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©2012 Gregory R Cook
Organic Chemistry I
CHEM 341: Spring 2012
Prof. Greg Cook
cook.chem.ndsu.nodak.edu/chem341
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©2012 Gregory R Cook
Instructor
• Prof. Gregory R. Cook
• office: Ladd Hall 104G, Dunbar 360A
• office hours: Tu/Th 10:30 am - 12:00 noon
• may vary - contact me
• phone: 231-7413
• email: [email protected]: drcookndsutwitter: drcookndsu
• cook.chem.ndsu.nodak.edu/chem341
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©2012 Gregory R Cook
A little about me
• I am a synthetic organic chemist
• Graduated High School 1984, Plainwell, Michiganphysical sciences and music
• Olivet College, BA 1988 - Chemistry and Math
• Michigan State University, PhD 1994 - Organic Chemistry
• Postdoctoral research at Stanford University 1994-1996
• Began my career at NDSU in August 1996
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©2012 Gregory R Cook
A little more about me
• I run marathons
• I have an organic vegetable garden
• I like to cook (what organic chemist doesn’t?)
• I make wine in my basement
• I want YOU to succeed in Organic Chemistry!
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O
OHOHLactic Acid
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©2012 Gregory R Cook
Web Page
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©2012 Gregory R Cook
Web Page
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©2012 Gregory R Cook
Supplemental Instruction
• Optional sessions with an SI leader
• review material, answer questions, solve problems
• SI Leader: Mike Kalinoski
• 612-597-6556
• Dunbar 152Mon 5:30-6:30Wed 4:30-5:30
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©2012 Gregory R Cook
More Help
• Organic Lab TA office hours (check web page)
• ACE Tutoring (free)
• http://www.ndsu.edu/studentsuccess/tutoring_schedule/
• On-Line resources
• Lecture Notes
• Lecture Video Capture
• Past Class Information (note: different text)
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©2012 Gregory R Cook
Textbook
• “Organic Chemistry” 8th edition, Francis A. Cary and Robert M. Giuliano
• “Solutions Manual for Organic Chemistry” 8th edition
• a molecular modeling set
• McGraw-Hill Connect withLearnSmart (on-line homework and e-book) - FREE
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©2012 Gregory R Cook
Grading
• Total of 500 points
• Three midterm exams100 pts each, 60% of grade
• Comprehensive final exam150 pts, 30% of grade
• Homework50 pts, 10% of grade
• Unannounced quizzes may replace a low test score
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A 85-100%B 75-84%C 60-74%D 45-59%F <45%
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©2012 Gregory R Cook
Exams
• Midterm ExamsFri, Feb 10Fri, Mar 9Mon, Apr 16
• Final ExamThu, May 10 - 10:30 am - 12:30 pm
• All hats, cell phones, PDAs and calculators, ipods must remain stored away during exams
• 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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©2012 Gregory R Cook
Quizzes
• Six unannounced quizzes21 pts each
• The best 5 out of 6 quizzes will be totaled(105 pts maximum possible)
• Quiz total will replace your lowest exam if it is higher
• Absolutely no make quizzes for any reason - must be present to get points for quizzes
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©2012 Gregory R Cook
Homework
• McGraw-Hill connect with LearnSmart
• on-line homework system
• Embedded directly in BlackBoard
• or go to the Connect web site
• free e-book
• Carey and Smith
• CONNECT CODE contact Dr. Cook
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©2012 Gregory R Cook
My Philosophy on Organic Chemistry
• It is not hard
• but - it IS hard work
• Similar to a foreign language
• Vocabulary
• terms, structures,functional groups
• Grammar
• electronic properties, reactivity, reaction mechanims
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©2012 Gregory R Cook
OChem is NOT about rote memorization
• If you depend on rote memorization for passing classes, you will most likely not do well in 341
• 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
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HO
H+ H+ H
OH
H
CO
H H HNH
H
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©2012 Gregory R Cook
Suggestions for Success
• Read ahead before coming to class
• Ask questions
• Rewrite your notes after every class
• Do problems as many times as necessary to understand the material
• Use the study guide but try to answer problems before looking up the answers first
• Use flash cards to help learn structures, names and reactions
• 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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©2012 Gregory R Cook
Flash Cards
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SUBSTRATES
REAGENTSPRODUCTS
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©2012 Gregory R Cook
Flash Cards
CH3
Br
KOH
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©2012 Gregory R Cook
Flash Cards
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KOH CH3 CH3+
minor major
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©2012 Gregory R Cook
Flash Cards
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CH3
Br
CH3 CH3+
minor major
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©2012 Gregory R Cook
Flash Cards
20
CH3
Br
KOH CH3 CH3+
minor majorH
H
Base-E2 eliminationOther strong bases can be used (NaOH, NaNH2, KNH2, etc)Most substituted alkene is the major product
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©2012 Gregory R Cook
Come to Class
• Attendance vs Performance
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60
65
70
75
80
76
71
6564
68
80
77
74 74
77
Exam 1 Exam 2 Exam 3 Final Total
Absent >2 (73 students) Absent <3 (199 students)
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©2012 Gregory R Cook
Tentative Schedule
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©2012 Gregory R Cook
OChem is a Blackboard Subject
• You must learn to drawchemical structures
• Practice drawing as muchas possible
• I have typically taughtthis class in StevensAuditorium with the blackboards
• Not possible in this room
• I will use technology to draw on the screen - let me know if I go too fast
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©2012 Gregory R Cook
Science
ChemistryAnalytical
Biochemistry
Organic
Inorganic
Physical
Theoretical
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©2012 Gregory R Cook
Chemistry
Organic• Chemistry (Merriam-Webster)
• A science that deals with the composition, structure, and properties of substances and with the transformations they undergo
• Organic (Webster 1913)
• 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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©2012 Gregory R Cook
Organic Chemistry
• 18th Century
• Organic compounds obtained from Living Organisms which posses the “vital force”
• It was thought that Organic Compounds could not be made or manipulated without the influence of this “vital force”
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©2012 Gregory R Cook
Organic Chemistry
• 19th Century
• Friederich Wöhler (1828) demonstrated for the 1st time that an “organic” molecule could be synthesized from inorganic materials
NH
HH
H O C N
Ammonium Cyanate
heat
H2NC
NH2
O
Urea
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©2012 Gregory R Cook
Organic Chemistry
• 20th Century
• Urey and Miller (1952) showed that amino acids, life’s building blocks, could be created from simple materials
e-CH4 NH3 H2O+ +
CH2
COH
H2NO
CHCOH
H2NO
CH3
+
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©2012 Gregory R Cook
Biomolecules
• Carbohydrates / Sugars
• Fats / Lipids
• Amino Acids / Proteins
• Heterocyclic Bases (DNA)
OH
HO
H
HOH
HOHH OH
OH
Glucose
O
O
O
O
O
O
H2NO
OHR
H3NO
OR
N
NN
N
NH3
HN
NN
N
O
H
H
NH2 N
N
NH2
OH
N
N
OH
O
H3C
H
Guanine ThymineCytosineAdenine
N
N
OH
OH
Uracil 29
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©2012 Gregory R Cook
Man Made (synthetic) Organic Molecules
• Polymers
• Dyes
• Pharmaceuticals
**
Ph Ph Ph Ph Ph Phpolystyrene
N NNaO2S NCH3
CH3methyl orange
acetaminophen(Tylenol™)
HO
HN CH3
O
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©2012 Gregory R Cook
Modern Organic Chemistry
• The chemistry of carbon compounds
• New, efficient, environmentally friendly tools to construct organic compounds
• ORGANIC SYNTHESIS
• make carbon-carbon bonds controlling all three dimensions of the molecule
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©2012 Gregory R Cook
Periodic Table
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©2012 Gregory R Cook
Periodic Table
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©2012 Gregory R Cook
Organic Molucues
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H
CH
HH
Methane
C
CC
C
CC
H
H
H
H
H
H
Benzene
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©2012 Gregory R Cook
Former NIH Director, Elias Zerhouni
• “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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©2012 Gregory R Cook
Natural Products and Medicine
• Paclitaxel (Taxol™): anticancer compound isolated from the bark of the pacific yew tree
• Epibatidine: analgesic compound isolated from the skins of an ecuadorian tree frog
OHO
AcO OH
AcO
H
PhOCO
O
O
PhCOHN
OH
O
HN
N
Cl
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