Download as PDF, PPTX
![Aramaticity
• Compound must be cyclic and Planer.
• Every atom in the ring must be conjugated.
• Molecule must have [4n+2] pi electrons
• Where n=0,1,2,3,……..n
• Cyclic and planer
• Conjugated
• 3 pi Bond i.e. 6 pi electron
• n =0 -------?
• n= 1--------?](https://image.slidesharecdn.com/heterocyclic-210425073113/75/Heterocyclic-Chemistry-pdf-ppt-7-2048.jpg)
Heterocyclic Chemistry pdf ppt
This document discusses heterocyclic and polycyclic aromatic compounds. It provides examples of heterocyclic compounds that contain nitrogen, oxygen, or sulfur atoms in their rings, including furan, thiophene, pyrrole, pyridine, quinoline, and isoquinoline. Naphthalene is discussed as an example of a polycyclic aromatic hydrocarbon. The document outlines synthesis methods and characteristic reactions for these compounds, such as electrophilic substitution, reduction, acylation, and nitration reactions.
More Related Content
Similar to Heterocyclic Chemistry pdf ppt
Heterocyclic Chemistry pdf ppt
- 1. “ Heterocyclic andPolycyclic Aromatic Compound” G. P. Sadawarte Assistant Professor Dept. of Chemistry, B.P. Arts, S.M.A. Science, K.K.C. Commerce College Chalisgaon
- 2. Introduction • Cyclic orring Compound Contain C & H - Homocyclic • Cyclic or ring Compound Contain at least one Heteroatom like S, O and N • Alkaloids, Colouring Matter, Vegetables • Five or Six membered Compound • Furan, Thiophene, Pyrrole • Pyridine • Quinoline, Indole, Benzofuran
- 3. Heterocyclic Compound This arecyclic rings compound containing at least one hetero atom other than carbon . N H S O Pyrrole Thiophene N N Quinoline Isoquinoline Pyridine N Furan
- 4. Numbering N S O PyrroleThiophene N N Quinoline Isoquinoline Pyridine N Furan 2 3 4 5 1 1 2 3 4 5 alpha beta 1 2 3 4 5 6 1 2 3 4 5 6 7 8
- 5. Example O NO2 S NO2 N Br N Br N 1 2 3 4 5 6 7 8 Br N N 1 2 3 4 5 6 7 8 2-Nitro furan3-Nitro thiophene 3-Bromo pyridine 3-Bromo pyridine 8-Bromo quinoline 5-Methyl quinoline 1-Methyl isoquinoline
- 6. Furan(C4H4O) • Furan isa Heterocyclic organic compound. • Having five member aromatic ring with four carbon atoms and one oxygen. • Furan is a colorless, flammable, highly volatile liquid with a boiling point close to room temperature. • It is soluble in common organic solvents, including alcohol, ether, and acetone, and is slightly soluble in water. • Its odor is strong, ethereal; chloroform like. • It is toxic and may be carcinogenic in humans.
- 7. Aramaticity • Compound mustbe cyclic and Planer. • Every atom in the ring must be conjugated. • Molecule must have [4n+2] pi electrons • Where n=0,1,2,3,……..n • Cyclic and planer • Conjugated • 3 pi Bond i.e. 6 pi electron • n =0 -------? • n= 1--------?
- 8.
- 9. Synthesis of Furan O CHO SteamDistillation Oxide Catalyst O + CO2 From Furfural Fufural Furan
- 10. Synthesis of Furan FromMucic Acid CO2 CHOH HOHC CHOH HOHC HOOC COOH Dry Distillation O COOH Mucic Acid - H2O - 2-Furoic Acid O COOH Boil Decarboxylation O + CO2 2-Furoic Acid Furan
- 11.
- 12. Reaction of Furan Sulphonation O O +SO3 Pyridine SO3H 2-Furan sulphonic Acid O O + CH3COCl COCH3 2-Acetyl Furan AlCl3 Furan Furan Acetyl Chloride Sulphurtrioxide Fridal Crafts Acylation
- 13. Reaction of Furan O O +CHCl3 CHO Furfual KOH Furan Chloroform Reimer Tiemann Reaction O O + HNO3 NO2 2-Nitrofuran Acetic unhydride Furan Nitric Acid Nitration 100 C
- 14. Reaction of Furan O O +H2 Tetra Hydra Furan Ni Furan Reduction Hydrogenation
- 15. Thiophene (C4H4S) •Thiophene isa heterocyclic compound •It is a planar five-membered ring. • It is aromatic as indicated by its extensive substitution reactions •It is a colorless liquid with a benzene like odor. S Thiophene
- 16. Synthesis of Thiophene •From n-Butane • From Acetylene Heat S + 3 H2S + 4 S 600 o C HC CH + H2S Al2O3 600 o C S + H2 2
- 17. Reaction of Thiophene Sulphonation SS + H2SO4 SO3H 2-Thiophene sulphonic Acid S S + CH3COCl COCH3 2-Acetyl Thiophene AlCl3 Thiophene Thiophene Acetyl Chloride Sulphuric Acid Fridal Crafts Acylation
- 18. Reaction of Thiophene SS + CHCl3 CHO Thiophene 2-Carboxyaldehyde KOH Thiophene Chloroform Reimer Tiemann Reaction S S + HNO3 NO2 2-Nitro Thiophene Acetic unhydride Thiophene Nitric Acid Nitration 10o C
- 19. Reaction of Thiophene SS + H2 Tetra Hydra Thiophene Ni Thiophene Reduction Hydrogenation
- 20. Synthesis of Pyrrole HCCH + H3N Heat Red hot tube H + H2 2 H O Stem N + H2O + H3N Al2O3 H From Acetylene From Furan
- 21. Reaction of Pyrrole Sulphonation N H N H +H2SO4 SO3H 2-Pyrrole sulphonic Acid Pyrrole Sulphurtric Acid N H N H + CH3COCl COCH3 2-Acetyl Pyrrole AlCl3 Pyrrole Acetyl Chloride Fridal Crafts Acylation
- 22. Reaction of Pyrrole N H N H +CHCl3 CHO Pyrrole 2- Carboxyaldehyde KOH Pyrrole Chloroform Reimer Tiemann Reaction N H N H + HNO3 NO2 2-Nitro Pyrrole Acetic unhydride Pyrrole Nitric Acid Nitration 5o C
- 23. Reaction of Pyrrole N H N H +H2 Pyrrolidine Ni Reduction Hydrogenation Pyrrole
- 24. Pyridine(C5H5N) • Pyridine isa basic Heterocyclic organic Compound • It is structurally similer to bnzene, with one methine group (=CH-) replaced by nitrogen atom • It is a highly flammable weakly alkaline, • unpleasant fish-like smell. • it is colorless, but older or impure samples can appear yellow. • The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and Vitamins. • It was produced from coal tar.
- 25. Synthesis of Pyridine FromAcrolein H2C CH CHO Heat NH3 N CH3 K2Cr2O7 dil H2SO4 N COOH 3- Methyl Pyridine 3- Pyridine Carboxylic acid N CaO Heat COOH N 3- Pyridine Carboxylic acid Pyridine
- 26. Synthesis of Pyridine FromAcetylene HC CH + HCN Heat Red Hot Tube 2 N From Acetylene Acetylene
- 27. Reaction of Pyridine Sulphonation +H2SO4 3-Pyridine Sulphonic Acid Sulphuric Acid N 350 o C Heat N SO3H Pyridine Nitration + HNO3 3-Nitro Pyridine Nitric Acid N 300o C N NO2 Pyridine H2SO4
- 28. Reaction of Pyridine Halogenation +Br2 3-Bromo Pyridine Nitric Acid N 300o C N Br Pyridine Heat + N Br Br 3,5 Dibromo Pyridine + H2 Ni Reduction Hydrogenation N Pyridine N H Piperidine Naphthalene
- 29. Naphthalene(C10 H8) •fused pairof benzene •It is the simplest polycyclic aromatic hydrocarbon •white crystalline solid with a characteristic odour that is detectable at concentrations • It is main ingredient of traditional mothballs •it had been derived from a kind of naphtha 1 2 3 4 5 6 7 8 1/4/5/8= alpha 2/3/6/7=beta
- 30. NOMENCLATURE OH OH NH2 Alpha- Naphthal Beta-Naphthal Alpha- Naphthyl Amine 1-Hydroxy Naphtahalene OR 2-Hydroxy Naphtahalene 1-Amino Naphtahalene OR OR SO3H NH2 Alpha- Naphthalene Sulphonic Acid 1,5 - Dinitro Naphthalene 2- Naphthalene Sulphonic Acid OR 2,4-Dinitro-1- Naphthyl amine NO2 NO2 NO2 NO2
- 31. Resonanace Naphthalene It is planar,like benzene. carbon–carbon bonds are not of the same length. The bonds C1−C2, C3−C4, C5−C6 and C7−C8 are about 1.37 Å (137 pm) in length, whereas the other carbon–carbon bonds are about 1.42 Å long. This difference, established by X-ray diffraction three resonance structures. Ref:Cruickshank, D. W. J.; Sparks, R. A. (18 October 1960). "Experimental and Theoretical Determinations of Bond Lengths in Naphthalene, Anthracene and Other Hydrocarbons
- 32. Synthesis of Naphthalene O O O + AlCl3 F.C.Acylation HOOC O HOOC Zn/Hg HCl Benzene beta-Benzoyl Propanoic Acid H2SO4 Poly Phosphoric acid O Zn/Hg HCl alpha-Tetralone Tetralene Pd/Heat -2H2 Naphthalene Haworth Synthesis Succinic Anhydride
- 33. Reaction of Naphthalene O2,V2O5 460-480o C O O O Naphthalene Phthalic anhydride CrO3,CH3COOH 25 o C Naphthalene O O 1,4-Naphthaquinone
- 34. Reaction of Naphthalene NO2 HNO3/H2SO4 50-60o C 1 -Nitro Naphthalene Naphthalene Nitration
- 35. Reaction of Naphthalene Halogenation Naphthalene Conc.H2SO4 300 o C + Br2 Br 1 -Bromo Naphthalene Naphthalene Conc. H2SO4 300 o C + Cl2 Cl 1 -Chloro Naphthalene
- 36. Reaction of Naphthalene Sulphonation 80o C Naphthalene 1- Naphthalene Sulphonic Acid H2SO4 SO3H 160 o C Naphthalene 2-Naphthalene Sulphonic Acid H2SO4 SO3H
- 37. Reaction of Naphthalene 1-Acetyl Naphthalene Naphthalene Fridel Crafts Acylation + CH3COCl AlCl3 CS2/ CCl4/ C2H2Cl4 COCH3 2 -Acetyl Naphthalene Naphthalene + CH3COCl AlCl3 COCH3 C6H5NO2
- 38. Reaction of Naphthalene DecahydroNaphthalene / Decalin Naphthalene H2/Ni Heat Reduction
- 39. Reaction of Naphthalene Naphthalene 1,4-DihydroNaphthalene Na/C2H5OH 1,2,3,4- Tetrahydro Naphthalene Reflux Naphthalene Na/C2H5OH Reflux Reduction