The document discusses several polynuclear hydrocarbons including naphthalene, anthracene, phenanthrene, and diphenylmethane. It provides their structures, classification, synthesis methods, chemical reactions, and uses. Naphthalene contains two fused benzene rings and can be prepared from coal tar or through Diels-Alder reactions. Anthracene and phenanthrene both contain three fused benzene rings and can undergo halogenation, nitration, oxidation, and Diels-Alder reactions. Diphenylmethane consists of a methane molecule with two phenyl groups and can be synthesized through Friedel-Crafts condensations. These compounds are used in dyes, plastics
Acidity of Phenols/OC -II PCI Syllabus/Effect of substituents on acidity of phenols
Hi dear students, in this video I had explained about acidity of Phenols and Effect of substituents on acidity of phenols. I had tried to explain all the points by animations. So don't hasitate to study now, See this video and you will come to know the facts about acidity and basicity of organic compounds. After watching this video it will be very easy to answer the following questions,
What are phenols?
what about acidity of phenols?
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Pka of phenols?
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Acidity of Phenols/OC -II PCI Syllabus/Effect of substituents on acidity of phenols
Hi dear students, in this video I had explained about acidity of Phenols and Effect of substituents on acidity of phenols. I had tried to explain all the points by animations. So don't hasitate to study now, See this video and you will come to know the facts about acidity and basicity of organic compounds. After watching this video it will be very easy to answer the following questions,
What are phenols?
what about acidity of phenols?
factors affecting acidity of phenols?
Pka of phenols?
Please do subscribe Online ustaad and share this video to as many as possible.
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POLYNUCLEAR HYDROCARBON : STRUCTURE AND USES OF NAPHTHELENE, ANTHRACENE,DI-PH...RishikaBehere1
Hello everyone, we the students of Gurunanak College of Pharmacy, Nagpur have created a presentation of subject pharmaceutical organic chemistry -2 of third semester, Unit 4 : polynuclear hydrocarbons . This presentation was made for the purpose of better understanding of the topic structure and medicinal uses of naphthelene , anthracene, diphenylmethane , triphenylmethane , phenanthrene and their derivatives . This portion covers topics like structure, properties , and medicinal uses of polynuclear hydrocarbons such as naphthelene , anthracene , di-phenylmethane, tri-phenylmethane , phenanthrene and their respective derivatives.
Benzene and its derivatives- According to PCI Syllabus Ganesh Mote
Benzene history, nomenclature, orbital structure, resonance structure, kekule structure,synthetic evidences, structural and analytical evidences, Directive effect of benzene, structure and uses of DDT, BHC, saccharine
Unit 1- Effects of substituents on Mono substituted benzene RingAnjali Bhardwaj
Effects of substituents on reactivity and orientation of monosubstituted benzene compounds towards electrophilic substitution reaction
Activating & Deactivating group
Ortho and Para Directing group
Meta directing group
substitution on the benzene ring
Halides are Ortho & Para directing group why?
Introduction of poly-cyclic compounds, resonance, molecular orbital structure, physical properties, preparation, reaction and uses of napthalene, anthracene, phenanthrene, napthaquinone, napthol, napthylamine, 9,10 anthraquinone and phenanthrequinone.
POLYNUCLEAR HYDROCARBON : STRUCTURE AND USES OF NAPHTHELENE, ANTHRACENE,DI-PH...RishikaBehere1
Hello everyone, we the students of Gurunanak College of Pharmacy, Nagpur have created a presentation of subject pharmaceutical organic chemistry -2 of third semester, Unit 4 : polynuclear hydrocarbons . This presentation was made for the purpose of better understanding of the topic structure and medicinal uses of naphthelene , anthracene, diphenylmethane , triphenylmethane , phenanthrene and their derivatives . This portion covers topics like structure, properties , and medicinal uses of polynuclear hydrocarbons such as naphthelene , anthracene , di-phenylmethane, tri-phenylmethane , phenanthrene and their respective derivatives.
Benzene and its derivatives- According to PCI Syllabus Ganesh Mote
Benzene history, nomenclature, orbital structure, resonance structure, kekule structure,synthetic evidences, structural and analytical evidences, Directive effect of benzene, structure and uses of DDT, BHC, saccharine
Unit 1- Effects of substituents on Mono substituted benzene RingAnjali Bhardwaj
Effects of substituents on reactivity and orientation of monosubstituted benzene compounds towards electrophilic substitution reaction
Activating & Deactivating group
Ortho and Para Directing group
Meta directing group
substitution on the benzene ring
Halides are Ortho & Para directing group why?
Introduction of poly-cyclic compounds, resonance, molecular orbital structure, physical properties, preparation, reaction and uses of napthalene, anthracene, phenanthrene, napthaquinone, napthol, napthylamine, 9,10 anthraquinone and phenanthrequinone.
What is a Heterocyclic Compound?
A heterocyclic compound has at least two different elements as a member of its ring.
The most common hetero atoms found on a cyclic ring are Oxygen (O), Nitrogen (N) and Sulphur (S).
Example:
Nucleic Acid that is present in the body responsible for storing and expressing genetic information, is an example of a Heterocyclic compound.
Essential micronutrient, Vitamins is also an example of a heterocyclic compound.
The majority of drugs, pesticides, dyes, and plastics are examples of heterocyclic compounds.
Classification of Heterocyclic Compounds
Based on the electronic arrangement, we can classify Heterocyclic compounds into two types:
Aliphatic Heterocyclic Compounds
Aromatic Heterocyclic Compounds
Aliphatic Heterocyclic Compounds
Aliphatic heterocyclic compounds are those cyclic heterocycles that do not contain any double bond.
The properties of aliphatic heterocyclic compounds are mainly affected due to ring strain.
Examples of aliphatic heterocyclic compounds are Aziridine, Ethylene Oxide, Thiirane, Oxetane, Azetidine, Thietane, Tetrahydrofuran (THF), Dioxane, Pyrrolidine, Piperidine, etc.
Aromatic Heterocyclic Compound
Aromatic heterocyclic compounds, as the name suggests, are cyclic aromatic compounds.
Aromatic Heterocyclic compounds obey Huckels Rule, i.e.
It should be cyclic.
It should be planar.
It should not contain any sp3 hybridised atoms.
It must have (4n+2) 𝛑 electrons.
Aromatic Heterocyclic compounds are analogous to Benzene.
Examples: Furan, Pyrrole, Thiophene, Indole, Benzofuran, Carbazole, Quinoline, Isoquinoline, Imidazole, Oxazole, Pyrazole, Pyridazine, Pyrimidine, Purine, etc.
Based on structure, we can classify Heterocyclic compounds into five types:
Three-Membered Heterocyclic Compounds
Four-Membered Heterocyclic Compounds
Five-Membered Heterocyclic Compounds
Six-Membered Heterocyclic Compounds
Condensed or Fused Heterocyclic Compounds
Three-Membered Heterocyclic Compounds
These heterocyclic compounds contain three atoms which may be saturated or unsaturated.
Based on the number of heteroatoms present, we can further classify them into two categories:
Aldehydes and ketones contain the carbonyl group. Aldehydes are considered the most important functional group. Ketones A carbon double bonded to an oxygen is called a carbonyl group. Compounds in which the carbon of a carbonyl group is bonded to two other carbons
This presentation is the second part of the previously uploaded presentation with the title amino compounds. please read that presentation first.
In this presentation, I explained the Derivatives of amino compounds with their reactivity.
This presentation will help students to understand the various topics related with halogen compounds in a very short time.it also help teachers during the recapitulation of the chapter content.it will also help students to revise the content in short time especially by those students who r preparing for various competitive exams after class 12th.
This presentation includes all the preparations and reactions of various Polynuclear hydrocarbons as naphthalene, Phenanthrene, anthracene,diphenylmethane,triphenylmethane and their derivatives.This is made by the b Pharmacy 2 year students of Gurunanak College of Pharmacy Nagpur as a group activity which focussed on student participation.
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3. • Polynuclear hydrocarbons are
hydrocarbons, organic compound
containing only carbon and hydrogen, that
are composed of multiple aromatic rings.
Polynuclear hydrocarbons are uncharged,
non polar molecules found in coal and tar
deposits.
• They are also produced by in
complete combustion of organic matter.
• Polynuclear hydrocarbons are lipophilic and
larger polynuclear hydrocarbons are
insoluble in water. And they are abundant.
• Polynuclear hydrocarbons are consider as
possible starting material for abiologic
syntheses of materials.
• The class of polynuclear hydrocarbons are
further classified as as- the simplest are
Napthalene , having two aromatic rings and
the three ring compounds Anthracene and
Phenanthrene. 3
Introduction
7. Structure of naphthalene can be explained on
the basis of Kekule formula, orbital model,
resonance model
(1)Kekule-Type Formula: The structure of
naphthalene is given on the basis of Kekule
formula as follows:
(i) Aromatic Nature: Determination of
elemental analysis and molecular weight
shows that naphthalene has the molecular
formula CoHg. The formula of naphthalene
shows its extreme unsaturation state and
can also be expected to be very reactive.
However, naphthalene is a very stable
compound and undergoes substitution
reactions. It does not undergo addition
reaction and Phenanthrene. On complete
hydrogenation (under drastic conditions), it
gives decahydronapthalene having
molecular formula C10H18 (decalin). These
properties show that naphathalene is an
aromatic compound with five double
bonds
7
Naphthalene
8. 8
Naphthalene
(ii) Presence of a Benzene Ring with Two Side-Chains: Oxidation
of naphthalene gives phthalic acid, thus, indicating that
naphthalene contains a benzene ring having two ortho side-
chains
(iii) Presence Two Fused Benzene Rings: Erlenmeyer proposed the
structure of naphthalene from the conclusion of Kekule-type
formulas and showed the presence of two fused rings at ortho
positions
(iv) Existence of Two Monosubstituted Derivatives Confirms
Kekule-Type Formula: The Kekule-type formula shows
symmetry and allows only two isomeric monosubstituted
derivatives to be formed. The H atoms present at marked
positions (X) and (~) remain identical
9. 9
Naphthalene
Resonance Model: According to the resonance
model, structure of naphthalene can
be described as follows
i) Resonance Hybrid of Three Forms: Naphthalene
is a resonance hybrid of three canonical forms,
hence the re-electron system of naphthalene
shows a continuous delocalisation on ring system
(ii)Not All C-C Bond Lengths are Equal: Bond
length of C2-C3 bond is longer than that of C1-
C2 bond (1.36 Å) due to double bond character
i.e., shorter length of C1-C2 as it is double in
two resonance forms (I and II). However, C2-C3
bond is single in two forms (I and II) and double
in only one hence making longer length
10. Synthesis
10
Naphthalene can be prepared by the following methods
• From Coal Tar: Coal tar is the main source of naphthalene. Decalin (decahydronapthalene) in the presence of a metallic
catalyst at 180°C undergoes dehydrogenation reaction to form naphthalene.
11. Synthesis
11
• From Diel's-Alder Reaction: Furan and benzyne reacts to form the Diels-Alder adduct. However, the reactions
of Diels-Alder adduct of furan and benzyne in the presence of H/Ni produces naphthalene.
• Haworth's Synthesis: Haworth's synthesis of naphthalene involves
• Friedel-Crafts acylation of benzene
12. Synthesis
12
• From 4-Phenylbut-1-ene: A compound 4-phenylbut-1-ene when passed over redhot calcium oxide yields
naphthalene
• From 4-Phenylbut-3-enoic Acid: Heating of 4-phenylbut-3-enoic acid with sulphuric acid results in the
formation of 1-naphthol, which on further distillation with zinc dust yields naphthalene.
13. • A:- Physical Properties:-
Naphthalene is colourless, crystalline solid, m.p. 80°C, b.p. 218°C with a characteristic strong odour.
It is insoluble in water but is soluble in organic solvents, e.g. ether, benzene etc.
It is volatile and sublimes on warming.
It is also steam volatile.
It burns with sooty flame
• B:- Chemical Properties:-
Naphthalene having similar chemical properties as that of benzene, though it is less aromatic than benzene and reacts
more rapidly.
Naphthalene is having 61 kcal/mole resonance energy, in benzene which is less than twice of 36 Kcal/mole
Properties
13
14. (A)Oxidation Reactions of Naphthalene:-
When naphthalene undergoes oxidation in the presence of chromic acid, it gives 1,4-naphthoquinone. Also when it
undergoes oxidation in the presence of vanadium pentoxide
ChemicalReactions
14
15. (B) Halogenation
Bromination or chlorination of naphthalene takes place readily and does not require any Lewis acid catalyst (as in case of
benzene). Halogenation of naphthalene occurs exclusively at position-1. Substitution at 1position of naphthalene can be
explained on the basis of resonance stabilisation of the intermediate carbonation, i.e., when the halogenating agent
attack on naphthalene at 1-position, the intermediate ion formed remains more stable apparently
ChemicalReactions
15
16. (C) Friedel-Craft
While, Friedel-Craft methylation of naphthalene leads to the product mixture of the β-methyl derivatives; the Friedel-
Craft ethylation though slightly less yielding, offers on β-ethylnaphthalene
ChemicalReactions
16
17. (D) Friedel-Craft Alkylation
While, Friedel-Craft methylation of naphthalene leads to the product mixture of the β-methyl derivatives; the Friedel-
Craft ethylation though slightly less yielding, offers on β-ethylnaphthalene
ChemicalReactions
17
18. (E) Friedel-Craft Acylation
Friedel-Crafts acylation of naphtahelne depends upon nature of solvent used. If the reaction is carried out in presence of
non polar solvent such as carbon disulfide then 1-substituted product is obtained while in presence of polar solvent such
as nitrobenzene then 2-substituted product is obtained
ChemicalReactions
18
19. (F) REDUCTION:
Napthalene can be reduced partially to completely to corresponding dehydro, tetrahydro
and decahydro derivatives under a reaction conditions.
ChemicalReactions
19
20. (G) NITRATION
Napthalene undergo nitration and produces 1-nitro naphthalene which further leads to 1,5-and 1,8-dinitronapthalene
ChemicalReactions
20
23. 1. As a fumigant = Napthalene has been used as a household fumigant. In a sealed
Container containing Napthlene destroy all forms of moths that attack textiles. The other
fumigant include fumigant pesticide, that repeal insect and protect the contents.
2. Laboratory uses = Molten naphthalene provides an excellent solubilizing medium
For poorly soluble aromatic compounds. It is used in industrial production of phthalic
Anhydride.
3. Wetting agent and surfactant = Alkyl naphthalene sulfonates are used as nondetergent wetting agent. Also in
agricultural chemical industries, in textile and fabric
industries.
4. Napthalene – Sulfonate polymer plasticizers are used to produce concrete and plaster
boards. Also used as dispersants in synthetic and natural rubbers, as tanning agent in
leather industries.
5. Use to produce dyes, explosive and synthetic resins.
Uses
23
24. 24
Anthracene
• Anthracene also called paranaphthalene or green
oil is a solid , aromatic and colourless
hydrocarbon
compound .
• Its molecular formula is C14H10 and it consist of
3 fused rings derived from coal ,tar or other
residues of Thermal Pyrolysis. Anthracene is a
constituent of insecticides, wood preservatives,
coating material and is also used in the synthesis
of ALIZARIN (red dye).
30. (A) Halogenation: Anthracene forms anthracene dihalide by reacting
with chlorine or bromine in the absence of a catalyst. Anthracene
dihalide further decomposes on heating to form 9-chloro or 9-
bromoanthracene
ChemicalReactions
30
31. B) Nitration: Anthracene forms 9-nitroanthracene and 9,10-
dinitroanthracene on treatment with conc. HNO3 in the presence of
acetic anhydride
ChemicalReactions
31
32. C) Sulphonation: Sulphonation of anthracene with concentrated
sulphuric acid at high temperature gives 2-anthracenesulphonic acid
and at low temperature gives 1anthracenesulphonic acid
ChemicalReactions
32
33. (D) Oxidation: In the presence of a strong oxidising agent (like
potassium dichromate under acidic conditions, anthracene gets
oxidised into 9,10-anthraquinone
ChemicalReactions
33
34. (E) Diels-Alder Reaction: The 9,10-positions of anthracene are highly
reactive and therefore undergo the Diels-Alder reaction with maleic
anhydride. Anthracene acts like a diene and forms
ChemicalReactions
34
35. (F) Reduction: Anthracene is reduced to 9,10-dihydroanthracene
sodium and ethanol or on catalytic hydrogenation (H2/Pd)
ChemicalReactions
35
37. • Molecular formula : C14H10
• Molar mass: 178.234 g·mol−1
• Phenanthrene a polycyclic aromatic
hydrocarbon (PAH) with formula C14H10,
consisting of three fused benzene rings.
• It is a colorless, crystal-like solid, but can
also appear yellow.
• Phenanthrene is used to make dyes, plastics
and pesticides, explosives and drugs.
• It has also been used to make bile acids,
cholesterol and steroids.
• All the fourteen carbon atom are sp2
hybridized. It occurs in coal tar in anthracene
oil fraction.
37
Phenanthrene
38. Haworth Synthesis
Synthesis
38
Step 1: naphthalene react with succinic anhydride
in the presence of aluminium chloride to form
naphthoylpropionic acid.
Step 2: naphthoylpropionic acid reduces to form
Naphthylbutyric acid in the presence of Zn and
HCl.
Step 3: Naphthylbutyric acid heated with H2SO4
to give 1-keto,1,2,3,4-tetrahydrophenathrene.
Step 4: 1-keto,1,2,3,4-tetrahydrophenathrene
reduces with Zn and HCl to form 1,2,3,4-
tetrahydrophenathrene.
Step 5: 1,2,3,4-tetrahydrophenathrene heated
with Selenium to form Phenathrene.
39. Bardhan Sengupta Phenathrene Synthesis
Synthesis
39
• Step 1: 2-β-Phenylethylcyclohexanol reacts with
diphosphorus pentoxide to give 1,2,3,4,9,10,11,12-
Octahydrophenathrene.
• Step 2: 1,2,3,4,9,10,11,12-Octahydrophenathrene reacts
with Selenium to form Phenathrene.
45. Uses
45
• Phenanthrene ring is present in various chemical compounds, which have the following medical uses
1. It is used as anticancer
2.It is used as antimalarial
3.It is used as antioxidant
4.It is used as antimicrobial
• It can be used in the manufacture of pesticides.
• After conversion processing it can be used to produce dyes and Drugs
• It is used as a stablizer of high effciency and low toxicity pesticides and smokeless powder expolsives.
• Phenanthrene quinone can be used as dyes, fungicides and polymerization inhibitors.
46. 46
Diphenylmethane
• Diphenylmethane is an organic
compound with the formula (C6H5)2CH22).
The compound consists of methane wherein
two hydrogen atoms are replaced by
two phenyl groups
• Appearance colourless oilMelting point 22 to
24 °C (72 to 75 °F; 295 to 297 K)Boiling
point264 °C (507 °F; 537 K)
The 2D chemical structure of diphenylmethane (also called
skeletal formula) is the standard notation for organic
molecules. The carbon atoms in the chemical structure of
diphenylmethane's are present at the corner(s) and
hydrogen atoms attached to the carbon atoms are not
shown. Each carbon atom is associated with hydrogen atoms
in order to provide its four bonds
The 3D chemical structure of diphenylmethane can be
explained with the ball-and-stick model displaying the 3D
position of the atoms as well as the bonds present between
them. The radius of the spheres is smaller than the rod
lengths so that a clearer view of the atoms and bonds
throughout the chemical structure model of
diphenylmethane can be obtained
47. Synthesis
47
Diphenylmethane is prepared by the following methods
1) Friedel-Crafts condensation between benzyl chloride and benzene yields diphenylmethane
2)Condensation between a molecule of formaldehyde and two molecules of benzene in the presence of
concentrated sulphuric acid yields diphenylmethane
48. Synthesis
48
3) Heating benzophenone at 160°C under pressure with hydriodic acid and red
phosphorus, the Wolff-Kishner reduction, or by LAH-AICI; yields diphenylmethane
4) Grignard reaction also yields diphenylmethane
49. Synthesis
49
3) Heating benzophenone at 160°C under pressure with hydriodic acid and red
phosphorus, the Wolff-Kishner reduction, or by LAH-AICI; yields diphenylmethane
4) Grignard reaction also yields diphenylmethane
54. Uses
54
1. Diphenylmethane group is found in numerous medicinal compounds,
Therapeutic drugs.
2. Examples of It are,
Pridinol (Antiparkinson , Anti cholinergic )
Pipradrol (Mild CNS stimulant)
Fexofenadine (Antihistaminic)
Sertraline (Antidepressant)
Cyclobenzaprine (Antipsychotic)
3. Other compounds are, Antacid, Antidiarrhoeal, Antiulcer, Prebiotics,Anti emetic and Sedative.
55. 55
Triphenylmethane
• Triphenylmethane is a hydrocarbon having the
molecular formula (C6H5)3CH. It is a colourless solid
soluble in non-polar organic solvents and insoluble in
water. It is the basic skeleton of many synthetic dyes
called triarylmethane dyes. These dyes are pH indicators,
and some of them are fluorescent indicators
• Structure -pka of hydrogen on the central carbon atom is
33. The acidity of triphenylmethane is more than that of
hydrocarbons because the trityl anion is stabilized by
delocalization over three phenyl rings since,
delocalization does not occur over all the phenyl rings
due to steric effects, each ring forces the other two out
of co-planarity of the anionic carbon is parallel to the p-
orbitals of one of the phenyl rings. The trityl anion
strongly absorbs in the visible region and makes it red.
This colour is used as an indicator for maintaining the
anhydrous conditions with calcium hydride reaction
between hydride reagent and water forms solid calcium
hydroxide, which is a strong base with the ability to
generate trityl anion if hydride is completely consumed,
the solution becomes colorless.
56. Synthesis
56
• Triphenylmethane (tritane) is prepared by the following methods
• Triphenylmethane can be synthesized by friedel-crafts reaction from benzene and chloroform
with aluminium chloride catalyst
3 C6H6 + CHCl3 → ph3ch + 3 HCL (33%)
• C6H5CHO + CHO ZnCl2 (C6H5)3CH + H2O
• 2C6H5 + C6H5CHCl2 AlCl3 (C6H5)3CH + 2HCl
57. • Triphenylmethane undergoes following Reaction
• 1.It Undergoes Bromination to yeild triphenylmethyl bromide
• 2.It undergoes Oxidation to yeild Triphenylcarbinol
• 3. Triphenylmethyl react with sodium to form Triphenylmethyl sodium
ChemicalReaction
57
58. Uses
58
I. Triphenylmethane dyes are used in medicine and experimental biology. E.g. in cytology, histology and microbiology to
stain cells.
II. Malachite green and Crystal Violet are some Dyes possessing antibacterial, antifungal and antiprotozoal properties.
III. These are also used as medical disinfectants.
IV. Some of the Triphenylmethane dyes are used as pH indicator and some display Fluorescence.