Academic Planner

JIK 327/4
CHEMICAL SPECTROSCOPY
2019/2020 Academic Session
WEBEX
Session DATE TIME

1.

2.

3.

4.

INTENSIVE COURSE

5.

6.

7.

8.

Students need to fill in the date and time of Webex sessions. Please refer to the Webex time table
for the Academic Session 2019/2020 provided.
JIK 327/4 – CHEMICAL SPECTROSCOPY

COURSE MANAGERS: Dr. Nurul Syafiqah Rezali

E-mail: nyafiqah@usm.my
Tel: 04-6535915

Dr. Noor Fatimah Yahaya

E-mail: noorfatimah@usm.my
Tel: 04-562 2071

A. COURSE CONTENT

The course comprises 4 units of which 3 units are theory and 1 unit is experimental. The
following spectroscopic techniques will be taught:

Proton Nuclear Magnetic Resonance (1H-NMR) Spectroscopy: shielding/de-shielding

phenomena and chemical shifts, coupling constant and splitting patterns – the use of these
data to elucidate structural formula. Chapter 3 of the textbook.

Carbon-13 Nuclear Magnetic Resonance (13C-NMR) Spectroscopy: coupled/de-

coupled spectrum, chemical shifts and DEPT techniques- the use of these data to identify
molecular structures. Chapter 4 of the textbook.

Molecular Symmetry and Point Group: identification of symmetry elements in some

molecules, symmetry operations that can be performed on each symmetry element, types
of point groups, simple applications of molecular symmetry as, for example, in molecular
bonding theory and in Raman and IR spectroscopy.
Note: Notes on these topics: Molecular Symmetry, Group Theory and Its Applications;
are made available in the PPPJJ e-learning portal.

Infrared (IR) Spectroscopy: correlation between infrared absorption and organic

functional groups. Chapter 2 of the textbook.

Ultraviolet (UV) Spectroscopy: calculation of λmax and its relation with chromophore
systems of the molecules. [Not discussed in the textbook], instead see:
• Paula 2nd Edition, Chapter 13
• Wade 7th Edition, Chapter 15

Mass Spectroscopy (MS): exact mass, molecular ion, parent ion, typical fragmentation
patterns of different compounds. Chapter 1 of the textbook.
B. LEARNING OUTCOMES

Upon completion of this course, students should be able to:

 Describe concepts, principles and techniques that are used in spectroscopy

methods
 Identify the presence of certain functional group of an unknown using IR
spectrum
 Identify molecular weight and molecular formula of a compound using MS
spectrum
 Identify the presence of chromophore in a sample compound using UV spectrum
 Recognizing functional groups and carbon skeleton of an organic compound using
1
H-NMR and 13C-NMR
 Suggest a plausible structure for the unknown compound if sufficient
spectroscopic data are given
 Identify a given compound into a specific point group and perform appropriate
calculation to predict IR and Raman activity of the compound
 Apply the knowledge of the point group in the chemical bonding theories
 Apply common techniques and theoretical knowledge in practical

C. LEARNING MATERIALS

Primary textbook:

 Silverstein, R. M., Webster, F. X., Kiemble, D. J. and Bryce, D. L. (2015).

Spectrometric Identification of Organic Compounds. 8th Edn. John Wiley &
Sons, Inc.

Supplementary materials:

 Wade, L. G. (2014) Organic Chemistry. 8th Edition. Pearson Education Limited

 R. M. Silverstein, F.X. Webster & D.J. Kiemle (2005). Spectrometric
Identification of Organic Compounds (7th Edition). John Wiley & Sons, Inc.
 J. A. Landgrebe (2005). Theory and Practice in the Organic Laboratory (5th
Edition). Brooks/Cole. (Reference for Experiments)

D. WEBEX SESSIONS

Four (4) Webex will be conducted before the Intensive Course and another four (4) after
the Intensive Course. You are advised to study the relevant topic that is going to be
discussed before attend the Webex session. Agenda for Webex are as follows:
Webex 1: 1H-NMR (Part 1: Introduction, theories and chemical shifts)
Webex 2: 1H-NMR (Part 2: Multiplicity and spin couplings)
Webex 3: 13C-NMR
Webex 4: IR Spectroscopy
Webex 5: UV Spectroscopy
Webex 6: Mass Spectrometry (Part 1: Introduction and interpretation of Mass Spectra)
Webex 7: Mass Spectrometry (Part 2: Mass Spectra of Some Chemical Classes)
Webex 8: Molecular Symmetry and Point Group

E. COURSE WORK

I. Laboratory Works

There will be FIVE (5) sessions of laboratory work that are scheduled during the
Intensive Course:

1. Qualitative Organic Analysis: Classification tests

2. Qualitative Analysis: Identification of unknowns
3. Isolation of Caffeine
4. Photoreduction of Benzophenone
5. Preparation of Homophthalic Acid

Important Note: You are required to submit the obtained products and written
laboratory reports following the completion of each experiments to the instructors.

II. Assignments

There will be TWO (2) written assignments for this course.

Assignment 1: 1H and 13C-NMR

Due date for this assignment is 29th December 2019 (Sunday).

Assignment 2: IR, UV and Mass Spectrometry

Due date for this assignment is 12th April 2020 (Sunday).

III. Continuous Assessment

The 1-hour Continuous Assessment comprises a test that will be carried out at Regional
Centers (Note: Please be alert with the announcement). The test will cover the following
topics:

 Proton (1H) Nuclear Magnetic Resonance

 Carbon (13C) Nuclear Magnetic Resonance
 IV. Contribution of Course Work and Final Exam

There will be a 3-hour Final Examination for this course, and it will cover the entire
syllabus taught during the academic session.

The overall grade for this course will be based on:

Final Examination: 60%

Coursework: Laboratory Reports 20%

Assignments 10%
Continuous Assessment 10%

F. INTENSIVE COURSE

You are required to attend the compulsory Intensive Course which will be held from 28
January 2020 to 13 February 2020.

Tutorial Classes during Intensive Course:

1. Spectroscopy Problems (Combined IR, UV, MS, 1H and 13C NMR)

2. Spectroscopy Problems (Combined IR, UV, MS, 1H and 13C NMR)

G. REFERENCES

Spectroscopy
1. D.L. Pavia, G.M. Lampman & G.S. Kriz (2001). Introduction to Spectroscopy. A
Guide for Students of Organic Chemistry (3rd Edition). Harcourt College
Publisher.
2. W. Kemp (1991). Organic Spectroscopy. MacMillan.
3. Williams & Fleming (1980). Spectroscopic Methods in Organic Chemistry.
McGraw-Hill.
4. R.T. Morrison & R.N. Boyd (1996). Organic Chemistry (6th Edition). Allyn &
Bacon Inc.
5. J.E. McMurry. Organic Chemistry (5th Edition). Brooks/Cole: Thomson Learning.
6. Y.B. Paula (1998). Organic Chemistry (2nd Edition). Prentice Hall.

Molecular Symmetry and Group Theory

1. G. Davidson (1991). Group Theory for Chemists. MacMillan.
2. H.H. Lowell (1986). Group Theory and Symmetry in Chemistry.
3. A. Vincent (2001). Molecular Symmetry and Group Theory: A programmed
Introduction to Chemical Applications (2nd Edition). John Wiley & Sons, Inc.
4. E.H. Catherine & G.S. Alan (2008). Inorganic Chemistry (3rd Edition). Chapter 4.
An Introduction to Molecular Symmetry, pp. 88‒110. Prentice Hall.