtflctio,i O?acnon is caUet) lll!uner-TU!ma.nn
,_ 0 --~• 4 'HQ OH
.... tt1, -t 2 Teen chloro~1~
(tarbor, ettlatJilon,k)

@.
C)P'"

• Chloroform .maY, be nlmued by conc:ena:ntd ~-3N;tltt ....

..-dOII •,. ..- chlorop1cnn. ~
pt,»~·ro10•"' He.it l
'""'~... 6fcl N02 - · ex~ J"N_Oi ~ Hi()
~ ChJ0101l1cnn
Ci is used as an insccclcide ,ind as a war gas. ~OlO • 3N,o f 2H:,O
~ 1 rne reacllon : When chloroform is Ylarmed with "Z-~
iij ca,t_, " '' mode or ahpharic grirnary amine and alcoholic ~)

:.:J°:;h
,~ble o,oh corresponding isocyantdt or carbylammr is D• Uses of Chlorororm
has an em:emely offensive (unpleasant) iTh -
' utrpo~t ~ ofchlo,ofonn ~ as follows.
(,J It IS Useii as an anaesuieo~ As hs slight overdoses an
,i,J- )!! + cy 'c'fiil • JKOH dan&CTC>usly lOlic. its use as an anaesthetic is oo, much
~s~, IB en/ lftl (llla,lJolit) Prei'emd. Nowadays it bas been replaced by some
other more Silk anaesth.e.iics.
,,,,;,,,,,,Anlltne
aromauc• amine
J ) Chlorofon;i
(II) It 1s widely used as a solven1 for oils; fins, rubbers,
restns, tl~
Warm G~s--\,•-•c + 3KC1 ... 3Hz0 (iii) hnweilmthepttp:sr.uionofcllloroplain.chloretone,
Pb.en~! ~nfde e,c.
(P.lleo,f mrbj{am,nd
{I,} It is~ as a pr1?:Se:rv.:uh e for arunomical SlJC?Cimens;.
M h is used {n medicines;.
'- CHC13 .;. 3t<OH ~ 1
\"i) lt is~ a.s a bboruory reagent;
Otlorofonn
2. lodofonn orTniodomelhane. CHl
3
CH3-CH 2 -N - • C ~ 3KO - 3H 0 lt LS n Di 1odo dmvam~ of methane and firuh sevm\l
2
E!h~l i.1oc)-arud~ phannateutiatl ond ~nical appucauons. It is commonly
(ttl'\Yf c:arb.rfarnlrit:) known .is iodoform.
Cue ro Its highly unpleas.:int smell, the carbylmnin~ formed
A. Preparaooo of 'odo~orm
•die l'tldion can easily be 1dermfied This ~aion is c:alled
~ ~ on and ~ used as n test for botli :iromatic lodafonn is pl"fpared by tieanng euianol or propanone
led lliphaac primary amines. wnh an 3lbli ~d M>dioc The ~Ctlon ~ c.illed haloform
reaction.
fl) liWa11n1t1on : When chloro(onn is heated with Sth-er
It unde oes dehalooenauon co gi\-e acetylene. ll) from eLAnol (ethyl ale1>hol) · When ethanol is heated (at
Cl -==io, ·
about 60"C) Wilh iodine ,n thi: presen~ of nn ruka1i (Na.OH
0 + 6Ag + ~C--H Hw or Na1C()J, iodofonn ls obt;itned When tl\e ruk.a1i used is
~ : : - -__ g NaOH. the maion rakes place as follows.
Ch\010rorm {ol Na0H f\:..l(tS wnh iodine to fonn sodium h)l>oiodit~
~\iJOH .. t.. - NaOl + Nal -.. H 0
.. Sod 1-t)--poiodhc 2
K-c-C-ff t ~
Elh)11e {b) Sodium hypolooite thus 'Produced oxidises ethanol co
(auljfm.tl
tlh:utal l~ce0ld!h>'ttd.
lion With acetone : Chlorofom, condenses with
~ Pre~ence of pornssium hydroxide to gt\'i! Otl CH,OH -
-+ N:iOl - . CH3CHO • Nal "" H~O
El~
~ (orua.l~f\)llt)

(Oxtd.ation)
(c) Elbonnl thus formed under&oes iodinntion to fonn '2. 2,
2-ufiodocth.,n:il. J

Ch)otttonc at OiO :I': 3~fa01 _,. Cl3CHO - 3NaOH

~ as n steep inducing (hypnotic) drug. __}l~dt)
.) -:.. 2, :1-~b,.-uw
(cnfa!i, arm:.ildt~)
< - I
n reaction : , vhen chlorofonn is ~ea~ <Iodinatio,o
SOdlurn hydro~ide (or pot. h)-dro;ode)
 532 I Nootan ISC Chemi5m':-Xll
0
(d) lliiodo acetaldchyde undergoes hydrolysis (cleavnge of
II
C--C bond) to give iodofonn. c1-13 - C-Cf J3 +. 3J 2
,- .,; : :.. -.. ---,.. ... -:-~ '--~
~13 CHO + Na>\
... _, ......
H'• --•lodofonn
CHJ3 + HCOONa
Sod. (offfl.1IC
Acetone
0
(Hydrolysis) II
CHl3 + GH3-C-ONa ._ JNnt
The complete reaction may be written as lodofonn + 2CQ
l •~
{J
Oi3CH20H .. 412 + 6NoOH
Etb.ano1 Sod. h.>iliodck 8. Physical Properties of lodoform
CH13 -+ HCOONn • SNal + SH20 The important physic:.,t p1-opcrtics of iO<I ,
rodoronn Sod. form.air • n ye11ow crystnllfnc !iOlld hnv1~ 0 ~ art11...
(i) It is
When sodium cnrbonate is usc.-d in pla~ ofsodium hydroxide,
the reaction Is (iil It has o chnmcteristlc unplcnsnnt:: rn.p.392~
(Hil It is insoluble fn woter but solubf~ ouc
1
CH3CH20H + 412 .a. 3Na1 co3 Heal ether. ncth)Ja%~
E.dwJot Sod.~ I

CHl3 • HCOONa -t SNaJ .. 3C02 + 2H10 C. Chemical Properties of lodoform

lodoform Sol fi1mmr The chemical behaviour o( lodoform is al
(11) From propanon1 (acetone) : lodoform ran also be prep:i.red that of chloroform. The onJy diffcrcnce is
by bearing propi1Done \\i th iodine in the P.resen~ of an alknli as co!"parcd to ch.loroform. Its imponant
are gwen below.
1
ca
~~
1~
lasi:t clt;on
,:~;
(NaOH or Na2 COj). On using sodium hydnmde. the reaction
takes place in the following $1eps. (I) Stablllly : On heating, iodoform decomposes •
1
(a) NaOH reaas wi lh iodine ro form sod.ium h)'J)Oiodite. vapour. Presence of air, moisture and light ~rrrt'ti.:i
2NaOH + 12 ---+ NaOJ • Nal + H1 0 decomposition o( iodoform. Due co liberation of fi ~
Sod. h)l>Oioditr iodoform shows annstptic action. rtt....._
(b) Acetone undergoes iodination ro form triiodoamone. (rt) Reduction : When teduced with red pb~ I?
0 hydroiodic aod, it gives methylene iodide.

Of3-1--ol3 + 3Na01 CHl3 + 2 H P◄ -+HI CH2l2 t HI

-
Propmoor Sod, h)-poiodale DlfodomethJnt
(oa:iont) (m~il,yluit Eodidt)

0 (UI) HydrolpJs ; When boiled with akoholk ~

II
013--c-a3 • 3NaOH hydroxide, it undergoes hydrolysis 10 give formJc addc
l.l,J ~-2-onr
{aflodq aaront) combines with KOH ro form gorassium[fonnate.OH l
(c) 'Jffiodoacerone undergoes hydrolysis (deavage) to yield
iodoform.
(Iodination}
~
lodo(onn
OH(cic.) -3KJ ➔ H
~:1~
0
II -----------
CH3--C-~_::___,.H.pt,za ---+ 0 0
'nfiocfoet:a~ Sod. h7dmfdc
- H10j
II
H--C-OH
~u~
-HJ.O I
0 Mcthonofc add J
II (f~nn(c add) ~p
CHl3 + CHj,-C-ONa (Iv) C1rbrJ1mlne reaction : When lodofonn ~ ~n~ ~
rodofonn Sod.1CCWe (Hydrolyrt.,J 8 primary (1") amine (aromatic or nllphotlc arb)~
The comP.lete reaction may t;e wrfuen u caustic potash, a corresponding lsocynnfde ~\t) Slfl',w
0
formed which has a very unpleasnnt (offc

"
CH3 i--C-CH3 + 312 +
Aatont
◄NaOH
Sod. h)drmMc
0
example,
C6H5NH2 + CHf3 + 3KOH (atc.J
~

AnUlne lodo(onn

CH13
rodofonn
+ 3
+ II
+ CH3-C-0Na + GH2o
Sc,d, M'.efate
When sodium carbonate JI used 1n place ofIOdJum fi)'droX,de;
the reaction ls
(J• aromatic amine)
 + CHl3 t 3KOH (ale.) ~► Haloal~.an~ and Haloaienes I S33
01,rafi~ (odoform Whtn a CllmPound •
~ lilt))
St<111p ls hea1cd • conra1nln& CH)CO- or CH3CHOH-
(!!!"~pc ornrne SOd1Um ~ilh fodfnc :ind an aqueous so1uuon of
(t'~ Jtreril1llCl.rbonatt' (or S<Jdiurn l1ydro-udr). a yellow c.oloun.d
CH3-N - • C • 3KJ • lli20
t-1c1hyl i,ocyanltlr: o:rrdt,,- ~~~ •ocJoform h obta1nl!d. Tue rearoon Im.-oh·es
d hLOil. '11G""" •1nd ll)'dtoJyru (clez,ilgc. of C-C bond)
~
(mcur,I CJJJbyf11mfnc)
:; lod0 0alrt-Jdy been disa.u.k(J In dc-1~·ul (.see, prep:mJtiun
. When heated \Vith silver powder. h r?.acti nn from ethanol and prop-anone). The complete
iwa,lol'"allofl enation
• to ~ve accr.yleoe. • fol~ns for ,thanol. propan-2-onc :ind P.fop3n-2-o1 are as
pl.,.
I'' ~ ~--
,_c,es•--•••· 61\ll----• ----,CLI
f3: r ~►
IIP'"attl)•• !'.--- ."l- --- "iodoCorm Otl0120H • 412 • 3Na2C03 - · cml
,_,tonis luunoi 1000,om:i
(nllDwr,r.)
Elhyn,. • llCOONa • SNaJ • 2.H10 -'t' 3C02
(a.utyl,nt)

1 Ith sliver nitrate . Wbe-n iodoform is heate,d with

~~•d "'1YI niuacc, a yellow coloured pr~pila1corsiher Ofl3
, ,_.....i~ s1 ver . . heh . .11.,.,. Jodo{onn
,svi...-- 0 t,cained. Jn this renct1o n, its avsour lS \lll1l'.fent l)dlol,, pp:.)
pf,lfe i, 0 r chloroform which does no, fonn a preopinue
toll that • Of3COONa ~ 3:-.T:il ... 2C02 + ll20
Jklrsih'et niuare. OH
I
DUseS of lodoform Ot3--cli-O-t1 .. 4li - 3Nn2CO-j-;. 003
· flllportnnt wes of fodofonn are .is follows. Pmpm-1~ lodofonn (ytllow ppc.)
1kl.i) Ir ls ustd os nn anclsepuc for dressing .w':unds. The - Oi.lCOONa. .. S~nJ - 2H10 - 3C02
and.septic action is due to the 1.lberaced iodine. Applkatioru of lodofonn. test ;
M Jt ls used in the manufoctunng of t'fflain , lodofonn test it wed for the dcteaioo of CU CO- or
3
plwmnceuncals. CHlOIOH- 3nJUl> \lt an organic compound.
(li) lodofonn IC!:51 c:an be used to dirungutsh ~raJ p;im
tlodoform Test (Haloform Reaction) of compound... So~ imf>'.Orram patrs rm: given i"n
l is an hnponan1 test used to detea cru: p ~ of Tablt3.
0

-
II Table 3 Distinction betwffn Some Palis of Compounds on lhe
~sat lodoform T~t
Oh~ group ln a compcu111d. The tat tS givm by all chCR
s
~ i1t which a methyl group is dirm1y anach(d LO a No Patt of CDmpouods C4lmpouno which gives 1

PQ:SlllVe iodofom, tes&

"""'-p (CH,J~) 0
or bj, th, compocmifs whidl am
l,

2.
Meilunol (mah](~-
and cth";mol (dffyl akoliof)
Eduno1 (trhyl alcahol)
Ethanol (ethyl alrohol)

Ethanol (trhyr a.lmho()

II .ind propan-\;ot (n-proPJl
alcohd)
,,___ CH3-c- group upon axfdarton. te.. by tht
J. Pn,p;an,1-ol (n•propj( Prvp.in-2"'.'0I {~ropyf
OH

~ COlltainin.g
a1tohol) ,ind prop.1n-2-ol altohol)
CH3 _}:__ group. Thus, ethanol (iu?PnJP]f abhol)
I
I 4. 8utlJl•l-ol (n-ba,')'i a.'a>hol) But.l.n-2,,ol ~-bun-f
ulcnltof) -
lnd lfuan-2-ol (.1«,fidyf

[:H,-!~,}P~~~2
11

c.1tohol)

r ff} ~ --2-ol
s
I
Z-mcdi)ipn,p;m-1-ol (isohuryt
aJrohol) 3rid buem·2~ Cs«·
tiiiij-f ak-c,hol)
Butan-2-ol (uc-bu')'I
ckoltor)

l
6. Mtlh.ln:i.l ({annal~) and Eth:uw ( o a t ~ )
cth:111.11 ( ~ )
7. Elhana1 (auu,!Jth.)-dt) and
ff Qi3 , lactic acid [ CH,-LCOOII •
8.
prop;in.,1 (propanalJth.)dt) ,
Ettun.,J (ar&raldt'Jydi)

Pentan-2--ont' (mdhyf P'DPJJ "PenCJn•2--one (m¢ayf

k.lto,icl and peruan-J.onc J1'-0ll)f ~ttont)
(ditthJi kttont)
io tlils test. The rest is as follows. I )