SYLLABUS

Organic Chemistry II

CHEM254

 

Spring 2006

 

                                                                       

Instructor: J. Brent Friesen

Office: 304 Science Building

Phone: 524-6972

Email: jbfriesen@dom.edu

Webpage: http://domin.dom.edu/faculty/jbfriesen/

 

Class Format:

 

Lecture: Monday & Wednesday 10:30-11:20; Friday 10:30-12:20

Lab: Section I – Monday 1:30-4:30       Section II - Wednesday 1:30-4:30      

 

Attendance is MANDATORY at all class meetings

 

Required Materials:

 

Organic Chemistry 6th ed. 2006

By L.G. Wade, Pearson Prentice Hall

 

Duplicate Page Lab Notebook: Hayden-McNeil specialty products, Jones and Bartlett Publishers, or W.H. Freeman.

 

Protective Safety Goggles. “Goggles” not “glasses.”

 

Many handouts will be distributed in this course.

You will need a three-ring binder to organize them.

 

Supplemental Materials: (on reserve at the library)

 

Solutions Manual for Organic Chemistry: 6th ed

J.W. Simek & L.G.Wade, Pearson Prentice Hall

 

The Organic Chem Lab Survival Manual, by J.W. Zubrick,

John Wiley & Sons, Inc. (The 6th editions is most recent but the 4th and 5th are fine.)

 

Preparing for Your ACS Examination in Chemistry: The Official Guide,

ACS Division of Education, 2002

 

Websites:

 

http://domin.dom.edu/faculty/jbfriesen/chem254.htm

http://www.prenhall.com/divisions/esm/app/wade/index.html

http://blackboard.dom.edu
Course Description:

 

Chemistry is often characterized as the "central" science because of the many connections to other fields. Organic chemistry is the study of compounds that originate in living systems; therefore, it is recognized as an essential ingredient in the education of scientists in a wide range of fields, particularly the life sciences. This course will be the second semester of an overview of organic chemistry. The major foci of the course are:

1)      to understand the reactivity of organic compounds,

2)      to appreciate the role of structure in chemical identity and

3)      to apply reactivity and structure to the understanding of organic molecule function.

 

This course is challenging and fast-paced. This means that a lot of material will be covered in a relatively short period of time. The crucial importance of organic chemistry dictates the pace. This course involves cumulative, vertical learning. That which is learned in the first and subsequent weeks is needed continuously, throughout the year, even into the last week!

 

Course Objectives:

 

1)      Think Molecular! Molecules are interesting and important. Molecular thinking helps us understand the way the natural world works.

 

2)      Continue gaining familiarity with the language of organic chemistry. Every discipline has its vocabulary and terminology associated with it. Organic chemistry has much representational language in the form of functional groups, molecular structural formulas and 3-D representations.

 

3)      Understand and apply mechanism-based chemical reactivity. Much of what we do involves using electron movement to explain and predict chemical reactivity.

 

4)      Synthesis and spectroscopy problem solving is a means of improving your problem-solving skills relating to real-world problems in the chemical sciences.

 

5)      Practice basic experimental techniques and appreciate experimental design with interpretation of results.

 

Text Box: “But the wisdom that comes from heaven is first of all pure;
Then peace loving, considerate, submissive, full of mercy and good fruit, impartial and sincere. Peacemakers who sow in peace raise a harvest of righteousness.” 
James 3:17,18
Academic Integrity Policy

 

Students of the university must conduct themselves in accordance with the highest standards of academic honesty and integrity. Failure to maintain academic integrity will not be tolerated. The following definitions are provided for understanding and clarity.

 

Definitions of Plagiarism, Cheating and Academic Dishonesty

 

Student plagiarism is the deliberate presentation of the writing or thinking of another as the student’s own. In written or oral work a student may make fair use of quotations, ideas, images, etc., that appear in others’ work only if the student gives appropriate credit to the original authors, thinkers, owners or creators of that work. This includes material found on the internet and in electronic databases.

 

Cheating entails the use of unauthorized or prohibited aid in accomplishing assigned academic tasks. Obtaining unauthorized help on examinations, using prohibited notes on closed-note examinations, and depending on others for writing of essays or the creation of other assigned work are all forms of cheating.

 

Academic dishonesty may also include other acts intended to misrepresent the authorship of academic work. Deliberate acts threatening the integrity of library materials or the smooth operation of laboratories are among possible acts of academic dishonesty.

 

Sanctions for Violations of Academic Integrity

 

Text Box: “The world looks so different after learning science. For example, trees are made of air, primarily. When they are burned, they go back to air, and in the flaming heat is released the flaming heat of the sun which was bound in to convert the air into tree. [A]nd in the ash is the small remnant of the part which did not come from air, that came from the solid earth, instead. These are beautiful things, and the content of science is wonderfully full of them. They are very inspiring, and they can be used to inspire others.”
Richard Feynman 
If an instructor determines that a student has violated the academic integrity policy, the instructor may choose to impose a sanction, ranging from refusal to accept a work product to a grade “F” for the assignment to a grade “F” for the course. When a sanction has been imposed, the instructor will inform the student in writing. The instructor must also inform the student that she/he has the right to appeal this sanction, and refer the student to the Academic Appeals Process described in the Bulletin of the Rosary College of Arts and Sciences. The instructor will send a copy of this letter to the Dean of the Rosary College of Arts and Sciences. The Dean will note whether a student has committed multiple violations of the academic integrity policy over time, and in such cases the Dean may institute a process leading to possible further sanctions, including suspension or expulsion from the university…


Tentative Course Calendar:

 

Date

Topic  

Text Selection

1/13

Syllabus, MRI

13-14

1/13

NMR: spin-spin splitting

13-8 & 13-9

1/16

NMR: C-13 NMR

13-12 & 13-13

1/18

NMR Problem solving

 

1/20

Alcohols: Intro, Naming & Properties

10-1 to 10-6

1/20

Preparation of Alcohols

10-7 to 10-11

1/23

Reactions of Alcohols

11-1 to 11-5

1/25

Reactions of Alcohols

11-6 to 11-10

1/27

Synthesis

 

1/27

Synthesis

 

1/30

Ethers: Intro, Naming, Properties

14-1 to 14-4

2/1

Synthesis of Ethers

14-5 to 14-8

2/3

Reactions of Ethers

14-11 to 14-15

2/3

Synthesis

 

2/6

EXAM I

Chapters 10, 11, 13, 14

2/8

UV/vis spectroscopy: The Chemistry of Color

15-13

2/10

Conjugated Systems

15-1 to 15-3

2/10

1,2 and 1,4 Additions

15-4 to 15-10

2/13

Diels-Alder Cycloadditions

15-11

2/15

Diels-Alder Cycloadditions

 

2/17

Pericyclic Reactions

15-12

2/17

 

 

2/20

Aromatic Compounds: Benzene

16-1 to 16-5

2/22

Aromaticity

16-6 to 16-12

2/24

Nomenclature

16-13 & 16-14

2/24

Spectroscopy

16-15

2/27

 

 

3/01

EXAM II

Chapters 15 & 16

3/03

Reactions of Aromatic Compounds

17-1 to 17-5

3/03

Activation and Directing

17-6 to 17-9

3/06

Spring Break

 

3/08

Spring Break

 

3/10

Spring Break

 

3/10

Spring Break

 

3/13

Activation and Directing

17-10 to 17-13

3/15

Side Chain Reactions

17-14 & 17-15

3/17

Ketones and Aldehydes: Nomenclature

18-1 to 18-6

3/17

Ketone and Aldehyde Preparation

18-7 to 18-11

3/20

Reactions of Ketones and Aldehydes

18-12 to 18-19

3/22

Reactions of Ketones and Aldehydes

18-20 to 18-21

3/24

Synthesis

 

3/24

Amines: Nomenclature & Spectroscopy

19-1 to 19-9

3/27

Preparation of Amines

19-10 to 19-13

3/29

Reactions of Amines

19-15 to 19-21

3/31

 

 

3/31

EXAM III

Chapters 17, 18, 19

4/03

Carboxylic Acids & Derivatives

20-1 to 20-5 & 21-1 to 21-3

4/05

Carboxylic Acids & Derivatives: spectroscopy

20-7 & 21-4

4/07

Carboxylic Acids & Derivatives: Preparation

20-8 to 20-15

4/07

Carboxylic Acids & Derivatives: Reactions

21-5 to 21-12

4/10

 

 

4/12

 

 

4/14

Good Friday

 

4/14

Good Friday

 

4/17

Condensations and α substitutions

Chapter 22

4/19

 

 

4/21

 

 

4/21

EXAM IV

Chapter 20, 21 & 22

4/24

Mass Spectrometry

12-13 to 12-15

4/26

 

 

4/28

Prepare for final exam

 

4/28

 

 

5/??

FINAL EXAM

 


Grading for Organic Chemistry :

The grade for this course consists of both the lecture grade as well as the laboratory grade. The distribution of the grades will be:

 

Midterm Exams (4)

100 points each

40%

 

Quizzes

Units of 5 points

9%

Homework Assignments (Best 14)

15 points each

21%

 

Laboratory

200 points total

20%

Final Exam (ACS standardized exam)

100 points

10%

 

                                                                                               

Letter Grade Assignments:

 

 

100  >  A  >  92%

92  >  A-  >  90

90 >  B+  > 88

88  >  B  >  84

84  >  B-  >  82

82  >  C+  >  80

80  >  C  >  76

76  >  C-  >  74

 

74  >  D  >  65

 

 

Attendance:

Class attendance is an essential component of this course. If you are absent you cannot receive the points designated for the in-class quiz. You will lose 2 points for every 10 minutes that you are absent during regular class time. Consistently missing class will not be tolerated. More than 8 missed class sessions will result in an “F” grade for the course.

 

Lecture and Reading:

The lecture time will be spent introducing new concepts, solving sample problems and going over “problems areas” that have been identified from graded homework and quizzes. Preparation for lecture is essential. The current text is very organized and readable. Make use of the many diagrams in the text, Organic Chemistry is a very visual discipline. Follow the problems solved in the text. Reading the book before lecture will help you assimilate new concepts easier and guide you to pose key questions about the material. Bring all graded papers and work-in-progress to class. Do not hesitate to ask questions about the worksheet you are currently doing.

 

Quizzes:

There will be at least 18 five-point in-class quizzes. The format of the quizzes will vary. You will be allowed to drop quiz problems if more than 18 are given. There are no make­up quizzes. If a quiz is missed, it will be counted as the dropped score. Quizzes will be 5-10 minutes in length. These quizzes are designed 1) to help you keep you up to date in the class, 2) to encourage you to do practice problems, and 3) to allow you to become used to my style of questions.

 


Homework:

The only way to learn organic chemistry is to do problems. Thus, there will be homework worksheets due regularly (about one each week). All homework sets will be collected and graded. Please do your homework problems as they are covered in class. Be sure to raise pertinent questions in class before homework problems are due. This effort should help you to keep up with the material and come to class with questions about the material that is being covered. Be forewarned these problems are a minimum requirement! You should attempt to solve many of the chapter exercises, end-of-chapter problems, and web page exercises.

 

Hand your homework in at the beginning of the class period the day it is due. Any homework handed in after it is due will receive a one-point deduction. Any late homework handed in after the homework has been graded and handed back will receive a one-letter-grade-deduction on the corrected score. For example: a late homework with a 14/15 (93%) score will be recorded as 13/15 (87%). Extra credit will not be accepted on late work.

 

Consistently handing in late homework will not be tolerated. In addition to the above penalties no more than two late assignments will be graded.

 

No late work will be accepted after the Final Exam has been completed.

 

The student is responsible for the successful receipt of any electronically submitted materials.

 

Exams:

All examinations will be cumulative with the emphasis on the newest material. I will be glad to schedule a review before any of the exams if the interest is there. Exams must be taken the day they are offered. No make-up exams will be offered until finals week.

 

Text Box: “We (the undivided divinity that operates within us) have dreamed the world. We have dreamed it resistant, mysterious, visible, ubiquitous in space and firm in time; but we have allowed into its architecture tenuous and eternal interstices of unreason to let us understand that it is false.”
Jorge Luis Borges, 1932
Final Exam:
The Final Exam will be the American Chemical Society standardized exam. This exam allows us to compare the performance of Dominican students with other students around the nation. The exam consists of 70 multiple choice questions and takes 2 hours to complete. Copies of the official preparation guide for the exam will be available on reserve. Copies can be ordered from the ACS website: http://www3.uwm.edu/dept/chemexams/ 

 


Encouragement and Advice:

 

The New Year is an ideal time to renew your efforts to develop good study habits. Here are some gleanings I have picked up from various places:

 

What SOME do:

What YOU should do:

 

Save money by not buying the textbook. 

Use the textbook to your advantage.

Copy answers from the study guide and your fellow students.

Try to do all assigned problems by yourself before seeking help.

Stick your class notes in a folder and forget about them.

Reorganized and shorten your notes.

 

Ignore examples.

Copy down (and understand) all examples

 

Stick your corrected homework in a folder and forget about it.

Review and rework homework questions.

 

Memorize what you don’t understand.

Insist on understanding

(i.e. memorize as little as possible)

Cram the night before the test.

Study daily; review each night.

Be a “lone ranger.”

Seek help.

 

How to Succeed in Organic Chemistry

1.                                          Never get behind, never get behind, never get behind. Get the picture? There is an enormous amount of material to be learned, and it can only be accomplished through very disciplined study. Get behind and you're sunk. You can't learn it all the night before the exam.

2.                                          Strive to understand, not just memorize the material. There is a fair amount of memorization that you will have to do, but it's much easier if you understand the material first.

3.                                          Practice, practice, practice. Do all of the suggested problems in the book. Do the old quizzes and exams.

4.                                          Come to class every day. Successful students rely more on their lecture notes than on the text, and remember, it's the person giving the lectures, not the author of the text, that is writing the exams.

5.                                          Do the readings and the suggested problems in the Study Guides before coming to class. The lecture will be much easier to follow and comprehend if you have already looked at the material. No doubt you will have questions or difficulties, but you can be prepared to have them cleared up in lecture. That's a lot better than coming into class clueless - I can guarantee that then you'll be lost for sure.

6.                                          Make a "roadmap" of the ground you've already covered, especially reactions. Keep the roadmap updated.

           Still interested? Try - http://chemistry.boisestate.edu/rbanks/StudySkills.html