Lahore University of Management Sciences

CHEM 531 – Advanced Organic Chemistry I

Fall 2018

Instructor Irshad Hussain

Room No. 9-519A
Office Hours TBA
Email ihussain@lums.edu.pk
Telephone 8133
Secretary/TA
TA Office Hours
Course URL (if any)

Course Basics
Credit Hours 03
Lecture(s) Nbr of Lec(s) Per Week 02 Duration 75 min each
Recitation (per week) Nbr of Rec (s) Per Duration
Week
Lab (if any ) per week Nbr of Session(s) Per Duration
Week
Tutorial (per week) Nbr of Tut(s) Per Duration
Week

Course Distribution
Core Graduate students (MS) of Chemistry
Elective
Open for Student Category
Closed for Student Category

COURSE DESCRIPTION
This course is designed to enable the students to understand and apply the concepts of organic chemical reactions based on the frontier orbitals
interaction of the reactants. These concepts will then be used to solve problems related to aliphatic addition/substitution reactions, carbonyl
chemistry, electrophilic/nucleophilic aromatic substitution reactions, pericyclic reactions and heterocyclic chemistry. We will discuss the synthesis
and reactions of various classes of organic compounds in more detail while explaining the orbital interactions and stereochemistry in particular.
The applications of such compounds in life sciences and industry, wherever applicable, will also be discussed. On completion of this course, the
students should be able to understand and propose mechanism of fairly complex organic reactions, especially those involving above mentioned
classes of organic compounds, while keeping in view the frontier molecular orbitals interactions.

COURSE PREREQUISITE(S)

• N/A
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COURSE OBJECTIVES
1. To give the students a general overview of the structures and reactivity of fairly complex organic molecules based on frontier
• orbitals interaction.
2. To enable the students to understand and interpret patterns of reactivity of fairly complex organic reactions on the basis of
frontier orbitals interaction and mechanistic reasoning.
3. To enable the students to propose strategies for the syntheses of fairly complex organic molecules not even discussed during
the course.

Learning Outcomes
At the end of this course, the students should be able to understand the mechanism and analyze the products of fairly advance
• organic reactions involving following concepts:

1. Nucleophilic substitution at saturated carbon

2. Nucleophilic addition and substitution at the carbonyl group

3. Using organometallic reagents to make C-C bonds

4. Elimination reactions (E1, E1cb and E2)

5. Aromatic substitution reactions

6. Stereochemistry of above-mentioned organic reactions.

7. Color chemistry, heterocyclic compounds and pericyclic reactions.

Grading Breakup and Policy

Attendance: 5%
Assignments: 5%
Quizzes: 15 %
Mid-term exam: 35 %
Final exam: 40 %

Instructor has the privilege to change the grading scheme which, if availed, will be conveyed to the students well in time.

Examination Detail

Yes/No: Yes
Combine/Separate: Combine
Midterm
Duration: 02 h
Exam
Preferred Date: During the university mid-term exam week
Exam Specifications: Closed books, course material in any form is not permitted

Yes/No: Yes
Combine/Separate: Combine
Final Exam
Duration: 03 h
Exam Specifications: Closed books, course material in any form is not permitted
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COURSE OVERVIEW
Recommended Objectives/
Topics
Readings Application
Period 2 elements and the building blocks Course package plus recommended To know the importance of period 02
of organic molecules; functional groups sections of the textbook (s) elements and draw the building blocks of
Week 1
&their stereochemistry etc. organic molecules; understand functional
groups and their stereochemistry.
Inductive effect, resonance and linear Course package plus recommended To enable the students to understand and
combination of atomic orbitals (LCAO) sections of the textbook (s) apply the concept of inductive effect,
Week 2
resonance and to build molecular orbitals
from atomic orbitals
Molecular orbital theory and frontiers Course package plus recommended To enable the students to understand and
orbital theory sections of the textbook (s) apply concept of the formation of
Week 3 molecular orbitals and the role of
frontiers orbitals in organic chemical
reactions.
Conformations and cycloalkanes; Course package plus recommended To enable the students to understand and
Structure, reactivity and acid-base sections of the textbook (s) predict the conformations of molecules,
Week 4 equilibrium etc. especially cycloalkanes, and understand
their reactivity based on their
energy/stability.
Substitution and reactions at SP3 centers Course package plus recommended To enable the students to understand SN1
Week 5 (SN1, SN2 etc.) sections of the textbook (s) and SN2reactions at SP3 carbon atoms in
detail.
Elimination reactions at SP3 centers (E1, Course package plus recommended To enable the students to understand E1,
Week 6 E2, E1cb etc.) with more examples. sections of the textbook (s) E2 and E1cb reactions at SP3 carbon atoms
in detail.
Addition reactions revisited Course package plus recommended To enable the students to understand the
Week 7 sections of the textbook (s) addition reactions of unsaturated
compounds and their stereochemistry.
Addition and substitution reactions of Course package plus recommended To enable the students to understand the
Week 8 carbonyl compounds and their derivatives sections of the textbook (s) reactivity and chemistry of carbonyl
compounds
Electrophilic and nucleophilic Aromatic Course package plus recommended To enable the students to understand the
Week 9 substitution reactions sections of the textbook (s) reactivity of aromatic compounds
specifically the substitution reactions.
Color Chemistry and pericyclic reactions Course package plus recommended To enable the students to understand the
Week 10- sections of the textbook (s) basis of color chemistry, its applications in
11 nanobiology and the introduction to
pericyclic reactions
Retrosynthesis and Heterocyclic Course package plus recommended To enable the students to understand the
Week 12-
Chemistry sections of the textbook (s) chemistry of heterocyclic compounds and
14
the concept of retrosynthesis.
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Textbook(s)/Supplementary Readings
Textbooks:
Organic Chemistry by Clayden, Greeves, Warren and Wothers (Edition 2009).
ISBN 978-0-19-850346-0

Others recommended readings:

Organic Chemistry as a 2nd Language, Part – II, by David R Klein

Organic chemistry by TWG Solomons and CB Fryhle (9th Edition); ISBN 978-0-471-68496-1
Organic Chemistry by L. G. Wade Jr. (6th Edition); ISBN 0-13-147871-0