king khalid university - kkuwith maleic anhydride with chlorine 2.3. phenanthrene 2.3.1 synthesis....

KING KHALID UNIVERSITY

COLLEGE OF PHARMACY

DEPARTMENT OF PHARMACEUTICAL CHEMISTRY

COURSE SCHEDULE

MALE SECTION

Pharmaceutical Organic Chemistry (PCH 218) FOR PHARMACEUTICAL SCIENCES

by

Dr. Kumar Venkatesan

Academic Session 1437-1438H

1st Semester

September 2016-January 2017

Course Specification

Course title Pharmaceutical Organic Chemistry

Course code PCH 218, Section – 12 (Theory)

Section 13,14 and 6156 (Practical)

Credit hours (3+1) Credit Units (45 hours) 3 Theory/week

1 practical / week

Program(s) in which the course is offered B.Pharm.Sc

College of Pharmacy

Name of faculty member responsible for

the course

Dr. Kumar Venkatesan College of Pharmacy King Khalid University,ABHA. Email: [email protected] 163/4/c- 0172417982

Lecture Timings: Theory Sunday 1.00 - 1.50 pm Wednesday 9.00 - 9.50 pm Thursday 1.00 - 1.50 pm

Lecture Timings: Practical Monday 10.00 - 11.50 am (Section 14, A) Tuesday 8.00 - 9.50 am (Section 13, B) Wednesday 1.00 – 2.50 pm (Section 6156, C)

Level/year at which this course is offered Level 3/year 2

Pre-requisites for this course (if any) Chem 111(General Organic Chemistry)

Co-requisites for this course (if any) None

Location if not on main campus Guraiger

Total number of teaching weeks 15 Weeks

Total number of Theory Hours 45 hours

Total number of Practical Hours 30 hours (15 Credit hours)

Course Description

The present course is a continuation of the basic organic chemistry (Chem-111). It deals with

the methods of preparation, identification and reactions of the aromatic and heterocyclic

compounds; with special emphasis on their pharmaceutical importance. The basic concepts of

stereochemistry as an important basic knowledge for pharmacy students is also discussed.

Moreover, the specifically important classes of amino acids and carbohydrates are also

included. Finally the different spectroscopic methods for the identification of basic organic

compounds are explained. These include Infrared spectroscopy – Nuclear magnetic resonance

mailto:[email protected]

spectroscopy – Mass spectroscopy instrumental techniques applied to investigate the structure

of the organic compounds.

THE MAIN LEARNING OUTCOMES FOR STUDENTS ENROLLED IN THE

COURSE

After completing this course, students should be conversant with:

The basic concepts in organic chemistry especially those related to the aromatic and

heterocyclic compounds of pharmaceutical interests.

The general methods for preparation and identification of the essential nuclei involved

in organic compounds. Preparation of organic compounds.

The basic concepts of stereochemistry.

The basic concepts of the instrumental methods of interest in the identification of

pharmaceutical and organic compounds.

The basic chemistry and significance of the carbohydrates and amino acids as

pharmaceutically important substances.

TEXT BOOK FOR REFERENCE

1. Solomons, T.W. Graham “Organic Chemistry” 8th

edition 2004; John Wiley & Sons.

2. R.T. Morrison and R.N. Boyed “Organic Chemistry” 6th

ed. 1992, Prentice-Hall

Int. Inc

3. Finar “Organic chemistry, the fundamental Principles” 6th

ed. 1994, longman

singabore publishers.

4. Peter Sykes “ A guide book to mechanisms in organic chemistry” 3rd

ed. John

Wiley & Sopns.

5. F.D. Gunstone “Guidebook to Stereochemistry” Longman, London

SCHEDULE OF ASSESSMENT TASKS

Assessment task (e.g. essay, test, group project,

examination, speech, oral presentation, etc.)

Marks

Quiz Exam (MCQs) 5

Mid-term Exam (MCQs) 30

Mid-term practical Exam 10

Three Assignments 5

Final Practical Exam 10

Final written Exam (MCQs) 40

Total 100 Marks

Examination protocol

Quiz-I

Final exam will consist of 10 multiple choice questions for 10 marks

Topics for Quiz- I

Introduction to Organic Chemistry:

Monocyclic aromatic compounds

Reactions of benzene

MID-TERM EXAM

Mid-term exam will consist of:

Part 1: 32 multiple choice questions for 24 marks

Part 2: 5 questions consisting of definitions or terms for 2 marks each (3 to be chosen for 2

marks)

Mid-term exam will take place In 6th

teaching week

Topics for Mid-term exam

The topics (lectures) covered during week 1 to week 5.

ASSIGNMENT

Each student will be allotted 3 assignments topic for 5 marks

Topics for Assignment

Topics for assignments will be communicated to the student via block board.

END SEMSTER EXAM

Final exam will consist of 80 multiple choice questions for 40 marks. The final examination

will consist of 64 MCQs from the topics after mid-term (from week 6 onwards) and 16

MCQs from the topics of mid-term examination.

TEACHING SCHEDULE FOR PHARMACEUTICAL ORGANIC CHEMISTRY

THEORY

week Day/

Date

List of Topics Name of the Faculty

1

Sunday

18/09/2016

17/12/1437

Introduction to Organic Chemistry:

Organic Compounds

Some functional groups and

corresponding classes of

compounds

How to name?

Dr. Kumar

Venkatesan

Wednesday

21/09/2016

20/12/1437

Thursday

22/09/2016

21/12/1437

1. Monocyclic aromatic compounds

1.1. Benzene

1.1.1. Preparation of benzene

1.1.2. Structure of benzene

1.1.3. Aromaticity (Annulens)


2

Sunday

25/09/2016

24/12/1437

Wednesday

27/09/2016

27/12/1437

Thursday

28/09/2016

28/12/1437

1.1.4. Reactions of benzene

Halogenation

Nitration

Sulphonation

Friedel-Crafts acylation

Friedel-Crafts alkylation

Limitation of Friedel-Craft

reactions

The effect of substituents on

reactivity

Substituent Effects: Orientation

3

Sunday

02/10/2016

01/01/1438

1.2. Alkyl benzenes

1.3. Alkyl benzenes

1.2.1. Nomenclature

1.2.2. Synthesis [Friedel-craft

reactions (Acylation and

Alkylation)


1.2.3. Reactions

Nitration (toluene to

trinitrotoluene)

Oxidation

Halogenation

Wednesday

05/10/2016

04/01/1438

1.4. Aromatic sulphonic acids

1.3.1 Nomenclature

1.3.2. Preparation

1.3.3. Reactions

Preparation of acid chloride

General reactions of acid chloride

Examples of sulpha drugs

Saccharine synthesis


Thursday

06/10/2016

05/01/1438

1.5. Aromatic halogen compounds

1.4.1. Nomenclature

1.4.2. Preparation of nuclear substituted

halogen compounds (Direct

halogenations- Indirect halogenations via

Sandmeyer reaction)

1.4.3. Reactivity of Aryl halides

(Resonance structures of halobenzene)

1.4.4. Reactions

Electrophilic substitution

reactions

Nucleophilic substitution

reactions

Preparation of D.D.T.

1.4.5. Side chain halides

Preparation of side chain halogen

compounds: Chlorination,

Bromination)


4 Sunday

09/10/2016

08/01/1438

1.5. Phenol

1.5.1.Nomenclature

1.5.2. Preparation

Wednesday

12/10/2016

11/01/1438

1.5.3. Acidity of phenols

Factors affecting acidity as

electron donating groups and

electron withdrawing groups

1.5.4. Reactions of phenols

Kolbe synthesis

Ester formation

Reactions involving benzene ring

Sulphonation

Nitration

Halogenation

1.6. Aromatic alcohols.

1.6.1.Nomenclature

1.6.2. Preparation

1.7. Quinones

1.7.1. Nomenclature

1.7.2. Preparation

1.7.3. Reactions

Dr. Kumar

Venkatesan

Thursday

13/10/2016

12/01/1438

Quiz (1)

Dr. Kumar

Venkatesan

5

Sunday

16/10/2016

15/01/1438

1.8. Aromatic nitro compounds

1.8.1. Nomenclature

1.8.2. Preparation

1.8.3. Reactions

Nucleophilic substitution (SN2Ar)

Reduction.


Wednesday

19/10/2016

1.9. Aromatic amino compounds.

1.9.1. Nomenclature

1.9.2. Preparation

via reduction

Hofmann rearrangement

Curtius Rearrangement


http://www.organic-chemistry.org/namedreactions/curtius-rearrangement.shtm

18/01/1438 1.9.3. Basic character

Factors affecting basicity as

electron donating groups and

electron withdrawing groups

1.9.4. Reactions

Acylation

Alkylation

Reaction with nitrous acid

Preparation of sulpha

drugs.

Thursday

20/10/2016

19/01/1438

1.10. Aldehydes and ketones

1.10.1.Nomenclature

1.10.2.Preparation

Oxidation

1.10.3. Reactions

Addition of HCN

Addition of grignard reagents

Addition of ammonia derivatives

Addition of carbanions

(Knoevenagel condensation)

Wittig reaction

Haloform Reactions

Oxidation reactions

Dr. Kumar

Venkatesan

6

Sunday

23/10/2016

22/01/1438

1.11. Aromatic carboxylic acids

1.11.1. Nomenclature

1.11.2. Preparation

Oxidation

Hydrolysis of nitrile and

cyanohydrin

1.11.3. Acidity

Effect of substituents on the

acidity of aromatic carboxylic

acids

1.11.4. Reactions

Reactions of carboxyl group

Acid chloride formation and its

reactions


Wednesday

26/10/2016

25/01/1438

Thursday

27/10/2016

26/01/1438

2. Polynuclear compounds.

2.1. Naphthalene

2.1.1. Preparation (Haworth synthesis)

2.1.2. Positions of the double bonds in

naphthalene

2.1.3.Nomenclature of naphthalene

derivatives

2.1.4. Reactions

Reduction

Oxidation

The Friedel-Crafts reaction with

naphthalene

Dr. Kumar

Venkatesan

7

Sunday

30/10/2016

29/01/1438

2.2. Anthracene

2.2.1. Synthesis

Elbs reaction

2.2.2. Positions of the double bonds in

anthracene

2.2.3. Reactions

With maleic anhydride

With chlorine

2.3. Phenanthrene

2.3.1 Synthesis.

Dr. Kumar

Venkatesan

Wednesday

02/11/2016

02/02/1438

Thursday

ISOMERISM

Constitutional Isomer

Stereoisomers

Geometrical isomers

Optical isomerism

(R), (S) Nomenclature

The Rules For Determining

Stereochemistry

Enantiomers

Biological Discrimination

Dr. Kumar

Venkatesan

03/11/2016

03/02/1438

Racemic Mixture

Fischer projection

Diastereomers

Meso compound

Reactions involving stereoisomers

8 Sunday

06/11/2016

06/02/1438

Wednesday

09/11/2016

09/02/1438

Thursday

10/11/2016

10/02/1438

4. Heterocyclic chemistry

Introduction

Heterocyclic Aromatic

Compounds and Hückel's Rule

Nomenclature of monocycles

Nomenclature of fused

heterocycles

Nomenulature of carbocycle fused

with heterocycles

Nomenclature of heterocycle

fused with another heterocycles

9

Sunday

20/11/2016

20/02/1438

4.1. Chemistry of six membered

heterocyclic (pyridine).

4.1.1. CHARACTERS OF PYRIDINE

4.1.2. Aromaticity

4.1.3. Basic properties of pyridine

4.1.4. Synthesis

4.1.5. Reactions

4.1.5.1. Chichibabin reaction

Dr. Kumar

Venkatesan

Wednesday

23/11/2016

23/02/1438

4.2. Five membered heterocyclic

compounds: (pyrrole, furan and

thiophene)

4.2.1. The importance of pyrrole, furan

and thiophene

Dr. Kumar

Venkatesan

Thursday

24/11/2016

24/02/1438

4.2.2. Preparations of Pyrrole, Furan and

Thiophene

PAAL-KNORR SYNTHESIS

4.2.3. Characters of pyrrole, furan and

thiophene

Aromaticity

Diene Characters

4.2.4. Reactions

Reduction

10

Sunday

27/11/2016

27/02/1438

4.3. . Monocyclic heterocompounds

with more than one heteroatom

(imidazole, pyrazole)

4.3.1. Basic and acidic characters of

imidazole

4.3.2. Electrophillic substitution (SE)

4.3.3. Synthesis of Pyrazole Derivatives

Dr. Kumar

Venkatesan

Wednesday

30/11/2016

01/03/1438

Thursday

01/12/2016

02/03/1438

4.4. Fused heterocyclic compounds

Quinoline and isoquinoline

4.4.1. The importance of Quinoline and

isoquinoline

4.4.2. Synthesis

Bischler -Napieralski Synthesis

Skraup Synthesis

Dr. Kumar

Venkatesan

Sunday

04/12/2016

05/03/1438

4.5. Fused heterocyclic compounds:

indole

4.5.1.The importance of Indole

4.5.2. Fischer indole synthesis

4.5.3. Chemical Properties of

Indole

Dr. Kumar

Venkatesan

11

Wednesday

07/12/2016

08/03/1438

Thursday

08/12/2016

09/03/1438

5. Carbohydrates

5.1. Introduction

5.2. Nomenclature

5.3. Classification.

5.4. D and L isomers

5.5. Epimers

5.6. Structural formulas for

monosaccharides

Open structure formula

Cyclic structure formulas

5.7. Reactions of monosaccharides

5.7.1. Oxidation reactions of

monosaccharides

Benedict's reagents

Bromine water

Nitric acid oxidation

5.7.2. Reduction of monosaccharides

5.7.3. Reactions with phenylhydrazine

5.8. Disaccharides

Reducing disaccharides

Non reducing disaccharides

Dr. Kumar

Venkatesan

Sunday

11/12/2016

12/03/1438

6. Aminoacids and protein chemistry

6.1. Structures and names

6.2. Physical properties of amino acids

6.3. Protein

Dr. Kumar

Venkatesan

Wednesday

7. Spectroscopic methods for

determination of organic compounds:

7.1. Infrared spectroscopy and its

applications;

12 14/12/2016

15/03/1438

Thursday

15/12/2016

16/03/1438

7.1.1.Theory

7.1.2.IR radiation source

7.1.3.Sample preparation

7.1.4.Requirements for absorption in IR

7.1.5.Types of vibration

Stretching

Bending

7.1.6.Interpretation of IR Spectra

7.1.7.Factors affect the stretching

absorption frequency of C=O group in

any molecule

Electron donating or electron

withdrawing groups

Conjugation

Ring strain

Hydrogen bonding

Intermolecular

Intramolecular

7.1.8. O-H absorption, peak shape

7.1.9.IR Spectra–Examples

7.1.10.Application of IR Spectroscopy

Dr. Kumar

Venkatesan

13

Sunday

18/12/2016

19/03/1438

Wednesday

21/12/2016

22/03/1438

Thursday

7.2. 1H NMR spectroscopy

7.2.1.The background to NMR

spectroscopy

7.2.2. Sample preparation

7.2.3. Solvents for NMR

7.2.4. Main parts in NMR spectrometer

7.2.5. NMR spectrum

Characteristics of Absorption Signal in

NMR

Dr. Kumar

Venkatesan

22/12/2016

23/03/1438

Position

Number of signals

Intensity of signals

Signal splitting

7.2.6. Assignment of 1H-NMR spectra

7.2.7. Examples

14

Sunday

25/12/2016

26/03/1438

Wednesday

28/12/2016

29/03/1438

Thursday

29/12/2016

30/03/1438

7.3. Mass spectroscopy MS and its

applications.

7.3.1. Theory of Mass Spectrometry

7.3.2. Some important peaks

Molecular ion peak M+

Base peak

Fragment ions

Isotope peaks( M+ + 1 and M

+ +

2)

7.3.3. Examples of fragmentation patterns

7.3.4. Principle stable isotopes of some

common elements

7.3.5. Mass spectra of haloalkanes

7.3.6. Applications of mass spectroscopy

Dr. Kumar

Venkatesan

15

Sunday 01/04/2017

03/04/1438

Wednesday

04/04/2017

06/04/1438

Thursday

05/04/2017

07/04/1438

Assigned problems in IR,1H NMR and

MS.

Dr. Kumar

Venkatesan

TEACHING SCHEDULE FOR PHARMACEUTICAL ORGANIC CHEMISTRY PRACTICAL

WEEK Day / Date Topic Faculty Name

1 Group A

Monday

19/09/2016

18/12/1437

Introduction about practical organic chemistry Safety measures in chemistry laboratory


Dr. Jaber Alshehri

Group B Tuesday

20/09/2016

19/12/1437

Group C Wednesday 21/09/2016

20/12/1437

2 Group A Monday

26/09/2016

25/12/1437

Physical properties:

Condition

Color

Odor

Solubility: H2O , NaOH , Dil HCl , Conc. H2SO4


Dr. Jaber Alshehri

Group B Tuesday

27/09/2016

26/12/1437

Group C

Wednesday

28/09/2016

27/12/1437

3 Group A

Monday

03/10/2016

02/01/1438

Chemical Properties:

Dry Ignition

The change in


Dr. Jaber Alshehri

appearance

Degree of flammability

Color of the flame

Nature of the residue

Action of Sodalime

Decarboxylation

Dehydration

Group B

Tuesday

04/10/2016

03/01/1438

Group C Wednesday

05/10/2016

04/01/1438

4 Group A Monday

10/10/2016

09/01/1438

Action of 30% sodium hydroxide solution

Action of sodium carbonate solution


Dr. Jaber Alshehri

Group B Tuesday

11/10/2016

10/01/1438

Group C Wednesday

12/10/2016

11/01/1438

5 Group A

Monday

17/10/2016

16/01/1438

Action of (FeCl3) solution;

Action of concentrated sulfuric Acid


Dr. Jaber Alshehri

Group B

Tuesday

18/10/2016

17/01/1438

Group C Wednesday

19/10/2016

18/01/1438

6 Group A Monday

24/10/2016

23/01/1438

General scheme for identification of organic compounds


Dr. Jaber Alshehri

Group B Tuesday

25/10/2016

24/01/1438

Group C Wednesday

26/10/2016

25/01/1438

7 Group A Monday

31/10/2016

30/01/1438

Revision


Dr. Jaber Alshehri

Group B Tuesday

01/11/2016

01/02/1438

Group C Wednesday

02/11/2016

02/02/1438

8 Group A Monday

07/11/2016

07/02/1438

First Practical Exam


Dr. Jaber Alshehri

Group B Tuesday

08/11/2016

08/02/1438

Group C Wednesday

09/11/2016

09/02/1438

9 Group A Monday

21/11/2016

21/02/1438

Introduction about synthesis of organic compound


Dr. Jaber Alshehri

Group B Tuesday

22/11/2016

22/02/1438

Group C Wednesday

23/11/2016

23/02/1438

10 Group A Monday

28/11/2016

28/02/1438

Preparation of acetylsalicylic acid (Aspirin)


Dr. Jaber Alshehri

Group B Tuesday

29/11/2016

29/02/1438

Group C Wednesday

30/11/2016

01/03/1438

11 Group A Monday

05/12/2016

Preparation of Acetanilide


06/03/1438

Dr. Jaber Alshehri

Group B Tuesday

06/12/2016

07/03/1438

Group C Wednesday

07/12/2016

08/03/1438

12 Group A Monday

12/12/2016

13/03/1438

Preparation of Iodoform


Dr. Jaber Alshehri

Group B Tuesday

13/12/2016

14/03/1438

Group C Wednesday

14/12/2016

15/03/1438

13 Group A Monday

19/12/2016

20/03/1438

Recrystallization and

purification of

organic compound


Dr. Jaber Alshehri

Group B Tuesday

20/12/2016

21/03/1438

Group C Wednesday

21/12/2016

22/03/1438

14 Group A Monday TLC ( thin layer Dr. Kumar

26/12/2016

27/03/1438

chromatography)

Spectroscopic elucidation of structures by using IR

Assigned problems ( IR , 1H NMR) and revision

Venkatesan

Dr. Jaber Alshehri

Group B Tuesday

27/12/2016

28/03/1438

Group C Wednesday

28/12/2016

29/03/1438

15 Group A Monday

02/04/2017

04/04/1438

Final Practical Exam Dr. Kumar Venkatesan

Dr. Jaber Alshehri

Group B Tuesday

03/04/2017

05/04/1438

Group C Wednesday

04/04/2017

06/04/1438

king khalid university - kkuwith maleic anhydride with chlorine 2.3. phenanthrene 2.3.1 synthesis....

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