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Anthracene
Structure of Anthracene
Introduction
• It is obtained from oil fraction of coal tar.
• The crude anthracene contains Phenanthrene
and carbazole
Phenanthrene Carbazole
Purification of anthracene
Anthracene is washed with Solvent
naphtha which dissolve phenanthrene and
remaining solid is then washed with
pyridine which dissolve the Carbazole.
Solvent naphtha
• A flammable liquid distillate
containing mainly xylene and
aromatic hydrocarbon.
• It has high boiling point than ligroin.
• It is obtained by cracking of
petroleum.
• It is used as solvent.
Structure
Xylene Ligroin
• Light ligroin; Light
petroleum; pether
Isomers of xylene
• Ligroin is the petroleum fraction consisting mostly of
C7 and C8 hydrocarbons and boiling in the range
90‒140 ℃ (194–284 °F). The fraction is also called
heavy naphtha.
• Ligroin is used as a laboratory solvent. Products under
the name ligroin can have boiling ranges as low as
60‒80 ℃ and may be called light naphtha.
• Petroleum ether is the petroleum fraction consisting
of aliphatic hydrocarbons and boiling in the range
35‒60 °C, and commonly used as a laboratory solvent.
• Despite the name, petroleum ether is not classified as
an ether; the term is used only figuratively, signifying
extreme lightness and volatility.
• Ligroin is assigned the CAS Registry Number
8032-32-4, which is also applied to many
other products, particularly the lower boiling
ones, called petroleum spirit, petroleum ether,
and petroleum benzine.
• "Naphtha" has the CAS Registry Number 8030-
30-6, which also covers petroleum benzine
and petroleum ether: that is, the lower boiling
point non-aromatic hydrocarbon solvents.
Structure of Anthracene
When anthracene react with bromine
gives bromo anthracene
Structure of Anthracene
• This reactions suggest that anthracene
contain two benzene ring.
• The presence of two benzene ring is
confirmed by the fact that on fusion with
KOH at 250C.
• It forms anthroquinone
• On oxidation gives two molecules of
benzoic acid
Structure of Anthracene
• It contain 14 carbon and 10 hydrogen
atom,the middle ring must be closed
to retain the quadrivalency of
carbon.
• The structure of anthracene is three
benzene rings are fused in a linear
manner.
Structure of Anthracene
Synthesis of Anthracene
Friedel craft reaction
Two molecules of benzyl chloride in the
presence of AlCl3 from
9:10dihydroanthracene, readily eliminates
two hydrogen atom under the condition of
the experiment to form anthracene
Friedel craft condensation
Anthracene is formed by condensation
between benzene and methylene
bromide
Friedel craft condensation
Anthracene is formed by condensation
between benzene and Acetylene tetra
bromide
By heating ortho bromo benzyl
bromide with sodium; the product
dihydro anthracene is converted into
anthracene by mild oxidation.
Elbs reaction
• It is prepared by refluxing ketone
under 400-450C.
• The yield is low.
• But Elb’s reaction is often used to
prepare polynuclear
hydrocarbon.
Elbs reaction
Diel’s alder reaction
Anthraquinone
Anthracene
1:4Naphtha
Quinone 1,4 butadiene
Position of double bond
• Structure I was accepted by may because
synthesis of anthracene by treating benzene
with acetylene tetra bromide.
• Synthesis of naphthalene from anthracene
ondicates the absence of para bond
Anthracene adds on maleic anhydride,
the addition occur in the middle
ring[because it behave as diene]
X ray analysis revealed that all the
carbons are lying in a same plane.
Anthracene is resonance hybrid of four
structure
• Anthracene is an alternate hydrocarbon
• Pie-electron densities are unity at all position.
• The self polarisability order is 9<1<2
• Position 9 will be more reactive.
Isomerism of anthracene
Isomerism of anthracene
• Three possible mono substitution product α,β
and ϒ [meso].
• There are 15 possible disubstitution product if
both the substituents are similar.
• If the substituents are not similar than large
number of isomers are possible.
Properties of anthracene
• Colorless solid
• Melting point 216 C
• It gives blue fluorescence.
• It is insoluble in water and sparingly soluble in
organic solvent.
• It is very reactive in 9: 10 position
• A saturated solution of anthracene in xylene on
exposure to light forms crystals of the dimer
[dianthracene – paranthracene ]
Xray analysis revealed that two
anthracene molecule are linked in 9th
and 10th position
• It adds on one molecule of oxygen to form
peroxide
• It forms a red picrate.
• It undergoes diels alder reaction
• It reduced in sodium ethanol forms 9:10
dihydroanthracene.
Anthracene treated with chlorine
forms dichloro anthracene.when it
is treated with alkali or HCl it gives
9 chloro anthracene
Anthracene treated with nitric acid
underwent oxidation to
anthroquinone
Synthesis of phenanthrene
• This is trans annular tautomerism
• Hydrogen atom migrates across
• X ray reveals that solid anthrone does not
exist in anthranol [enol form]
Anthracene

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Anthracene

  • 3. Introduction • It is obtained from oil fraction of coal tar. • The crude anthracene contains Phenanthrene and carbazole Phenanthrene Carbazole
  • 4. Purification of anthracene Anthracene is washed with Solvent naphtha which dissolve phenanthrene and remaining solid is then washed with pyridine which dissolve the Carbazole.
  • 5. Solvent naphtha • A flammable liquid distillate containing mainly xylene and aromatic hydrocarbon. • It has high boiling point than ligroin. • It is obtained by cracking of petroleum. • It is used as solvent.
  • 6. Structure Xylene Ligroin • Light ligroin; Light petroleum; pether
  • 8. • Ligroin is the petroleum fraction consisting mostly of C7 and C8 hydrocarbons and boiling in the range 90‒140 ℃ (194–284 °F). The fraction is also called heavy naphtha. • Ligroin is used as a laboratory solvent. Products under the name ligroin can have boiling ranges as low as 60‒80 ℃ and may be called light naphtha. • Petroleum ether is the petroleum fraction consisting of aliphatic hydrocarbons and boiling in the range 35‒60 °C, and commonly used as a laboratory solvent. • Despite the name, petroleum ether is not classified as an ether; the term is used only figuratively, signifying extreme lightness and volatility.
  • 9. • Ligroin is assigned the CAS Registry Number 8032-32-4, which is also applied to many other products, particularly the lower boiling ones, called petroleum spirit, petroleum ether, and petroleum benzine. • "Naphtha" has the CAS Registry Number 8030- 30-6, which also covers petroleum benzine and petroleum ether: that is, the lower boiling point non-aromatic hydrocarbon solvents.
  • 10. Structure of Anthracene When anthracene react with bromine gives bromo anthracene
  • 12. • This reactions suggest that anthracene contain two benzene ring. • The presence of two benzene ring is confirmed by the fact that on fusion with KOH at 250C. • It forms anthroquinone • On oxidation gives two molecules of benzoic acid Structure of Anthracene
  • 13. • It contain 14 carbon and 10 hydrogen atom,the middle ring must be closed to retain the quadrivalency of carbon. • The structure of anthracene is three benzene rings are fused in a linear manner. Structure of Anthracene
  • 15. Friedel craft reaction Two molecules of benzyl chloride in the presence of AlCl3 from 9:10dihydroanthracene, readily eliminates two hydrogen atom under the condition of the experiment to form anthracene
  • 16. Friedel craft condensation Anthracene is formed by condensation between benzene and methylene bromide
  • 17. Friedel craft condensation Anthracene is formed by condensation between benzene and Acetylene tetra bromide
  • 18. By heating ortho bromo benzyl bromide with sodium; the product dihydro anthracene is converted into anthracene by mild oxidation.
  • 19.
  • 20.
  • 22. • It is prepared by refluxing ketone under 400-450C. • The yield is low. • But Elb’s reaction is often used to prepare polynuclear hydrocarbon. Elbs reaction
  • 26. • Structure I was accepted by may because synthesis of anthracene by treating benzene with acetylene tetra bromide.
  • 27. • Synthesis of naphthalene from anthracene ondicates the absence of para bond
  • 28. Anthracene adds on maleic anhydride, the addition occur in the middle ring[because it behave as diene]
  • 29.
  • 30. X ray analysis revealed that all the carbons are lying in a same plane. Anthracene is resonance hybrid of four structure
  • 31. • Anthracene is an alternate hydrocarbon • Pie-electron densities are unity at all position. • The self polarisability order is 9<1<2 • Position 9 will be more reactive.
  • 33. Isomerism of anthracene • Three possible mono substitution product α,β and ϒ [meso]. • There are 15 possible disubstitution product if both the substituents are similar. • If the substituents are not similar than large number of isomers are possible.
  • 34. Properties of anthracene • Colorless solid • Melting point 216 C • It gives blue fluorescence. • It is insoluble in water and sparingly soluble in organic solvent. • It is very reactive in 9: 10 position • A saturated solution of anthracene in xylene on exposure to light forms crystals of the dimer [dianthracene – paranthracene ]
  • 35. Xray analysis revealed that two anthracene molecule are linked in 9th and 10th position
  • 36. • It adds on one molecule of oxygen to form peroxide
  • 37. • It forms a red picrate. • It undergoes diels alder reaction • It reduced in sodium ethanol forms 9:10 dihydroanthracene.
  • 38. Anthracene treated with chlorine forms dichloro anthracene.when it is treated with alkali or HCl it gives 9 chloro anthracene
  • 39.
  • 40. Anthracene treated with nitric acid underwent oxidation to anthroquinone
  • 41.
  • 43. • This is trans annular tautomerism • Hydrogen atom migrates across • X ray reveals that solid anthrone does not exist in anthranol [enol form]