Pharmaceutical Organic Chemistry II – Theory

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Chinmaya Chidananda Behera

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Core Courses

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Course Name: Pharmaceutical Organic Chemistry II

Code(Credit): BPHT2101 (4-0-0)

Course Objectives

This subject deals with general methods of preparation and reactions of some organic compounds. The reactivity of organic compounds are also studied here. The syllabus emphasizes on mechanisms and orientation of reactions. Chemistry of fats and oils are also included in the syllabus.

Learning Outcomes

  1. write the structure, name and the type of isomerism of the organic compound
  2. write the reaction, name the reaction and orientation of reactions
  3. account for reactivity/stability of compounds,
  4. prepare organic compounds

Course Syllabus

Module I

Benzene and its derivatives

A. Analytical, synthetic and other evidences in the derivation of structure of benzene, Orbital picture, resonance in benzene, aromatic characters, Huckel’s rule
B. Reactions of benzene - nitration, sulphonation, halogenationreactivity, Friedelcrafts alkylation- reactivity, limitations, Friedelcrafts acylation.
C. Substituents, the effect of substituents on reactivity and orientation of monosubstituted benzene compounds towards electrophilic substitution reaction
D. Structure and uses of DDT, Saccharin, BHC and Chloramine

Module II

• Phenols* - Acidity of phenols, effect of substituents on acidity, qualitative tests, Structure and uses of phenol, cresols, resorcinol, naphthols
Aromatic Amines* - Basicity of amines, effect of substituents on basicity, and synthetic uses of aryl diazonium salts
Aromatic Acids* –Acidity, effect of substituents on acidity and important reactions of benzoic acid.

Module III 

• Fats and Oils
a. Fatty acids – reactions.
b. Hydrolysis, Hydrogenation, Saponification and Rancidity of oils, Drying oils.
c. Analytical constants – Acid value, Saponification value, Ester value, Iodine value, Acetyl value, Reichert Meissl (RM) value – significance and principle involved in their determination.

Module IV 

• Polynuclear hydrocarbons:
a. Synthesis, reactions
b. Structure and medicinal uses of Naphthalene, Phenanthrene, Anthracene, Diphenylmethane, Triphenylmethane and their derivatives

Module V 

• Cyclo alkanes*

Stabilities – Baeyer’s strain theory, limitation of Baeyer’s strain theory, Coulson and Moffitt’s modification, Sachse Mohr’s theory (Theory of strainless rings), reactions of cyclopropane and cyclobutane only

Session Plan

Session 1

Analytical, synthetic and other evidence in the derivation of the structure of benzene, Text Note: Synthetic and Spectral Evidences of Structure of benzene,

Further Reading: Benzene Structure and its evidence, Video Link: Evidence of Structure of Benzene

Session 2

Orbital picture, Video Link: Orbital Structure of Benzene, Resonance in Benzene,  Aromatic characters, Huckel’s rule, Text Note: Aromaticity of Benzene, Aromaticity of Arenes

Session 3

Reactions of benzene - Electrophilic substitution reaction of benzene, Video Link: Electrophilic Substitution reaction of Benzene, nitration, sulphonation, halogenation reactivity, Video Link: Halogenation reaction of Benzene

Session 4

Friedel crafts alkylation- reactivity, Text Note: EAS reactions_Friedel crafts alkylation and acylation, Friedelcrafts acylation, limitations, Text Note: Limitations of Friedel-Craft's reaction

Session 6

Structure and uses of DDT, Text Note: DDT, Saccharin, Text Note:Saccharin

Structure and uses of BHC, Chloramine, Text Note: BHC, Chloramine

Session 7

Phenols* - Acidity of phenols, the effect of substituents on acidity, Text Note: Acidity of Substituted Phenols - Chemistry LibreTexts, Effect of substituents on Acidity of Phenol. Video Link: https://youtu.be/h-dXz6E-kBw

Session 8

Qualitative tests, Text Note: Qualitative Test for Phenol, Structure, and uses of phenol, Text Note: Phenols and Their Uses - Chemistry LibreTexts Video Link: https://youtu.be/HSGlfbV7W84

Session 9

Preparation and chemical reactions of Phenol, Text Note: Phenol Preparation and Chemical reactions

Session 10

Structure and uses of cresols, Text Note: Structure and Uses of Cresol

Session 11

Structure and uses of resorcinol, Text Note: Structure and Uses of Resorcinol

Session 12

Structure and uses of naphthols, Text Note: Structure and Uses of Naphthol

Session 13

Aromatic Amines* - Basicity of amines, Text note: Aromatic Amines_Basicity of amines_effect of substituents on basicity and synthetic uses of aryldiazonium salts, the effect of substituents on basicity. Video Link: https://youtu.be/T3EdL1vs48Q

Session 14

Synthesis and chemical reactions of Aniline, Text Note: Aryl amines

Session 15

Synthetic uses of aryl diazonium salts, Text Note: Aryl diazonium salt, Also see session - 13 note

Session 16

Aromatic Acids* – Acidity, the effect of substituents on acidity, Text Note: Aromatic Acids and Effect of substitution on aromaticity. Video Link: https://youtu.be/H3c9TIGxaVk

Session 18

Fats and Oils: Reactions of Fatty acids-Hydrolysis, Hydrogenation, Text Note: Reactions of Fatty acid

Session 17

Preparation and chemical reactions of Benzoic Acid, Text Note: Preparation and Chemical reactions of Benzoic acid

Session 19

Reactions of fatty acid: Saponification and Rancidity of oils, Drying oils, Text Link: Reactions of Fats and Oils

Session 20

Analytical constants – Acid value, Saponification value – significance and principle involved in their determination, Text Link: Reactions of Fats and Oils

Session 21

Analytical constants – Ester value, Iodine value – significance and principle involved in their determination, Text Link: Reactions of Fats and Oils

Session 22

Analytical constants – Acetyl value, Reichert Meissl (RM) value – significance and principle involved in their determination, Text Link: Reactions of Fats and Oils

Session 23

Polynuclear hydrocarbons: Structure, Synthesis, reactions, and medicinal uses of Naphthalene. Text Note: Napthalene-Structure Properties and Uses

Session 24

Polynuclear hydrocarbons: Structure, Synthesis, reactions, and medicinal uses of Phenanthrene. Text Note: Phenanthrene_Structure Properties and Uses

Session 25

Polynuclear hydrocarbons: Structure, Synthesis, reactions, and medicinal uses of Anthracene. Text Note: Anthracene_Structure-Properties-and-Uses

Session 26

Polynuclear hydrocarbons: Structure, Synthesis, reactions, and medicinal uses of Diphenylmethane.

Session 27

Polynuclear hydrocarbons: Structure, Synthesis, reactions, and medicinal uses of Triphenylmethane.

Session 28

Cycloalkanes: Structure and Stability, Text Note: Stability in cycloalkanes Video Link: https://youtu.be/b0QJdfJku9w

Session 29

Baeyer’s strain theory, limitation of Baeyer’s strain theory. Text Note: Cycloalkane_Bayer Strain Theory and Limitation of Bayer Strain Theory Video Link: https://youtu.be/MsiYYr1kv-I

Session 30

Coulson and Moffitt’s modification, Sachse Mohr’s theory (Theory of strainless rings). Text Note: Refer Text note of Session-29. Video Link: https://youtu.be/gHZGKFf1Qc4

Session 31

Preparation and Chemical Reactions of cyclopropane. Text Note: Preparation and Chemical Properties of Cyclopropane and Cyclobutane

Session 32

Preparation and Chemical Reactions of cyclobutane. Text Note: Preparation and Chemical Properties of Cyclopropane and Cyclobutane

Book References

1. Organic Chemistry by Morrison and Boyd
2. Organic Chemistry by I.L. Finar, Volume-I
3. Textbook of Organic Chemistry by B.S. Bahl & Arun Bahl.
4. Organic Chemistry by P.L.Soni

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