CHEMISTRY 534

SYLLABUS

SPRING SEMESTER 2015

Course Description: A detailed study of the structural and mechanistic underpinnings of organic chemistry.
Standard synthetic transformations will be discussed from a structural, stereochemical and mechanistic point of
view. Common functional group transformations in multi-step synthesis including retrosynthetic analysis will
also be discussed. A thorough understanding of all of the topics discussed in CHEM 330 is a necessary
prerequisite, 3 hrs. Lect.
My expectation is that you will attend all classes, read the text, do the assigned work, and complete all quizzes
and exams. Study of organic chemistry is very cumulative in nature; i.e., each topic (in fact, each lecture)
builds upon the material discussed and mastered during the previous class. Students who repeatedly miss
lectures or do not attempt to remedy any of their existing organic chemistry deficiencies on a timely manner
during the course do it at the risk of failing the course.
Suggested Texts:
Organic Chemistry by J. Clayden, N. Greeve, S. Warren and P. Wothers (Oxford University Press, 2001)
(This textbook is available for free download as a PDF file and we will use this as our primary text book)
Organic Chemistry-An Acid-Base Approach by Michael B Smith (CRC Press, 2011)
Structure and Reactivity in Organic Chemistry by Mark G. Moloney(Oxford University Press, 2008)
Perspectives on Structure and Mechanism in Organic Chemistry by Felix Carroll (John Wiley, 2010)
Organic Chemistry: An Intermediate Text by Robert V. Hoffman (ISBN-0-471-45024-3)
Molecular Orbitals and Organic Chemical Reactions by I. Fleming (John Wiley, 2010)
Course Instructor:

Dr. T. K. Vinod
mftkv@wiu.edu

Currens Hall 438-A

298-1379

Meeting Times:

5.00-6.15 PM M, and W in Currens 206. The instructor may hold extra lectures on
weekends if necessary in order to adequately cover all the required topics.

Office Hours:

Monday, Wednesday, Friday 10.00 AM-11.00 AM or by appointment

Assessment

4 Quizzes (50 points each), 2 Midterm Exams (125 points each), and a Final
Exam (200 points): Total points for the course is 600 points.

Grading:

A+AA- (100-85%), B+BB- (84-70%), C+CC- (69-50%)

Quizzes & Exams:

Four in-class quizzes (30 min. duration) will be administered during the term and the best three
scores for the quizzes will be considered along with other scores when assigning the final grade
for the course. The class may meet at 4.00 or 4.30PM on Exam and Quiz days and such changes
will be announced well in advance. Students will not be allowed MAKE-UP missed quizzes
after the quiz has been administered.

Additional and Relevant Information

ADA policy: In accordance with University policy and the Americans with Disabilities Act (ADA), academic
accommodations may be made for any student who notifies the instructor of the need for an accommodation. It
is imperative that you take the initiative to bring such needs to the instructors attention, as he/she is not legally
permitted to inquire about such particular needs of students. Students who may require special assistance in
emergency evacuations (i.e. fire, tornado, etc.) should contact the instructor as to the most appropriate
procedures to follow in such an emergency. Contact Disability Support Services at 298-2512 for additional
services.

Grades and class attendance: http://www.wiu.edu/policies/grdclatt.php

Code of student conduct: http://www.wiu.edu/policies/stucode.php

Policies of all kinds may be found at: http://www.wiu.edu/provost/policies/

Jan 21

Jan 26

Jan 28
Feb 2

Feb 4
Feb 9
Feb 10
Feb 16

Feb 18
Feb 23
Feb 25
Mar 2

Mar 4
Mar 9
Mar 11
Mar 16-20
Mar 30

Apr 1

Apr 6

Apr 8

Orbitals, bonding schemes, molecular orbitals, anti-bonding orbitals, hybridizations,

HOMO, LUMO HOMO-LUMO interactions lead to reactions, Resonance, resonance
energy,
Bonding in conjugated -systems, Aromaticity, aromatic compounds, ions, antiaromatic
compounds, Hckel rule etc. Oxidation states of carbon atoms in different functional
groups, oxidation level changes.
Oxidation levels continued, nomenclature of organic compounds-some common themes,
introduction to organic reactions. Summary
Brnsted and Lewis acids and bases, strength of acids, definition of pKa, pKa values,
factors effecting pKa values, bascity of amines, amidines and guanidines Acid-base
equilibria, amphoteric compounds, structural effects on acidity/basicity continued
Spectroscopic identification of organic molecules-Nuts and Bolts of IR, 1HNMR, 13CNMR
and mass spectrometry
Spectroscopic identification of organic molecules-Nuts and Bolts of IR, 1HNMR, 13CNMR
and mass spectrometry, cont.
Quiz 1 (30-40 minutes). Discussion of problems on quiz to follow
Curved arrow symbolism, heterolytic and homolytic bond cleavages, Heterolytic and
homolytic bond cleavages, use of fish-hook arrows, use of resonance arrows, Depiction of
reaction mechanisms
Guide to drawing mechanisms with curved arrows. Nucelophilic addition to carbonyl group
Nucelophilic addition to carbonyl group, Molecular orbital explanation for the reactivity of
carbonyl group, addition of H-, CN- and other nucleophiles to carbonyl group
Exam 1
Addition of oxygen nucleophiles to aldehyde and ketones, acetals as protecting groups.
Acid-base catalysis of O nucleophile addition, Organometallic reagents, organolithium
reagents, Grignard reagents, metal halogen exchange, C-C bond formation using
organometallic reagents
C-C bond formation using organometallic reagents ortholithiation, conjugate addition
Molecular orbitals control conjugate addition, conjugate addition or direct addition?
Kinetic and thermodynamic control of reactions, Amines react with aldehydes and ketones,
imines and enamines, reduction amination, and Witting reaction
Quiz 2 (30-40 minutes). Discussion of problems on quiz to follow
No Classes, Spring Break
Stereochemistry, enantiomers and chirality, configuration and conformation, enantiomers
and diastereomers, Configurational assignments, R and S nomenclature, optical activity,
resolution of enantiomers
Nucleophilic substitution mechanisms, classification of substrates, solvents, nature of Nu,
and leaving groups, rates of substitution reactions, Stereochemical consequences, special
leaving groups, Mitsunobu reaction
Conformational analysis, conformation of alkanes and cycloalkanes, conformational
energies, A values, ring strain, Conformations of disubstituted cyclohexanes, substitution on
cyclohexanes.
Conformations of cyclohexene, cyclohexanone and reactions on these ring systems
Elimination reactions, E1 reactions, stereoselctive and regioselective reactions, E1cB
mechanism Quiz 3 (30-40 minutes).

Apr 13

Apr 15

Apr 20
Apr 22
Apr 27
Apr 29
May 4
May 6
May 11-15

Molecular rearrangements during reactions. Electrophilic addition to alkenes,

stereochemistry of bromination and epoxidation-ring opening. Oxymerurationdemercuration, hydration of alkynes
Formation and reactions of enols, keto-enol equilibrium, MO picture of allyl anion and
enolate anion, stable enols, reactions with enolate anions/enols as intermediates, kinetic and
thermodynamic enolates
Condensation reactions, aldol, crossedaldol, Claisen, Dieckman condensation etc.
Conjugate addition to ,-unstaurated systems
Diels-Alder reaction, FMO description, regioselectivity in Diels-Alder reaction, Ozonolysis
and hydroxylation reaction as cycloaddition reactions
Quiz 4 (20-30 minutes). Discussion of problems on quiz
Aromatic electrophilic and nucleophilic substitution reactions, Mechanisms and synthesis of
derivatives, Benzyne mechanism for Nu substation on benzene systems
Exam 2
Review and Discussion of Exam 2
Final Examination will be held during this week