Paqe No.:
Unit-9 - Heiexocyclic Compounds
Date:
Hetexocycliccompounds AXe cyclic compounds ncohichAhe sing
atoms xe afcaxbonand some theY elenents.
- The ctann of Hhe othex elementCN, S. o)is called 4he hetero atom
’5- Membexed Hetexocuclic Campounds i
H
Pyxale Thiaphene Indale
6 Membexed Hetexocuclic campounds i
Pyridine. Quinoine Tsaqungline
Pysxolei 1+ is found many natural products includin
an alkalgids
hamaglabinchlaophy
Sp- sp 2
H
sp -s
(c- H o bond
H
sp' sp
(eN G band)
(N-H S bond)
, Page No.:
Date:
H
d mixtuxe f fuxcn dnd
Tndusiyially pyszxale is abdained by passing
clumina 400
Aloo3
H
yiale
he
amnanicd undex ressure
NH3 heat +
Pxesse
dial Pyxole
Physicel Propenties -
is a colawrless iquid
3 J4 is anly slighdly solable cadex but toBally nniscihle asith
e4he
4, IA duns bocn in dheciy and
gxadally Kesinifies
, Date:
Chamical Paopexties -
Pysxale is axomatic andnmoxe xeuctive hdnbenzene.
J4 qiNes electiaphiic subs4idution z actions. Such as.
haloginatian,
nHxtion anl Sulfonation.
also
3.14undexqoes diazotizction and Reinmex- Tiemunn Renetionschile
benene does not..
a. Dyxale undaqaes electophilic substitution xeuction at the 9-position.
5. Att ack f the electrophile at 3- position in pyxxale leads to an
inienAediate caitla ony two Yesanance styuetures
6. hxee Yesonance Stuctuxes
uYe passible fox the intexmediate pxoduced
by cttick at 2ndpositia
Thit is i the intexmedictepxoduced bu attack at9-position is.
moe stable.
SThis is +he xeasanA +hat
electyophilic cittack occuYS at 9-positian
Iuthex 4han a t 3-position
Attack at
H
Less stable
Attack CAt 2-positign i
H H
H H
H
More steble
FavouYed
Prouct.
d Acidic chaxactex i- Ryrzole can
also dct As ca ceck acid its ucidity is
ahout +he Sume
dS that of acetylene. Fox excAmple ,if pyxrole
isAe
caifh metallic potassiuM
innheDtane cs Soluent steble potassiun
p4salide is faxmed.
heat
NKt
Pyaxale Patassium puzide.
Unit-9 - Heiexocyclic Compounds
Date:
Hetexocycliccompounds AXe cyclic compounds ncohichAhe sing
atoms xe afcaxbonand some theY elenents.
- The ctann of Hhe othex elementCN, S. o)is called 4he hetero atom
’5- Membexed Hetexocuclic Campounds i
H
Pyxale Thiaphene Indale
6 Membexed Hetexocuclic campounds i
Pyridine. Quinoine Tsaqungline
Pysxolei 1+ is found many natural products includin
an alkalgids
hamaglabinchlaophy
Sp- sp 2
H
sp -s
(c- H o bond
H
sp' sp
(eN G band)
(N-H S bond)
, Page No.:
Date:
H
d mixtuxe f fuxcn dnd
Tndusiyially pyszxale is abdained by passing
clumina 400
Aloo3
H
yiale
he
amnanicd undex ressure
NH3 heat +
Pxesse
dial Pyxole
Physicel Propenties -
is a colawrless iquid
3 J4 is anly slighdly solable cadex but toBally nniscihle asith
e4he
4, IA duns bocn in dheciy and
gxadally Kesinifies
, Date:
Chamical Paopexties -
Pysxale is axomatic andnmoxe xeuctive hdnbenzene.
J4 qiNes electiaphiic subs4idution z actions. Such as.
haloginatian,
nHxtion anl Sulfonation.
also
3.14undexqoes diazotizction and Reinmex- Tiemunn Renetionschile
benene does not..
a. Dyxale undaqaes electophilic substitution xeuction at the 9-position.
5. Att ack f the electrophile at 3- position in pyxxale leads to an
inienAediate caitla ony two Yesanance styuetures
6. hxee Yesonance Stuctuxes
uYe passible fox the intexmediate pxoduced
by cttick at 2ndpositia
Thit is i the intexmedictepxoduced bu attack at9-position is.
moe stable.
SThis is +he xeasanA +hat
electyophilic cittack occuYS at 9-positian
Iuthex 4han a t 3-position
Attack at
H
Less stable
Attack CAt 2-positign i
H H
H H
H
More steble
FavouYed
Prouct.
d Acidic chaxactex i- Ryrzole can
also dct As ca ceck acid its ucidity is
ahout +he Sume
dS that of acetylene. Fox excAmple ,if pyxrole
isAe
caifh metallic potassiuM
innheDtane cs Soluent steble potassiun
p4salide is faxmed.
heat
NKt
Pyaxale Patassium puzide.
