Introduction to CBE-2206Industrial Organic Chemistry 1
• Organic Chemistry-the chemistry of carbon
compounds
• CBE 2206-Industrial Organic Chemistry deals
with understanding the basic principles of
organic chemistry, and applying them to
analytical instruments and simple industrial
processes with a focus on sustainability
Instructor Info.
Prof. Paul A. Charpentier
-Call me Paul
pcharpen@uwo.ca
Office Hours: CMLP 3333-Open, come anytime.
Course Web page:
OWL
Text: “Organic Chemistry” Wade 9th Edition
Course Outline- Prerequisites
-Chemistry 1024A/B or Chemistry 1050 or the former Chemistry
1020 or 023. Open only to students registered in the Faculty of
Engineering.
Class Schedule
• Monday →9:30-11:30 am, FNB 3210
• Thursday →10:30-11:30, SEB 2100
Course Materials / Lab Manuals
Required Course Notes-On Brightspace
Required Laboratory Manual-On Brightspace
UWO Course Website
Course materials such as course outline, schedules
(deadlines), and announcements , etc. are posted on the
Brightspace course website :
Notices
Students are responsible for regularly checking Brightspace.
Evaluation
Laboratory (and pre-labs)
Mid-term exam (2 hrs)
(tentative Oct. 27)
Assignments
Quizzes (4)
Participation
Final Examination-Dec
25 %
20 %
Optional
15%
5%
35 %
100%
Course Textbook
L.G. Wade Jr., “Organic Chemistry”, 9th
edition, Prentice-Hall, 2017.
• Textbook-useful
https://www.pearson.com/en-ca/subject-catalog/p/organicchemistry/P200000007007/9780135213728
Assignments
Text problems will be assigned with dates
given out, then solutions provided.
Attendance
→Attendance in all labs is mandatory.
→On the recommendation of the Department concerned, and with the
permission of the Dean, the student will be excluded from taking the regular
examination in the course.
Sickness
• Talk to instructor if anything chronic that
effects performance
• For tests and labs get doctors note and bring
to either the UG office in TEB 477 As Soon
As Possible.
• Services for Students with Disabilities (SSD)
at 661-2111 x 82147 for any specific question
regarding an accommodation.
Lab Schedule
CBE Students
Section 2) Weds→ 1:30-4:30pm
Section 3) Tues 9:30-12:30
Section 4) Friday → 9:30-12:30
Section 5) Thurs → 3:30-6:30
Section 6) Tues → 12:30-3:30
→All labs in SEB 1082
Lab Technician: tba
Laboratories-Bench Scale
1) FRACTIONATION DISTILLATION AND ANALYSIS
OF HYDROCARBONS USING GAS
CHROMATOGRAPHY (GC)
2) PURIFICATION OF ORGANIC COMPOUNDS BY
EXTRACTION AND RECRYSTALLIZATION
3) SN1 AND SN2 REACTIONS
Lab 1- (3 weeks Lab, Labs on Thursday Sept. 21, Friday Sept 22, and Thurs Sept
28, Fri. Sept 29, Thurs Oct. 5)
Lead TA and Marking: -Rasoul Salami
Homecoming –Sept 23
Lab 2: “Purification of Organic Compounds by Extraction and
Recrystallization”
2 week lab on Thurs Oct. 19, Fri. Oct. 20, Thurs, Oct. 26 and Friday Oct. 27
Lead TA and Marking: Johana Amaya
Lab 3: “SN1 and SN2 Reactions”
(2 week Lab)
Starts Thursday Nov. 9, Fri. Nov. 10, Thurs Nov. 16, Fri. Nov. 17)
Lead TA and Marking: Fatemeh Dodangeh
No labs the week of Mon. Oct. 9 (Thanksgiving Holiday) and
Mon. Oct. 30 (Fall Reading Week)
Skills Learned in Labs
• familiar with basic laboratory equipment
(glassware, titration, heating units, etc.)
• familiar with spectroscopic instrumentation
(FTIR and UV)
• familiar with chromatography (GC)
• gain experience with basic laboratory
techniques such as distillation, column
chromatography, re-crystallization
Labs-Safety
→Labs will start week of September 18th.
→Consult the lab schedule on OWL for the dates of particular experiments.
→Students will form groups of 2 to perform the experiments.
→Lab reports will be written up by both group members.
→**You must have safety goggles and a laboratory coat or will not be allowed into
the laboratory and will receive a mark of zero for that particular lab.
→Students must read the lab manual and complete the pre-lab questions prior to
attending the lab.
2) Students must attend all labs, turn in all laboratory reports, and achieve a
passing grade in the laboratory component to pass this course.
If you miss a lab for medical or compassionate reasons, you must notify the instructor
immediately to make arrangements to make up the lab and provide adequate
documentation for your absence. Failure to provide the adequate documentation
will result in a mark of 0.
CBE 2206 Course Description
• This course deals with the fundamental
principles governing the structure and
reactivity of organic molecules.
• Organic molecules form the basis of industrial
chemical and environmental processes.
• The laboratory section focuses on bench
scale processing of organic chemical
products, and the use of modern instruments
for analysis of organic materials and
monitoring of chemical processes.
Final Exam Text Coverage
Text: Wade 9th Edition
BASIC CONCEPTS FOR ORGANIC CHEMISTRY
Intro. and Review
Ch. 1-All
Structure and Properties
Ch. 2-All
Alkanes
Ch. 3-All
Chemical Reactions
Ch. 4-All
Stereochemistry
Ch. 5: Sections 1-8, 10-13, 15,16
FUNCTIONAL GROUPS SECTION
Alkyl Halides
Ch. 6: Sections 1-14,16-21
Alkenes
Ch. 7: 1-2, 4-11
Ch. 8: Sections 1-4, 8, 10, 12-13,
15b, 16
Alkynes
Ch. 9 1-8 (except 9-7b), 9(a,b,d,e)
1.2 Principles of Atomic Structure
Structure of the Atom
Orbitals
• Electrons have properties of both particles and waves
• wave equation provides a probability plot of finding an
electron at any particular place
• orbital defn- region in space where an electron is likely
to be found
• think of electron in an orbital as being smeared to form
a cloud
• different types of orbitals with different sizes and
shapes (s,p,d, f)
• energy of electron determines which orbital type it is in
→ the shape of the cloud is the orbital where it’s density is
highest at highest probability of finding electron
1s Atomic Orbital
2s Atomic Orbital
2p Atomic Orbital
Electronic Configuration of Atoms
• Aufbau principal-"fill-up" electrons into lowest
energy orbitals first
• Pauli exlusion principle-only 2 electrons are
put in each orbital
• Valence electrons are in the outermost shell
• Group number in Periodic Table corresponds
to the number of valence electrons
Valence Electrons
Bond Formation
• octet rule- atoms are most stable when
the outer shell is full corresponding to
the nearest noble gas configuration
→ He, Ne, Ar
• Filled shell is 8 electrons for elements
in the 2nd row of Periodic Table
Ionic Bonding
• ionic bond→electrostatic attraction
between opp. charged ions (i.e. salts)
• results from a transfer of electrons
Covalent Bonding
• results from a sharing of electrons
• typical of the compounds of carbon
• most important bond for organic
chemistry
H• + •H →H2
Lewis Structures
• each valence electron is represented as a dot
• a bonding pair of electrons is represented as
a dash
Cl
Cl
Cl
Cl
Cl
Cl
Multiple Bonds
Polarities of Bonds and Molecules
• polarity of bonds can lead to polarity of
molecules
• polarity affects a compounds chemical
properties i.e. reactivity and physical
properties such as MP, BP, and solubility
• a molecule is polar if the center of negative
charge does not coincide with the center of
positive charge
Electronegativity and Polarity of Bonds
• in covalent bonds, sharing of electrons is not
equal
between
atoms
of
different
electronegativity
→ hence polarity or polar bond
• most electronegative elements in upper right
hand side of periodic table
• F > O > Cl,N > Br > C,H
for electronegativity
Electronegativities of Elements
Formal Charges
• Provide a method for keeping track of charges on elements
• Formal charge =
grp. number -nonbond. electrons - 1/2(shared elect.)
H
H
For C = 4 - 0 -1/2 (8) = 0
C
H
H
H
H
H
N
H
B
H
H
For
N = 5 - 0 -1/2 (8) = 1
Ionic Structures
• Organic structures can contain ionic
bonds
H
e.g. CH3ONa
=
H
C
H
CH3COONa
Na
O
O
H
C
H
H
C
O
Na
Resonance
• Some molecules require >1 Lewis
Structure
• resonance structures→2 or more
structures of a molecule where the
atoms do not move, but the electrons do
• the charge is said to be “delocalized”
over the relevant atoms
Resonance
O 1/2 H
C
H
H
O 1/2 -
Structural Formulas
Molecular and Empirical Formulas
• Molecular formula gives the number of atoms
of each element
• Molecular formula of ethanol is C2H6O
• Condensed structural formula is CH3CH2OH
• Line Formula is
OH
• Get emperical formula from elemental analysis,
e.g. gives C2H6O, then molecular weight gives
you the molecular formula
1-12 Wave Properties of Electrons in
Orbitals
• quantum mechanics-describes the motion of
an electron in terms of its energy
• must solve the Schrodinger equation or wave
equation
• solutions from the Schrodinger equation are
called “wave functions” 
• widely accepted as the best theoretical
method to understand atomic and molecular
structure
Molecular Orbitals
• When orbitals on different atoms interact,
they overlap and hybridize forming molecular
orbitals (MO's)
• shapes of MO’s are related to the shapes of
the atomic orbitals
• assumed that each pair of electrons is
localized near two nuclei
• why do atoms form molecules?
→more energetically stable –each electron is
attracted by 2 positive nuclei instead of one
Recall- 1s Atomic Orbital
2s Atomic Orbital
2p Atomic Orbital
Molecular Orbital for H2- Sigma Bond
Pi Bonds
Pi Bonding
Hybridization
s-s
3
sp
sp2
s-p
'hybrid'
C
sp
H H
sp Hybridization
Forming BeH2-sp Hybridization
sp2 Hybridization
sp3 Hybridization
i.e. Tetrahedron Shape
Unshared Pairs of Electrons, e.g. NH3
sp3
2p
2s
1s
1s
H
N
H
H
Unshared Pairs of Electrons, e.g. H2O
2s
sp3
2p
1s
1s
H
O
H
Summary of Hybridization and Geometry
Hybrid
Orbitals
Hybridization
Geometry
Bond Angle
2
s + p = sp
linear
180
3
s + p+ p = sp2
trigonal
120
4
s+p+p+p=
sp3
tetrahedral
109.5
Drawing 3D Structures
H
H
H
C
H
C
H
H
H
H
H
H
C
H
C
H
Bond Rotation
Double Bonds
Ethylene = 1 sigma + 1 pi bond
-double and triple bonds are rigid i.e. do NOT rotate
Triple Bonds
Acetylene (Ethyne) = 1 sigma + 2 pi bonds
Isomerism
-structural isomers differ in their bonding
sequence
H3C
H3C
CH2
CH2
CH2
CH3
H3C
CH3
CH
CH2
CH3
H3C
C
CH3
-stereo isomers differ in the orientation of the atoms in
space
H3C
CH3
C
H
H3C
C
H
C
H
H
C
CH3
CH3