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Course Detail

Course Name Pharmaceutical Organic Chemistry
Course Code PD.104T
Program Pharm. D.
Campus Kochi

Syllabus

LECTURE WISE COTENTS:

UNIT I – Structures and Physical properties                                                            4 hours

  • Structure of organic compounds, hybridization, protic and aprotic solvents, and Inter molecular forces. (1hr)
  • Acids and bases, Lowry Bronsted and Lewis theories (1hr)
  • Oxidation and reduction reaction. (2hrs)

 

UNIT II – Classification, Nomenclature and Isomerism of organic compounds 18 hours

  • Classification of Organic (1 hr)
  • Common and IUPAC systems of nomenclature of organic compounds, alkane and complex substituents. (1 hr)
  • IUPAC nomenclature of alkene, alkyne, and cycloalkane (1 hr)
  • IUPAC nomenclature of functional groups like alcohol, aldehyde, and ketone (1 hr)
  • IUPAC nomenclature of terminal functional groups like carboxylic acid, acid halide, acid amide, ester, cyanide, amine and ether (1 hr)
  • IUPAC nomenclature of Polyfunctional groups (1 hr)
  • Electron displacements in organic chemistry (such as inductive effect, resonance, hyperconjugation). (2 hrs)
  • Reaction intermediates (such as free radicals, carbocations, carbanions, carbenes and nitrenes). (4 hrs)
  • Types of reagents – electrophilic & nucleophilic (1hr)
  • Structural and stereo isomerism in organic D &L system of nomenclature of optical isomers, sequence rules, R&S system of nomenclature of optical isomers (5 hrs)

UNIT III – Organic reactions and mechanisms

  • Nucleophilic aliphatic substitution (SN2 & SN1) 4hours
    • Nucleophiles and leaving groups – reaction, mechanism
    • Kinetics of second and first order reaction
    • Stereochemistry and steric hindrance
  • Carbocation and their stability
  • Rearrangement of carbocation
  • Solvolysis
  • Role of solvent in substitution
  • SN2 versus SN1.

 

     Elimination (E2 & E1)                                                                                   4 hours

  • Reaction, mechanism, kinetics, evidence, orientation, and reactivity
  • Role of carbocation, 1,2 eliminations
  • Absence of rearrangement isotope effect
  • Absence hydrogen exchange
  • Elimination versus substitution 4 hours

   Electrophilic addition in alkene

  • Electrophilic addition reaction
  • Orientation and reactivity of Markownikoff rule
  • Addition of hydrogen halides
  • Addition of halogen and halohydrin formation
  • Heat of hydrogenation and stability of alkenes 4 hours

   Free radical addition in alkene

  • Reaction, mechanism, orientation, peroxide effect (Anti- Markownikoff rule)
  • Mechanism of peroxide-initiated addition of hydrogen bromide,
  • Additions of carbene to alkene,
  • Comparison of free radical substitution with free radical addition,
  • Allylic

   Conjugated dienes                                                                                             3 hours

  • Conjugated dienes – stability and resonance, stability of allyl radical, hyperconjugation, reactions of conjugated dienes

  Electrophilic aromatic substitution (reaction of benzene)                       10 hours

  • Nitration, sulphonation, halogenation, Friedel-craft alkylation (2 hrs)
  • Friedel-craft acylation mechanism, reactivity and orientation (1 hr)
  • Effect of substituent groups on reactivity and orientation of benzene (1 hr)
  • Activating and deactivating O, P, & M directing groups – reactivity and orientation (1 hr)
  • Effect of halogen on electrophilic aromatic substitution in alkyl benzene (1 hr)
  • Basicity of amines and Acidity of phenols (1 hr)
  • Diazotisation, Mechanism and applications (1 hr)
  • Hoffman rearrangement and Reimer Tiemann reaction (1 hr)
  • Sandmeyer’s reaction, Williamson synthesis (1 hr)

   Nucleophilic addition reaction                                                                         8 hours

  • General principle, Addition of HCN, Addition of alcohol, and addition of Grignard reagent. (2 hrs)
  • Aldol condensation and crossed aldol condensation (1 hr)
  • Cannizzaro reaction and crossed Cannizzaro reaction (1 hr)
  • Claisen condensation, Benzoin condensation (1 hr)
  • Perkin condensation, Knoevenagel reaction (1 hr)
  • Reformatsky reaction, Wittig reaction (1 hr)
  • Michael addition, Kolbe reaction (1 hr)

    Nucleophilic aromatic substitution                                                           2 hours

  • reaction, mechanisms, orientation
  • comparison of aliphatic nucleophilic substitution with that of

Unit IV- Alkane & cycloalkane                                                                                4 hours

  • Free radicals chain reactions of alkane; mechanism, relative (2 hrs)
  • Cycloalkane (alicyclic compounds); preparations of cycloalkanes, Bayer strain theory and orbital picture of angle strain. (2 hrs)

Unit V- Carboxylic acids                                                                                           5 hours

  • Ionisation of carboxylic acids, acidity constants, acidity of acids, structure of carboxylate ions, role of carboxyl group. (2 hrs)
  • Effect of substituent on (1 hr)
  • Nucleophilic acyl substitution reaction, comparison of alkyl nucleophilic substitution with acyl nucleophilic substitution. (1 hr)
  • Conversion of acid-to-acid chloride, esters, amide and (1 hr)

 Unit VI- Introduction of Heterocyclic rings                                                              5 hours

  • Classification, and nomenclature of Heterocyclic compounds (3 hrs)
  • Aromatic character of different class of Heterocyclic compounds (five-membered, six- membered, and Fused) (2 hrs)

Objectives and Outcomes

SCOPE:

This course is designed to impart a very good knowledge about the classification and nomenclature of simple organic compounds, structural and stereo isomerism, intermediates forming in reactions, important physical properties, reactions and their basic reaction mechanisms. This also covers the important name reactions and their applications. It includes the nomenclature, chemistry and aromaticity of important heterocyclic compounds.

The syllabus emphasizes mechanisms and orientation of reactions such as electrophilic addition, free radical addition, nucleophilic aliphatic substitution (SN1 & SN2), nucleophilic addition & elimination (E1 & E2), electrophilic aromatic substitution, and heterocyclic chemistry. This syllabus also includes the synthesis, qualitative tests, identifying the preliminary test, and detection of elements of some organic compounds. They also include the physical property evaluation such as boiling point and melting point determination of organic compounds. This course cultivates a professional mindset by emphasizing the importance of good laboratory practices in the synthesis and analysis of organic compounds in pharmaceuticals.

LEARNING OUTCOMES:

Upon successful completion of the course, the student shall be able to

KNOWLEDGE

K1: Outline the classification of organic compounds. (Remembering)

K2: Interpret the structure, IUPAC name of the organic compounds (Understanding)

K3: Interpret the structure & types of isomerism (structural and stereo) of organic compounds (Understanding)

K4:   Explain the general principles of       different mechanism of     organic reactions. (Understanding)

K5: Describe the basic concepts of alkane, alkene and conjugated dienes. (Understanding) K6: Articulate the basic knowledge regarding alkyl halides, alcohols, carbonyls, carboxylic acids, and aliphatic amines. (Applying)

SKILL

S1: Prepare organic compounds. (Preparation of different organic compounds) S2: Determination of melting point and boiling point of organic compounds. S3: Identify the preliminary test and detection of elements.

S4:Identify the group of organic compound to which it belongs to (based on solubility of compounds in different solvents)

S5: Classify various organic compounds based on their functional groups.

S6: Analyse the physico-chemical properties of various organic compounds.

ATTITUDE

A1: Appreciate the basic knowledge of subject. A2: Follow professional and standard procedures. A3: Participate in group discussion.

A4: Follow the SOPs when using lab equipment and instruments. A5: Assist fellow students and others in executing the experiments. A6: Take responsibility for self and group outcomes.

Text Books / References

TEXT BOOKS:

  1. Morrison, T., & Boyd, R. N and Bhattacharjee. Organic chemistry. 7th ed. Pearson Education India; 2010.
  2. Arun Bahl and S. Bahl. A textbook of organic chemistry. 22nd ed. S. Chand; 2016.
  3. L. Soni & H. M. Chawla. Textbook of organic chemistry. 29th edn. Sultan Chand & son: India; 2012.
  4. P. Agarwal. Organic chemistry: reactions and reagents. 56th edn. Goel Publishing House. 2018

REFERENCE BOOKS:

  1. Mann G & Saunders B C. Practical organic chemistry. 4th edn. Pearson Education India; 2009
  2. Bruice Y. Organic Chemistry. 8thedn.Upper Saddle River, NJ: Pearson Education; 2015.
  3. Brian F, Antony J.H, Peter W.G.S & Austin R.T. Vogel’s textbook of Practical Organic Chemistry. 5th edn. Pearson Education India; 2003.
  4. Donald Pavia, Gary M. Lampman, George S. Krizet al. A small-scale approach to organic laboratory techniques. U.S: Cengage Learning; 2014.

 

*Latest edition of the text books & reference books can be referred

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