cook.chem.ndsu.nodak.edu/chem240
Survey of Organic
Chemistry
CHEM 240: Spring 2014
Prof. Greg Cook
cook.chem.ndsu.nodak.edu/chem240
©2014 Gregory R Cook
Monday, August 25, 14
Instructor
cook.chem.ndsu.nodak.edu/chem240
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Prof. Gregory R. Cook
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office: Ladd Hall 104G, Dunbar 360A
office hours: Tu/Th 1:45 pm - 3:00 pm
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may vary - contact me
phone: 231-7413
email: gregory.cook@ndsu.edu
cook.chem.ndsu.nodak.edu/chem240
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©2014 Gregory R Cook
Monday, August 25, 14
cook.chem.ndsu.nodak.edu/chem240
A little about me
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I am a synthetic organic chemist
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Postdoctoral research at Stanford University
1994-1996
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Began my career at NDSU in August 1996
Graduated High School 1984, Plainwell, Michigan
physical sciences and music
Olivet College, BA 1988 - Chemistry and Math
Michigan State University, PhD 1994 - Organic
Chemistry
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©2014 Gregory R Cook
Monday, August 25, 14
cook.chem.ndsu.nodak.edu/chem240
A little more about me
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I have run 9 marathons
I have an organic vegetable garden
O
OH
OH
Lactic Acid
I like to cook (what organic chemist doesn’t?)
I make wine
I want YOU to succeed in Organic Chemistry!
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©2014 Gregory R Cook
Monday, August 25, 14
cook.chem.ndsu.nodak.edu/chem240
Web Page
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©2014 Gregory R Cook
Monday, August 25, 14
Supplemental Instruction
cook.chem.ndsu.nodak.edu/chem240
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Optional sessions with an SI leader
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review material, answer questions, solve
problems
SI Leader: Sandeep Reddy
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sandeepreddy.vemula@my.ndsu.edu
1-7117
SI Sessions TBA
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©2014 Gregory R Cook
Monday, August 25, 14
More Help
cook.chem.ndsu.nodak.edu/chem240
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Organic Lab TA office hours (check web page)
ACE Tutoring (free)
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http://www.ndsu.edu/studentsuccess/tutoring_schedule/
On-Line resources
Lecture Notes
Lecture Video Capture
Past Class Information
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©2014 Gregory R Cook
Monday, August 25, 14
cook.chem.ndsu.nodak.edu/chem240
Textbook
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“Fundamentals of Organic Chemistry” 7th
edition, John McMurry
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“Solutions Manual” 7th edition
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OWL on-line homework
bundled with your book
includes ebook
a molecular modeling set
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©2014 Gregory R Cook
Monday, August 25, 14
Grading
cook.chem.ndsu.nodak.edu/chem240
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Total of 500 points
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Three midterm exams
100 pts each, 60% of grade
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Comprehensive final exam
150 pts, 30% of grade
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Homework
50 pts, 10% of grade
A 85-100%
B 75-84%
C 60-74%
D 45-59%
F <45%
Unannounced quizzes may replace a low test
score
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©2014 Gregory R Cook
Monday, August 25, 14
cook.chem.ndsu.nodak.edu/chem240
Exams
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Midterm Exams
Tue, Sep 23
Tue, Oct 21
Tue, Nov 25
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Final Exam
Thu, Nov 25 - 10:30 am - 12:30 pm
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All hats, cell phones, PDAs and calculators, ipods
must remain stored away during exams
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Please bring a picture ID to the exam
Arrange to take the exam ahead of time if you
will be absent for an authorized school function
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©2014 Gregory R Cook
Monday, August 25, 14
cook.chem.ndsu.nodak.edu/chem240
Quizzes
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Six unannounced quizzes
21 pts each
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The best 5 out of 6 quizzes will be totaled
(105 pts maximum possible)
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Quiz total will replace your lowest exam if it is
higher
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Absolutely no make quizzes for any reason - must
be present to get points for quizzes
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©2014 Gregory R Cook
Monday, August 25, 14
Homework
cook.chem.ndsu.nodak.edu/chem240
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OWL
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on-line homework system
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Embedded directly in BlackBoard
or go to the Connect web site
free e-book
instructions to access OWL on web page
contact Dr. Cook
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©2014 Gregory R Cook
Monday, August 25, 14
My Philosophy on Organic Chemistry
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cook.chem.ndsu.nodak.edu/chem240
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It is not hard
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but - it IS hard work
Similar to a foreign language
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Vocabulary
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terms, structures,
functional groups
Grammar
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electronic properties, reactivity, reaction
mechanims
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©2014 Gregory R Cook
Monday, August 25, 14
cook.chem.ndsu.nodak.edu/chem240
OChem is NOT about rote memorization
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If you depend on rote memorization for passing
classes, you will most likely not do well in 240
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OChem is about problem solving
We will build a foundation of knowledge
I expect you to be able to reach beyond what you
have ‘memorized’ and make new connections
with this knowledge
H
H
O
H
+ H+
H
O
H
O
H
C
H
H
H
N
H
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©2014 Gregory R Cook
Monday, August 25, 14
cook.chem.ndsu.nodak.edu/chem240
Suggestions for Success
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Read ahead before coming to class
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Use the study guide but try to answer problems before
looking up the answers first
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Use flash cards to help learn structures, names and reactions
Ask questions
Rewrite your notes after every class
Do problems as many times as necessary to understand the
material
Find a friend or form a study group
Buy a set of molecular models
Utilize instructor, SI and TA office hours
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©2014 Gregory R Cook
Monday, August 25, 14
Flash Cards
cook.chem.ndsu.nodak.edu/chem240
REAGENTS
SUBSTRATES
PRODUCTS
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©2014 Gregory R Cook
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Flash Cards
cook.chem.ndsu.nodak.edu/chem240
CH3
KOH
Br
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©2014 Gregory R Cook
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Flash Cards
CH3
KOH
CH3
cook.chem.ndsu.nodak.edu/chem240
+
minor
major
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©2014 Gregory R Cook
Monday, August 25, 14
Flash Cards
CH3
CH3
CH3
cook.chem.ndsu.nodak.edu/chem240
+
Br
minor
major
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©2014 Gregory R Cook
Monday, August 25, 14
Flash Cards
H
CH3
CH3
KOH
CH3
cook.chem.ndsu.nodak.edu/chem240
+
Br
H
Base-
minor
major
E2 elimination
Other strong bases can be used (NaOH, NaNH2, KNH2, etc)
Most substituted alkene is the major product
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©2014 Gregory R Cook
Monday, August 25, 14
Come to Class
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Attendance vs Performance
cook.chem.ndsu.nodak.edu/chem240
Absent >2 (73 students)
Absent <3 (199 students)
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80
77
76
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74
74
71
70
68
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Exam 1
75
65
64
Exam 2
Exam 3
60
Final
Total
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©2014 Gregory R Cook
Monday, August 25, 14
cook.chem.ndsu.nodak.edu/chem240
Tentative Schedule
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©2014 Gregory R Cook
Monday, August 25, 14
cook.chem.ndsu.nodak.edu/chem240
OChem is a Blackboard Subject
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You must learn to draw
chemical structures
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Practice drawing as much
as possible
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I will use technology to draw on the screen - let
me know if I go too fast
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©2014 Gregory R Cook
Monday, August 25, 14
Science
Chemistry
cook.chem.ndsu.nodak.edu/chem240
Analytical
Physical
Organic
Theoretical
Biochemistry
Inorganic
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©2014 Gregory R Cook
Monday, August 25, 14
Chemistry
cook.chem.ndsu.nodak.edu/chem240
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Organic
Chemistry (Merriam-Webster)
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A science that deals with the composition,
structure, and properties of substances and with
the transformations they undergo
Organic (Webster 1913)
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Pertaining to, or denoting, any one of the large
series of substances which, in nature or origin,
are connected with vital processes
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©2014 Gregory R Cook
Monday, August 25, 14
Organic Chemistry
cook.chem.ndsu.nodak.edu/chem240
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18th Century
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Organic compounds obtained from Living
Organisms which posses the “vital force”
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It was thought that Organic Compounds could
not be made or manipulated without the
influence of this “vital force”
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©2014 Gregory R Cook
Monday, August 25, 14
Organic Chemistry
cook.chem.ndsu.nodak.edu/chem240
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19th Century
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Friederich Wöhler (1828) demonstrated for the
1st time that an “organic” molecule could be
synthesized from inorganic materials
H
H N H
O
heat
O C N
H
Ammonium Cyanate
H2N
C
NH2
Urea
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©2014 Gregory R Cook
Monday, August 25, 14
Organic Chemistry
cook.chem.ndsu.nodak.edu/chem240
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20th Century
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Urey and Miller (1952) showed that amino
acids, life’s building blocks, could be created
from simple materials
e-
CH4 +
NH3 +
H2O
O
H2N
C
H2
C
O
OH
+
H2N
CH
C
OH
CH3
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©2014 Gregory R Cook
Monday, August 25, 14
Biomolecules
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H OH
Carbohydrates / Sugars
HO
HO
cook.chem.ndsu.nodak.edu/chem240
H
H
O
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HO
OH
H
Glucose
OH
O O
Fats / Lipids
O O
O
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Amino Acids / Proteins
O
H2N
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O
H3N
OH
R
R
Heterocyclic Bases (DNA)
NH3
N
N
N
N
H
Monday, August 25, 14
NH2
O
N
N
N
N
H
Adenine
©2014 Gregory R Cook
O
H
NH2
O
H3C
N
N
O
H
Guanine
Cytosine
O
N
N
H
O
N
N
H
H
Thymine
Uracil
H
O
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Man Made (synthetic) Organic Molecules
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Polymers
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Ph
Ph
Ph
Ph
Ph
Ph
cook.chem.ndsu.nodak.edu/chem240
polystyrene
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Dyes
CH3
NaO2S
N N
N
CH3
methyl orange
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H
N
Pharmaceuticals
HO
CH3
O
acetaminophen
(Tylenol™)
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©2014 Gregory R Cook
Monday, August 25, 14
Modern Organic Chemistry
cook.chem.ndsu.nodak.edu/chem240
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The chemistry of carbon compounds
New, efficient, environmentally friendly tools to
construct organic compounds
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ORGANIC SYNTHESIS
make carbon-carbon bonds controlling all three
dimensions of the molecule
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©2014 Gregory R Cook
Monday, August 25, 14
cook.chem.ndsu.nodak.edu/chem240
Periodic Table
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©2014 Gregory R Cook
Monday, August 25, 14
cook.chem.ndsu.nodak.edu/chem240
Periodic Table
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©2014 Gregory R Cook
Monday, August 25, 14
Organic Molucues
H
C
H
H
cook.chem.ndsu.nodak.edu/chem240
H
Methane
H
H
H
C
C
C
C
C
C
H
H
H
Benzene
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©2014 Gregory R Cook
Monday, August 25, 14
Former NIH Director, Elias Zerhouni
cook.chem.ndsu.nodak.edu/chem240
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“One interesting result of the NIH Roadmap
development process came when we surveyed
scientists to find out what the stumbling blocks for
biological sciences were. The number one stumbling
block turned out to be synthetic organic
chemistry. I was shocked because I thought the
limiting factor was computational biology. So the NIH
Roadmap really changed my view of the importance of
chemistry and chemical engineering.”
~ Chemical & Engineering News
July 3, 2006
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©2014 Gregory R Cook
Monday, August 25, 14
Natural Products and Medicine
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Paclitaxel (Taxol™): anticancer compound
isolated from the bark of the pacific yew tree
AcO
PhCOHN
O
O
H
O
cook.chem.ndsu.nodak.edu/chem240
OH
OH
HO
O
AcO
PhOCO
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Epibatidine: analgesic compound isolated from
the skins of an ecuadorian tree frog
Cl
H
N
N
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©2014 Gregory R Cook
Monday, August 25, 14