Survey of Organic Chemistry - The Cook Group @...

©2014 Gregory R Cook

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Survey of Organic Chemistry

CHEM 240: Spring 2014

Prof. Greg Cook

cook.chem.ndsu.nodak.edu/chem240

Monday, August 25, 14

http://cook.chem.ndsu.nodak.edu/chem341





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0Instructor

• Prof. Gregory R. Cook

• office: Ladd Hall 104G, Dunbar 360A

• office hours: Tu/Th 1:45 pm - 3:00 pm

• may vary - contact me

• phone: 231-7413

• email: [email protected]

• cook.chem.ndsu.nodak.edu/chem240

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mailto:[email protected]

mailto:[email protected]

http://cook.chem.ndsu.nodak.edu/chem341/

http://cook.chem.ndsu.nodak.edu/chem341/


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0A 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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0A little more about me

• I have run 9 marathons

• I have an organic vegetable garden

• I like to cook (what organic chemist doesn’t?)

• I make wine

• I want YOU to succeed in Organic Chemistry!

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O

OHOHLactic Acid





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0Web Page

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0Supplemental Instruction

• Optional sessions with an SI leader

• review material, answer questions, solve problems

• SI Leader: Sandeep Reddy

• [email protected]

• 1-7117

• SI Sessions TBA

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0More 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

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http://www.ndsu.edu/studentsuccess/tutoring_schedule/

http://www.ndsu.edu/studentsuccess/tutoring_schedule/


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0Textbook

• “Fundamentals of Organic Chemistry” 7th edition, John McMurry

• “Solutions Manual” 7th edition

• a molecular modeling set

• OWL on-line homeworkbundled with your bookincludes ebook

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0Grading

• 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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0Exams

• Midterm ExamsTue, Sep 23Tue, Oct 21Tue, Nov 25

• Final ExamThu, Nov 25 - 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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0Quizzes

• 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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0Homework

• OWL

• on-line homework system

• 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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0My 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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0OChem is NOT about rote memorization

• If you depend on rote memorization for passing classes, you will most likely not do well in 240

• 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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0Suggestions 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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0Flash Cards

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SUBSTRATES

REAGENTSPRODUCTS





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0Flash Cards

CH3

Br

KOH

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0Flash Cards

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KOH CH3 CH3+

minor major





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0Flash Cards

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CH3

Br

CH3 CH3+

minor major





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0Flash 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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0Come 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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0Tentative Schedule

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0OChem is a Blackboard Subject

• You must learn to drawchemical structures

• Practice drawing as muchas possible

• I will use technology to draw on the screen - let me know if I go too fast

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0Science

ChemistryAnalytical

Biochemistry

Organic

Inorganic

Physical

Theoretical

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0Chemistry

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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0Organic 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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0Organic 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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0Organic 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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0Biomolecules

• 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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0Man 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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0Modern 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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0Periodic Table

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0Periodic Table

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0Organic Molucues

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H

CH

HH

Methane

C

CC

C

CC

H

H

H

H

H

H

Benzene





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0Former 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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0Natural 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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Survey of Organic Chemistry - The Cook Group @...

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