Hydrocarbon NEET Study Materials Download PDF

be b bbeebb bbeebb bbeebb bbeebb
ew bbeebb ee bbeebb e e eew bbeebb eew eew

vi ee w w w w w i w w i w
i w i i w eew w i w w w i w
v v
ww
ii vvi i ww
u
i i
vvruuvv w i i
uu
i i
vvruuvv i
r u
r u vvrruu v v vv
w w
ii vvi i w
u v v i
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i
u
w
vv i
uu vvruuvvi
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r uuavv
r
uruarru u r u r rr r a uu r u u rr u r r rr r
r
alailila
r
alailiala
ilim a
alailila
ilim a
ilima
l ii l l a r
lialariliala
r alailiala
ilim a
alailila
ilim l ilila
a
ilima
ilim m m m
m m mm a m i m m m
m m aa//ttam
mm a
mm m m
t/taea//ttaa ttaea//ttaa ttaea//tta mmtaamm aa mttaa aa//ttaa tt
t//taea//ttaa /
eem e /
eem e / /
eem e/ taa
//tee// t / tt
eem/ ee
// /
eemee
t
/t //
eemee
eem e m m . m eem m m m .m
/ t..m/m//tt..m
t / //
mm .
tt.:.////tt. m
/ /
/ /
mm .
tt.:.////tt . m
: /
:
. .
//tt::////
/
t t .
/ t
/ ..m/m//tt..
t
m
/ /
mm .
tt.:.////tt
/
.m
/ /
/
. mm
tt:.////tt
/
. .
: /
: //t::////t.
/ t . . t
/ // /
ss:: ss: ss:: ss : sspss / / /
:: s : ss:: ss : ss ss
ss::/ss:: ttphpttttpp ttphpttttpp ttttphphttttp sst:p:p/ss:: ppststttpps ttphpttttpp ttphpttttpp
t tttphpttttpp t t t t h h t ttpp t t t tttt t t h h tt h
hh h hh h hh h hht hh hh hh hh h
b b bbeebb bbeebb bbeebb bbeebb
we ee bbeebb eewbbeebb
w w eew
i w i w
i w
eew
i i w e e bbeebb
w eew w w w
eew
i w iw
i
iwvviw iw w
vvriuiuwvvii w
vvriuiuvv i v iwvviw iw vvriuiuwvvii vvriuiuvvi
uu vvriuwu r uu r r u
r u r rruuavvrruuv uu vv iw
u u r uu r r u
r u r rruuavvrru
alariliala alailila r alariliala alailila
l
alarrilialar
ilim ilim ilimalailiala
m m
ilim
m alarrilialar
ilim ilim ilimalailiala
m m
ilim
m
m m m m m m ma m a a ta a mmttaa m mm m mma m aa t aa
m
t//taea//ttaa /ttaea//ttaa
/ //ttaea//tta /e/ttee//t ttaa / /t
/ aa//ttaa
t //taa//tta
t / tte//t
/ e
ee e ee e ee e e m ee// ee / ee ee ee ee e em
t. mm/tt..mm
. / t..m/m//tt..mm
t / t
/ ..m/m//tt..mm
t / /
/ tt.:.m/m///tt..m
/ t .
t mm/tt..mm
. / t ..m/m//tt..mm
t / t
/ ..m/m//tt..mm
t / /
/ tt.:.m/m///tt..m
/
t
/// /// / // / / ss:: ss : /// /// / / / :://s:: / :: s :
ss::/ss:: ss::/ss:: ss::/ss:: ttphpttttpp sst:p:p/ss:: sst:p:p/ss:: ppststttpps ppststttpps
ttttphpttttpp t tttphpttttpp t ttphpttttpp
t t t t p
ttp t t ttpp ttt t t
t t t ttt h
hh h hh h hh h hh h hhtt hht hht hh hh hh hh h
b eb bbeebb
Organic compounds composed of only carbon and
bbeebb bbeebb bbeebb bbeebb
wveiw ,. e e bbeebb e e e e w w w
eew
i i w eew bbeebb eew eew
hydrogen rare uruarrknown as hydrocarbons.
w w w w w i w Sawhorse i i Projection w i w w w i w
i i vvruuvvi
Itis a view of molecule down a particular C-C bond, and
w i w w i i w i i i v v w i w i i w i i i
v v iiwvvi
uu uu vvruuvv
r r uu vvruuvv
r " r ru u v vrruu
u v v u
w
ii vvi
u u u v v
r ru u vv
r u u r r ruuav
groups connected
lialatorilialaboth the front and back carbons are
rr
alailiala r
alaililaa ilima a
l ii l a
l a r u r r rr
alailiala r
alailila a iliml ilila
a a
i
alailila
ilim ilim ilim i ilim ilim
m aa//ttam
eemee drawn usingee/sticks /tee// at 120 angle.ee/The ee left-hand bottom eemeeend
mmtaam Hydrocarbons mmttaa m mm aa m m m
aa//tta a mmtaamm m mttaa m mm aa m m m a
aa t ta
t a / / / ttaa //t t //tt aa t ° ta
t a / / / tta a / t
/ t //t t
of this locates ..m/m//tt..matoms nearer////ttot.:.///the tt. observer and///tright-hand
//ttee// // ee eem/ ee t / / eemee
•
eem eem m m . m m m m m .m
m m m m . m . . t . m m m . m m m . . //tt::////t.
. . t
top end sst:p:p/satoms
/ s::/ that is further
ppststttppsaway.
..m/m//tt..mOpen chain ////tt.:.////tt. m . / tt.:.Cyclic .
//tt chain / //tt:://// t t / t.:.:////tt / /
/ /t t / / / /
: / : : / / / t :: s : / : :
/ /
ss::/ss:: ss:: ss: ss:: ss sspss ss:: ss ss ss
t tttphpttttpp
t hh h t ttphpttttpp
t
t hh h t ttphpttttpp
t h h ttttphphttttp
+ t
hht hh
ttp p t t t t
hh hh
t
t t
2H - .H
hh httttphpttttpp
}H -- H
h h t ttphpttttpp
t h
bb --H
hh h
Alicyclic Aromatic H
•
be b Saturated Unsaturated b
ew (Alkane) bbee I b b b
eewweeb b b b
eewwe b e b b e e b e e b bee b b eew bbeebb eew bbeebb
i ee w w w i i w
i w i w
i w 60 0 e e w i w w w i w i
vv iwiwvviw iw
u vvriuiuwvvi i
uuvvriuiuvv i
r ru u vvruuvv
r � v v iwiwvviw iHw H
u vvriuiuwvvH i
H uu vvriuiuvvi r ruuavvrr
u u rr
Alkenc u u r u r r r r a u u r uu r u r r r r
arriliala
al�C=c::: alariliala
ilim ilimalailiala ilimalailila alarrilialar alariliala
ilim alailiala
ilim ilimalailila
H
ilim m m m m m m m m a a m H H
ilim ·-tt m m m H ·-H m m m mm a a m
mm m ttaea//ttaa ttaea//tta a aa
/e/ttee//t t mmttaa m aa//ttaa aa//tta a aa
tte//t t
t//taea//ttaa ee e/ / ee e// e t a
t
// ee a // / t
/ t
eemee Gauche or skew /
ee ee
t
/ t e em/ / e
ALKANES eem e Eclipsed form Staggered mm/ttform ..m/m//tt..mmform
" :://// ::/General fonnula:://s/C::/11/H2n + 2
m eem
t . m
. m t .
t . m / t t..mm/tt..mm
/ / t
/ ..m/m//tt..mm
t / /
/ tt.:.m/m///tt..m
/ t .
t m
. m t .
t . m / t t.. / ..m / t
/ t / // tt.:.m/m///tt..m
/
t /// / / ss:: ss: Newmanss::/Projection //s/s:://// / / / / :://s:: / :: s :
ttttphpttttpp Due to inertness tttphpttttppknown as paraffins ttphpttttpp .
ss::/ss::
ss ss .. ss s
t ttphpttttpp
t • hInhttthNewman p p p
projection,
t p sst:p:p/ss::
hht hh the two carbon
p t ttppststttpps
hh hhatoms fonning hh h
t t
t ppststttpps
t
hh h Only C - Chh and C - H single bonds are present.
p t t t
..
t t t t t t t tt h
hh h htt
the a-bond are represented by two circles, one behind the
h hh h
b All carbons areebsp
.. b 3b
hybridised . ebb ebb b ebb other, soeb that
b ebb
only front carbon b b is seen. The hydroge.
b ebb n atoms b eb b ebb b eb
attached to the front carbon are shown by the bonds from
e b e e b e w e w eb
evwiwe i weviwiw e ebwe e b e ebw e wew w evewbw e weiw
wvi w i w e i w e wi w v i i
w i
w i vi w i w e i i
w w vi i
w i i i
w i i i
the centre of the circle while the atoms attached to the back
Isomerism w vi w vi vi u v uv w v i w vi v v
uvarur ruvruv
i uv
: iliAlkanes exhibit ionly amil chain
v iruv uvaruruv uvarur uv r larur viruv uvaruruv ruvru uv
u
" Structural r
u uv u ur ar r
u l ar u i r
u u v u ur ar r
u l a larurliala
t/a carbon are shown by the bonds from theacircumference.
ar l ar l l i l ia l a ar l ar l a l i a l i
a
il ia isomerism m
ar l i a ar l i a l
isomerism.Methane, Ethane,
tt aem/t/atam Propane tdo taem/t/atnot exhibit e/t/ataem
amil a i l
mtiammi ialmilia ilaim
amil il ia a l i
amil
ilam i i mi mi l
milamil mlam mtilam amm mtam amm mtam taem/t/atam /ta
isomerism.
tt/aaem/t/atam / a /a / t am / a /at /
t t
a t /at
t e/ t/at / t a / t/a
e/me e/me t/aee/t e/mt ee/ e/ e/ e/m e e/me e
m etem /me
. . m/e.tm. .
m m/e.tm . t
. m.m/t/e.tm.me m etem/m
. . m/e.tm. m . m t .
m m/e.tm. e t.mte.m / t
. m.m/t/e.tm. .mt.m
.
tt m:/t/. /.tm / t
. t / /
t tm. /.tm . t / . t / / t : t /
s:
/ .
/:/pss:/ s :
/t
/:pss:/ :/ t
s: : / t
/pss:/ :/
p s
:
/
s:tps: s /:
s:
/ .
:/ts:/:
/ / /
t .
s:
/t :/ t
/:pss:/ sm:/betwee / t
s : / /
s : : / t :
/pss:/ s: s / / / : /
p s s:tps: s://s:/
/: s /
ps t tps t
tp ttp ps ps p s
tpt ht tpt ttp tt p t
tp ttp tp tt p
tptpstNo. tpt of possible isomers tpt t tpt 2 3 httpht tp 5
hht 18hh tptpsttpt tpt t tpt tp ttp hht hh ht h
hht hh hht hh ht h �hht h h h
9
hht hh h h hht hh
..
Conformations b ebb
The different mTangement of atoms in space that results
b ebb b ebb b ebb bw b ebb b ebb b b b ebb b eb
ew b eb e b ebw e e ebw e w evew i e eb e ebw e e e e ebw e e
from freeuruvrotation of groups about
e
C - C bond axis are
e w e w i i w i i e w e w i i w
wuvviw viuwviw
i
vi vi iwviwi
w uv v i i viw
w u v uvv i wuvviw
r uv w
viEclipsed
r
u uv i
v i w wviwi
iStaggered
uv vi i viw iSkew
w uv v wvi w
uv vi r r uvavriuwr
called iconformational isomers mil mi or rotational isomers mil mi and this t•amm/atamm
ur uv r
uialar ur r
u
r lialar ur u
larilial ar uv r u v
r laru (CH - CHilar)uialar ar lar r r
u u u a r
u u
r lialar ila ila r u r u
larilial
ar l ar l a Conformations
i
a of Ethaneu l i
a
/ae/t An infinite number of conformations tam(relative arrangement
l
i a a r i l ia l i
a i l l a
amilar i a 3 l l i ia i l
phenomenon as confonnational taem/t/atam or rotational isomerism.
3 il mi
mlamil ilaim amm
il mi mi m
amm tam /tam/tam
m mm
taem/t/atam amm ataem/t/ata /tam
.me of hydrogen t eeatoms) are possible e/mee/for eethane,
. .mt.me /if .m/one .meoft.m the
tt aem/t/atam /a t t t /a a t a / t
a / a t/
: In /.tthis . fonn the bigger
/a /
t a t e/ /at /t/a t/a t / t / t e / t e/
" tm.mFully
e/me e/me
.mt/e.tm e/m etem/ eme .mt/e.tm .me .mte.me
methyl :/t/.s:groups is rotated/:along
s:t/pss:/: sthe ://s:C/ -C paxis s:/t:pss:keeping
/: s:/ s:the pss:/pss:/ s://s://
/me
etem eclipsed conformation .m/t/e.tm .m/t/e.tm m/e.tm .m/t/e.tm
/:p/sts:/:/atoms are nearest s:/t:/pss:/:to each other.pssThese :/t:pss:/: conformerstpshave
. .tm . m /
t tm
. t .
m . /.tm t
. m /
t . / t . t/.tm : / t
/. / : / t /
rest tpsof tpt molecule undisturbed.
/. t t / t : /
s:/tpss:/ t / / t / : /
/:/t
tpt t tpt maximum henergy t tphhtt and minimum hht hhstability.
s: ps t p s: / p s p s s p p t t pt p t p
hht hh : hIn hthis conformation hht hh h hrotationh h h h
ps t p tpt ttp tp t tpt ttp ttp ttp tpt ttp tt tt httpht tt t
hht hh" Staggeredh form : In this form the bigger atoms are
hht hh • httphht
Eclipsed conformation
about Cb -b C single bond is by an angle such that
h
farthest to each other.
b ebb These confonners b ebb have minimum hydrogen ebweeatoms of front carbon
b ebb atom completely b ebbcover b ebor
energy and maximum stability.
b eb b ebb b bw b ebb b eb
ebw evew
eclipse the hydrogen atom ofrcar carbon atom , only
e e b e w e e b w e w e i e i w e wi e b e w e e b w e e w i e weiw
i
uvaruruv 0 ° to 60 ° generates
i
uv : Rotation between
w e w
..
e i
i.e.
wvi w w
ii viw i wi v i w v i
w vi w vi w vi i w i wi vi w i w i w v w i i
vi i u v w vi uvarur ruvruv
i
three hydrogen atoms of front carbon are visible. This
v w uvaruru v u v
r larur v w
iruv v i uvaruruv ruvru v uv uv
Gauche oruruvskew r u uv r arurlial
one ofm the almimany arrangements amil in between staggered amil and
u a r r
u ar r
u l r
a u l i l ar ia r
u ar u ar r
u l ar u l a a i l
conformationtais mtmost unstable. /atamm
a r l l ia i l ia a l a r l l ia a a i l ia l i l l a
ilaim lia ilaim ilam mil mi almilia
ilaim amil il il
ilaim ilamamil i mi mi
eclipsed t/aee/t forms. Theseee/m tarrangements aree/tcalled Gauche ee/me
amm amm taem/t/atam mtam amm mtam taem/t/atam /t
." Staggeredmeconformation : In m/e.this con±ormation m/erotation
t am t /at / at /at t/ at t/a m / at a /at /
t at t a / t/a
or eteskew form.
/ a t e/ t/aee/t / a t
t ee/ e/ e/ t t e/ / e/me e
/m ee/ .me e/m e/m e/m
. e t.mte.m
e
.m/t/e.tm
about C � C single bond is by an angle so that hydrogen
m/.tm . . m/e.tm tm.m/t/.tm . m . tm . .mt.m
/60 Staggeredpss: pss:
m . . t m
Gauche�/:pss:/ 60 Partially /pss:-.:::.::..+
. . tm m
/:/pss:/ F u 11Y �
.
tt m:/t/. m /.tm / t
. m t / /
t . t .
m tm /.tm . t . / t
. m t . / / /
t . : t /
t : /. t t / s:tps: s://s:/
atoms tpstof ptps two carbon atoms tps pt arettat p tmaximum t distance p from
/. 60 ° /t :/ ° :/ t :/ ° /: / / .
:/ts:/: /t /t :/
/:pss:/ s:/ s: / / / :/ t
/pss:/ s: s :/ / : / /: s /
tptpsttpt eclipsed httpthht tp
s s: s s:
eclipsed
s : : p s t t s: / : p s p t p s
tp ttp tp tt p
ps t t tpt tp ttp tpt
each ht tphhtother making it
hstable
ttphht t by h h2.9 kcal/mol
tp
as compared
t
httphht httphht htt ht
l
hht hh hht hh ht h
b
hht hh h
b ebb 180°
h
b ebb
j ebw b ebb to eclipsed
h
ebw b ebb conformation.b b
h h
b ebb b b ebw b ebb b eb
e be eb e ebw e w e e i w e i e e b eb e ebw e e e w e e e
wviw w e
iwviwi w e
v i w w
i viw i v i i
wuvviw i viw uv vi w e
iwviwi
w w e
vi w w i
i viw iwviw v i wuvviw viuwviw
i i vi
r
u
vi
uvaruruv a r rulvarur
u u v
a r u uv
r larur l a r
uv
urialaru r
r
u
vi
uvaruruv a r r
u uv
uvarur ru ru v
a r u uv
r larur ruar l a r uriualvar
ar lial ialmilia ialmilia i
ilamamil ar lial l
ialmilia ila ila ialmilia il il a i
ilamamil
ialm
mtilam i mtilam mtilam amm t m alm
ilaim i mtilam m mtilam mtam amm t
am am t a am m am t / a
t /a
e/t/aee/t
am t
t/a /t/a t
e/t/ae/t
/a /a
e/t ee/
/
t am
t/at /t/a t t / a
t/a /t ta /t a t /
e/t/ae/t /t e/
a a e/t ee/ /tae
/a t
ee/mee me me .me.m ee/ ee ee/mee e/ e me me em .me.m em
v v
ww
ii vvi i ww
u
i i
vvruuvv w i i
uu
i i
vvruuvv i
r u
r u vvrruu v v vv
ww
ii vvi i w
u v v i
u
i
u
wvv i
uu vvruuvvi
i i
r uuavv
r
uruarru u r u r rr r a uu r uu rr u r r r r r
r
lialailila
r
alailiala
ilim a
alailila
ilim a
ilima
l ii l l a r
lialariliala
r alailiala
ilim alailila
ilim a l ilila
a
ilima
i i
Hydrocarbons
mm mm m
m
t/taea//ttaa
m m
m
ttaea//ttaa
m mm a
ttaea//tta
m mmtaamm aammttaa m m
m
aa//ttaa m ttaa//ttam
mm a
t//taea//ttaa / / / aa t tt // /tt //
..
/
eem e eem e / eem e t
//tee// /
eem/ ee eemee/ eemee
..m/m//tt....m Skew conformation : The tinfinite number of //tt:possible .Clemmensen reduction tt.:.////tt : In this method tt:.////tt aldehydes and
eem e m m . m eem m m m .m
mm .
tt.:.////tt. m m m .
t.:.:////tt . m . . / t
// t . mm/tt.. m m m .. m . mm . . //t::////t.
t . . t
intennediate ttphpttttpp conformations ttphpttttpp between the pststttpp extreme ppsst:tp:p/ssketones
ttttptwo are reduced ppststttpps1,vith Zn - HgtttaL. pp"1.ststtalgam
tpp and cone.htHCl.
//tt //// / /
/ / : /
: / : / / t
/ t ./ / / /
/ / //// : : /
: /
/ / ss:: ss: ss:: ss ss / ::/ :: s : :: ss ss ss
ss::/ss::
hh hh Zn - H g/H CIhh RC
ttphpttttpp
confonnations ( eclipsed hh and h staggered) are referred to as hht hh
RCHO + 4 H H3 + Hp
t tttphpttttpp hh ht t t t h h h h t tt t t tttt t hh h t h
skew conformations.
hh h
b b
eewwee RCOR + 4Heebbeebb
b b R -eeCH, bbeebb- R + H,O eebbeebb
b Zn - Hg/HCI
b b
we
..
bbeebb bbeebb bbeeb
uuavvrruuv Wolff-Ki.shner iwreduction : vIn vriruiuwvvthis
iw method aldehydes
ee eew eew w i iw
iwvviw iw w
vvriuiuwvvii w w w
vvriuiuvv i i w i i wv i iwiwvviw w i w iwvviw
vvriuw iw i
vvriuw uuavvrru
and ketones alarrilialarare reduced with alarilialhydrazine. (NHiliiala-:iN lialaH2 ) and
uu u r uu r r u
r u r rr uu vvr u u r uu r u
r u r u rr
alarrilialar alariliala alailiala alailila alailila
KOH.
ilim ilim ilim ilim ilim ilim a ilim
m m m m m m m ma a m mm m mm mm m m aa m
CH m
m
ee e H H
m m m a a
ttaea//tta a a
/e/ttee//t t mmttaa aa//ttaa a
aa//tta aa
tte//t t
t//taea//ttaaH !Hee//ttaeae//tta
R
/ aa t t / tt / /
I //t3t../m
/ t / /
l
t / / e
NH .2.m/m-//tt.NH
ee e e m ee// ee / eemee ee ee e em
..m/m//tt..mm tt.:.m/m///tt..m tt..mm tt.:.m/m///tt..m
sst:p:p/ss::R - C - CH3ttpp----.
mm/tt..mm ..m/m//tt..mm mm/tt..mm .m 2
Eclipsed Staggered ttphptSkew
t.
t . //tt / t
/ t / / /
/ / : t .
t . / t
/ t /
/ / / /
/ / :
/// /// / /
ss::/ss::
/
ss::/ss:: sst:p:pss /// /// / /
sst:p:p/ss:: R - sCs::/= /s::NNHz :: s
ppststttpps
ss::/ss::
KOH/glycol
ttttphpttttpp tttphpttttpp t ttphpttttpp t t t t p p t ttt t t ppttttpps
t t ttt
H H
t t hh h t tt t
hht hh t hh h h
i
hhtt hht
!
hh hh
or C1H,ONa
hh h hh h hh h
l 2.6jkJ/mol H· bb bb
Hwweeiw .,eeH R -iwCH - CH3 + N 2 w
b eb bbeebb bbeebb bbeebb
ii vviwH
wveiw bbeebb eew bbeebb bbeebb
..
e eew eew
ruu rEclipsed
e
: In this method, the
vv carbonyl compound
e e w w i w w i w
i w i i w eew i w w i w
w i i w i vvruuvvi
i
H
w
iiwvvi i w vv i
vvruuvv v vrruu v v w w
ii vvi i w v v i 2 i uuav
u
Hilim ....
alaiL..--H is converted lialarilialinto
a its dithioacetal alaior liala ketal using ethanedithi.ol
v u v
H-••. L.-Hilim
uruarruv u ruu rruu r r r a Mozingo method
uu vr u u r u
r u r ruu r u
r u r r r
r
alailila
r
alailiala a
lila ilima a
l ii l l a r r
ilim ilimalailila a iliml ilila
a a
in the presence of a Lewis
ilim i mttaa acid. Dithioacetal aa is then //ttaa//tta
H eei // eeH ee/ ee H 0 H
mm m m m m
A mmttaa m mm m aa//tta a mm m m mm m a
mm/tHt..mm H
mmtaam a aa t mm a
hydrogenated over Raney mm/tt..mm nickel.
aa t a t t / t a a a a t a t t
mm/tt..mm Staggered
a t t / / a t t /
Staggered
//ttee//a t t // / / ee ee t a
//tee// t t / t / / / / / e
ee/ ee ee ee ee e
//// :///Et,O' - BF3- s::///s/s:://
eem ..m/m//tt..mm eem ..m/m//tt..mm
R> CH2sSH
. mm .. m t . . t .
t . / /t t . m m . . m t . . t .
t mm/tt..mm
. / /t t
sst:p:p/°ss:: °
.
tt / t t t
/// /// /// // / / / .
tt / t t t / / /
::///s/s::/// sst:p:p/ss:: ::///s/s::/// sst:p:p/ss::
60 120
sst:p:p/ss:: C= o + 1 st:tp:pss: - ---- sttpp
ChhHzSH
s s p p t s s p p t
Anglehhof rotation from
p p p t pp t oo t tpp t t t t
t t t t p
ttpttt p p t pp
ttthhtt t tpp t t t
t t t t
ttpttt
hhtt hht hhtt hht
tt tt hht hh hh hhtt hhRt hhtt hht hh hh
staggered conformation
Fig. : Degree bb of rotation from bbeebbthe staggered eform
ew b eb
b bbeebband eew bbeebb bbeebb bbeebb bbeebb
iw energy of vthe vriruiuwvvmolecule of ethane.
i ee b e e eew eiw w w w i i w e e eew eew w
w w w w i i w i w w w i i
vv iwiwvviw u
i i
uuvvriuiuvv i
r ru u vvruuvv
r vviwiwvviw iw
u vvriuiuwvvi uu vvriuiuvvi r ruuavvrr
u ur u u r u r r r a u u r u u r u r r r r
alarrilialar of Preparation alariliala ilimalailiala ilimalailila alarrilialar alariliala alailiala
ilim ilimalailila
..
ilim ilim
t//•taea//ttaa Hydrogenation
Methods ilim ilim
ttaea/of ttaaunsaturated /hydrocarbons (Sabatier Decomposition of Grignard aa//ttaa reagent : Grignard aa//tta reagent //tte//t
m mm m m m m a mm aa m m m m m m m m m a mm a a m
m
m ttaea//ttaa a
/e/ttee//t t mttaa a a t
mm/tt..mm and Senderen's ./ .m/m//tt..mm reactions)//tt..m/m :/tThe
..m method involves tt.:.m/m///tt..m the
a t t t
(RMgX), m an organometallic mm/tt..mm compound on ..m/mreaction
..m with active
/ / / / e t
// eet a / / // t /
eemee / e em e
ee e ee e eem e m eem ee ee
tt.:.m/m///tt..m
reduction ss::/ss::of unsaturated ss::/shydroc arbons (alkenes sst:p:pss: and ://// :hydrogen (hydrogen :://ss::/ attached to strongly :://s:: electronegative
t .
t . / t t / t / /
/ / t .
t m
. m / tt.. / t
/ .
t ./ / / t
/ t ///tt / // / :
/// /// / / / s::/ :/// ss:: ss
alkynes) tttphpttttppwith nickel catalyst. ttphpttttpp Raney nickelhhtistttphpmore thtt reactive ttppststttp:pssatom like 0,ttttpN, pststttppS or F) compounds ppststttpps like HOH, tROH,
ss::/ss:: ttphpttttpp
ttttphpttttpp
than supported nickel catalyst.
tt t
hhtt hh RNH , RCOOH, RC ""' CH, etc. decompose to give alkane
hh ht hh ht t hh hh t
hh hh t hh h
hh h
b ebb CH2 + H2 200 bNi_ebb 0c RCH2CH3 bcorresponding to balkyl b group of Grignard b ebb reagent.
=
2
300 dry etheriweebiwe ewe

b ebb ebb b ebb b eb
Alkene Alkane + M
b eb RCH ebw b b bw
e b ebw e evew
g
e eb e w e e e w e i ebweeb e weiw
Alkyl irhalide
e w w i i w w i
uvaruruGrignard
v uvru reagent uruv ur ruvruv
e w i i e i
Ptaruror uvarurPd uv can also be used uvaruruvas catalyst for urabove uvarur reactions. arur larur
wvi w w w
ii viw i v i i
w vi w vi w vi w v vi w uv vi RX wi w vi wi vi w v i w RMgX i w v i vi w i i uv
v uv u v uv
uv u v arurliala
milThis
ialmilia method cannot abemil used for the preparation of methane
u r r
H2 <X
l l ar u ial i l ar ial ial lia ar r
u l ar u l ar u ial a r a i l ar i
a la r l a i l a i
a l
ilaim ilamamil mi mi l ialmilia ilaim
amil il i l amil
ilam i mi mi l
tt/aaem/t/ataCH amm amm t taem/t/atam mtilam 0
amm mtMg m amm t mtam taem/t/atam /ta
m • t /at /at /a /
t a am .----+ t / t
a RH · a+ a /at /a t a / t/a
"'
/a t t t /a /a t t t /
Reduction m/of a l kyl h alides m/e.t:m. Alkyl halides .can . be
t ee/ e/me t ee/ e/ e/ t e/ e/me e
m/e.tOH
/m
etem
t ee/ e/m t/aee/t e/m e/m e
. e t.mte.m .m/t/e.tm
C, ,
etem/me 4
. m/e.tm etem/m m/e.tm . . .mt.m
/:pss:/ s:/�s:RH + pMg /ps,......
. t m m . t m
reduced with
/:pss:/ zinc and acetic /pss:acid/ or zinc-copper s:tps: couple
. m
tt m:/t/. . /.tm. . / t
. m t / /
t . /t tm. m . / t
. .
m . m t . /.tm t m / / /
t . : t /
/ . /t :/ t : / t : / :
/ s /: / . /t/. /Ht : /
OHt / t // : / t :/ X // /
: s:tps: s://s:/
/: s /
ht tphht 'htOC,H,
/:/pss:/ :/ts:/: s:/ s: s
in ethanol.
s: s: ps s : t ps s: / s : s s: p t ps p
tptpsttpt
ps
tpt t tpt t tpt tp ttp tptphsttpt
ps tpstpt p t tpt tp tt tp ttp tp tt
hht hh hht hh hZnhttphht
- AcOH
hht hh h h t h h httphht httphtt h h hht hh ht h
Zn - Cu/EtOH
RX + 2H RH + HX b ebb
Order of reactivity of different alkyl halides is
b b ebb b ebb bw b ebb b ebb b b b ebb b eb
ew b e b eb b e b e e b w e w e ebw e i w evewi e eb e ebw e e e w e ebw e e
vi vi iwviwi
w e w e
v i
w
i viw
w uv
i
uvv i i
wuvviw i
uv w
viruvi v
i w e
iwviwi w e
v i
w
uv
i
i viw iwvi
w v
w
uv vi wuvviw viuwviw
i i
uvavriuwr
uvarur> R - F r u uv r
lliaaReduction can also il mbe i carried out by mtilamLiA1H
Ruru- varurIuv> R - Br > R -arurCl r
u ur u
larilial ar uv r u v r r
u
uialar ar ar u u r
u r
u r u r u
larilial
r lial i
a l ial i
a l ar lialar li
a l a r urialaru ial a r l ial ar lialar ila ila li
a
tt aem/t/atam1 ° and 2 ° alkyl taehalides
tam are readilyt/atam reduced by LiAJH but
l mi 4. i
mtamm iamil il mi i l l i il mi i
m mm
mi mi mm / at4aem /a mtilam amm tam tam/tam t amm tam /tam/tam /ataem/t/ata /tam
e/me 3 ° halides give . mainly alkenes.
/a t/a /
t a e/ t/a e/ t / t /at am /a t/at t/a /
t a e / /
t a e/ t
e/me/ e/me .me t ee/t e/mee/ e/ e e/me e e .me .mte.me
R'COOH
.m/t/e.tm .mt/e.tm e/m
.m/t/e.tm .m/t/e.tm .mt/e.tm
NaBH 4s:/:reduces
.m/t/e.tm
2 and 3 s:/halides : s:/: but not 1 ° halide.
m/e.tm . m/e.tm . .mt.m . t.mt.m
s:/t:/pss:/: s://s:/ RH +pssM <X
t .
m . /.tm / t
. m /
t tm
. / t .
m . / t
. m / t
. m / t/.tm : / t /
/. t /ts:/: ° ° / t :/
s:/tpss:/ :
:/t/.s:/:/t t t / / t
:/t:pss:/: ps:p/ s:
/ / s:/tpss:/ s://s:/
:/
Alkyl tpt ttiodides are conveniently reduced httpto ht alkane by tptphst tpt
s: /:p/sts:/:/ ps ps ps t ps t p s t p s: / p s t p s tp p p
..
t tpt ttp ps tpt ttp tp ttp tpt ttp g_ tt hOOCR' tt tp t t
heating
hht hh with red phosphorus hht hh and HI. h h
ps p t t
tpt t tpt hht hh ht h
hht hh hht h Wurtz reaction hht hh : hInt hthis reaction hht hh ether h
solution of alkyl
Red P
halide b is treated withbsodium to fom1balkane.
• b eb dry ether eb eeb eb eb
- H + I2
Reduction of alcohols, aldehydes, ketones, evefatty
bweeb acids
R - I + HI --+ R b b b ebb b eb
---+
b b b b b e b b
b eb b eb ebweeb weviewiwRe - X + 2Na +weX evew bw e weiw
anduvtheir iruv derivativesru:v On uv heating withuruHI varuruand red P at arur larur This methodruviisuruvuseful with single
e ebw e w e i w i i ebw e- R w e R i w - R + 2NaX w i
uvaruruvtype vruof alkyluruhalide.
wvi w i w e i i
w vi w v i
w i w vi w i i i
w v i w i w i w v i
w i i
w vi w vi i u v uv w vi w vi v varur ruvruv
i uv
425
ialmiliaK in a sealed mtube, iliamil alcohols, aldehydes, milamil ketones and
v v v uv
r arurlial
If two different ialmilia alkyl halides are
il used
mtam a mixture
amof il three
u ur a r u ar u l a r u l r
a i l i l ia u ar ar r
u l r u l ar i l a l a i l
l a l l i a a
tt/aaem/t/atacids get reduced tt aem/to atamalkanes. e/t/ataem/t/atam
a r l ia i a mil mi a r l iam a a
il il i
ilam a i l i mi mi l
mtilam
different t/aee/t alkanes is obtained. t ee/ For / eexample,
milam taem/t/atam mtilam amm mtam taem/t/atam /t
/me ROH + 2HImeeRed /me P RH + Hp
a m t a
.m+e I2
/a / /
t a t am /at / a a /at /
t a t / t/a
mCH .me -t.mCH
t e/me / a t t / /t e/ e e / e/me e
etem .m/t/e.tm etem/m e/m em etem .m/t/e.tm
/ Red P RCH
. . m/e.tm tm . m/e.tm . . . m tm . .mt.m
/pss:/+ Hp + 21 pss:tpss:
m . m . .
+ /:p4HI
.
tt m:/t/. . / t
. m / t
. m / t
. m t / /
t . tm. /.tm . m t . / t
. m /
t . / t / /
t . : t /
t t : : /. t t / t / / s:tps: s://s:/
:
/. / t :/ / /. /t :/ 3 3 /
:/ :/ / :/ts:/: /t :/
/:pss:/ s:/ s: / / : /
/pss:/ s: s / : / s
/:/pss:/ RCHO s
: s: s: / s: s:
Aldehydes hht hh and ketoneshcan httphhtbe reduced by other hht hhalternative hht tphhttp
s : s p s t s : ps p s p t ps
tp ttp tp tt p
tptpsttpt
ps
tpt t tpt t tpt tp ttp tps tps tpt t tpt tp ttp tpt t tpt ttp tt
3 2
hht hh hht hh ht h hht hh h h hht hh ht h

methods also. b ebb
b b b ebb ebw b ebb ebw b ebb ebw e b ebb ebw b ebb b b ebw b ebb b eb
e e eb e e w e e i w e i eb e e e e w e e e
wviw w e
iwviwi w e
v i w w
i viw i v i i
wuvviw i viw uv v
i w
w e
iwviwi w e
vi w w i
i i vi
r
u
v i
u uv
a r u uv
r larur l a r
uv
urialaru r
r
u
vi
uvaruruv a r r
u uv
uvarur ru ru v
a r u uv
ilamamil ar lial l
ilamamil
mtilam
ialm i mtilam mtilam amm t m alm
a
t /a
e/t/aee/t
m t
t/a /t/a t
e/t/ae/t
/a /
e/t ee/a t/ am
t/at /t/a t t / a
t/a /t ta /t a t /
e/t/ae/t /t e/
a a e/t ee/ /tae
/a t
ew bbeebb ee bbeebb ee eew bbeebb eew eew
vv
ww
ii vvi i ww
u
i i w
vvruuvv i i
uu
i i
vvruuvv i
rruu vvrruu v v vv
w w i
ii vvi w
u vvi
u
i
u
w
vv i
uuvvruuvvi
i i
rruuavv
u
uruarru r u r rr r a uu r u u rr u r r rr r
r
alailila
r
alailiala
ilim a
alailila
ilim a
ilima
l iil l a r
lialariliala
r alailiala
ilim a
alailila
ilim l ilila
a
ilima
ilim m m m
m m mm a m i m m m
m m aa//ttam
m
m a
mm m m
t//taea//ttaa / // /
eem e/ taa
//tee// t / tt
eem/ ee
/ / /t
/t //
eemee
• tt..m
eemee
tt.:.////tt. : This is similar tt.:.////ttto Wurtz reaction
eem e eem e eem e mm . m eem m mm .m
..m
m//tFrankJand mm . m mm .. m .. tt .
//tt:://// Mechanism ..m/m//tt.. m mm .
tt.:.////tt .m . mm .
tt:.////tt. //t::////t.
t .. t
•
reaction
tttphpttttpp with the difference ttphpttttpp that instead ttphptof
sst:p:psssodium, zinc tistppstsused A preaction
sst:p:p/ss:: taking placettppin sst:p:sunlight or in presence ttphpttttpp ofperoxidehhttttphphttttp
// / t //
/ / //// : ::// /
/ / t
/ t //// //// : :://
/ /
ss::/ss:: ss:: ss: pss ss: ss:: ss sspss
tt hhtttp
here in inert hh solvent. hor
ht athh high temperaturehhalways hh follows freehhradical h mechanism.
t tt tt t t hh t tt p tt t t t t ttp tt
h hh h
In this bbeereaction hydrogen is substituted by halogen, thus it
hh h
isiw a eefree-radical substitution bb reaction: For

b b R fx + zn + x +R - Rbb- R + ZnX2 b bb bb bbileelbustrating thewweeiw
•
we b bbeebb
Corey -viHousei synthesis vv:iw
iwItvviw
i is a better reaction for
beebb
eebw eebw
bee bee b b
uuamechanism, let usvviconsider iw the chlorination vvriuiuwvvi of methane.
w eeww w i w
i w ee e e e e w w w iw
iwvviw i i w i i i
vvruuvv iwvviw w i vvriuiuvvi i
coupling alarrilialatwo different types alariliala of alkyl halides alailiatogether to
w vvu vv w uuavvrru
uu vrruu r uu r u
r u r ruu rr u alailil)-a Chain initiation
r r r
alarrilialar step : ilialailiala
uu r uu r ruu r r ruu r r r
alailila
fonn alkanes with either even or odd number of carbon
ilim ilim la ilim alailiala
ilim ilim
Cl - Cl mttaa� 2C( ttaa//ttaa
ilim m m m m ilim m m mm m
tatoms.
mmttaa m mm
aa//ttaa m mm
aa//ttaa aa
tte//t t a a m m mm m mma
aa//tta a a
tte//t t aa
)- Chain
mm/tt..mm propagation step
eemee:
taa // //tt //tt e / / e ttaa // // / t
/ t e // e
ee// ee ee ee ee ee em ee// ee ee ee em
tt.:.m/m///tt..m tt.:.m/m///tt..m
/// /// 2R - X � Li � :://Rss:2: CuLi + Lilss:p:pss ///CH /// + c1· - / :/ ; + H - Cls:://ss::
sst:p:p/ss:cH
..m/m//tt..mm ..m/m//tt..mm
ss::/ss:: Alkyl halidettppststtp:pss -
mm/tt..mm ..m/m//tt..mm ..m/m ..m
Ether
t.
t . //tt / / /t t / / /
/ / : t .
t . / t
/ t //tt / /t t / / /
/
:: s / :
:// ::2R
ppststLithium diall 7l . . so on.
CH3 CI + hh Cf hh . . . and
ppststttpps
hhtt hht CH; + C l - Clhh --
tpp ttphptttt sst:p:p/ss:: 4 p p p p sttpp tt
ttttphpttttpp t tt t t tt p p t t t tt t t t t t t t t
)- Chain terminating step :
t
hht hh t
hh hh cuprate hh h t tt t t hh t hh h h
hh h
b eb R2 CuLi + R'bb-bbX - R - R'bb+eebbRCu + LiX ebbeebb bbeci'+ ebb c(° - bbeebc1
CH; + Cl - CH Cl
b2 bbeebb bbeebb
wveiw eew
•
eew
In
vvruthisvv method a concentrated
ee e e w ee w w w w e
i w w i w
i w i i w eew w eew w w w i w
w i ww i i w i i i i i v v w i w i i w i i vvruuvvi
i i
l ii CH; + CH; lialari--+ CH3 - CH
Kolbe's electrolytic iiwvvi method : vvruuvv vvrruu w
ii vvi 3 v vv uuav
solution alaof
ililasodium or potassium alailiala salt of a carboxylic alailila acid
v v u uu u u u r rruu vv u u u u vr uu u u r r r
ruruarru rr r r r a aa l a
l a r u u r r r r
alaili3ala r r r
alaililaa l ilila
aa
a'"a//tta Finkelstein aareaction
ilim liala ilim
mmtaamm : Iodoalkanes mttaa can be conveniently
ilim ilim
is electrolysed to give higher
mttaa alk:anes. taa ttaa
ilim ilim i ilim
m m m m m mm a m m m mm m aa//ttam
mm a
Electrolysis
mmtaam aa
prepared eeby
//tee/treating alk--ylm echloride or bromides eemee with
a a ta
t a / t / / / t
/ t ta
ta/ ttaa / t
/ t //tt
+ RCOOK -----+ - + 2CO + H + 2KOH
//ttee// t eem // ee / /
eem/ ee eemee t / t // ee / // eemee
emm
sodium ..m/iodide
m//tt..m in acetone//tor methanol. This tis
t.:.:////tknown as
eem m m . m m m m .m
RCOOK m m R R mm . m . . t . mm . //tt::////t.
. . t
s•s::/ss:: Hydroboration
..m/m//tt..m m .
tt.:.////tt. .
tt.:.////tt 2 //tt:://// t m m
..///tt.. .
ss:: ssof: alkenes : In
ttphpttttpthis
ss::pss reaction diborane
/ 2 / t / t /
Finke sst:p:pl/sstein reaction. ttttpptstttpp
//tt /// / // / : :: / / t
/
/ s::/ t // : / // / :: /
/ / sspss s:: ss: ss:: ss ss ss
tttphpttttpp (B H ) adds hh toh an olefinic bond
ttphpttttpp
hh hforming trialkyl borane
ttttphphttttp
hh Acetone
ttphpttttpp t ttphpttttpp
CH3 I + NaCl
p t
hht hh CH Cl + Nal
tt tt tt p t t tt h
3
t h h t t hh hh h hh
which on treatment with acetic acid or propionic acid yield
hh h 2 6
• Reactivity bbeebb and Selectivity bbeebb : For a particular bbeebb type of eebbeebb
corresponding bbealk:ane.
b eb bbeebb bbeebb
abstraction ofH (say iwvv1iw °)
iw reactivity of halogens vvriuiuwvvi is in order:
ew bb eew eew eew eew
i ee e w i w ee
w i w i iwvviw iw i
R -rruCH == CH - - CH -) B
iwvviw iw w
i iw i i w w w
vvriuiuvv i i i
vvruuvv w i w vvriuw
alarriFliala2 r> Cl2 > Br2 > iIlial2ailiala ° °
vv iw B2H 6 uvvuuvv u uu r v v iw u u uuavvrr
u r u u r
iAlkene Tria!J...71 borane
u rr u u r u(RCH
rr r r r r a uu u u r u r r r r r
1C
alariliala alailila r r alailila
m For a given mhalogen, abstraction of 1 °, 2 , 3 , hydrogen
lialailiala 2
ilim 2 2 laa3ila
iiml ila ilim alailiala
ilim ilim
ilim m
H ttaeaCOOH
m m mm m mm a m mm m
m m m m a
follows the // eeorder:
m m m m m a a a t a mttaa m m
aa//ttaa aa//ttaa aa
tte//t t a
t//taea//ttaa ttaea//ttaa / //tta /e/ttee//t aa tt /t t / /
// /tt..////tt1-r
/ / t / /
3 0 >//t2t../0///t>t. 1 0
ee e / ee 3e e t / / /
ee ee ee ee ee e
eem e mm.mm mm..mm ..mmt..mm eem mm.mm mm.mm ..mmt..mm
tt..mm//tt..m //tt..////tt. /: ///tt::////t tt..mm//tt..m // /tt..////tt. /: ///tt::////t
Bromine
ttphpttttpp is less reactive ttphpttttpp than chlmine ttphpttmvards alkanes ttttphphttttpp
/// //
ss::/ss::
/
ss::/ss:: sst:p:p/ss:: ss: ss
ttphpttttpp ss ss :://// ::// ss :://ss:: sttpp s::/ss:: ss: ss
tttphpttttpp ttphpt3RCHz
Alkanc hhbuth bromine is more hh selective in the site h of attack when ithh
ttttphpttttpp t
hh h tt
hh h t t - CH tt
3 hh h t t tt h h t t h t
hh h
Physical Properties reacts.ebb ebb
: C - C odourless, colourless gases
b ebb b eb
weviwiwe : Lowerwealkanes undergo vapoure wewphase
b eb b ebb b ebb b ebb b ebb b ebb b b bw
State e b e b ebw e ebw ebw e evew e weiw
Cru5v-uruvC 17 odourless, colourless liquids uruvarur
e e w e we i e w
nitration under drastic iruv conditions atru400-500
e
varuruv ruv°ruC to give
wvi w
11
1 we 4
ii viw i w e i
w w v i i
w v i
w vi i
w Nitration
vi w i i i
w w v i i
w i i v i
w i i i
v w vi
uvaruruv i v
u uv
r larur u v v w v
i w vi v uvarur ruvruv
i uv uv
il Cia onward odourless, iamil colourless solids
arurliala
mi minitroalk:anes. milialmilia
u u ar r
u r
a l l ar uia r
u uv u ar u l r
a r
u l a l
a r lar l ial i l i
a ia l ar l ar l ia a a i l i
a l a i l i
a
400 C
l ilaim l amil mi mi l
milamil
•
amil il i ilam i
tt/aaem/t/atam : Increases very tt aem/t/slowly with increase in molecular
milamil 1 8 mtilam amm mtam
CH4e(g t/laee+/t HN0 3 (g) - t ee/CHe3 N0
Density a tt aem/t/atam
/a /
t taem/t/atam
a am t m
a °
t amm / t
a a mtam /t
a /at t a / /
t taem/t/atam /ta
a
mass.
/ a e/me t / a /a t t
/ e/ 2 t e/ t / e/me e
methane
e/me e/me e/m e/m e
/me
etem m/e.tm m/e.tm .m/t/e.tm. etm/m m/e.tm m/e.tm . e t.mte.m .m/t/e.tm. .mt.m
•:/:/ s:/ Solubility : Insoluble
. . . t m . m . tm
/:pss:/ in polar psolvents, /pss:/ soluble inpssnon Vapour :/ts:/phase nitration causes/:pss:/ cleavage / s: of Cs:/-C s:/ ands: Cs - H pss:tps: s:p/ s:/
. m
tt m:/t/. . /.tm. t /.tm t / /
t . : tm. m /. . /.tm. t Nitrot . m t . /.tm t / / /t/. : /t /
/. /t :/ :/ t :/ :
/
:tps: s / /. : /t /t :/ / / / :/ t :/ / : / /: s /
s :
tptpsttpt polar solvents.
:
bondtptpsttpt resulting in thehttfonnation
h hh ht h of mixture hht hh of nitroalk:anes
s s : s t s :/ s : s p s p s p t
ps ps
tpt t tpt tpt t tpt tp ttp ps ptpst tpt tp ttp tpt t tpt ttphtt tp ttp tp tt
hht hh• hht hh hht hh hht hh hht hh ht h
Boiling points : Boiling point of normal alk:anes increases as a product.
hht hh h
regularly with bnumber of carbon

batoms. CH e CH3 ( l + HN0eb3be(gebJb-=--+
b ebb
g
b b b ebb bw b ebb b b b ebb b eb
b eb ev3ew
400'C
eb ebw
Normaluvvisomers have higher
i viwboiling point viw than viw the
ew b e eb e b e eb w e we w e i w i - eebw e e e we e e
e w i w wuvviw viuwviw
i
CH - CH - N0 + CH - N0
e w i i e w i i
vi iwviwi v i w w
viruvi iwviwi vi wi viw iwvi w vi uvavriuw
branched lliaariulialarchain isomer. iGreater arulialar the branching, ar liallower vvill
iw u v uv r uv v
u r uv r
u uv u v
i w uv u v r u v v u uv r u r
u r
il mi i Nitromethane
r u r r u r
u ar u i larilial a r uv r
urialaru 3 2 ar r u
uialar2 ar ar3 u r
u
2ar ia l u
ar la ila r r i larilial
l l
betam the
mtiammboiling point. tamm/atam
ilalm i i
a
il mi i
m mm la l r
a
iamil ial l l i l ia
il mi l i mm i la
t ee/t : Replacementeeofhydrogen / e/ e/ e atom by e/msulphonic
amm mtilam Nitroethane
amm tam /tam/tam
" ee/Melting points :.mAlkanes
tam ataem/t/ata Sulphonation .. amm tam tam/tam taem/t/atam /tam
.me with even .m/t/e.tnumber of C-atoms
/ a /a t / t
a /
t a t/ t am / a /at t/a /at /
t a t/a
acid group (-SOi{) is known .meas.msulphonation.
/a
t e/t t
/ e/ t e/ e / /a t t e/ e /
etem e/me
.mt/e.tm.me e/m
.m/t/e.tm. e t.mte.m
e
.mt/e.tm .me .mte.me
/:p/sts:/:/ have higher pm.pt. s:/t:/pss:/:than the last lower s:/t:pss:and/: next higherpsalkane
me . m/e.tm .m/t/.tm
S0 s:/t:p3ssH
tm. m/.tm
. /.tm /. /.tm m /
t tm
. / tm. . /t
. m t . m /.tm / t/.tm :/ t /
/. t t /t /t :/
s:/tpss:/ :
:/t/.s:/:/t t
s:/t:/pss:/: s://s:/
t / /t :/: s:p/ s: / / s:/tpss:/ s://s:/
:/
having odd tptm;mber of C- atoms. ht tphhtHt 2 S,0
T'
s: p s t s: / ps t ps p
h 7h CH hh�t hhIt - CH
s tpt ttp tp t t p ps ps
t p ttp ttp tpt tp tt htt p tp t tp p t
hCHhttphht HCH2CH CH HzCH
ps
tpt t tpt ttp tpstpt t t
hht hh hht hh ht h
39 3 2 3
hht hh Chemical Properties hht hh hht hh h h
C
•
2 3
Halogenationeb:bRep b l acement of ehydrogen b ebb of an alkane b ebb CH

b ebb
CHe3bbeebb eb eb b ebb b eb
with halo vgen ii viw by rea cting valkane with hal o gen in
b eb3w b ebb bw
be eb b ebw e e evew e weiw
The
r larur ease ofreplacement iruv ofhydrogen ratom uvaruruv isru3vr>u 2 > I uruvarur ruvruv
w e e e w i ebw w
wveiw we i w e i we i i w i
w i
w vi w we i e i we i w i w i i
presence of sunlight or at elevated temperature is cal l ed
w i w v
i w v
i w v vi u vvi uv v i
w v
i w vi w v
i w ° i w v i ° vi wuv i uv
uvaruruv uvaruru
mil miSulphonation malso almiliafollows free radical amil mechanism.
arurlial
0
u r v
u r uv r
u r
u ar u r v
u u •
halogenation.
a r u l r
a u l r
a i
a l i l r
a ial i
a l lia a r u l r
a u l ar i
a l a a i l r
a ial l a i l a lial
il ia i
milamil milamil ilaim il il amil i mi mi
:
milamil ilaim ilam
t..aem/t/atamReed's reaction amm mtam
m,-Cl2
tt aem/t/atam amm mtamof alkanes taem/t/atam /t
eCl
tt aem/t/atam t
e/mCle
tt/aaem/t/atam /a m
a t t t / a a /a
Alkanes.mundergo chlorosulphonation on treatment . e with
/ a / a t t t or chlorosulphonation /a / a a /a t t / t
CH Cl /.t- Cl3
/ a t t /
C�Cl/t/.t-�- +
t e/ e e e/me e
. i
e/me t ee/ e/ e/
CH/.t4m · .-m- -
etem /e t/aee/t e/m
- z z -
/ e/m
h
.m/t/e.tm .m/t/e.tm
hu, HCI 1 H c 1
/m
etem
.
.me2
/:/psts:/: hu, -HCL
.mt/e.tm . m/e.tm m/e.tm . .mt.m
a mixture :/ts:/: of sulphur dioxide /:pss:/ and / schlorine in
/pss:presence
/ s: s of pss: ps: s://s://
.m/t/e.tm m m. / . CH l /.tm . tm. . m .m t .
m . m t . m /.tm t
. t
Cl2 lrn,
/t t / . / /t
tp t-tpHCl
:/ :/ t :/ t :
/ /: /.tm //
t . //
t . :/ t / t / / :/ t :/t / / : / :
/ s /:
ps pt tp tpsul honyl
t p httpthht tchlmides.
s:tpss:
ultraviolet ps light to form
tpt ht talkanes
s
: s
: /:pss:/ s: /pss:/ s
ps s: / s: s : : s: t p
ps ps t ps pt ttp tt p t
tp ttp tp tt
tpt t tpt tpt t tpt
hht hUV light
tptpsttpt hht hh tptpsttpt hht hh ht h
hht hh hht hh ht h h h
CC1 4 b eb+b SO 2 + Cl z ---"--+ RS0 2 Cl + HCl
hht hh hht hh h
500c
RH
be b b ebb eb b ebb eb b ebb ebw e b bb ebwb ebb b b ebw b ebb b eb
eb we e w e we i eb e e e e e e e
wveiw e
iwviwi
w we
vi w w e
i viw i v i i w
wuvviw i viwi
uv vi w e
iwviwi
w w e
vi w w e i
i viw iwviw vi i w
wuvviw viuwviw
i vi
r
u
vi
uvaruruv r
a rulvarur
u uv
ar u v
u
r larur lar
uv
urialarur
r
u
vi
uvaruruv a r r
u uv
uvarur ru ru v
a r u uv
r larur ruar l r
a uriualvar
amil
ilam ar lial l
amil
ilam
mtilam
a m a m t a am m am t / a
a
t /a
e/t/aee/t
m t
t/a /t/a e/t/ae/t
t / a /a
e/t ee/
/
t am
t/at /t/at t /a
t/a /t ta /t a t /a
e/t/ae/t /t e/
a e/t ee/ /tae
/a t
vv
ww
ii vvi i ww
u
i i w
vvruuvv i i
uu
i i
vvruuvv i
rruu vvrruu vv vv
w w
ii vvi i w
u vvi
u
i
u
w
vv i
uuvvruuvvi
i i
rruuavv
u
r
alailila
r
alailiala
ilim a
alailila
ilim a
ilima
l iil l a r
lialariliala
r alailiala
ilim a
alailila
ilim l ilila
a
ilima
ilim
Hydrocarbons m m m
m m m
m a m i m m m
m m aa//ttam
m
m a
mm m m
eem e/ taa
//tee// t / tt
eem/ ee
/ / /t
/
eemee
t //
eemee
mm/t2t..hybrid orbitals//tt.are .////tt inclined to each tt:.////tother at an angle
eem e
..m/m//tt..•m Isomerization tt.:.////tt. : In this reaction tt.:.////tt straight chain::alkanes //tt:://// on
eem e eem e mm . m eem m mm .m
mm . m mm .. m .. tt . m mm .. m . mm .
t. //t::////t.
t .. t
heating ttphptttintpppresence ofA1Cl ttphpttt3tppand dry HCl gas pststttppconverted ppsst:tp:p/ssof
ttttpare 1 20 ° and lie ppstin
st:tp:psas: plane. The unhybridised p orbital ttphpttttpisp
//tt //
/ / / /
/ / : // / t
/ .sp
t ./ / // : //// : :://
/ / ss:: ss: ss:: ss ss / ::/ ss:: ss ss ss
ss::/ss::
intohhmore h symmetrically hh hstable branched chain alkane. hht hh at right angle hh to hh this plane. Allhhthe h four (3 sp -hybrid +
ttttphpttttpp tt tt hh hh t tt tt t t
t t t tttphpttttpp
t 2 hh tt h
1 unused p-orbitals) orbitals are singly occupied. Two of
hh h
CH.
the hybrid orbitals bbeebbon each carbon bbatomeebb overlap with bbeelsbb
b b
CH
I eewbwbeeCH- bbeebb
CHpEfiCH°i CH CH -
bb
we beebb
,
bbeebb AlCl3 +eebHCl eew
uuavvrruuv orbitals ofuuvtwo iwH-atoms to form vvriuiuwvvCi - H bonds. uThe vvriuiuvvthird
e e .:>
w w i i w e e eew eew iw
w i iw
ii-Butane iso-Butane
iwvviw iw -- w i
iwvv0 ci
_--- w -
3 vvi i vv w w i i i v iwvviw w i w w w i i
vvriuw 3·
vvri2, iw uuavvrru
sp2 hybrid alarrilialaorbital of one carbon alariliala overlaps withilialathe iliala similar
u u u v
..mmilimalmarOxidation : Oxidation
alariliala of alkanes gives different products
uu u r u u r u r ru u r r r r rru u r u u r r r u r r r
alailila
rilalar alailiala ilialailila
orbital of the other carbon to form a sigma C - C bond.
ilim ilim ilim ilim
t//taea//ttaa according toee/reaction ttaea//ttaa conditions//ttaand a//tta catalyst used. //ttee//t
i m m m mmtaamm ilim m m m m m m m
The // eetwo unutilised p-orbitals at right angles eemee to the planemm.emm
m m m a a a m mttaa m mm
aa//ttaa m
aa//tta a a a
tte//t t aa
ee e Completemmoxidation (Combustion) : Alkanes tt.:.m/m//produce
/ e t a
t a / / /t
/ t / t
/ t e / / e
ee ee e
mmcontaining hybrid orbitals
m//tt..mm are parallel ..m/m//ttto
..meach other and
e eem ee ee
tt..mm
CO2 and /:/ssH /2O on combustion.
mm/tt..mm ..///tt..mm ..m/m//tt..mm / . m ..m //tt.:.:////tt.
sst:p:p/ss::overlap sideways sstp:pssto form a pi (1t) ppststtCtpp-
ss C bond.
t .
t . / t
/ t / t
/ t / / /// : t .
t . //tt . / t
/ t // / / t
/ t / : / /
/:://s/s::/// : //ss:: : : / / / / / : / : : :
tttphpttttppCH4 + 20 2 -- ttphpttttppCO2 + 2Hphhttttphphttttp
: : : : s / / : : : : s
ss ss ssp s ppststttpps
hhtt hht p-p (n-bond)hh hh
ss p p t t
ttttphpttttpp p p t t t t t t t t
1t-cloud
hh ht hh ht t t tt t t t t t
hh hh t hh h h
hh h
C 2 H6 + 0 2 -- 2C02 + 3Hp
b eb
wveiw Incomplete beebbcombustion/controlled2
7
bbeebb
oxidation : A
bbeebb
mixture cr
A-.!. (.) .
H.._eebbeebb
·-.V w cr V/a
H ll.bbeebb\ H
eeH bbee1-2bb1 H bb bb
/ wweeiwwee
vvr1uu1vv6.6� C uuvvriruiuvvi
b e e e e w
ofmethane
uruavvrruuv and oxygen uuaon vvruupassing over a rcopper uuavvrruuv tube under aarruluaarruu
e e w w w i w w i w
i w i i eew a "'-n:/4 w w
/ t ),_
w i w w i w
i w i i i i w i v v w i w i w
i w i i
iiwv i vv v v v w
vvriuiuvvi uuav
ihigh
lialailila temperature and alaipressure
r r
gives methyl alailila alcohol. ilil ii H�·----O�Hlalariliala H
r uu /4 �d'- ailiala H
r u u r
ilifm
ala"Hr r r r
1 34 p
r r r r r a l ilila
a a
mttaa Cu tube taa ttaa aa' 1 1 o pm //ttaa//tta
ilim lila ilim l ilimalH ilila ilim
aa//tta p-p (1t-bond)
CH4 +e/½/ ee0 z
i
ee/ eeCH3 0H
m m mm m m m a m m i m m m m
m m m m a m
mmtaamm mmtaamm mttaa
100 atm, 2OO0c (a)eem mm/tt..m(c)
t a
mm/(b)
aa t t ta
a / / / t / / // t t aa t / ta
t a / / / t
/t a / t
/ t e
//ttee// eemee //tee// eem/ ee ee ee ee e
This method
mm/tist..mmused for industrial
mm/tt..mmpreparation of methyl
eem e ..m/m ..m m m ..m/m//tt..mm
mm . m . . . . t t / t
/ t m m . m . . t . . . . t t
alcohol.
..
tt / t t . t t
/// /// t
/// //t / / / / / . .
tt / t t . t t
/// /// t t
/// //t / / / / /
::///s/s::/// sst:p:p/ss:: sst:p:p/ss:: sst:p:p/ss:: Isomerism ::///s/s::/// sst:p:p/ss:: sst:p:p/ss:: sst:p:p/ss::
With hhtt potas sium permanganate (KMnO hh 4h)h a tertiary hhtt"tthphtttt Alkenes show hhttfour
thhtt types of isomerisms, viz.,
p s s p p t p p t t p
t p t t t t
t p
t p t t t p s s p p t p p t ttp p t t t t
t p
t p t t t
ttpttt thhtt hhtt hht hhtt hht hh hh
(a) Chain isomerism (b) Position isomerism
hhtt hht
hydrogen gets oxidised to hydroxyl group.
bbeebbCH3 CHe3ebbeebb
bbe(ec) Geometrical bbeeisomerism
ew b eb bbeebb bb bb bbeebb bbeebb
vvruuvv ( d) Functional iwisomerism vviuiwvvi
eew
vvriuiKMnO
i eew eew eew
iw l vIvriuiuvv
ee w w w i i w ee
CH CH + [O]
w i w i
CH C - OH
iw iwvviw wwvvi i w w w i i i iwiwvviw w i w w w
vvriuiuvvi i
uuavvrr
These are alarrildescribed belowilialariliala
u urvv u u r uu r u 4
r ruu r r ru u
a r u u vv uu r u u r r u r ru u r r r
alariliala alailila rr alailila
alarrilialar 3 I alailiala alailiala
- -
I ilim ilim
Chain mttaaisomerism : This aa//ttaisa due to the difference in the //tt //t
iala
CH/t3taa//ttaa
i3lim ilim
ttaea//tta CH3
ilim ilim m m m m • ilim m m m m mm m
m m mm a m m a
t//•taea//ttaa
m a m a
structure
// ee of the carbon
m
mm/tt..mmchain. For example,
ee eebut- 1 -ene andmm.emm
m a a
ee e Aromatization m//tt..mm : Alkanes /tcontaining
ee e six to tenmmcarbon
m
m a a
/e/ttee//t t a a m t t t aa//tta
t a a t
ee ee / // e t t // /
ee ee / / / e ee
2-methylpropene are chain isomers.
mm/tt..mm atoms are//tt..m
/:/ss:converted into benzene //ss::/ and its homologues at
m eem
. . ..m/m//tt..mm
t / tt.:.////tt..m
/ . m
. m t . . m t .
t . t ..m/m//tt..mm
t //tt.:.:////tt.
hightttemperature in thetpresence ttphpttttpp of catalyst. tAromatization
t t // / / / : t t / t / / / / / / / / /
ppststttppsCH3 - C = CH
/:://s/s::/// : : / / / / / / : : :
sst:p:p/ss::CH - CH - CH= CH
: : : : s / / / / : / : : : : : s
ss s sstp:pss s ppststttpps
0
ss ss tphphttttpp
0
1/
ss
involves cyclisation isomerisation and dehydrogenation. hht hh
ttphphttttpp t
I
ttttphpttttpp t t t t p p t t ttpp t t t tttt t t th2
hh h hh t t tt 3 2
hht hh 2 hh hh hh h
CH3
hh h hh but- 1-enc
( I bCr b2 3 - A12 3 b ebb -3H 2 b ebb ebw b ebb b ebb b ebb2-methylpropene b eb b ebb b eb
b
� ii viw 600 C {-H2 ) viwuvvi I
0
Position isomerism : Position isomerism in alkenes

0
be e b e b eb w e e ebw e w e i e e b e b w e e evew bw e weiw
wveiw w e i w e ° i w e wi v wi w vi i
w • vi i
w v i w i w e wi w e i
w w e vi i
w i w i w v i
w w
uvarur ruvruv i i i
n-Hexane Cyclohexane arises from the difference in the position of the double
v w uvaruri u v ..._...._ u v
r larur uv v w
iruv vi vi
uvaruruv ruvru v i uv uv
u r
u uv r
u uv ur uvarur
ar r
u l l ar u i r
u uv u ur ar r
u l a larurliala
bond in mtithelialmiliasame chain. But- 1 -ene mtaisma position isomer mtaof
ar la r l ar i l i l ia Benzene ia l a ar l ar l ar i l a i l i
a l a i l i
a
•/atamm Pyroly s i s / C rt/ataam cki n g/T h e r m al D ec o mp o s itio n
almilia iamil a amil
ilam mi mi l ilaim
amil il ia a l amil
ilam im mi mi l
ilaim mtilam amm taem/t/atam amm amm taem/t/atam /ta
but-2-ene t/aee/t because these t ediffer
e/ e/only e/ in the . position
t ee/ e of
m the/.tm
t t
t ee/t Decomposition e/meeo/ f a compoundee/m
. by applicationtm .om/t/ef.tm . heat
/ t
a t/ a /at
t ee/ /
t a e/met/a t am / a a m /at /
t at t a /at /
t a / t a / t/a
e/me e
e/m e/m e
double bond
etem /m /m
etem .m/t/e.tm
is known as pyrolysis . But when applied to alkanes, the
m . . m/e.tm. t .
m m/.tm / . m . . m/e.tm . m . m t m.m/e.tm . m t . . .mt.m
-
:/tsCH - CH - CH= /:pss:/ CH CH
/pCH s:/ =s: CH - CH
.
tt m:/t/. /.tm / . t / t tm. /.tm . t / . t t / / t : t /
t t : : /. t t / t / / s:tps: s://s:/
:
process tpt t tptis known as hcracking and leadsht tptohttpformation
/ . /t
/:pss:/ :/ : /
/pss:/ : / /
s:tps: s / /. : /t /t : / /
/ s: / : / :/ / : / s /
s: /:/pss:/ s : ps s: t ps s: / : / ps s : s : p s s: s p s t ps p
ps
tpt t tpt ps tps 3 tp t t ttphtt tp tt3p tp tt
of lower hht hh alkanes, alkenes ht hh and hydrogen.h For h example, ht tpthhttp tpt t tpt tp ttp
2 2 3t tp
tptpsttpt hht hh but-2-ene hht hh ht h
hht hh ht h
b Geometrical isomerism : When two carbon atoms are
but-1-ene
hht hh h
propane on b cracking givesebbvarious products. b b
h•
joined
ebb by a double b ebbbond, they cannot b ebbrotate b ebfreely. eAs b eabb b eb
b
w 2 + CH2 = CH
ebw
Ciig viw iwv_iwi 0 CH3 CHvi= i vCH wuvv2iw+ CH4 + H2 uvviruvi result, the relative iwviwi positions of the i variousw viwvgroups attached
b b e b e b e b ebw
eb e eb e b e e e eb ebw e e
45O 5O0 c
Cracking e w e w e w i w i e e e w
viw
e w e w i i i w v w e w e w i i w wuvviw viuwviw
i i
uvavriuw
to these lcarbon urialaru atoms get fixed uialarandagive r lar rise toialargeometric
w uv i v i vi w vi w uv vi u v vi r
lliaaMechanism of m cracking is believed mil mto i be free-radical
uv r u v r uv r
u r
u uv r
u r
u ar u uv r uv r uv r
u u u r
u r
u r u r r
u
rurlialaru arulialar ar lialar larilial ar la ila larilial
isomers.
amilSuch compounds
tam twhich
il mi mi m possess
tamthe
il mi msame
i l i al li
a a r i l a r lial lia
tt aem/t/atammechanism. e/t/ataem/t/at
a
ilammi i
mamm ilaim a l l i i i
m mm
mi mi amm m
structuralt ee/t formula but e/mediffer
e/ e/ine the spatial / aITangement
/ataem/t/atam t/ataem/t/at t amm /at /at amm t/a a t a / t
a /
t a / t a /ta t/ataem/t/ata /tam
/a t e/ /a t / t e / e /
of the groups about .m/at/e.tm.double bond are .m/called
etem.me t.geometrical .me .mte.me
e/me .me e e
m/e.tm
e/me
.m/t/e.tm.me .m/t/e.tm. tm .mt/e.tm e/m
m/e.tm m m/t.m tm.mt/e.tm
/:p/sts:/:/ • Organic
. . m
:/t/.s:/:isomers and the s:phenomenon
/:/psts:/: s://s:/ is known s:/t:pss:/: as sthe :/ sgeometrical
t m .
s:/t:/pscompounds containing s:/t:pss:/: C = C tare s:/tpsknown as
t .
m ALKENES /.tm / t
. m t/ . / t m. /.tm . t . / . t/. t/ : / t /
/. t ts:/: /t :/ s:/ :
/ /t t / / t / : / s:/tpss:/ s://s:/
:/
alkenes.hht hh General formula hht hhC nH211 • Alkeneshwith
httphht two double httptphst tpt isomerism. hThis
ht hh type
tpt ttp ttpof
h h isomerism hht hh is halso knownhhtash cish h
s: ps p s p s t p s: p s ps t ps p p t ps tp p t p
ps
tpt t tpt tpt ttp tpt ttp ttp tpt ttp tt htt tpht tt t
bonds are known as dienes. trans isomerism. The necessary and sufficient condition
hht hh h h
Dienes b b eforb ebba compound tob exhibit geometrical b ebisomerism
b b b is that b ebb b eb
the two groups
ebattached to the same
e carbon ewe mustiweebe
be b b eb b e b b eb b
ebweeb b e ebb ebw bw
e b w e e w e i w e weiw
wveiw e i e
uConjugated Cumulated
e w w i w e w i
Isolated
i i
r larur different, i.e. ,
iralkenes of the following
uvaruruv ruvrtypes show uvarur elsruvruv
w
ii viw e � i w vi wi vi w vi wi vi w vi w uv v i wi w e v wi w vi i
w v i w i w i vi w v i w i
v w varuruv uvaruru v u v v i v uv uv
uv u v arurlial
milamil dienes ammtilammi dienes
r u u r
trans isomerism.
u v uv
milamil dienes
u ur a r r
u ar r
u l l r
a u i l i l ar ia r
u ar u ar r
u l l ar u i l a l a i l
ar l l i a i a mil mi a l a r l l ia
amil il il a a i a l i l a
il ia i al ialmilia ilaim ilamamil i mi mi
e/t = Cab, abCee/=m e/ = Cax, / = Cbx
tt aem/t/atam taem/t/atam mtilam amm t mtam amm t mtam taem/t/atam /t
tt/aaem/t/atam I tt e/t/a /a am t / a a t / a t a /a
• .metIn
/ a /a t t
t/aeabC /a
t eeCed,
/ e/ abC /a
/t eabC t / t
the cis-form, the m/.tgroups or atoms ofhigher
.me t.mtepriority
e/me / a t t / e/me e
etem /me - C= C-C-C = e/Cme- - C=C-C =ee/m
m/e.tm. . m/.tm .CIe- - CI =C=/.tC m.Im/t/e-.tm. e/m . m . m etem . m
e
tm.m/t/e.tm. .mt.m
ts:/: lie on the same : side / of:/ the : double /psbond.
. m
tt m:/t/. . 1 I I /I.tm. I I I / I
t
. m t / t t m .
m / t
. .
m m . m t . / t
. m /
t . / / t/. : t /
/. / t
/:Double /:/ t :/ t
/pss:/ :/ /:
s:tpss: /: / . / /
t . / t :/ t / t / / :/ t :/
s:/ s: s / / : / s:tps: s://s:/
/: s /
hht hh orbitals, hht tphhttp• In the trans-form,
/:/pss:/ Structure of s : / / s
hht hh ht hthe groups hht hh or hatoms
tpt t tpt ttphtt of higher
s: : s: ps / s : : s s: ps
tptpsttpt •
s : ps Bond pt tpt s: ps s p
In ethene hht hh carbon atomhht having sp2 hybridised
ps p s t
tp ttp tps tps ps p s p t
tp ttp tp tt
tpt t tpt t hht tpt t tpt tp ttp hht hh ht h
priority lie on the opposite sides of the double bond.
hht hh
one of the p- orbitals remains
be b b ebb e b b ebb unhybridised. e b b Thee b b three ebw b ebb
e b ebb ebw b ebb b b ebw b ebb b eb
eb w e e w e w e i eb e e e e e e
wveiw w e
iwviwi w e
vi
w e
i viw
w i v i i w
wuvviw i viw i
uv vi w e
iwviwi
w w e
vi
w e i
i viw iwviw
w v i i w
wuvviw viuwviw
i vi
r
u
v i
u u v
a r u uv
r larur l a r
uv
urialaru r
r
u
vi
uvaruruv a r r
u uv
uvarur ru ru v
a r u u v
ilamamil ar lial l
ilamamil
mtilam
a m am t a am m am t / a
a
t /a
e/t/aee/t
m t
t/a /t/a t
e/t/ae/t
/a /
e/t ee/a /
t am
t/at /t/a t t / a
t/a /t ta /t a t /
e/t/ae/t /t e/
a a e/t ee/ /tae
/a t
v v
w w
ii vvi i ww
u
i i
vvruuvv w i i
uu
i i
vvruuvv i
r ruu vvrruu v v vv
ww
ii vvi i w
u v v i
u
i
u
wvv i
uu vvruuvvi
i i
r uuavv
r
uruarru u r u r rr r a uu r uu rr u r r rr r
r
alailila
r
alailiala
ilim a
alailila
ilim a
ilima
l ii l l a r
lialariliala
r alailiala
ilim a
alailila
ilim l ilila
a
ilima
ilim m m mm m mm a m i m m m
m m aa//ttam
mm a
mm m m
t//taea//ttaa / /
eem e/ /
eem e/ taa
//tee// t / tt
eem/ ee
// /
eemee
t
/t /
eemee/
//tt:://// ., Colour ..m/m/and
.. odour : Al]//tare ..///ttcolourless, all /are tt:.////ttodourless
eem e eem e m m . m eem m mm .m
..m/m//tt..m mm .
tt.:.////tt. m m m
tt.:.////tt.. m . . t t . m mm .. m . mm . . //t::////t.
t .. t
except sst:p:p/ss:ethene. [Ethenc ppststt:tppPleasant odour]ttppststttpps
//tt //// / /
/ / : : /
: / / t
/ t t
/ t / / t: / / / / : :://
/ / ss:: ss: ss:: ss sspss / :/ :: ss: :: s ss ss
ss::/ss:: ttttphphttttp ttphpttttpp
., hhSolubility
ttphpttttpp
: Insoluble hh hh in water, soluble hh h in organic
t tttphpttttpp tttphpttttpp
t t t h h t ttpp
t hh t t t tttt t t h h htt h
hh h hh h
solvents.
hh h
.. Functional isomerism : A lkenes andbbcycloalkanes have bbeebthe
same molecular bbeebformula (C"H "). The cycloalkanes eedo not ., Boiling point and Melting
bbeebb point : Gradual increase with
b b bbeebb bbeebb bbeebb
we b eewbbee b eew eew eew
behave as vvrunsaturated hydrocarbons. vvriuiuwvvi Therefore,ualkenes vvriuiuvv and uuavincrease in molecular mass. b.pt. of cis-isomer > b.pt. of
ee 2
w w w w i w w i w
i w i i w e e w i w w w i w iw
i
iwiwvviw iw i i vrruuvv iwiwvviw iw vvriuiuwvvi vvriuiuvvi uuavvrru
cycloalkanes alarrilialar are termedilifimctional isomers.ilialFor ailiala example,
m trans-isomer.
uu u u r uu r r r u r rr uu vvr u u r uu r r u
r u r rr
alariliala alailila
ilim alarrilialar alariliala ilimalailiala alailila
ilim
propene
t//taea//ttaa is isomericee/with ttaea//ttaacyclopropane /(or ttaea//ttrimethylene).
ilim m mm m m ilim ilim m m m m
m m m m m m m ma a a t a a mmttaa m mm
aa//ttaa m mma
aa//tta aa
tte//t t aa
ta /t
eeCHe
/e/ttee/Chemical a a t t / tt / /
"- tt.:.m/m///tt..m • The most
/ / t
Properties t / // / e
mm/tt..mmimportant reactions ..m/m//tt..mmof alkenes are ..m/m/the
tt..mmaddition ////tt.:.m
e / e
..m/m//t/t..mm
ee e e m ee// ee ee ee ee ee e
m//tt..mm
..m/m//tt..mm
CH3 - CH :://s= ::/ CH2 ss::/H
/ ss:: C - CH
7
mm/tt..mm
2 2 reactions.
sst:p:p/ss:: Alkenes ttpare sst:p:p/sreactive due to ppststtthe
:://ss:: presence of ss:p:pss
t.
t . //tt / t
/ t / / /
/ / : t .
t . / t
/ t / t
/ t / / /
: /
/// /// ss:: ss /// /// / s::/
ss::/ss:: tttPropene ttphpttttppCyclopropane
hhtdouble
tthhtt bond. Thehhn-electrons are looselyhh hh held and are,hh hh
ttttphpttttpp ppststttpps t t tttphpttttpp p p t p ttt t t t tpp ttttpptttt
In alkenes, the functional group is the double bond, while
t t hh h t tt hh t
therefore, easily polarisable.
hh h hh hh hh h
b eb in cycloalkanes, bbeitebbis the closed ring bbeewhich
bb represents bbthe bbeebb Heterolytic bb bb Homolyticbbeebb
wveiw functional group.
eew eew eebb )c - c( eew w fission weewwee fission
eew )c- c( vviwiwveveiwbiwbeebb
Charged uuaspecies uuvvrruuvMene Ditadicalrruu rruu
eew w w i
w i
i iw i w i w
i w
vvi i w i w
i
v vv w i i w
vvruu vvriuiuvvi iiwvii iwviw
iw i
vvruuv uuav
uu vvruuvv r uu r rruuavrruu rr r rru u r r r
r a a l ilila
•
Methods ofaarPreparation r r a l l r a a a
alailiala alailila lialariliala alailiala alailila
By adehydration of alcohols mttaa :
l iliala
ilim ilim ilim ilim
l ii ilim ilim ilim
•
Ionic Mechanism i
1 step//tee:// The reagent Eee/-eeNu ionises toeegive
aa//ttam
ee an
m m m m m m m
I//ttee//I
m m m m
95% H2S04ee// ee
mmtaam aa m a a mt aa
t ttaa//tta a mmtaamm a a m mttaa a a mt aa
t t t a
a t t / t t / / // aa tt / t t / / //
-
eCem - C - , .,,,. - ,
t / / st t / /
electrophile
..m/m//tt..m and nucleophile.
eem/ ee eemee t / / eemee
'c _ c/
..m/m//tt..I m I '--'
m m . m eem m m m m m .m
m m m m m . m . . t . mm . m m m . . //tt::////t.
. . t
/ / E -Nu ss:E'
ppttttpps+ : Nu- ttttppststttpp
m .
tt.:.////tt. tt.:.////tt . //tt:://// t tt.:.////tt. tt.:.////tt
ss::/ss:: H OH ttppststtp:pss
/ /t t / /// / /// : : /
: / / t
/ t / /// / /
/ / : : /
: /
/ / : : ss:: ss sspss :s: :: ss ss ss
•
sst:p:p/ss::
hht hh2 step : The electrophile attackshhtheh carbon-carbon
tttphpttttpp Saytzeff rule hh :hhIf a single starting hh hcompound can yield two
ttphpttttpp ttttphphttttp ttphpttttpp
----f
t t t tt h t p
t p t t t
nd t t
t t h t t h
double bond and fonns a covalent bond with one of
t h t hh hh h h
or more isomers then more substituted alkene is formed in
hh h
greater amount. ethebbeecarbon atoms eby bbeeutilising the re-electrons.

be b bbeebb bb bbeebb bbeebb
ew bbeebb bbeebb eew eiw bb eew
+uvviuiuwvvi
eew eew
., By dehydrohalogenation of vvrialkyl
iwvvi halides : vviui vv
i ee w w i w i w
i w i w e w w i w i
E rr a+)
iwiwvviw iw w i w i vvruuvv w iww w
vvriuiuwvvi i w
vvriuiuvvi uuavvrr
lialIarilialal alaililar tl c ( � alariliala )7 - c(
v u u
ale. KOHilim
u v uu r u u ru u r ruu r r u r r a r u r u u r r ruu r r r
r u rr alariliala ilialailila r alailila
-miC -C- )C = C(
alailiala alailiala
Alkene
ilim ilim ilim ilim
E //ttaa//tta
m mm m mm m mmtaamm ilim m m m m m m mm a a m
Carbocation
m m �/ttaa//ttaa ttaea//ttaa aa
/e/ttee//t mmttaa m aa//ttaa a aa
tte//t t
t//taea//ttaa1 I / // t a a / t t / /
..
t / / e
3
em e H X ee ee ee e e // ee / ee ee ee ee e em
..:////tt.:.m:/m///tt.ePartial hydrogenation ./ .m/m//tt..mm of alkynes//tt..m : step
/// :/// : The nucleophile / / now attackss:the // : carbocation ss:: ss
m eem
.m t t m//tt..mm
/ / tt.:.m/m///tt..m
/ rd . m
. m t .
t . m t t..mm/tt..mm
/ / t ..m/m//tt..mm
t / / tt.:.m/m///tt..m
/
ttttphptttto
ss:p:p/ss:fmm an addition tttphpttttpproduct.
ttttphpttttpp R - C Chh-ttttpRhphttt+tpH2 Pd/CaC03hhttttphphtttt "c - c/ hhtttthhttt
/
/ / / / / /
:: s : t t / / / / / / / :
ss:p:/ss:: ss:p:p/ssR:: ss::p/ss:: s: ss:
ss: ss
Alkyne
= (Lindlar's catalyst) H/ - "H
R ppsstpps
t t ttttphpttttpp h h ttttphphttttp
p
)i-vNu-
hh h hh h hh h hh h
cis-alkene +<
Fast
• Birch reduction b eb:b b ebb b ebb b
bweeb b b ebb b b b ebb b eb
H
b eb weview b ebb
ii viw Na/Liq. NH·"viwuvvi
ebw evewbw ebw e wewe evewbw e weiw
Addition uvaruruv product
e ebw e w e e w i e i i ebw e w e w i
wvi w w e i i Rwi v i
w i vi w i w e i i
w vi wi i i v i
w i i
w i uv w v w vi uvarur ruvruv
i
Alk e
i
mi mAs i the addition reaction ialmilia is initiatedmiliby a il an electrophile, athe
v uvarur "c= c ( uruvarur uv u v
r larur v iruv v uv uv
il ia yn
u R - Curuv='=uruC v -R r ar u uv ur u vru r
u arurliala
u ar l i r
u u r ar a l
milamil H/trans-alkene
ar l ar l l i l ia l a ar l ar l a l i l a l i
a
taem/t/atamreaction is termed as electrophilic amt/aaddition.
ar l i ia i a l ar l ia a l i a l i mi mi l
milamil milam Ril il i ilam mil mi m
..Electrolysis
tt/aaem/t/atam
of saltmeof e/medicarboxylic acids
tt aem/t/atam
/
°
a e/me :
tt aem/t/atam
/ a
. • Addition
t
e/me
.m/t/e.tm
/a
toft
/ae/t
mtilam
e halogens : .Alkenes
am / a e/m /at
t ee/ e/ e/t amm amtam
readily
t
add
e/m /a amm
. eont.m
t
t e/ e e t/at
the.m
/ t a / t a t/a
e/me e
.m/t/e.tm
taem/t/atam /ta
CH
etem/me etem/m
tt m:/t/. CH2 COONa:/t/.�%i� CH
m/e.tm
halogens :/ts:/: in the presence /:psof / an :inert / s: solvent /pssto :/ form : s1 , 2 pss:tps: s://s:/
m/e.tm m/e.tm . .mt.m
2 2 pss: ps:
m . . t .
m . . t m m . . m m . t m
. t m /. coo- tm / . . t m . . tm t / . t /
I ps � i � ii + 2CO
/ . t t/. / t : / t /: / t
. m / . /t/. t t / t t/. :/ t / / / : / t /:
ortptpvicinal
s ptps dihalides. tptphst tpt ttp ttp
:
tpt t tpt Anode CH2hht tphhtt 2
/pss:/ : / :/
/pss:/ / s / t :/ / / : / / : / s
/:/pss:/ s :
CH2 COO-
s
CH2 COONa
s: s : ps s: t t s :/ s : s p s : s p t p
tptpsttpt tpt t tpt
p t tpt
ht tphht htt ht
pt tp ttp tp tt
hht hh• Hofmann hht hh hht hh ht h
elimination :
hht hh ht hhtt --..___
ht h h h
,,,, _ I I
C = C + X2 � - C - C b e-
h h h
(C2 H5) 4NOH - eb�

(C H hN ebwe+ CH = CH w
b ebb
2 + HzO
b b bb eb eb b ebb b eb
be b b b b eb ebwe b eb e b
evwiwe b eb b I ebw I ebw e e
Tetraethyl
ew eb e e i w eb e e w e
e w i i e w i wuvviw viuwviw
i
,,,, .._.____
e w i e w i
iwviwi i viw w
viruvi iwviwi i viwX iwvi w uvavriuw
2 5 2 wuvviw
w X w
larilialAddition of dihydrogen (H ) (Hydrogenation) uialar ar ar : Alkenes
vi vi vi
ammonium lliaariulialahydroxide
vi vi
..
uv vi w u v v
u r uv r uv ur r
u uv u uv v
i w uv uv r u v v u r uv ur u r r
u r
r ru r r
arulialar u u
ar lialar ar urialaru r r u u u
ar lialar ila ila r larilial
.. Wittig tt aem/t/atam reaction : e/t/ataem/t/at /ataem/t/at undergo hydrogenation in presence tam taofm/tacatalyst alike tamNi,
iilalm ial i li
a l a r 2 ial ar l l i l ial i li
a
mami mil mi mamm ilaim
amil il mi i m il mi m m m mm
mi m amm mm ataem/t/ata /tam
Pt, Pd, etc., t ee/to t form corresponding e/mee/ ealkane. (Sabatier e/me and
taem/t/atam amm t t /a t / a t a /ta /
C= 0 + (C 6H .m/5t/ehP.me = CH2 �
/a t/a e/ t /at /a /
t a t /
t a e / t / e/ t
.,..-
R, �-.mee./me / e .me .mte.me
Sanderen's reduction.)
.mt/e.tm .me e/m . .mt.me /.tm . t.mte.m .mt/e.tm
/. tH
e/me .m/t/e.tm
.m/t/e.tm
s:/t:/pss:/:Methylene
t .
m m/e.tm . / .tm t
. m / .tm t/tm
. /
t tm
. / tm. m/e.tm . /.tm / /
t tm
. : / t /
/t / :/ : t / / t / / s:/tpss:/ s://s:/
:/
ps CH 2 = CH2 + tH t p---P. CH p - CH
t s:/t:pss:/: s:/tpss:/ :/t/.s:/:/t t :/: :// :/ s:/t:pss:/: s:p/ s:
tpt ttriphenyl phosphorus
s: /:p/sts:/:/ ps ps t ps t p s: / ps p s s:/t:/pssNi s s ps p t p s t p p t p
R -hCH = CH2 + (C6Hh5)_iP = 0 Ethane
t p httphht t p t tp t
Ethene h h h
ps t t
tpt t tpt hht hh
tp ht tphhtt tpt t tpt ht pht2t ttphtt 3 hht tphhtt3 htt ht hht hh ht h
hht hh hht hh
. H202 or (.JJ e
• Cope reaction : bR3N CF,COOH )
b - N - 0 ebb ebb .. Birchebreduction
R3 :
3 ° amine
b ebb
3 -N-axide
b ebb b b b ebb b eb
= CH + 2H ----... R - CH
e CH_i
b b b ebb NH,
2 2
b e b e b e b eb w e e b ° e w e w e i w e ebNa/liq. ebw ewe evewbw e weiw
wvie w w
ii viwe i w e j
i
w w ev wi i
w w vi wi R -vi i
w CHvi w i w e i w e i
w w ev wi w i i
w w i i i
w vi i vi u v w vi w vi i i v
uvarur ruvruv
i
mil mAd i dition of hydrogen halide i:liaAlkenes il ilmil react mwi thil
v uvaruruv uvaruru v u v
r larur viruv C2 H5 0H uvaruruv ruvru v uv uv
il 0
uv arurlial
isooc mCH
u � uv e R r r u u v r r
r r
u u u ,. l ar r u u u l
R - C�
u ar ...._, lar il l r
a i l ia ia u a r ar l a l ar i l a l a ia
taem/t/atamhydrogen halides or halogen acids ato
mmgive mtacorresponding
a r l a i a l a r l l ia a i a l i mi mi l
ia iliamil milamil ialmilia ilam i
tt/aaem/t/atam N
milamil I + � tt aem/t/CH mtilam amm amt/atam tam/tam taem/t/atam /t
2
atI aIm tt aem/t/atam
alkyl halides.
/a /a t
e/me/a t am / a /at /
t
t ee/ e/ e/at t a /at
t e/ / t/a
e/me e
e/me e/me t/aee/t e/m e/m e
H X
m etem/me
. CH{\}
'-
R . m/e.tm . t .
m m/e.tm . / .tm.m/t/e.tm. m etem/m
. . m/e.tm. m . m t .
m m/e.tm . e t.mte.m / .tm.m/t/e.tm. .mt.m
/:pss:/ s:/ s: I Ipss:/pss:/ s:ps
.
tt m:/t/. 2 / t
. m / . t / t t .
m / t
. m . t / . t / / t : t /
/ . /t
/:pss:/ :/ t : / t
/pss:/ :/ /:
s:tpss: /: /.
:/ts:/: /t/. /t :/ t / t / / : / t :/ / / : / s:tps: s://s:/
/: s /
tps = c< + HX
/:/pss:/ s: s: p s / s: p s
hht hh• Physical State
Physical
s : Properties s: p
hht hh C 5 - C 1 7 li quids, hht hh ht h )c-c<
tptpsttp)c
hht hh : C 2 - C4 gases,
p s t t
hht hh C 1 8
ps tp ttp tp tt
tptpsttpt
ps
tpt t tpt tpt t tpt tp ttp tpt t tpt--+- tp ttp tpt t tpt ttp tt hht hh ht h
hht hh Alkene hht hh h h
onwards solids. b ebb Alkyl halideb b ebb b eb
b b b ebb e b b ebb e b b ebb ebw e b e b b ebw b eb b b ebw
e e eb e w e w e w e i w e i eb e e e e w e e e
wviw e
iwviwi
w w e
v i w w
i viw i v i i
wuvviw i viw uv vi w
w e
iwviwi w e
vi w w i
i i vi
r
u
vi
u uv
a r u uv
r larur la r
u v
urialaru r
r
u
v i
uvaruruv a r r
u uv
uvarur ru ru v
a r u uv
ilamamil ar lial l
ilamamil
mtilam
a
t /a
e/t/aee/t
m t
t/a /t/a t
e/t/ae/t
/a /a
e/t ee/
/
t am
t/at /t/a t t / a
t/a /t ta /t a t /
e/t/ae/t /t e/
a a e/t ee/ /tae
/a t
vv
ww
ii vvi i ww
u
i i w
vvruuvv i i
uu
i i
vvruuvv i
rruu vvrruu v v vv
w w
ii vvi i w
u vvi
u
i
u
w
vv i
uuvvruuvvi
i i
rruuavv
u
r
alailila
r
alailiala
ilim a
alailila
ilim a
ilima
l iil l a r
lialariliala
r alailiala
ilim a
alailila
ilim l ilila
a
ilima
ilim
Hydrocarbons m m m
m m m
m a m i m m m
m m aa//ttam
m
m a
mm m m
eem e/ taa
//tee// t / tt
eem/ ee
/ / /t
/t //
eemee
//tt::////addition • //tt..m/m/Self .. addition or//tpolymerization : /Alkene
tt:.////tt molecules :l:/ink
eemee
tt.:.////tt.o ff's rule : It////tstates t.:.:////tt that during::/the
eem e eem e eem e mm . m eem mm .m
..m/m//tt..m• Markownik mm . m m m .. m .. t t . m mm .
..///tt .m . m
m .. m //t::////t.
t .. t
ssppss etc. to ss:://ss::/together in presence
of unsymmetrical reagent ttphpttttppsuch as HX, HOH, ttttphphttttHOX, ppststttpps of acid catalyst ttphpttttpat
ss::psshigh temperature ttphpttttpand
//tt //
/ / / t
/ t // t: / /
/ / : /
/ / ss:: ss: ss:: ss :: s : ss pss
ss::/ss::
unsymmetrical alkene, hh the h positive pai1 of the addendumhht hh pressure tohhgive hh new bigger molecule hh h with high molecular
ttttphpttttpp ttttphpttttpp tt hh t tp
t p ttttpp t t
t t tt hh tt h
mass. The process is known as polymerisation.
hh h
(i. e. , molecule to be added) goes to less substituted carbon
hh h
atom of bbdouble bond i. ee.ebbcarbon atom of the
bbedouble bond bbeHigh bb temperature eebbeebb
b b bbeebb
and pressure
we bb bb e bbeebb
n CH2 =vvCH
b e
which iw carries greater vvriuinumber of hydrogen vvriuiuvv atoms.
b e e
vvriuiuwvvi -fCH2 - CHuuv2vrt,;-
ee e e e e e w w w i w
i w ee e w eew iw
iwvviw w wvvi i w w w w i i w i i v iwvviw i2w--------''------ w i w ii vviw
w w i i
vvriuw uuavvrruuv iw uuavvrru
alarrilialPeroxide effectilior alariliKharasch effect ala: ilKharasch and Mayo Ethylene alarri(Monomer) alariliala Polyethyleneiliala(Polymer)
u
.. uu u r uu r u r ruu r r r
alailila u u r uu r uu r r r r u r r
alailila
ar ala iala ilim lialar iliala ilim
t//taea//ttaa in 1 933 observed ttaea//ttaa that addition /ofHBr ttaea//tta to an unsymmetrical
ilim ilim mm m ilim ilim mm mm m
m mm m m m
m m a a a m mm m mm a aa
alkene inm m/presence
eem e of peroxides
..m/m//tt..mm such as benzoyl tt.:.m/m///tperoxide
mm a a
/e/ttee//t t mmttaa aa//ttaa t a
aa//tta / a
tte//t t
-fC�tt..m -m .CH-t,;-
// / e t t
// eeaa // //tt // t e / e
ee e ee ee eemee em
gives::/the / product contrary / to Markownikoff's : rule. It is :://// ::///
ee e ..m t..mm eem mm/tt..mm .m tt.:.m/m///tt..m
mm/tt..mm . . t t t / m m .. m .. t t /
:://s:: 1
. . t t t / . . t t t / / /
ppststttpps Cl
t / / /
lmown tttphpttttppas anti-Markownikoff's
ss::/ss:: addition.ttppststtp:pss
t t
/// /// / / / / // / / / : t t / /
/ / / / / / / /
:: s :
ss::/ss:: ss /ss:: sst:p:p/ss:: ppststttpps
Polyvinyl
hh hh chloride (PVC)
ttphpttttpp sstppss
Vinyl chloride
t
hh No h Peroxide
ttttphpttttpp t t t t t h t t p
ttp t t t p
t p t t t t t
t t tt t h
hh h hhtt hht hht hh hh h
CH. _ CH _ CH3 ..
hh h hh h
, I ebbeebb bbeeOxidation reactions of alkenes : Oxidation of alkenes
Br yields different bbproducts under different bbeebb conditions. eebbeebb
b eb bb
HBr
wveiw bbeebb
vvruuvv addition) rruuvrruu • Complete
bbeebb eew eebb
CH3vv-iuiuwvCH i = Cl-Iz (Markownikof!'s ii vvoxidation (combustion) vviw : Alkenes vvroxidise
ee ee e w i w eew eew
w i ww i w
i w i w
i w i w
i w i w
i w v i i wv v i w w i i w i w
i w i iwvviw
iw iw
uuav
completely
lialariliala in air to yield alailiCOala 2 and H2 0. The alaililareaction
vvruuvv vv
alailila Propene
uruarr v r u u r r u
r u r a uu v v u u r u u rruu r u
r u u
r u rr
r a a r r r l ilila
a
mttaa Peroxide taa ttaa
r a a l l r a a
ismmtalso mm known as combustion.
alailiala
ilim alailila
ilim ilim
l ii ilim ilim ilim
C� - CH - CH Br
ilim i
aa//ttam
2 ee e2e
m m m mm m m m m mm
/tee//2 = CH 2 + 30e2e�
/CH / ee 2C0 2 + 2H 0ee +ee1 4 1 I kJ mol- 1 ee ee
mmtaam aa m m ttaa//tta a a aammttaa aa mttaa tt a
Anti-Markownikoff's addition
aa
//ttee// t tt
// ee // / t / / // ta a t a / tt / / /t
/t // //
eem/ ee
•/m ..mOxidation with tt.:.////tt. potassium permanganate : :On
eem eem m m .m m eem m 2 m mm.mm
m m m . . m tt.:.m/m///tt..m //tt.:.:////tt.
Addition ss:: ssof : water : ss:: ss
..m/m//tt..m mm .
tt.:.////tt. m
tt.:.////tt. . . tt mm .
//tt .. //// /// / : ::/ //tt::////
/ / t
/ ..m
sst:p:p/ss:: oxidationttppstswith
t //tt
ttpp KMn0 4, ttttpdifferent
//// //// :
products ttphpttttare
/
: /
• htDirect
/ / ppststttpps
s / / :: ss: :: ss ssppss
ss::/ss:: ttphpttttpp hydration ttof ttphptttalkenes : Water ttttmolecule adds
pststttpp
obtained hh depending upon hreaction h h conditions.
tttphpttttpp tpp h t pp t t t t t
up to the alkene in presence of some mineral acid,
t t hh h t t tt t h h h h
Oxidation with cold dilute neutral or alkaline KMn04 :
hh h h h hh h hht hh hh
tobbyield bb alcohol. Addition bbeebb takes placeeein bbeeaccordance Allcenes on reaction bb with cold dilute bbeebb neutral or alkaline
ew b eb bb bbeebb bbeebb
iwvwith
viiw Markownikoff's vviuiwvvi rule. uuvvrruuv KMn04 get ihydroxylated to form vviuiuwvv1,i 2 glycols oru1,vviui2-diols.
i ee ee ee w ee w w e e bb ee e e eew
w w i ww ww i w
i w i i w i i wvviw w i ww w w i iw i
vviw vviuiuvv v
vviw iw uvv uuvvrr
lialariliala cold OHilialailialaOH
uu ruu uuarru ruu rr alarriliala uu ruu ruu rr rru rr alarriliala
alarrilialar alarrili+o lalariliala alarrilialar
CH2 = tCH ttaea//ttaa...,. CH3 - CHe2e//t-taeae/OH
taeae//tta2a + H - OH e__
la ----6 ilim ilim
aam/m/ttaam KMn04 //ttaaI m/m/ttaa I
ilim ilim E i im
t
l i
C
m m i i m m
// eeH2 = CH2 + Hp ee ee+ [O] ee CH ee 2 - C H2
mm m mm m m m m m m
mm m /ttaa mmtaamm ttaea//ttaa
ee e • Oxymercuration-demcrcuration : Reaction tt.:.m/m///tt..m of
t//taea//ttaa / / / / t a
t a // t / t
/ t e em/ / e
Ethylene Glycol
ee e e m eem -----''-,I,
tt.:.m/m///tt..m
alkenes
:://ss::/ with mercuric ss::/ss::acetate in presence ss:: ss: of water
t . mm/tt..mm
. / ./ .m/m//tt..mm
t t //tt..m/m//tt..mm / /
/ / t . m
. m t .
t . m / t �
t..mm/tt..mm
/ / t
/ ..m/m//tt..mm
t / // /
ttphpttttppborohydride ttppstst:tp:pss Cold alkaline sKMn0
st:tp:pss: is known ppBaeyer �<; reagent tand
ppststttppthe
/// ///t / / t
//// :://// /
// :From // KMn04 :://ss:: / :: ss :
ss::/ss:: tttphfollowed by reduction ttphpttttpp with sodium
sstpp
pststttpp p t
test is known
hht hhas Baeyer '.Y test.
ttttphpttttpp t p t t t
also results in hydration of alkene according tohh
t t t hh h t tt hht t tt t t 4 t t t t t hh h t h
hh h hh h hh h hh hh
Markownikoff's rule.ebb ebb b eOxidation with bhotbKMn04 : On reaction b ebb with b ebhot alkaline
l
b ebb bb b ebb b eb
KMn0 or higher e orweacidic KMn0
b ebb ebw ebweeb cone. of KMn0
ii viw RCH = CHv2iwu+vvi Hg(OCOCHu3v)vi2 uvi
e b eb eb e w e w e w e ebw
i e i w e i
w e w e ebw w evew bw
i e , weiw
i i
alkcnes are oxidatively cleaved uvarleading
uv uvrto the formation uvarur rof
wvi w w e i w i w wi v w vi w vi 4 i w e w i i
w vi w 4 i i w v i
w i 4 i v
THF
v w u v
r larur u v v w
iruv vi vi v i uv uavru uv
u uv uv r uvarur r r
u u v
u r r
u u r arurliala
different ialmicompounds depending
amil upon
mtam structure of alkene.
r r
u ar r
u l ar ui l l ar ui l ar ial ar lia ar r
u ar u l ar u i l r a l ar u ial a l i
a l
a l i a i a mi mi l l ilaim a a l i
amil l i mi mi l
il ia
milamil milamil milamil lia il i ilam i
t/aee/t = CH KMnO,, t e[OJ
mtilam amm
e/me raxymercuration)
tt aem/t/atam taem/t/atam amm mtam taem/t/atam /ta
tt aem/t/atam
RCH
tt/aaem/t/atam / a / a t/a t am / a /at /
t t
a t a /t
a
t ee/ e et/at / t a / t/a
e/me e/ eRCOOH / e/ /m e/me e
e/me
.m/t/e.tm
e/m +etem .m/t/e.tm
OH
etem/me m/e.tm. m/e.tm . . etem/m 2 mI',./e.tm. m .HCOOH m m . .mt.m
. m
tt m:/t/. . /.tm. / t
. .
m t / /
t t
. m tm. m . /.tm. . m t . m / t
. m. /
t . t . / t . / t/ t
. m : t /
t : / . t t / s:tps: s://s:/
tpt t tpt ttp tt l[OJ httphhttp httphtt
/ . /t
/:pss:/ :/ :/ t
/pss:/ :/ :
/
s:tps: s / /.
:/ts:/: / t /t :/
/:pss:/ s:/ s: / / / : / t :
/pss:/ s: s/ / : / /: s /
s : /:/pss:/ s: s: I tphttp ps s:/ s : s
: p s
h 2
p
hht hh h hC02 + Hp
ps t ps p s p t
I
ps
tptpsttpt tpt t tpt tpt t tpt R - CH h-ht CH tps ptps
ht tphhtt tpt t tpt tp ttp
hht hh hht hh hht hh ht h
NaBH4
hht hh I h h
(Demercuration) b ebb HgOCOCH
b ebb •ebbeebbOzonolysis ofb ealkenes : Ozoneebbon ebb passing b eb through b ebba b eb
Hydroxymercurial wuvviw compound uvviruvi solution ofviwialkenes in an ine1tvisolvent i viw iwlike i CC14 or wuvCHCl
ew b eb eb b ebb
e ebw e w e ebw e 3
i w evwiw eb bb e w e e w e ebw e e
e w e w
i viw i i i w e w e w i w i viw v3iwviw
i
uvavriuw
at low temperature oxidises uthe ar alkene r lar to a cyclic ar lialar product
iwviwi w wviwi w
vi v i vi vi
rulialar - CH3
uv vi w u v uv r uv r uv r
u r
u u uv uv u v r uv v u v r uv ur u r u r
u r
r r u u ar r r u u u r
called ozonide which ais ilmmi mi mand on m
taunstable amtreduction with tamm
r u
lliaariulialar R -ialaCH i l ar lialar li
a larilial ar urialaru l ar ial a i l la i l a li
a larilial
mil mIi
a i l i a l l i a i i
taem/t/atamOH
mil mi mamm iam
mtilam il il mi mm
reducing agents like e/mee/zince/ and e water e/meor hydrogen ine me e e
mi m
tt aem/t/atam /a / ataem/t/atam t/ataem/t/at t am /a /at mm /
t a t a t a / t
a /atam /tam/tam t/ae/t/ata /tam
m/epresence of palladium . .gives m aldehydes . and or ketone
/a t t e/ /a
t ee/t t / t e/ e/
Addition .m/t/of .malkanes : Alkanes
. add on to /alkenes in
/e
etem e/me .me e e
m/e.tm
e/me
• .m/t/e.tm .mt/e.tm e/m
.m/t/e.tm .m/t/e.tm m/t.m .mt/.tm . mm
tm tm / ://t.://t.
ps:tptpsHF to give pss:/t:pss:/ depending upon s:/pss: i.e.s s C = part ps:tps of s s
.
tphsttptpsstructure
s:/ s: s: s: of alkene,
. tm . m . t m . / .
presence tphsttptps of acid catalyst tptphsttpt such as H2 S0htt4pthhtor tptphsttpt ttphttp) httpthht tp httphttp
t .
m /.tm . /t/. : / t : / /.tm. t
. m t/.tm t / t / /
t . : / t / :/ t :
/
//: t/.s:/:/t :
s:/ s:/ t /: :
s:/pss: :
/ s / s: / /t :/ t : / /: / / / : / : / : s / s:
addition
h h product. h h the alkeneh which h hgeth converted h hto ) C = Q . h
s:
ptphst tptps t p t
p tp tp t t p ttp
CH3 CH3
t ht ht h t ht ht h t h
hht h hht h
CH3 w-
bI ebb - CH
CH + CH
b ebb I
C - CH
b ebb b ebb xox:
(y< b ebb 0b b b ebb b eb
H SO
b eb eb ebw )c ebw e= c < + 03 e-> b ebb y\ ebw z_:;
e wewe 2 )ciwe= ebw eo weiw
uvaruruv bo-butene uruvaruruo;c
e bw
v]so-butane
e e eb w e i w e 2i w e =
i w e wi e wi w vi i
w w e e i w e i i
w
1
w ii viw i w 3 w vi vi i i w i w vi i
O -i--t O
wvi w 3
vi w vi vi u v u v v w vi w vi w v i i v v
uvarur ruvruv
i uv uv
'' iliam
v v iruv
' il
u 4
r larur
u uvaruruv ruvru r arurlial
am. amtam
u r
u uv a r r
u r
a r
u l r
a l i l ar ia r
u uv ar u ar r
u l ar u l a a i l
a r l l ia i l ia a l a r l l ia a a i l ia l i l a
tt a3em/t/atam CH3 e/t/ataem/t/at
i milammi il il amil mi mi l
CH
milamil
il ia milamil milamil mtilam
ialmilia
amm amm
ilam mtam
i
taem/t/atam /t
tt/aaem/t/atam tt aem/t/atam / a am t / at / t
a / at t a / t/a
•
/ a ALKYNES t / a /a
t ee/ e/ e/t t t e/ e e t / e/me e
Alkynes are unsaturated hydrocarbons
m/e.twhich
. e t.mcontain a
e/me t/aee/t e/m e/m
CH - C - CJ--I - CH - CH
e/me I /t/.tm.m/t/e.tm.me /m .m/t/e.tm
m etem/me
. m/e.tm . . m/eI.tm. m etem . m/e.tm . m . m . m tm . .mt.m
:/ts:carbon-carbon tJiple
/:pss:/ bond / s:(C = C). /psThe s:/ general : s formula
.
tt m:/t/. . / t
. m / t
. m t t .
m . /.tm . m t . / t
. m t / t / /
t . : t /
/ .
/:/pss:/
/ t
/:pss:/ : / t :/ t
/3pss:/ I :/ /:
s:tpss: /: / . : /t/. /t :/ t / t / / :/ t :/ / / : / s:tps: s://s:/
/: s /
hht hh CH.�
3
/ :
ht tphhtt of alkynes hishttC,,H
ptphst tpt 2n _ttp, twhere
hnht ishh 1, 2,h ....h Alkynes hht hwere
s: s: ps s: t ps s: / s: s p s s: s p t p s p
tptpsttpt
ps
tpt t tpt tpt t tpt tp ttp
i'-2
tps ptps tp tpt t tpt ttp tt tphttp ttp tt
hht hh
/so-octane earlier called acetylenes.
hht hh hht hh h h h 2h h h
b b ebb b ebb b ebb ebw b ebb b ebb b ebb b b b ebb b eb
e b e e b e eb w e w e eb w e i w e i e e b e ebw e e e w eebw e e
wviw w e
iwviwi w e
v i ww
i viw i v i i
wuvviw i viw u v vi w e
iwviwi
w w e
v i w w i
i i vi
r
u
vi
u uv
a r u uv
r larur l a r
uv
urialaru r
r
u
v i
uvaruruv a r r
u u
uvarur ru ruv v
a r u uv
ilamamil ar lial l
ilamamil
ialm
mtilam i mtilam mtilam amm t m ilaimalm i mtilam m mtilam mtam amm t
a m a m t a am m a m t / a
a
t /a
e/t/aee/t
m t
t/a /t/a t
e/t/ae/t
/ a /a
e/t ee/ t/ am
t/at /t/a t t /a
t/a /t ta /t a t /
e/t/ae/t /t e/
a a e/t ee/ /tae
/a t
vv
ww
ii vvii w w
u
i i w
vvruuvv i i
uu
i i
vvruuvv i
rruu vvrruu v v vv
w w
ii vvi i w
u vvi
u
i
u
w
vv i
uuvvruuvvi
i i
rruuavv
u
r
alailila
r
alailiala
ilim a
alailila
ilim a
ilima
l iil l a r
lialariliala
r alailiala
ilim a
alailila
ilim l ilila
a
ilima
344 ilim m m m
m m m
m a m i m m m
m m aa//ttam
m
m a
mm m m
t//taea//ttaa / // aa t tt / / /tt //
//tt:://// • Reaction ..m/m/of.. iodoform with tt : Iodof01m
tt.:.silver .////ttheating
tton
/
eem e /
eem e eem e t
//tee// /
eem/ ee /
eemee eemee
eem e mm . m eem m mm .m
m m mm . m .. t . m m mm . //t::////t.
.. t
with ssilver st:tp:pss: powder gives ppststtpure
:: ss: acetylene. ss:: ss
..m/m//tt..m of Triple /Bond m .
tt.:.////tt. in Alkynes////tt.:.:////tt . t m m .. . . t
tttp•hpttttpp Alkynes can pststttppdescribed bytttthe
ttpbe ppststttppcondensed formula
Structure//
/ /tt /
/ /
:: ss: :: ss ::// / t
/
// : /t t
/ t //// //// //// :: :://
ss::/ss:: sspss ss ss
hht ;---------------;
ttttphphttttp ttphpttttpp
hh h R - C - C h-h Rhhwhere R may be hh an h alkyl group or H. hh hAlcohol
t p t tpp ttphpttttpp tt
I3 + 6Ag + !,:CH
CH:,_______________ ----,. CH= CH + 6Agl
t tt h hh t tt p tt t t t h t
hh ht hh h
The simplest member of this homologous bbeebb series (putting,
hh
,
n = 2) has the molecular formula eeCw H
b b
Kolbe's iw electrolysis i:wwElectrolysis of concentrated iw solutionvviw
b
we bbeebb bbeebb eebbeeb bbebb b
eebbeeb
b
eebbeeb
eew •
uvvrruupm cr
cr u120
e iwvviw eewwe
of sodium or potassium
vii salt of maleic or fumaric acid
e w w i w vvriuw iwvviw iwvviw
iw iw
i
iwvviw w
vviiwvvii w
vvii vvi vvriuw
•
iw iw 2 2
u u v i v u uuavvrru
rruu rruu rruu rruu u r v u
aammtaamgives acetylene
ilialat
m anode.
rr u uu u uu r r r
ialat c106 pm
a
alailila u u rr u rr r rr r alailila
H -ilialcarril= - H ilialailiala alailiala
ilim ilim arriliala ilialailiala ilialailiala ilim
one // ecr-bond + two n -beeonds
m m
CHCOONa
mmamm m
// ee Electrolysis CHCOO-
m mttaam m mm
aa//ttaa
m m mm
aa//tta a m tte//t mm mm mm
mttaa aa//ttaa aa//tta a a
tte//t t aa
a t tt / / a t tt //
I I
t t a / / // t // e e t t a / / / / t ee ee// eem e
-
ee ee em
mm/The./ .m triple bond//tpresent ..m/m//tt..mm in alkynes
/ -C C - iss::the
eem e ee eem ee ee
mm/t1t.1.mm
CHCOONa
tt.:.m/m///tt..m tt.:.m/m///tt..m
ss::/ss:: CHCOO ppsst:tp:pss:
..m/m//tt..mm ..m/m//tt..mm
l
. t t / / . m m .. m t . . t t / /
ttttphpttttpp functional hhgroup ttttphphttttp for alkynes.hhtThe tttphphtttt properties ofhhalkynes
t t . t t t / / / / / : t t . / tt / / t / / / / / / / :
/// // / /
ss:p:/ss:: ss:p:p/ss:: spss /// /// / / // : ss:: ss
ss::/ss:: ttttphphttttp ss::/ss:: ttphpttttpp
hh h are largely determined by the triple bond (- C C - ). In
tttphpttttpp
= ttttphpttttpp t t tthtt
t hh ht t
hh h hh h
2Na
hh h
ethyne (or in alkynes in general), the triple-bonded carbonb
atoms exhibitspeehybridisation. Therefore, eiww ethyne molecule CH
b eb �;;d,
2H,
bbeebb
+
bb bbeeb bbeebb bbeebb
wveiw b b b b
vv 1
b b b e e e b b b
o
is a linear molecule.
e e e e e eew
ee w w eewwee
111 2co, eiw
CH
w w w i w w i w
i w i i w w w w i w
w
iiwvvi i w w i i
vvruuvv w i i i
vvruuvv i v vrruu v v w w
ii vvi i v i i w i vvruuvvi
i i uuav
C2H2 ior lialaiHC liala "' CH), atomic
In ethyne ala(acetylene, alailiorbitals
v v u uu uu r u
r u v v u u u v u u u u r r
2NaOH + H
r uruarru rr r rr a r a a l a
l a r u u r r u rr r r r r a r l ilila
a a
ilila ilim la iliml ii lialariliala ilimalailiala ilimalailila ilim
of carbon
mmtaamare sp hybridis·ed. The two hybrid
aorbitals are
ilim i
mmttaa m m mm a m m m
aa//tta a m mmtaamm m mttaa m mm aa 2 m aa//ttam
m m a
Synthesis efrom C and H (Berthelot's synthesis) :
a aa t t t a a a t t t
inclined to each other at an angle of 180 . The other two
aa t tt a / / / tt / / t / / t aa t / tt a / / / t
/ t / / t eemee//
//ttee// // ee e°em/ ee eemee //tee// eem/ ee eemee
eem •
t2t.:.////tt.
eem
Acetylene by passing ss:: ss a stream
sst:p:p/ss:: can also bettppstprepared
m m e m .m
: ssthe hybrid orbitals
ss::/ssunused p-orbitals sst:p:pliess: at right angles ss:to
m . m m
t ..m/m//tt..m
t /
m m .
tt.:.////tt.
/
m
/ /
mm
tt.:.////tt
/
.. m
: /
. .
//tt::////
/
t t .
t ..m/m//tt..m
t
m
/ /
m m . m
/ /
m m
tt.:.////tt
/
..
: / //tt::////t.
/
. . t
of hydrogen through electric arc between ttphpttttpp carbon hhttttphphttttp

/ / / / / : : /
/ / / / / / : :
/ ::/ st:tp:pss:
tttphpttttpp and also to each thtt Each ofthe
ttphpother. tphphttttpporbitals (twohhybrid
tfour
sspss sspss
ttttphphttttp
electrodes.
t p p t t t
and two unusedp-orbitals) contains only one electron. The
t t t t h t tt t t t t t
hh h hh hh hht hh hh hh hh h
b parallel toeebeach beebb other give rise bbeto bbeebb Electric arcbb bb
unused p-orbitals bbeeblying e2ew H RC - = CH weeiww
b eb bbeebb
ebb bbeebb
two n bonds iwdue iwto sideways overlap.
ew
i ee ww w eew w vvruuvv + 2 3000'C
i w w i icw e e e e w eew w i
• ilialaIndustrial preparation alarrilialar of acetyleneilial(Wohler's reaction) alai:liala
w i w i i i iwvviw w
vvriuiuvvi i
vv iw
u vviw u uvvriuiuwvvi uuvvriuiuvv
r r ru u r v v iw
u
iw
u u vvriuiuwvvi uu r r ruuavvrr
u u
mmAcetylene is prepared by action of water on calcium
u ur r r r r a u u r r r r r
alarrilialar
ilim
1t a r aa
ilimlailil alailiala
ilim ilila
ilim ariliala ilim ilimalailila
m
carbide. ee// ee
m m m m m m m a m a a mmt a a mmttaa m m m m m m m a m aa mmt a a
m
t//taea//ttaa / ttaea//ttaa
/ / ttaea//tta
/ /e/ttee//t t a
t a / //t aa//ttaa
t / t
/ aa//tta
t / tte//t
/ e
ee e e / ee ee ee ee e em
:CaC
:///s/s:://2 + 2H,O --------> / CH/ - CH + Ca(OH),
ee e ee e m
. mm/tt..mm ./ .m/m//tt..mm
t t ..m/m//tt..mm
t / tt.:.m/m///tt..m
/ . m
. m t . mm
. t . mm/tt..mm
. t ..m/m//tt..mm
t / tt.:.m/m///tt..m
/
----
. t t
=
t / / / / / t t / / / / / /
Mg + 2Mg(OH) + CH
ssC + 4H O ppsts-tttppCs CH
/// /// t / / / / ss:: ss: t / / / / :://s:: / :: s :
ss::/ss:: ss::/ss:: ss::/ss:: ttphpttttpp sst:p:p/ss:: ppststttpps
tttphpttttpp ttphpttttpp
Propyne
ttttphpttttpp t t t t t t p
ttp t p
t p t t p
t p t t t tttt t t
t th
hh h hh h hh h hh h hhtt hh2 t 3 2 hht hh 2 hh h3h hh h
• ecan
Methods of Preparation
Dehydrohalogenation ofvicinal dihalides : Alkynes
b ebb b ebb b ebb Physical Properties b ebb b ebb b ebb b b b ebb b eb
•
b ebw
r larur State : C2ru-viurCuv4 colourless gases
Physical
bw evew bw
be prepareduvfrom iruv vicinal dihalides uvaruruby v treatment with uvaraur base
be e b e b w e e e w e i e ebw ebw e wewe e weiw
wveiw i w e wi w e
v wi w e vi i
w vi i
w w vi wi vi i
w v v i w i w e wi e
v i
w w e vi i
w i i v i
w w
uvarur ruvruv
i i i i
so that two almiliamolecules of hydrogen halide getilaeliminated
v w vi i uv u v u v w vi i v uv uv
ialC mi5la- C13 liquid,am Cmi14 il il i solidsmilamil mi m
liamonwards
u r u ur r
u a r u ur uvaruruv ruvru r
u arurliala
u ar l ar l l ia u ar l ar l a i l
from/ataadjacent carbon atoms to give alkynes.
ar l ar l ia i l ia lia l ar l a r l ia a l a i l i
a l a i l la
ilaimamil il mi mi i mi mi
e/•me Polarity : Weakly
ilaim
t/aee/t polar and lighter t ee/ than / ewater.
mm amm amm amm taem/t/atam mtilam am amtam amt/atam ta /ta taem/t/atam /ta
Htm
t
H X
/ t
a /at /
t t
a /at /
t a /
t a t am / a /at t/at t /t
a / t/a
•
t ee/ t e/ / t e/ e/me e
: Insoluble in water but highly soluble in
t ee/t e/m e/m e/m e/m e
etem/m m/e.tm m/e.tm .e .m/t/e.tm. etem/m m/e.tm em m/e.tm . e t.mte.m .m/t/e.tm. .mt.m
/:/pss:/ R - C - C -psRs:/t:pssKOH :/ (ak.)
m . . . . X / .tm m . .
m . m . tm. / .tm
organic tps ptpssolvents. httptphst tpt ttp ttp
.
tt m:/t/. I I tm / . / t Solubility tm. t
. . t /. t / / t t /
s:/tpIss:/ I
/ . /t/. :/ t : / t :/ t /: s /: /. /t/. / /
t : / t / t // : / t :/ / / : / s:tps: s://s:/
/: s /:
s: p s s:tps: s: :/ts:/:
/ s : /:pss:/ s:/ s: s: /pss:/ s: s ps
•
p s
Rtpt -tpC = C - R ht tphttp t p s
tpt tpt ttphtt p t
tp ttp tp tt p
Melting than
tptpsttpt tpt t tp -HX ht tphhtt point and hBoiling h h pointhht :hhtHigher
NaNH2
hht hh ht h
l
c-1----f-, hht hh hht hh
t
LK__ J! i b b
hht hh h h h
corresponding alkane and b ebb alkene. Boiling b b band ebb ebb b eb
b ebpoints
h h
Vicinal dihalide melting points increases with increase in molecular
b b b ebb bw b ebb
eb e
b eb eR e b
bwe- C = C - R weebiw evew e ebw e e
Alleyn,
e b e w e b e e
i i viw iwveiw
mass.
viw vi iwviwi
w e w e
v i w w
u v
e
i viw i
uvv i i
wuvviw u v wi
viruvi vi w e
iwviwi w e
vi w w
uv
e i
v uv vi wiuwveviwiw viuwviw uvavriuwr
uv r r u uv r r
mil m:i Geminal • mamm
uv u v u
• Dehydrohalogenation ofmtilamgeminal dihalides
uv r r u u uv r u r u r u
taem/t/atamalkyne, by e/t/ataem/t/at Order of B.pt, mm : Alkynes/ata>mm
ilaiM.pt tAlkenes > Alkanes
urialaru r a r r
uialar u l u
ar lialar i larilial ar urialaru r a r r u
uialar ar ar u l u
ar lialar ila ila r i larilial
l a r ial l ia i la l a r i
a l l l i l ia
il mi i l a
tt aem/t/atam on treatment
dihalides taem/witha base alsoe/t/give
i
milamil mi a il ilammi mi m m mm
amm a tamm / tam /tam/tam
a /ataem/t/ata /tam
mdouble dehydrohalogenation.
/a /
t a t/ a / at /at t /
t a t a / t t/a e/ t e/ t
t ee/t e/mee/ e/ e e/me e e .me .mte.me
s:/tpss:/ • Acidic
e/me .meChemical Properties
:/t/.s:nature : Acetylene s:/t:/pss:is/: acidic ://s:/ in nature. s:/t:pss:The /: sacidity
/me
etem .m/t/e.tm .m/t/e.tm.me .mt/e.tm e/m
.m/t/e.tm .m/t/e.tm .mt/e.tm
s:/t:/pss:/: X Ale. KOH
. . tm . t m / tm
. . m/e.tm. t m . .mt.m t
. m . t.mt.m / tm
. t /
/ . t / / t
tpt t-tp CH <
t m / . : / t m / . : /
s:/tpss:/ s://s:/
can tphstbe tpt explained onht tthe pt ttpbasis tphtof tp percentage tpt http s-character
/. t /
l
/. t t / t : / t / / t / :/
s: /:p/sts:/:/ p s s:/t:pss:/: t p s s: / /:/t s ps
:/ s:
p t p s p
hofhttphthe hybrid orbitals. h hh Ashts-character h ht h acidichht h h h
hht increases
ps t p p s tp p
NaNH,
ps R - C"' t p RCH = CHX tp t p s p
t tt tpht tt t t
tpt t tpt "2
hht hh X hh-H t tphhtXt hht hh
hht hh
liq.NHb3 b nature increases.
Acidic nature
e : Alkyne >ebAlkene > Alkane
b ebb b ebb ebw b ebb b ebb b ebb b b b ebb b eb
be b e b e b e e ebweeb w e i ebw e wewe evew bw e weiw
• Dehalogenation v of tetrahalides uvaruru:v Alkynes mayurualso varuru be
wveiw e w i e
Hybridisation :
w w
p
w
ii viw e i w e w i w v i i
w RC =CH v i
w vi wi vi w v i w i w e i w e wi w v i i
w i i v i
w i i i
v w vi i v u v
r larur u v v w
iruv vi w vi
uvar3uruv ruvru v uvarur ruvruv
i uv uv
arurlial
prepared ialmby ilia dehalogenation amiof l 1 , 1 ,2,2-tetrahalides on
u uv r u r u sp u v sp 2 r r
u
taem/t/atas-character : ammtilam 50% > 33.3%tamm >atamm25%
a r ur l a r u l ar u i l i l r
a ial i
a l a r lia a r r
u l a r u l ar u
0
ial a i l ar ial l a i l a ial
ilaim a amil milmmi ialmilia ilia il milmil a amil i mi mi l
treatment t/aee/t with zinc and talcohol. For example,
mtilam ilam ilam
amm amm amm mtam taem/t/atam /t
. The electrons t/aeofe/t the C - H bond in acetylene are.mstrongly
t am / a /at /
t at /at /
t at t/a t / a /a t/ t a t a /at /
t at / t a / t/a
e/m ee/ e/mt e/ e/me e/mt ee/ e/ e/
etem/t e/ e e/me e
/m .m/t/e.tm etem/m .me t.mte.m .m/t/e.tm
held by :/ts:carbon nuclei.s:/:This / facilitates /pss:/ s: sof
removal
etem X X m/e.tm m/e.tm .e m/e.tm . .mt.m
/:pss:/ Alcohol pss:/pss:/
. m . t .
m . / t
. .
m / /
t t
. m .
m m . t
. .
m . . m t . m / t
. m /. / / /
t .tm t /
tt m:/t/. / . t t : t /. / t t t / s:tps: s://s:/ :
tptpsttpt R - C - C -htH tpt ht+tpt 2Zn ----,.httpR tpt C = CH + 2ZnX
/:/pss:/ I I
/. / t t :/ : / / . /t / t :/ / : /
H-atom.
s :/ :/ /
s:tpss: :
/ / t s: :/ : /
/ s: / s: : / / : / s
s : : t p s s: / ps p s s p s p t ps
tp ttp tp tt p
ps t t- tp ttp
hht hh 2
tps ptps tpt t tpt tp ttp tpt t tpt ttp tt hht hh ht h
Acidic nature
b ebb : HOH > ROH > HC CH > NH3 > RH
h hh ht tphhtt hht hh ht h hht hh h h
hht hh
X X
I I h h
b ebb b ebb
h
b
= b ebb b b b ebb b eb
b eb eb b ebb e b e e b w e w e ebw
i e eb b e b ebw e e e e ebw e e
w e
wveiw w e
iwviwi w e
vi w w
i viwe i v i i w
wuvviw i viw i
uv vi w
w e
iwviwi w e
vi
w e i
i viw iwviw
w v i i w
wuvviw viuwviw
i vi
r
u
vi
u u v
a r u uv
r larur la r
u v
urialaru r
r
u
v i
uvaruruv a r r
u uv
uvarur ru ru v
a r u uv
ilamamil ar lial l
ilamamil
ialm
mtilam i mtilam mtilam amm t m alm
am
t /a
e/t/aee/t
t
t/a /t/a t
e/t/ae/t
/a / a
e/t ee/
/
t am
t/at /t/a t t / a
t/a /t ta /t a t /
e/t/ae/t /t e/
a a e/t ee/ /tae
/a t
vv
ww
ii vvi i ww
u
i i w
vvruuvv i i
uu
i i
vvruuvv i
rruu vvrruu v v vv
w w
ii vvi i w
u vvi
u
i
u
w
vv i
uuvvruuvvi
i i
rruuavv
u
r
alailila
r
alailiala
ilim a
alailila
ilim a
ilima
l iil l a r
lialariliala
r alailiala
ilim a
alailila
ilim l ilila
a
ilima
ilim
Hydrocarbons m
m m m
m m m
m a m i
mmtaamm mmttaa m m
m m 345 aa//ttam
m
m a
mm m
t//taea//ttaa t/taea//ttaa / ttaea//ttaa / ttaea//tta
/ taa t / ta
ta/ / /t
/taa//ttaa //tt
eemee
Nucleus : It is benzene tt.:.////tt ring where all .////tt six carbon atoms
ttthe
/ /
..m/m//tt..m Reactions tt.:./showing acidic nature tt.:.////tt :
eem e eem e eem e eem e eem//tee// eem/ ee eemee
mm . m m mm .m
m m mm . m .. t . m m mm . //t::////t.
.. t
sst:p:p/ss::are in sp hybridized ppststttpps state as there ss:is: ssalternate double ttphptand
m
/ .
tt.
/ / . / //tt:://// t ..m/m tt.. m m .. / . . / t
//tt //
/ / / // / : :: / / t
/ t // //// // / :: :: /
tthtt Na C = CHhht+tttphphlttttHp2
/ / ss:: ss: Na/liq NHpp3sst:tp_:pss + __ sspss / / :: s : sstppss
ss::/ss::
single bond. It is represented as
2
2
ttttphpttttpp ttttphpttttpp tt t tp
t p tt t t t
t t tttphpttttpp
t hh tt h tt
-
hh h hht hh hh hh hh h
2NH4OH b C Cu
hh h hh h
b�beebIll + 2NH,CI
Cl
b b
== - Cu
bbeebb
CH CH C - Cu
we b b bb eew eew bbeebb eew bbeebb eew bbeebb eew bbeebb
e e e e w w w w i w i w
i w i i w ee w i w w w i w iw
i
iwvviw
vvriuw iw i
vvriuiuwvvi Redppt. uuvvriruiuvv i
uuavvrruuv
v iwiwvviw iw vvriuiuwvvi vvriuiuvvi
2 2
uuavvrru
Side chain alarrilialar : Alkyl or any alaother i aliphatic group alailialaattached
u u u r u u r r r r r u u vv u u r u u r r ru u r r r
C - Ag
lialariliala alailila r rilala alailila
alarrilialar alailiala ilim ilim
I l l/ttaa//tta + 2NH,NO, +//tt2H,O
ilim ilim
totabenzene nucleus is ttaa side chain.//ttaThis
aacalled a//tta is obtained //ttee//t
ilim i2AgN0_
m 1 m mm m ilim ilim m m m m
m m m m m m m m a a a ta a m mttaa m mm m m m a a a t aa
ttaea//ttaa //t
mm/tby
// ereplacing one m or eemore
m hydrogentt..matoms m//tt..mm in the ring//tby
t//taea//ttaa ee -eeAg
C
// / e e e t a / / / t
/ t / / e
ee e em ee ee ee e
//// ::///alkyl groups. ss:://ss::/
ee e eem e ..m/m//tt..mm
. mm/tt..mm t ..m/m//tt..mm t t tt..mm
..m/m/Whiteppt. / /tt.:.m/m///tt..m . . . m t . . m//tt..m t
=
. t / / / . t t / / /
ttphpttttppC- Mg -X ttppstst:tp:pss Monosubstituted pp derivativestttpp:ststtIf pp one of the hydrogen
t
/// /// t / // / / / / ss:: ss / : t t / / / /
:://ss:: // ss:: ss / : :
��'-----_... ttphpttttpp R - H + CH
ss::/ss:: ss::/ss:: R-Mg-X ss::/ss:: ttphpttttpp
tttphpttttpp
atom of ring hht hhis substituted byhh an hh alkyl radical orhha hgroup
ttttphpttttpp t t t p p t t t t t
• Addition Reactions : Reactions are electrophilic addition. hh
t hh htt hh h tt hht t t t t t
hh h hh h
then it is called as monosubstituted derivative.
bbeebX bI XI x
a
b eb bb bbeebb bbeebb bbeebb
wveiw b
eewweeb b b X 2 X
w e b b e e
eiww = c< -"-+
)c
R X
w w
e e
Ri w w - C - C - R i w
i w
e e
i w
i w eew bbeebb
w eew
i w w w
eew
i w
v v
w
iiwvvi i i i w
vvruRuvv i X uuvvrruuvv I I
i i i
u u v vrruu v v v v
w w
ii vvi i w i i
vvruuvvw i vvruuvvi
i i uuav
alailiala trans-alkenc ilialailila
uruarru u r u u r rr r r a u u r u u rru u r r ruu r r r
r X X a l ilila
Disubstituted
lialariliala derivatives : The position of second
r
alailila a ilima a
l ii l l r r alailiala ilimalailila a ilima a
ilim ilim i ilim
m m m m aa//ttam
m m
substituent with respect / eeto first one will eemfonn ee different eemmee
mmtaam mmttaa m a mm aa m t aa//tta a mmtaamm m mttaa m a mm aa m t a
aa t t a
ta / / / t t a / t
/ t // t t aa t / ta
t a / / //tt a / t
/ t // t
//ttee// // ee / ee eemee
m//tt..m For example
forms. tt.:.////t2t. and 6 positions tt.:.////tt of a ring with
//tee//
//tt:://// I
eem eem R - CH eem = CRX --,. RCH m - m CX, eem eem mm.
ss5 thss
mm . m m m . . m . . m 2
t .
t . mm . m m m . . m //tt.:.:////tt.
sst:p:p/ss:respect to firstss:pare
ppttttps called ortha-positions. 3 rd and
/ t ..m/m//tt..m
t / / tt.:.////tt.
/ / /
/ tt.:.////tt
/ : /
: / / t ..m
t / //
nd th
/ /
/ / : /
: /
/ /
ss::/ss::
/ ss:: ss:/ ss:: ss : sspss R / :// / /
:s: sst:p:pss :
positions of a ring with respect
ttphpttttpp HgS0 ttphpttttpp ttttphphttttp ttphptto t first one arehtcalled ttphpttttpp
CH2 =CH � CH3 CHO hh hh meta-positions
tttphpttttpp t tt t p p t t tt tt t t
and 4th position of ring is called as para
t hh h t 4 hh h h h t t t t t hh hht hh h h h
hh h
bbeebposition.
dil. H2SO4 I Tautomerism
b eb b
ew
i ee bbeebb When R = H eebbeebb OH eew bbeebb
w w
eew
i w e e bbeebb eew bbeebb eew bbeebb
w w w w w i w i i i w i w w w i w i
vv iw iwvviw iw
u vvriuiuwvvi i
uuvvriuiuvv i
r ru u vvruuvv
r v v iwiwvviw iw
u vvriuiuwvvi uu vvriuiuvvi r ruuavvrr
u ur u u r u r r r r a u u r uu r u r r r r
alarrilialar alariliala
ilim alailiala
ilim ilimalailila alarrilialar ilimalariliala alailiala
ilim ilimalailila
Cis-alkene
ilim mm m m m m m m a a m ilim m m m m m m mm a a m
m
m m aa//ttaa ttaea//tta a aa
/e/ttee//t t mmttaa m aa//ttaa aa//tta a aa
tte//t t
t//taea//ttaa / t
/ tee catalyst
eeLindlar's ee e/ / e t a
t
// ee a // ee ee/ t
/ t /
ee ee
t
/t e em/ / e
4
ee e m eem
tt.:.m/m///tt..m
.mm reduction //tt..m/m//tt..mm tt.:.m/m///tt..m ..m/m//tt..mm
://ss::/ alkene pss:p:pss:
mm/tt..mm ./ .m/m//tt.Birch mm/tt..mm
NH ss:Trans-
m m . m ..
tttphpttttpp Na/1tq. 3ttttphphttttpp
t .
t . / t t / /
/ / t t. . / t t . / t
/ t / / / t
/ t / / // / :
/// /// / /
ss::/ss:: /// /// / /
sst:p:p/ss:: :://s:: :: s
¢
A
ss::/ss:: sst:p:p/ss:: ppststttpps
hhAt hh
ttttphpttttpp t t tthptttt
t t p p t t ttpp t t t ttttppststttpps t t
t th
hh h tt hh h
AROMATIC hh h HY!lROCARl!ONS hh hhtt hht Ahh hh
•
hh h
Aromatic b ebhydrocarbons areb now
ebb called arenes. b ebbBenzene b ebb 6 �b b
QA
A
is theiwesimplest aromatic hydrocarbon.

b b ebw b ebb b b bwb ebb b eb
be ebw e b w e e ebw e w e i e ebweeb ebw e wewe evew e weiw
wveiw e i e w
• Arenes iruv are the aromatic uvaruruhydrocarbons uvarur contain one arur larur
which
i e i
w w v i i
w v i
w w vi wi vi w vi w i w e i i
w w vi i
w i i v i
w i i i
v w vi w vi v i uv u v u v 5 ""-- v w
iruv vi w 3 uvaruruv ruvru A uruvarur ruvruv
vi v i u v
arurliala
uv
iloriliamore benzenemirings. liamil Benzene ring milamisil a six-membered
u r
u uv r u ar ur l ar r
u l i l ia r
u u v a4
r u ar ur l ar l a i l
a r l a l ia i l ia l a l ar l l ia
liamilmetailmi (1, 4-) a l a i l ia l a i l la
mi mi ial(1, i
mila2-)ortho
a il i mi mi
tt/aaem/t/atamring containing atam atoms linked
tt aem/carbon tt aem/t/atamto each othere/t/awith
milam mtilam (1, i3-) ilapara
mm tamtam
taem/t/atam amm amm taem/t/atam /ta
Ifeeside t/aee/t chain containsee/m / e/ e/ group,
taeefunctional
. ethen
t e/ ethese
m are/.tm
am t at am amta t / at /a
/me an alternatemee./single and double . bonds. Arenes/.tm .m/contain
/a t/ e/me/ a t / a /a /
t t e/m /a t / e / t
e/me e
.me
said to be phenyl derivatives of the corresponding aliphatic
etem me m/e.tm etm /m m/e.tm .m/t/e.tm. .mt.m
higher sproportion of carbon /pss:as / compared topsthe s:tps:aliphatic
. m . t .
m /.tm t .
m t/. . m t .
m t .
m m/.tm . . m . m tm. t . m t . t /
/ . t t /. / t
ps compounds. ptpstpt tp ttp
tt m:/t/. / . t / tm / . t / :
/ . / t :/ t : / t : / /: s :
/ /. / /
t . /t :/ t / t // : / t :/ / / : / s:tps: s://s:/
/: s /
hydrocarbons and constitute httphht a unique class hht of
tphttunsaturated
s: /:/pss:/ : /:pss:/ ps s: t s: /:/ts:/: s : /:pss:/ s:/ s: ps s: /pss:/ s: s
p t ps p
tptpsttpt tpstpt t tpt p
tptphsttpt t tpt
ht tphht htt ht
pt tp ttp tp tt
hydrocarbons.
hht hh h httphht h h
h h t h h htt hht ht h h hht hh ht h
• Arenesb can ebb be describedweeby b ethe bb general formula b ebbCnHzn---6m, b ebb b ebb b b b ebb b eb
where iwviwi n is the numberviof i vcarbon atoms and wum viwis the number uvviruvi
b ebw evewbw b ebb ebw
eb e e e b w e bw
i e w e i e i w i e
e eb w e w e ebw
i e e e w e
wuvviw viuwviw
i e e
rof benzene rings. larular
i i
viw vi w uv uv w
r uv i w
uvv i r v r
w
u vi wiwviwi 1 -Phenylethanolviwiuvviw viwvi
uv uv r
w
uv vi r u r
u uvavriuwr
mamm • Resonance
uv r u r u u ar uv r r u u u r u r
amil : When a molecule il mi mi mcan be m
amgiventam /taseveral
r u u r larilial
mi mFor monocyclic marenes, m = 1 and
taem/t/antam= 6, or more.e/t/ataem/t/at
lliaariulialar
u iilamilia iilalm ar lialar lialarilial l a r urialaru ial a r uialar ar ar
l l l ial ar lialar ila ila lia
m i i ilaim i il mi m m i
m mm
molecular structures but
tt aem/t/atam e.g / taem/t/atam
a / a t amm /at / t
a amm t/atamnone a t a of them / t
a /
trepresents
a / t a
it t/ataem/t/ata /tam
mcompletely, the/.tm molecule . .mt.mis said/.tm to .mbe a.m/resonance
/a t t /a
t ee/t t
e/mee/ e/ e t / t e / e/
m/e.tm
e/me . e/me
.m/t/e.tm.
e/me
.m/t/e.tm . .mt/e.tm .me etem/m
.m/t/e.tm .m etem/e e e
.m .mt/e.tm .me .mte.me
0
:/t/.s:/:/hybrid of those
ts:/: :// :/ and thes/: phenomenon
s:/t:/pstructures :tpss:/: ps:p/ s: is tcalled
t .
m . /.t m / t
. m t/ tm
. / tm. . /t/. t t t/.tm : / t /
/. t
/:p/sts:/:/
t
s:/t:/pss:/:
/ t
s:/t:pss:/:
: /
s:/tpss:/ : /
t . t / / t / / s:/tpss:/ s://s:/
:/
tpt t tpt resonance. ht tphhtt httphtt
s: ps ps t p s t p s: / p s ps s s s ps p s tp p t p
ps
tpt t tpt tpt ttp tpt ttp tp t ps t p p tpt ttp tt tt tp t t t
hht hh hht hh Benzene isha resonce hht hh ht h
hybrid of the following five structures:
hht hh hht hh hht hh hht hh h h
Benzene
0 0
0 - 0 0 -0� 0
b b b b b b b e b b b b ebb b b b ebb b eb
b b eb ebweeb Ethyl benzeneweebiweeb weviewiwe b eb
evew bw
For vbicyclic ii viw arenes, n =viw10 = 2
be ebw
,
ebw ebw e wewe e weiw
wveiw e e w e i i i e e w e i i w i
0-
w i i w w v w vi w w i i w i w i
0
v i v i i w v i i v i
,;;; 0-
i uv w vi uvarur ruvruv
i
0
w w v i
1
uvaruruv m uvaruru v u v
r larur vir1uv uvaruruv ruvru v u v uv
- arurlial
u u v uv r r u u v r r
00
elar.g r
uial. ar r
u l ar u i l l r
a u i l ial ar lia a r r
u ar u l ar u i l a l ar u ial a l a ial
i a i a mil mi l 0milaim a
amil il il a iamil l i mi mi l
milamil
i milamil milamil taem/t/atam mtilam
ialmilia
amt/at tamtam amm
ilam mtam
i
taem/t/atam /t
tt/aaem/t/atam tt aem/t/atam
/a tt aem/t/atam
/a t/a t am / a /at /at /
t at / t a / t/a
e/me e�/ e/me ae/t
t/Structures e/mt ee/ e/ eDewar's / structures e/mt e/ e e/me e
etem /me .me .m/t/e.tm etem/m . e t.mte.m .m/t/e.tm
Kekule's
. m . t .
m m/e.tm . h t .
m m/e.tm / t
. m .
. m . e
t .
m m/e.tm . m . m t .
m m/e.tm / .tm . .mt.m
t /
tt m:/t/.
/. /t/ . :/ t t/ . : / t � : / t /: /.tm /t/. /t/ . :/ t / t . / t /
t . : / t / / / / : / t
s:tps: s://s://:
=©
/:/pss:/ Naphthalene
/:pss:/ :/
/pss:/ /
s:tpss: :/ts:/: /:pss:/ s:/ s: / : /
/pss:/ s: s : / s
• Nomenclature of aromatic
hht hh compoundsh: The
ht tphhtt aromatic ht tptphsttptps
s : s: p s s: Anthracene t p s s: / s
: p s s: p t ps p
tptpsttpt tpstpt tpt t tpt
p tpstpt p tpt t tpt ttp tt tp ttp tp tt
httphht httphht httphtt hht hh ht h
compounds has two main parts
hht hh h h h h hht hh h h
Resonance hyblid
b b b b b b b e b b e b b ebb b b b ebb b b b ebb b eb

be eb eb ebwe e e ebwe w e i w e eb eb ebw e e e e ebw e e
wveiw w e
iwviwi w e
vi
w e
i viw
w i v i i w
wuvviw i viw i
uv vi w e
iwviwi
w w e
vi
w e i
i viw iwviw
w v i i w
wuvviw viuwviw
i vi
r
u
v i
u uv
a r u uv
r larur l a r
uv
urialaru r
r
u
v i
uvaruruv a r r
u uv
uvarur ru ru v
a r u uv
ilamamil ar lial l
ilamamil
mtilam
a
t /a
e/t/aee/t
m t
t/a /t/a t
e/t/ae/t
/a /a
e/t ee/
/
t am
t/at /t/a t t / a
t/a /t ta /t a t /
e/t/ae/t /t e/
a a e/t ee/ /tae
/a t
vv
ww i
ii vvi w w i i w
vvruuvv i i
u
i i
vvruuvv i
uu vvrruu v v vv
w w
ii vvi i w vvi
u
i
u
w
vv i
u vvruuvvi
i i uuavv
346
u
uruarru r uu r rr u r rr a uu r u u rruu r r rr u r rr
r
alailila
r
alailiala
ilim a
alailila
ilim a
ilima
l iil l a r
lialariliala
r alailiala
ilim a
alailila
ilim l ilila
a
ilima
ilim m m m
m m m
m a m i m m NEET Guide m
m m aa//ttam
m
m a
mm m m
t//taea//ttaa / t /
• m
/ a t t /
•
a t /
Aromaticity or Huckel rule : A compound is said to be
/ t / /
Cyclisation ..m/m//tt.. of long chain////tt.alkanes : Long chain tt:.////tt alkanes
/
eem e eem e/ eem e t
//tee// /
eem/ ee /
eemee eemee
eem e mm . m eem m mm .m
m m mm . m .. t . m m mm . //t::////t.
.. t
ss::/ss::aromatic if itttpmeets
:: ss: all ofthe following ss:: ss criteria. ttppststtppss
m . . t m . .
(C6 -C sst:p:9p/s)s:on
/ :/ passing overss:a: scatalyst generally ss:: smetal oxide tppssttppss
t../m//tt..m / tt.:.////tt. //tt.:.////tt ////tt:://// t m .////tt . // . // t
//
/ / t // / // : :: / / t :: // : ::
tttphpttttpp • Aromatic
s
hh hcompounds contain hh h one or more rings that (Cr,
hht hhV and Mo) supported hh hh over alumina hh at h 500 C under hht hh
tt pststttpp ttttphpttttpp tt hht tp
t p t t t t
t ppttttpps
t tttphpttttpp °
t t t tt
t hh t t
have a cyclic arrangement ofp-orbitals. pressurebbget converted into aromatic hydrocarbons. The
hh h h
• Aromaticeerings bbeebb are planar. eebbeebb reaction involves cyclisation bbeebb followed byeearomatization.
b b bbeebb bbee bbeebb bbeebb
we eew
Aromatic iwvvisystems are conjugated vvriuiuwvvi cyclic systems vvriuiuvv .
e
e eew
• vvriuw
w
iw w i w
w w w i w
i w i w
i w
v
uuavvrruuv
i i w ee
iwvviw
iw iw w i
vvriuiuwvvi
ww w w i
vvriuiuvvi
w iwi
uuavvrru
Aromatic
alarrilialar systems must alarilialcontain (4n + il)n lialailialaelectrons
v
• u u u r uu r rruu r rr u u v
r uu r uu r rruu r rr
alailila alarrilialar alariliala alailila
c5
ilim a ilim ilim alailiala
ilim ilim
t//taeaused
/e/ttaa in delocalisation, ttaea//ttaa where n = integer ttaea//tta (0, 1 , 2, ...). ee//ttee//t
ilim m
m m m
m m m mma a m ilim m
m m m
m m m
m aa m
mm m a aa t a m
mttaa m t aa//ttaa t a
aa//tta
t // aa t
tte//t
a t
mm/tt..mm Examples of//tt.aromatic mm/tt..mm compounds
/ // t / //
•
/ t / / e
mm/tt..mm CrO3 , V2O//t5t.,.m/m Mop/Al
/ e
ee// ee ..m 2O3
ee ee e ee e m eemee ee ee em
..m/m//tt..mm tt.:.m/m///tt..m ..m/m//tt..mm tt.:.m/m///tt..m
°ss:: ss -
0
. t
500 tppC,ttpp10 20 atm
t.
t . / / //tt / //// : t.
t. / / t //tt / //// :
/// /// :://s::/ /
ss::/ss:: ss:p: ss ::///s/ ::/// // ::/ /
ss::/ss:: ss:p: ss
ttppttt
hhtt hht
ss:p:p/ss:: ppssttpps
tt t
hhtt hht i�1 hhttCJ"
tpp ttpp
thhtt tttppttttp hht hh psspps ttpttt
hhtt hht
ttpptttpp tt
hhtt hht
ttttppttttp
Methyl cycloheptane
hhtt hht hh hh
b eb bbeebb bbeebb n-Heptane bbeebb bbeebb bbeebb
wveiw
H3vii vvi
eebbeeb
Methods of Preparation
b e e e eew bbeebb eew eew
•
e w
Decarboxylation
iiwvvi of aromatic acids vvruuvv : This is a convenient
w w w w w i w w i w
i w i i eew w i w w w i w
v v
w i ww i i w i i
u
i i
vvruuvv i
u u v vrruu v v C
v
ww i w v vi i
u
w
u vv i
u vvruuvvi
i i uuav
methodilito alaiprepare benzene iin
lialalaboratory in which aromatic
uruarru u r u u r rr u r r r a uu uu r u u r r r r u r r r
6
r r a a a l a r r r r a l ilila
a a
3H, +
lila iliala ilimalailila iliml ii l lialariliala ilimalailiala ilimalailila ilim
acids or their sodium or potassium salts are
aheated with Ar o matization
i
mm mm m mttaa m m a mm a m t
m m
aa//tta a m mmtaamm mmttaa m a mm aa m t aa//ttam
m m a
500 e°eC, 10-20 atm
aa t a a t a
ta / t t a/ t
/ t // t aa ta
t a / tt a / t
/ t // t
sodalime (NaOH + CaO).
//ttee// t // ee / /
eem/ ee eemee t
//tee// t / / ee / /
eemee/ eemee
..m/m//tt..mToluene
eem eem m m . m eem m m m m .m
..m/m//tt..m mm .
tt.:.////tt. m mm .
tt.:.////tt . m . .
//tt:://// t t . mm .
tt.:.////tt. m m m
tt.:.////tt. . //tt::////t.
. . t
@
/ / / /
Polymerization oftttalkynes
ppststttpps : Alkynes ppststttppon passmg ttttphpttttpp
/ /t t / /// / / / : : : / / t
/ t / /// / / / : : : /
tttphpttttpp @- coONa ttphpttttpp + NaOH � + Na ttt2tphphtttO
/ / ss:: ss: ss:: ss ssppss • / / :: s : :: ss ss ss
ss::/ss:: ttphpttttpp t sst:p:p/ss::
through
hht hh red hot ironhh tube
3 hh at high temperature undergo
t t t t t h h C
t ttp p t t t t tttt h h h h
hh h hh h hh h hh h
b b Sodium benzoate Benzene polymerization b to yield aromatic hydrocarbons.
•
b b b b bbeebb
Reductioniw of diazonium salts vvriuiuw:vvAryl i diazoniumvvisalt i vv can
ewe bbeebb eew bbeebb eew bbeeb eewwee bbeebb eew bbeebb eew
C �uuvviuiuvvi
i e e w w w w i w i w
i w i i ee w i w w w i w i
i i vvriuiuvvi
be reduced
alarrilialarby number ofireagents lialariliala but most powerful alailiala one
iwvviw iw vvruuvv ww iww vvriuiuwvvi uuavvrr
alarriCH
v u u u
ili�
0
v u u r H u
u u r u u r r
lialar Red hot Fe itube
u ur uu r u r r r r r r a r r u r r r r
alailila lialariliala alailila
is heating with h ophosphorus acid.
ilim alailiala ilim
H
ilim ilim
ilim
yp
m m m m m m m
t m m m m mm m
// ee CH
m m a m m a
Nee2//Cl 11 f--/
m
mttaa m m
aa//ttaa aa//ttaa aa
tte//t t a C mmttaa m m m
aa//ttaa aa//tta a aa
tte//t t a
m "l2
aa t t t t / / a a t t / tt / /
@
tt // / / / / e e t t / / / / / e e
Benzene
ee ee em ee ee em
H
ee ee ee ee
'
ee eem
./ .m/m//tt..mm ..m/m//tt..mm tt.:.m/m///tt..m mm/tt..mm ..m/m//tt..mm tt.:.m/m///tt..m
C
t .
t mm/tt..mm
. / t t / t
/ t / /
/ / t .
t m
. m/ t .
tC. / t
/ t.. / / / t
/ t / / // / :
/// /// / / / / ss:p:pss: /// /// / / :://s:: :: s
ss:p:/ss:: ss::/ss:: sst:p:p/ss::
ss::/ss::
ttttphpttttpp + H3hPO thtttphph2tttt+p H2O ---+ @ t tttphpttttpp+ N2 + H l +hhttttphph3tttPO t t p p sst:p:p/ss::
t t t p
t p t t t ttttppststttpps t t
t ppststttpps
th
Hypophosphorous
C H tt t hh h
hh h hh h Chemical hhtt hht Properties hh hh hh hh
b ebb • Aromatic
3
Benzene b b b ebbhydrocarbonsbare b less reactiveebthan b ebb alkenes

acid ebb ebb
and alkynes because theirebweebn-electrons are einvolved in
b eb eb ebw b eb bwb ebb b eb
e e e e b w e w e ebw
i e i w e i e e w ew w evew i e weiw
delocalisation and notiruv available for raddition uvaruruv ruvreactions.
wvi w w
ii viw e i w wi w vi i
w v i
w vi w vi w vi w i w e i i
w w vi i
w i w i v i
w i i
v i uv w v uvarur ruvruv
i
N2 Cl ialarulialar
v w i
uvaruruv uvarur u v u v
r larur v w vi i v uv uv
arurliala
milamil + N2 + H lam+mtilammH
a il 3 CHO
u v uv r u uv u r
taem/t/atamBut the benzene ringilia is electron rich amilso the
mtamelectrophile
u r r
u ar ur l l ar ui l i l ar ia r
u ar u ar u l r l ar u i l a l a i
a l
@ l ia i a l a l ar l l ia a l a i a l i l
i mi mi ialm ilaim il i amil
ilam i mi mi
@
C C
e/me can replacee/t/aH-atom of the benzene t ee/ ring. / e/ Thus earomatic

mil mi tt aem/t/atam mtilam amm t amm t mtam taem/t/atam /ta
tt/aaem/t/atam /a tt e/t/a
/a t/a t am / a /at /
t a t a /at
t e/ t/a / t a / t/a
e/me e
hydrocarbons
ee/ undergo electrophilic substitution
e/me e/me t e/m e/m e
m etem/me
. . m/e.tm. t .
m m/e.tm. / t
. m.m/t/e.tm. m etm . m . m/e.tm . m
em
. tm.m/.tm . e t.mte.m / t
. m.m/t/e.tm. .mt.m
reactions.
. t m
SnCI/NaOH
.
tt m:/t/. /.t m / . t / t tm /. . t /. t / / t : t /
/ . /t :/ t : / t :/ :
/ s /: /. / /
t . /t :/ t / t // : / t :/ / / : / s:tps: s://s:/
/: s /
tptN, t tp + H l
s /:/pss:/ s: /:pss:/ s: /pss:/ p s s:tps: s /:/ts:/: s : /:pss:/ s:/ s: s
: /pss:/ s: s ps
hht +2H
: :
• Mechanism of electrophilic hht hh ht hsubstitution hht hh reactions :h h h h
ps ps t
tp ttp ps p s
tpt t tpt ttphtt p t p p
tptpsttpt tpthht tpt @ h+ t C
hht hh tptpsttpt
ps
tpt t tpt tp ttp httphtt ttp tt
hht hh ht hh hht hh h
Benzene b ebbundergoes substitution because itbis ban electron
• Deoxygenation b ebof b phenols : Phenol b ebb or derivatives b ebof
rich evsystem e due to delocalised n-electrons.
b ebw b ebb ebweeb eb eb b ebb b eb
phenol onviw iwdistillation withuvvizinc wiuvviw dust yield uvaromatic
b eb e b ebw e ebw e w i eb ebw e e
Step 1 : Formation ofan electrophile
ew e w e w e i i w e i i w e w e w e i i w e
wuvviw viuwviw
i
vi wi v wuvviw w
viruvi iwviwi i viw iwvi
w w vi uvavriuw
hydrocarbons.
u v vi i r r uv u v
i w uv uv vi r uv v uv r u r r
uv r r r
u r
u u u
larilial ar u v r r u
uialar ar ar u u r
u u r r u
larilial
r u
lliaariulialar iilalm arulialar ial ar lialar i li
a l a r urialaru ial a r l l i l ial ar lialar ila ila i li
a
mil mi mamm lia il mtilammi mi m il mi m mm
E - Nu +
m i
� E :Nu
©
mi m
tt aem/t/atamOH / taem/t/atam
a / taem/t/atam
a t/ataem/t/at (YItammtiamm EB
a
E> am
/at /a a t a / t
a amm /
t tam /tam/tam
a t/ataem/t/ata /tam
/a t t e/ /a
t ee/t / t
e/mee/ e/ e t t / t e / e/
e/me e/me
.mt/e.tm .me e/me e e
.mt/e.tm .me .mte.me
Step:/t/2. :/:t Electrophile attacks on aromatic/: sring
s:tps:/: sto:p/ sfonn
e/me e/m
© +/:/ts:/: Distill atinn /: s:/:
m/e.tm .m/t/e.tm. .m/t/e.tm. tm m/e.tm .m/t/e.tm. .mt.m .m/t/e.tm. t.mt.m tm
s:tpsZn + ZnO tpss:tp/tpss:
t .
m . /.tm / t
. m /
t . / tm. . /.tm / t
. m / t/. : / t /
/ t : / : t / / t / / s:/tpss:/ s://s:/
:/
er-complex.
/. t / t
s: /:p/sts:/:/ ps p s s:tps s: / p s s: / ps s:/t:/pss:/: s://s:/ ps p
:
t p s tp p t p
ps
tpt t tpt tpt ttp tpt ttp tp t ps
tpt t tpt tpt ttp tp ttp tpt ttp tt tt tp t t t
hht hh hht hh hht hh hht hh ht h hht hh h h hht hh ht h
Wurtz - Fittig reaction : In this reaction substituted
hht hh• hht hh
aromatic hydrocarbons are obtained b ebbby the actionebbof
b ebb ebb ebw b ebb b ebb b ebb b b b ebb b eb
sodium metal ii on a mixture of alkyl halide and aryl halide
b e b e b e b w e e w e w e i e ebw ebw e wewe evew bw e weiw
wview w e i w e wi w ev i
w i
w w vi wi vi i
w vi w i w e i e i
w w ev i
w i i
w w i i i
i i i
in etherilsolution.
v w vi w vi
uvaruruv vi
uvaruru v u v
r larur u v v w v i w
iruv (cr-complex) ruv uruv uv u vi v v
uvarur ruvruv
i uv uv
u r uv
uialar r
u uv
ar r
u l r
a r
u l l ar u ia r
u uv u ar u l ar r r ar r
u l a l arurlial
@-{_
a r l ia i l ia ia l a r l ar l ia a a i l ia l a i l lia
milamil milam
iamil
milamil mil mi ialmilia stabilises duemitoliamresonance il il il ilamamil i mi mi
0
taem/t/atam mtilam amm mtam taem/t/atam /t
tt/aaem/t/atam 13_r ;:_�'.".�-�e/- �rj /tataem/t/at H tt aem/t/atam amt/atam tamtam
3 ----+
/a t/a t am / a /at /at
t e/ /
t at / t a / t/a
e/me e/me t/aee/t t ee/ e/ e/ e/m e e/me e
"', tm E tm
e/m
. e t.mte.m
C CH
etem/me m/e.tm me m/e.tm .m/t/e.tm. etem/m
H m/e.tm m/e.tm .m/t/e.tm. .mt.m
�
2
+ s:Nu /:pss:/ - /p+ss:H / - sNu

m . . . t .
m . / .tm . m . . . m . m . / .tm
/.
/:/pss:/
.
tt m:/t/. /t/
/:pss:/
t
. m:/ t
@- s /pss:/cH,CH + 2NaBr
:/ /
t . :/ t /: /
s:tpss:
t /: Steps/:3/ts::/: / t
. m /t/. E /t/ . 0:/ t
: /
/ s:t . / / t
s : / /
t . :/ t /
:s / : / / / / t
s:tps: s://s:/
: s /: t /
3
: :
tps ptps V httptphst tpt ttp ttp
s : s
: p s t p s : : s p s p t ps p
h h h h Substituti hht ohnhproduct
tptpsttpt
ps
tpt t tpt tpt t tpt tp ttp tpt t tpt httphtt tp ttp tp tt
hht hh hht hh ht h
Ethyl benzene
hht hh hht hh hht hh h ht tphhtt
b b b b ebb b ebb ebw b ebb b ebb b ebb b b b ebb b eb
e be e b eb e ebw e w e ebw e i w e i e eb e ebw e e e w e ebw e e
wviw e
iwviwi
w w e
vi w w
i viw i v i i
wuvviw i viw uv v i w e
iwviwi
w w e
vi w w i
i i vi
r
u
vi
u u v
a r u uv
r larur l a r
uv
urialaru r
r
u
vi
uvaruruv a r r
u uv
uvarur ru ru v
a r u uv
ilamamil ar lial l
ilamamil
mtilam
a
t /a
e/t/aee/t
m t
t/a /t/a t
e/t/ae/t
/a /a
e/t ee/
/
t am
t/at /t/a t t /a
t/a /t ta /t a t /
e/t/ae/t /t e/
a a e/t ee/ /tae
/a t
ew bbeebb e e bbeebb e e eew bbeebb eew eew
vi e e w w w w w i w w i w
vv
ww
ii vvi i ww
u
i i
vvruuvvw i i
uu
i i
vvruuvv i
r u
r u vvrruu v v vv
w w
ii vvi i w
u vv i
u
i
u
w
vv i
uu vvruuvvi
i i
r uuavv
r
uruarru u r u r rr r a uu r u u r r u r r r r r
r
alailila
r
alailiala
ilim a
alailila
ilim a
ilima
l ii l l a r
lialariliala
r alailiala
ilim alailila
ilim a l ilila
a
ilima
ilim mm m i
aa//ttam
mm
Hydrocarbons
mm m
t//taea//ttaa
m
m
t/taea//ttaa
m
/
m
m
ttaea//ttaa
m
/ /
a
ttaea//tta ta ammtaamm
t / ta
tammttaa
//
m
/ t
/t
m
m
aa//ttaa m 347 //tt a
eem e
/
eem e eem e / eem e eem //tee// eem/ ee eemee eemee
here
..m/m//tt..Xmay be - OH, tt.:./-///ttF, - Cl, - Br, -1.
m m . m m m m .m
t..m/m//tt..m /
mm .
tt.:.////tt. m
/
mm
tt.:.///Cl
/ / .
tt . m
/
. .
//tt::////
/
t t .
t m /
m m . . m
/ / . mm
tt:.////tt. . / //t::////t.
/ t . . t
on o- and
t / t /
sst:p:p/Thus electrophile ppststttpattacks ttphptttp-positions because
// // / / : : : / /
/ ss::/ //
:: ss: / / : : :
/ / ss:: ss: ss:: ss ss ss ss:p:pss ss ss
@
ss::/ss:: ttphpttttpp ttphpttttpp ttphpttttpp
tElectrophile p ttphpttttpp
hht hh these arc electron hh rich hh positions whilenucleophile will attack on
tttphpttttpp t Cl t t t t pp t t tt tt t tt
hh ht hh h t 2 hh. h h h h t t t t t hh h h h h
dB
meta position because m-position is less electron rich. bb bb
FeCI3
0-
eewwGroups with negative bbeebb mesomeric eeeffect decreases
b b b b b b b bbeebb
we bbeebb bbeebb eew bbeeb • ee
( - .M) eewwee
@H
eew
uuarruu electron density vv on o- andp-positions vvruuv so electrophile vvruuwill
ee w w w i w w i i e e w w w iw
i w
i w i w
i w i w
i
vvruuvwv i i i i
vvruu w vv i i vv i v v i w
i w i w
i w i w
i wv i i i i wv vii i
uuavvrru
alailila attack onaarrmeta
vvruuvv
l iliala position m and alarinucleophile willilialaattack
iliala on
u u u r r u u r rr u v v u u uu r r u u r rr
u H2SO r
ala4 riliala r u rr r r alailila
alarrilialar alailiala Ncf, ilim liala ilim
© o- and p-positions.
ilim
6-�-�
ilim ilim m m m m ilim ilim mm m m m
m m m HN0 m m m m ma a a ta a m m m m
aa//ttaa m mm
aa//ttaa aa
tte//t t aa
t//taea//ttaa /ttaea//ttaa3
/ //ttaea//tta e /e/ttee//t t a
t a //taa
t / t
/t //tt e / / e
ee e ee e ee e m ee// ee ee ee ee ee em
t. mm/tt..mm
. / t..m/m//tt..mm
t / t
/ ..m/m//tt..mm
t / /
/ tt.:.m/m///tt..m
/ t .
t mm/tt..mm
. / t..m/m//tt..mm
t / t
/ ..m/m//tt..mm
t / /
/ tt.:.m/m///tt..m
/
t
/// /// / // // : / :: ss : /// /// / // :://s:: / :: s :
ss::/ss:: ss::/ss:: H2SO4 + SOp3psst:tp:pss: pststttpp
ttpS0 sst:p:p/ss:: sst:p:p/ss:: ppststttpps ppststttpps
ttttphpttttpp tttphpttttpp tthtt t p t pp t tt tttt
O 6:
t tt t
hh h 3 h t ttp t t t t t tt h
hh h hh h (Oleum) hh h hhtt hht hht hh hh hh hh h x
b eb
wveiw bbeebb bbeebb bbeebb eew bbeebb bbeebb bbeeb3. b - 1 eebbeebb
vrruu Here, Xmay be ii -vvN0 i 2, - S03H, -vvuCN.
e e ee e e w i w eew eew /,
w w w
iiwvvi r Alkylation vvuuvv
i i w
i w i w
i w i w
i
vvruuvv w i w
i w
u v i i wv v i w w i w i w
i w vv i i w vvriuwiwvviw iw
uuav
v
uruarruv u r u u r r r ru u r r r ua uu v v
r u u r ru u r r u r ru u r u r r
r
alailila R-X+AICI ilim
r
alailiala ilimalailila a ilima a iil l a
l Carcinogenicity r
lialariliand
r
ala toxicity ilialailiala ilimalailila a iliml ilila
a a
3
aa//tta 5 PAH'saagenerally have a low mttaadegree of acute toxicity to
ilim m m mm m m m a m i m m m mm m aa//ttam
m m a
mmtaam mttaa aa mmtaamm aa
humans.
//tee//(Polycyclic Aromatic eem/ ee Hydrocarbons).
aa t t a
ta // / t a
t a //t t //tt t ta
t a / / / ttaa / t
/ t //t t
//tFriedel
tee// - Crafts ee// ee eem/ ee eemee t / eemee / eemee
The ..m/m//tt.most
.m significant///tt.endpoint ofPAH toxicity
tt.:.////tt is cancer.::////tt::////t.
eem mm . m m mm . . m . m
. m t t. . m eem mm . m m m . . m . m
. m t .m
..m/m//tt..m tt.
tt.:.//RCOCI
/ tt.:.////tt //tt:://// .////tt.
• ppsst:tp:Increased
t t // / + AICl / / / / t t / /
incidences ppststttppsoflung, skintand ttphpttttpbladder cancers tare
/ / // 3 ss:: ss / / : : : 0
/ /
//ss::/ /
:: s : : / / :
/ /
ss::/ss:: ss:: ss: sspss ss::pss ss ss
tphphttttpp
ttphpttttpp, Acylation ttttphphttttpp ttttphphttttp
hht hh associated with hh occupational exposure hh h to PAHs. Data for
t tttphpttttpp hh ht t hh h h t t t tt p t t
t thh t h h t t
hh h
bbother
eebb sites is much less persuasive. b bb
e iw
b
P AH' s toxicity is bvery
beebb structurally dependent, with isomers
be bbeebb bbeebb
ew bbeebb Gattennann eebbeebb eew bee
vvriuiCHd'
eew eeww eew
vvruuvv (PAHs with the iwvsameviiw formula and vvrinumber
iwvvi ofrings) varying
i Koch reaction
vvriuiuwv,vi
ee w ww ww i w i w i i w e e w i ww i w i
iwiwvviw iw i vv i iw w vvriuiuvvi uuavvrr
alailila from being alarrinon-toxic to being alariextremely toxic.ilialailiala
vv u uu u r ru u r vv u uu uu r r
• iOxidation :
uu CO + HCl u r uu u r
u
r u rr
lialariliala ala+rilialAIC1
r a 3 r r r
alailiala ilim a u u
lialar
r r liala r r r ilimalailila
/e/ttee//t • One/PAH
ilim ilim ilim
mttaa compound, benzo[ aa//ttaaa]pyrene, is notable ttaea//tta for being ee//ttee//t
ilim
t//taea//tta•a Combustion ttaea(//tcomplete oxidation) ttaea//tta :
m m mm m mm m a m m a a m m m m m m mm m m a mm a a m
mm taa a a t a a t
theefirst / ee chemical carcinogen
mm/tt..mm to be discovered ..m/m//tt..mm (and is one////tt.:.m/m///tt..m
a a t t
C6H6t+t..mm
/ /
15/2
..m 02 ---, 6C0 ..m/2m//tt.+.mm3H,O
/
eem e / ee e / e t t / / /
ee ee / ee e /
ee e
of many carcinogens found in cigarette smoke).
m emm m
tt.:.m/m///tt..m
• Oxidation ss: ss with V20p5ps:sttppss
t . mm/tt..mm
. / / t
/t / t
/ t / /
/ / t . m
. m t .
t . / t t.. / / t
/ t
•ttppstst:tp:p/sHigh
s:: prenatal texposure ss: ss to PAH isppsassociated with lower
t
/:://s/s::/// : / / / : /
: / : /
: / : : / sspp: : ss : / / / t / /
/ / : / / / : /
: / : /
: / :: / ssp : : s s :
s ss
ss ttphpttttpp ttttphphtttt0 tphphttttpp tthttttpp ttttphphttttp
hh hh IQ and childhood hh asthma.
ttttphpttttpp t t t tthtt
t h h h t t t t t t t h h h
"
hh h hh II h h
VO CHCOOH b CH - C ..____
hh h
b eb_______. 1 1 ebb ebb o
• Some P AH's known for their carcinogenic, b ebb mutagenic andb b b b
© + 0e2bb� teratogenic properties are
b
500 C
b
II
CHCOOH CH i -viwC__.,..
b eb e b b° eb e ebweeb e b b ebb eb b eb eb eb e e
e
wviw ii weviwiw e e
iwviwi
w w e
w w e i w e
v i i w
wuvviw i
i weviwiw e e
iwviwi iwviw
w w e e iweviwiwe viwviw
w
uriualvarur 0I I
v w vi vi uv u v v w vi vi uv uv
u rulvaruruv
u ar uriualvaruru
v
ar l arurlialaru
r
r
u uvariuruv ar
v
uriualvaruru aruavru ar uriualvarur arularu larurliala
mtialam
l i l i
Benzo[ ]pyrene
ar l i l a ar l l l i l i la
milamil
il ia iamil acid
milaMaleic milam amMaleic
il anhydride mi mi ialmilia ilaim
amil il i amil
ilam i mi mi
/tataem/t/at KMn0 e/Only taem/t/atam amm mtam amm mtam taem/t/atam /ta
side chains e/are
tt/aaem/•t/atam Oxidation e/with
m /tataem/t/at t/a t am /at / t
a a /at t/at t a / t/a
t/aee/t / a e/m t
t ee/ e/ e/ t e/m t e/ / e e/me e
.me . e t.mte.m
oxidised to carboxyl groups.
. m etem/me
. t .
m m/e.tm . me 4 me me
t .
m / .tm. / t
. m.m/t/e.tm . m etem/m
. tm. m/e.tm. m . m tm.m/e.tm /.tm.m/t/e.tm. .mt.m
t /
/ . / t . t /. / /t
t tpt COOH
tt m:/t/. /. t tm /. t :
s:tps: s://s:/
tCH
/ . /t :/ t : / t : / :
/ s /: /. / /
t . /t :/ t / t / / : / t :/ / / : / /: s /
/:/pss:/ /:pss:/ /pss:/ s:tps: :/ts:/: /:pss:/ s:/ s: /pss:/ s: s
httphht 3 KMn0 0hhttphrht �
s : s: / s : s:
Chrysene
s: ps t p s s: ps p s p t p s p
tptpsttpt
pstpt tp ttp tptpsttpt
ps
tpt t tpt tp ttp tpt t tpt ttp tt tp ttp tp tt
h� hht hh hht hh ht h hht hh h h hht hh ht h
/ 1- O
hht hh hht hh
O
b e b � e b b ebb 100°-120°c ebbe� ebb ebw b ebb
e w bw
evewi
b ebb
e eb b ebb ebw b ebb b b
e e e e ebw b ebb b eb
e e
ew e w e w w e i i e w e w
wuvviw viuwviw
i
CH
e w i i e w i i
vi v iwviwi
w v i wi viw v i wuvviw uv w
viruvi v iwviwi
w v i wi viw iwvi w v i uvavriuw
Coronene
uv i r u v r uv r
u uv r
u uv r
u r
u ar u u v i r uv r u v r
u uv u v u r
u uv r
u r u r r
u r
r u arulialar ar lialar larilial urialaru uialar ar ar ar lialar ila ila larilial
CH - CH mami
3
lliaariulialar
COOH
iilalm i
a l i li
a l a r ial a r l l i l ial i li
a
�
o
mil mi mamm ilaim
amil il mi i il mi m mm
mi m
tt aem/t/atam � e/t/ata3em/t/at taem/t/atam /ataem/t/at amm amm tam tam/tam amm tam /tam/tam ataem/t/ata /tam
- .metem
/ a t t t /a / t
a / a t/
.KMnO/OH
/a t e/ /at
t ee/t /a t/a
e/mee/ e/ et t e / t e /
m/e.tm
e/me
.m/t/e.tm me
/
.me .mt/e.tm .me e/m
m/e.tm .m/t/e.tm. .mt.m
e/me e e
.m/t/e.tm. t.mt.m .mt/e.tm .me .mte.me
s:/t:/pss:/: 100°-12ooepss:/t:ps�
tm tm
�
t .
m . /.tm / t
. m /
t . /
t . / t m. . /.tm / t
. m / t/. :/ t /
/. t
/:p/sts:/:/
t /t s:/:
/ : /
s:/tpss:/ :
:/t/.s:/:/t t
s:/t:/pss:/: s://s:/
t / / t
s:/t:pss:/: s:p/ s:
/ / s:/tpss:/ s://s:/
: /
Pyreneht tpt http ttphttp
s: s
p t p s t p s: / ps p s p s p t p s t p p t p
ps
tpt t tpt tpt http tpt ttp tp t ps
tpt t tpt tpt ttp tt tt tp t t t
hht hh Directive hht Influence
h hht hh hht hh hht hh h h h hht hh h h hht hh ht h
• Groups withposit:ivemesomeric beffect (+.M) increasesbelectron
density on
bo-ebband p-positionsedue ebbto delocahsation.
b ebb
&� �� o
ebweeb
b ebw b ebb b ebb b b b ebb b eb
xjuruv uruv x•
b eb e b b e e w e i e ebw ebw e wewe evewbw e weiw
Triphenylene
wview w
ii viwe i w e i
w w ev wi w i
w w vi wi vi i
w vi w i w e i e i
w w ev i
w i i
w w i i i
v w v i
uvaruruv x• i v i
uvaruru v u v
r larur uv v w
iruv v i w v i
uvaruruv ruvru i i v v
uvarur ruvruv
i u v uv
u
a r l ar l ar r
u i l i l r
a r
u ial ial ar u
lia a r r
u uv
l ar u l a r r
u ial a i l ar r
u ial l a i l a ial arurlial
i a mil mi amil il il
ilaim a amil mi mi l
milamil
il ia milamil milamil taem/t/atam mtilam
ialmilia
amm amm
ilam mtam
i
taem/t/atam /t
��o �6
tt aem/t/atam tt aem/t/atam t mtam t
tt/aaem/t/atam /me/a e/me /a t
e/me/a t am
t/aee/t / a e/m /at /
t
t ee/ e/ e/a t a e/m /at
t e/ /
t a / t a
e / t/a
e/me e
etem
. m
tt m:/t/.
etem
.
/me
/ t
. .
m "{)
m
t/. . '&/ t
. .
m m/e.tm
t
.
/ /
t .tm.m/t/e.tm
:
.
t .
m m etem
/ .
/m
. /.tm. m/e.tm
t
.
t . m t . m /
t t
. .
m m/e.tm
t
. e t.mte.m
/ / / /
t t
. m.m/t/e.tm
:
s:tps: s://s:/
. .mt.m
t /
ps Ovalene ptpstpt tp ttp
/. /t
/:pss:/ :/ : / t
/pss:/ : / /:
s:tpss: / / .
:/ts:/: / t /t :/
/:pss:/ s:/ s: / / / : /
/pss:/ s: s:/ / : / :
/ s /
s : /:/pss:/ s: p s s: t p s s : / s: p s s: p t p s
tp ttp tp tt p
tptpsttpt
ps
tpt t tpt tpt t tpt hht hh
tp ttp tptpsttpt t t tpt t tpt ttp tt hht hh ht h
hht hh hht hh hht hh hht hh hht hh ht h hht hh h h
b ebb b ebb b ebb ebw b ebb b ebb b ebb b b b ebb b eb
e b eb eb e ebw e w e ebw e i w e i e e b e ebw e e e w e ebw e e
wviw e
iwviwi
w w e
vi w w
i viw i vi i
wuvviw i viw uv v
i w iwviwi
w e w e
vi w w i
i viw iwviw vi wuvviw viuwviw
i i vi
r
u
v i
u uv
a r u uv
r larur l a r
uv
urialaru r
r
u
vi
uvaruruv a r r
u u
uvarur ru ruv v
a r u uv
ilamamil ar lial l
ilamamil
mtilam
a
t /a
e/t/aee/t
m t
t/a /t/a t
e/t/ae/t
/a /a
e/t ee/
/
t am
t/at /t/a t t / a
t/a /t ta /t a t /
e/t/ae/t /t e/
a a e/t ee/ /tae
/a t
b eb b eb b eb beebb beebb
eb ew ew ew bbeebb bbeebb ebw beebb eebw bbeebb eew bbeebb ebw beebb eebw
i wv i i w vi
uvru
i wv i
w w
eew
i i w i w
i w
eew
i iw i w
i wvveiw i v iwiwvviw i w w
eew
i i w i w
i w i iw i w
i wvveiw i v iwiwvviw i
uvru uvru arila
i
uuvvruuv
i v v
uuvruu
v v v
uu ruuv uu r uv u i
vv vv i v
uuvruu
v v v
uu ruuv uu r u v u
arila arila ilm alarrilialar alarrilialar alarrilialar alarrilialar ruu rruu alarrilialar alarrilialar alarrilialar
ma
ilm
ma
ilm ma ilim ilim
m m
ilim
m mm
ilim
m i lialariliala ilim
m m
ilim
m mm
ilim
m
/tae/t m m a mmamm m ma m a
/tae/t /tae/t em
mma m
//ttaeae//tta
ma
//ttaeae//tta //ttaeae//tta
a
eem //ttaeae//tta //ttaeae//tta //ttaeae//tta //ttaeae//tta
a
eem //ttaeae//tta
...
em em m . eem eem eem m eem eem eem m
m. .mt. . t m m m . mm . . m m mm m . m m . .
/t.://t //t // //t // ..mmt.. m m
.. t m
///s/tst::////t
. . . .tm
///s/tst::////t
. . t t/.
:s:///s/s::///
t t tt.:.m/m///tt.. m m
//tt.:.:////tt
. . .
//tt:.:////tt
. . t .
///s/st::////
t t
st:ps: st:ps: /:://s/tst::////t : : : : / /
/ / : /
: / : /
: / : : w
ps s
ttttphphttttCONCEPT
s
ttphpttttpp MAP hhttttphphttttp
p ssp ssp pp ss:: ss : sspss sspss sp
ht h
p
t t ht h
t t
t
ss
ttphpttttpp thtttphphttttp ttttphphttttp h h t t ttttphphttttp h h ttttphphttttp 0,
hh ht h h h hh h hh
b b eb b eb b eb bbeebb bbeebb bbeebb bbeebb bbeebb bbeebb
ew w ew
i i wveiw e e bbeebb eew eew w w
eew
i w e e bbeebb eew eew w w
eew
i w
i w v i i
uavru
v v iwiwvvii w w i w w
vvruiuvv i i w i w
i
vvruuvvw i i w i
vvruui v v i iw
iwvvii w w i w
vvruiuvvw i i w i w
i
vvruuvvw i i w vvruu i
i i v v
r uavru r a rularu u urv v u u r u u r r ru u r r ru u
a r u urv v u u r ru u r r ru u r r ru u
a r
ila il ila il mm
il i alarrilialar
ilim
r
ilialailiala ilialailiala ilialailila alarrilialar
ilim ilialailiala ilialailiala ilialailila
mm mm tae/ta mmtaamm mmtaamm mmtaamm mmtaamm mmtaamm mmtaamm
t/ ae/ta tae/ta m m m a t a a t m m m a t a a t
Cyclic chain
/ a a t / a a t /
Acyclic ..m/m//tt..mmor Open Chain
/ a a a t a t t t / t / / / a
tta/tt aa t t/a t t t / t // /
e em m .m
e tta/tt
ee// ee/ ee// ee/
t/ ee// ee/ eemee ee// ee/ ee// ee/ ee// ee/ eemee
.m//t.m
/ / t.:m//t. : / /t.://t t . mm/tt..mm
. / t t / t
/ ..m/m//tt..mm
t / // tt.:.m/m///tt..m
/ t .
t mm/tt..mm
. / t ..m/m//tt..mm
t / t
/ ..m/m//tt..mm
t / /
/ tt.:.m/m///tt..m
/
s : s :s s s / / t
// ::// / : : /
//ss:: / : /
: / s : : / s s: : ss : / /
/ / ::/ / / : /
: / / : : / : /
: / s : : / s s: : ss :
tp tt p : : ss ss s ttpptttpp :
ss ss : ss s s ss s ttpptttpp
tp ttp ht h
ss ss ttpptttpp ttpptttpp ttpptttpp ttpptttpp ttpptttpp
ht h ttpptttpp
hhtt hht hhtt hht hhtt hht hhtt hht hhtt hht hhtt hht hhtt hht hhtt hht
b b eb b eb !saturated ew b eb (Alkanes),cnH2n+2 I bbeebb bbeebb I Unsatee�bbrated eebb I I Alicyclic j

bbeebb bbeebb bbeebb
j Aromatic j
ew ew bbeebb bbeebb eew
we w i w i ee e e eew w w i w w e e Contain a ring e e of3 or Contain eew one or more benzenew w i w rings C,,H2" 6m
uuavvrruuv n = number
w i i i v v iww ii ww w
iiwv i i w i i i iw w w w
iiwv i i w i i i
vi v iwvviw vv vv iwvviw iw iwvii vvuuvv
rularu Have carbon-carbon single bond. Show chain
v v rularu vvriuw ior
w
nuclear uuvvrruiuvv vvriuw
rularu uuavvrruuv rrulualarruu morc C atomsuuavvrruuv where, rrulualarofr carbon atoms,
I I m = number ofaamrings,
a uu u r r r u u u r r r r
isomerism mam and conformational stereoisomerism
a
il i a
il i i l i r r r r
alailila a alailil a a a
ilil ii r r r alailila alailil a a a
ilil ii
ilialailiala ilim ilim ilialailiala ilim ilim m mm disubstituted products
/
mm
tae/ta
e /
mm
tae/ta e /tae/t Physical Properties ttaam/mttaamm
// ee/ I / t
/ aam/m/ttaam
t /
ee ee/t t
m
aam/m/ttaaIAlkenes, C,H,,
ee / / e
mm mm
ttaea//ttaa I t
ee// ee/
a
t amAlkyneo,
mttaamm
/ C,H,�, //t aam/m/ttaam
t / / aam/m/ttaam
ee ee � positionmmisomerism-a,
t t eem / /tte//ttaa
e m,p.
t.m/t.�
e m eem ee ee eemee
.mt.m .mt.m mm.mm mmt..mm ..mmt..mm .m
tt.:.m/m///tt.triple mm.mm .m
//tt.:.:////tt.
ttpptttpp Physical Properties
//st :// //st :// ://s:/ t/ t.:.m/m///tt..m Have carbon-carbon /: /tt.:.:////tt. double //tt.:.:////tbond, show ///s/tst::////t
structural Have t ..m/m//tt..mm carbon - c arbon / bond, //tt.:.:////tt. / /
Boilingpointss:s:: ss:
: s / / / : // : /
: / : : / / / t / : // / : : /
: / : : s s
s tp ttp andtttgeometrical
ss ss
isomerism
ss ss ss
ttpptttpp sst:p:p/ss:: structural isomerism ss: ss ss ss ss
ttttphpshow
p tp ttp ht h In straightttttphpchain tpptttpp ttpptttpp (cis, trans). ttpptttpp ttpptttpp
ht h htt
ttpp
hh hht hhtt hht hhtt hht htt
t hhtt hht hhtt hht hhtt hht
alkanes, molecular=
.t
hh h h
Melting and Boiling points
---,. B.pts. Physical bbeebb Properties I
eb w e
i
b eb
w w e
i
b eb
w iIn
w ew
i
b eb
isomeric alkanes, ee bbeebb t eew bbeebb eew bbeebb
w t i w w
eew
i
bbeebb
i w ee eew bbeebb eew bbeebb = molecular
w i w w
eew
i
bbeebb
i w size
II
i i v w i w w w i i i w i w w w i i i
j Physical Properties
w w w w
Chemical alarrilialar Propertfos
v uvru iwvviiw vvii vv i i iv vv vv iwvviiw vvii vv i i
vvuiuvv vv vv
vviw vviw
'
v uvru arila branching = 1/B.pts
arila
uvru
arila rrulualarruu rrulualarruu uuvvruuv ruu rruu
lialariliala I rrulualarruu Boiling ilalapoints rrulualarruu and lalarriuliualarr Solubility
ruu rruu
lialariliala Insoluble in
-+I
ilm ilm ilm la a i l i i i
mmtaamm --+ meltingttaam
a
points
mttaamm of alkyncs
la a i i i l i i i l a i i i i i
Melting points 'taamm
ma ii l i mm mm ii l i mmtaamm soluble in orgamc
ttaeawater,
m m m m mm mm
aam/m/ttaam aam/m/ttaam
/tae/t
I
tae/ta tae/ta aam m ttaea//ttaa > alkanes and alkenes ttaea//ttaa //t
/ / t t Boiling points t t : ee e �
/ tt Und rgo electrophilic // addition a a t / / / / /
..mmt..mmsolvents (large hydrophobic
e t / // / e t t // / / / e e
__. Even no. of C atoms
em e m /
eem/ ee / ee ee e e e /
eem/ ee ee ee ee e e
//tt.:.:////tt. react10ns. ::///s/tst::////t
m t.m/t. ..mmt..mm
tt.:.m/m///tt..m cis > trans
-+I
t.m//t. t.m/t. ://s:/
mm.mm
//tt.:.:////tt.
mm.mm
tt.:.m/m///tt..m
mm.mm
//tt.:.:////tt.
mm.mm
//tt.:.:////tt. ///s/tst::////t hydrocarbon part).
s: ://s:/ ----* higher m.p. while (higher
/ / :
ss dipole
// / / : / / / / / : / :
ttppttSolubility : Insoluble ttppttttpp in
s / / : : : / / :: :
odd� lowerm.p.
s tp ttp ss:: ss : ss ss s s s s ss:: ss : ssppss ss s s s s
Discharge ttppttttpp ttpptttpp
hhtt hhorange red colour ttpptttppof
tp ttp ht h ttpptttpp ttpptttpp
ht h ttpptttpp
hhtt hht moment hhtt hht of cis) hhtt hht hhtt hht
t
hhtt hhtwater, solublehhttinhh organic hhtt hht
bromine test for unsaturation.
b ebb
..-,. solvents.
I Chemical Properties b ebb b jb b eb
b ebb b ebb b ebb b b b ebb b eb
b b b b b e b
MeJtingpoints: e b b ebb e b Order of reactivity
e b e of addition w e of
ebw e e b b ebb eb e e e b e e w e ebw e wewe wveiw b eb
be b e e e e w e
-,. w e i w i i e e w e w e i w w i i i wveiw
__.jruSolubility
e e e w w i i w e w w i i w i w i
I I
e i w vi i w w vi i
halogens to alkenes:
w w i w w vi w i w w i v w i vi
in non-
v w v
arurliaChemical Properties
w w i i w w vi v w i i w w vi i v i v v i
trans uv ru>v cis (symmetry
w i w i w i w i i v vi w vi vi u v uv r i uv uv r u v vi w vi vi u v v v uv r i uv uaru Reactivity:
v uv r uv v u u r u v
uvru
v uvru
v vu
arur aru
uv r
arurlialaru F,>Cl,>Br,>l, arurlialaru arurlialaru uvaruruv uv r
arurlialaru lariularu arurlialaru ilarif-+ arurlialaru lariular arila u ru
arila arila ilma ilpolar
ar solvents and
lialmilial well packing alm
ilaim iof ilaimalm i mtilam
ialm i ialm l alm
ilaim i im alm
ilaim i m m l Alkenes mtilam
ialm i and i m alkynes > arencs ilm arila
ilm
�1
ilm l m
halogen halides: t/at e/t/a
ilm i m m am m i i m m am m a
/tae/t Chemical Properti'es e/t/atee/t/attrans in crystal t/lattice) t/>
m m at e/alkanes a a t m
.
ma taem/t/at am am a
ma ma am am ataem/t/at am am
t/atee/t/at t/atee/t/at e/tae/ta t/atee/t/at e/tae/t t/a /ta /t t /
e/ e /tae/t
a
"-+
/tae/t /tae/t t/aHI>HBr>HCl e/me e/m
em em em m e . m . m etem/m
. e . m etem/m
. e
tm. m/e.tm. m e e/m
. Have . m etem/m
. acidic m m acetylenic . m etem/m
. . m . m tm. m/e.tm . e .mte.me t . m/t.m m
em
.m//t.
e
Undergoes electrophilic
t m / . . tm t / . .
hydrogens.
. m . .m t . t . m/ t . / t
. m. /.tm / t/ t
. m /
t . /
t . :/ /
t . : / t /: /t / t
. m. /t/.tm / /
t t
. m / t/. t . / t /
t . :/ t/. / t / / : / t /: /t / / t / / : / / : / / t . / t / t
Solubility pss: ps::
t /t :/ :/ / : / / : / / : /
s: s: : : / / :
pss: ps: Additiontptphstof
t / //t / / // / t
s:/t:/pss:/: /: s/ / s/ s:tpss: unsymmetrical t
s:/:/pss:/: /: s/ / : / s/ : s ps /
s: s: s:ps
://s:/ s: s: psst:ptps: tpst::ps pss: ps: s ps tpstptps stps
tp tphttp
s: s: tphttp Least reactivetptps(inert) tp cis ht> tpthhttpttrans (less tpthhttpt reagents ht(HX,
tp
HP,HOX tptphst tpt
etc.)� tpthhAcidity t tpthhttpt httphtt ht tphht httphtsubstitution reactions.
h ttphtt tphttp ttphtt
-? alkynes > alkencs > alkancs
t ht h h t t t ht t
because of h hstrong symmetry
t h ht h t h h h h
h h t h h h h h h h
ofcis)
and C�H
h
---,. f+ b Markovnikov's b rule. In presence b ebb b(ass-character= acidity). b ebb bInebabsence b eofbb sunlightb eb and in eb eb
--
c�c of peroxides, b addition is anti- b ebb b b
-.1
b b b b eb e b b ebw b
eb b eb b eb er
b
ebonds e � paraffins. ebweeb e b
evwiwe e b e b
weviwiwe iweviwiw e ebw eeb evew bw e wewe weview bw
i e weiwpresence iweviof i ehalogen ew carrier �viwviw eb e
Markovnikov's - Peroxide or
e w e w w i w i w e wi v i
w w i vi i
w vi w u v i w e i
w v i
w w i i i i vi i
w i v vi w uv w v i w v i iwviw
w i i w vi i w vi i r ru ru test arur larur ruar substitution v u
arulialar larilareactions
uv
butlain
w i uv v
arur aru Gives brnmin, arurlialaru wate,
i i v v v vi
uv ruv uv uv uv r uv r r
u vi
uv ruv uv uv v uv uv u r r
u u u r u r v
Kharaseh arurlialaru effect.
v uvru r arulialar r u ru
uvru ru ru arurlialaru i mila
i--
la ila U dergo 0 Iy substi- ilialm arurlialaru arila
ialm ialm
°: 11:
alm ila formilialmilia ilm a il
.]
arila arila
ilm i alm
ilaim i ilaim i mtilam i lialmilial and Baeyer's alm
ilaim i ilm atest presence
mtilam i i m of sunlight mand ilm
ilm m m m m am m i m m a m m am m a a t a m
unsaturation.
m am am t t /a
t/ae/t colour of t/ataem/t/atam am am t a t /a a t
/tae/t
ma
/tae/t
ma
/tae/t
a tut10nreactlons. am am
t/atee/t/at t/atee/t/at I-> t/atBaeyer's
e/t/a test m:ee/pink t/atee/t/at e/tae/ta t/at e/t/a /tae/t e/m /t /t /tof halogen carriers
t/aeabsence e/ e �
/
/tae/t
a /t
etem/m e/m e/m
. eK.Iv1nO4 solution .meis dischargedmee./m e/m e/m
. e t.mte.m .m/t/e.tm . e .mte.me em em
....
em em em m . m/e.tm . . m/e.tm t . /t/.tm
m e . m/e.tm . m . m/e.tm t m addition reaction. t .m//t.m m .
Undergoes
t/. t t :// electrophilie
m . . . t m /.t m / /
t . . tm t m . m t . / t
. m / /t/ . t / / . m t . t . / t
m.
/t.://t .mt. . t
//t // /t/.tm/t/. t/. t t t
s:/:/ s:/:/ /:
s:/t:pss:alkenes. /.tmt/. t t / /
s:/:/ s:/:/ :/ s: s:/:pss:/: s://s:/ /
s:ps: t / ://s:/
s:/:/ s:/:/ s:/t:/pss:/:/ s://sand ://s:/
//t // Halogenationpssoccurs :/t:pss:/: tphst tptps . on addition tptphsttpto /:/ts/:/
�I
st:ps: st:ps: tphst tptps psst:ptps: tphst taddition nucleophilic
tphst tptps ttpsttp tptphsttpt ____ll,,_I tphttpnn nnt ,--,; ,,. °Rhttphtt '� tP.�t psttp psttp
ps p t p p t p p ttp ttp p t I t
H- by a free hht hhradical
p t h t t ht t t
hht h addition h h reactions.
p
t t t t tp t t ht t p t ht h t h
ht h t hht h h h hht hh to
t h h h h h h h
,r <1P>rPr
ht h h h h h
mechanism. Ozone oxidises alkanes
ozonides. b b eb b b b b b
b ebb eb b ebb eb eb eb iweebiweeb ew b eb eb e
uv ruv 4
b eb b eb b eb b ebb ebb eb ebw
ie b ebb ebb eb b eb b eb
b b ew ew Ease
ew
of substitution weview bw e iweviwiwe More substituted iweviwiwe
alkenes
wiuwveviw ---;
weview bw e iweviwiwe iwveiw iweviwiwe viwviw wuvviw viwvi iwviw ew
we w i i w w vi i i w w vi v w i
is
i v vi i
4
w i w
i v i i v w vi i uv uv v w vi uv uv u u v
i v uof v uv uviruv uvarur arurliheat
laru
r uviruv uv ruv v uv r
arurlialaru ilariular
u r
arurlialaru lariularu arila
r uvru
uvru
arila
uvru
arila aril30
ilm ar hydrogens 20 > 1 0.
arur aru
lialmilial
arurlialaru
alm
ilaim highly arurlstable.
alm
ilaim i ia
l Lowermthe alm
ilaim i a of arurlialaru
ialm arurlialaru lariularu
alm
ilaim alm
ilaim i mm mtilam
ialm i im ilm arila
ilm
>
ilm i l i i im m
hydrogenation of t/an
e/maee/t alkene � e/t/ataem/t/atam
ilm m i m m a m t m i m m m a m m a a ma
ma ma ma
/tae/t
am am
t/atee/t/at
am
t/atee/t/at
am
t/atee/t/at
t /a am
t/atee/t/at e/tae/ta
am
t/atee/t/at e/tae/t
a
e/m t/at e/t/a /ta /ta e/ e
t /t
/tae/t
em /tae/t em /tae/t em e e/m m etem/m
. m etemmore
/m
. stable. tm . m/e.tm . e m e m etem/m
. m etem.
/m
m m . m/e.tm . e .mte.me . m/t.m em m
e
m . . m . . m . . t m t m
t.m//t. /t .m//t. /t.:m//t. /.tm
t
. t/.tm
:/
.
: /t/.st:m/:/t/. /:
t m
/t/.s:/:/t/. s: /
/ .
:/ts:/:/t /.tm
t
. t/.tm
:/ : /t/.st:m/:/t/. ://t.://t m .
/:
tm
/t/.s:/:/t/. ://t :// . t
s
: /
/ .
:/ts:/:/t ://st :// s ://s:/ / / t.://t .
: / /t.://t
/ / / : / / /
s: ps s: ps ps : / / /
s: ps s: s ps ps s : s
/
st:ps: s: s: s: s pss: ps:
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