ORGANIC CHEMISTRY

      CHEM 211B (Lec. & Lab.)

FALL 2009

Fullerton College

 

                                                Lec.     M W 1:30 – 2:50 pm. (Rm. 402T)

                                                Lab.     MW   3:00 - 5:50 p.m. (Rm. 415T)

                                                           

 

Instructor:                   Dr. Tilahun Yimenu

Office:                         2023-R4

Telephone:                  (714) 992-7442, Email:  tyimenu@fullcoll.edu

Office Hours:              T R 11:00-12:30 / T R 5:30-6:00 p.m. / M W 12:45-1:30 p.m.

Text books-                - Brown, Foote, and Iverson, Organic Chemistry, 5th Ed.

- Iverso and Iverson, Student Study guide and Solutions Manual

                                    - Williamson, Kenneth L., Macroscale and Microscale

  Organic Experiments, 5th Ed.

                                    - Lab Safety Packet

Recommended Collateral Reading:

- Wade, L. G. Jr., Organic Chemistry, 4Th Ed.

                                    - Ege, Seyhan, Organic Chemistry, 4th Ed.

- Solomons, T.W. Graham, Organic Chemistry, 5th Ed.

- R.T. Morrison and R.N. Boyd, Organic Chemistry, 5th Ed.

- S.H. Pine, Organic Chemistry, 5th Ed.

 

Additional Supplies:   -Framework Molecular Model Set.

                                    -Case hardened goggles.

 

Prerequisites:             CHEM. 211A

 

Reading and Problem Assignments:

 

It is important to complete reading before class to maximize benefit from the lecture.  Your success in this course will be based to a large extent on how well you grasped important principles and how well you are able to solve problems.  If your textbook is not clear on some topics refer to other textbooks.  Additional textbooks will be on reserve in a limited loan section of the library.  In addition to this, an on-line resource center is available at http://now.brookscole.com/bfi4.  Problem assignments will be made periodically through the semester.   Some test questions will be taken from problem assignments, lecture and the reading material.  You should solve as many additional problems as time permits.  Remember

 

                                    I hear and I forget

                                    I see and I remember

                                    I do and I understand

                                                            Chinese Proverb


 

Tentative Lecture Schedule

 

Week              Topics                                                                                Chapter

1                      Review                                                                                     9,10

                                                                                                                       

2                      Ethers, Sulfides, and Epoxides                                                  11

 

3                      Organometallic Compounds                                                      15

 

4,5                   Aldehydes and Ketones                                                            16

 

6                      Carboxylic Acids                                                                      17

 

7                      Functional Derivatives of Carboxylic Acids                                18

 

8                      Enolate Anions and Enamines                                                    19

 

9                      Conjugated Systems                                                                 20

 

10                    Benzene and the Concept of Aromaticity                                   21

 

11                    Reactions of Benzene and Its Derivatives                                   22

 

12, 13              Amines                                                                                     23

 

13, 14              Carbon-Carbon Bond Formation and Synthesis                        24

 

15,16               Carbohydrates                                                                          25

 

16,17               Amino Acids and Proteins                                                         27

 

 


 

Grades and Distribution of Points

 

                        Course grade will be based primarily on the total points accumulated as follows:

                                                                                                                                                                                                            Points

 

                                 Examinations (4)                                                              300

                                 Final Examination                                                             200

                                 Special Assignments                                                         100

                                 Laboratory                                                                       200

                                          Total                                                                       800

 

                                 Final Exam - Wednesday, Dec. 9, 2009, 1:00 – 2:50 p.m.

 

                                          85.0 - 100%      A

                                          75.0 -84.9%      B

                                          60.0 - 74.9%     C

                                          50.0 - 59.9%     D

                                          Below 50%        F

 

There are no make-up exams.  Any missed exam is considered a dropped exam, regardless of the reasons.  A student planning to miss a second exam for serious reasons must consult with the instructor.  The instructor may decide to give more exams, unannounced quizzes or any other assignments when deemed necessary.  The instructor may also change the exam dates and due dates for various assignments.  Everyone has to take the final exam. The exams could be in the form of multiple choice questions or essays or calculations or any combination of all these forms.  Students should bring calculations, pens, pencils (#2), and scantron (#882).  Wide window calculators, or calculators capable of storing text, are not allowed during exams or quizzes.

 

Students have to participate in group activities in both lecture and problem solving sessions.  Turning laboratory/activity reports for missed sessions is considered cheating.

 

Student Wait Time for Instructor

If the instructor, due to unforeseen emergencies, does not arrive at the scheduled start time for class, students are to remain in class for fifteen minutes, unless otherwise notified by the Division.  If you do not receive notification to wait for your instructor to arrive, you may leave after fifteen minutes with no penalty for absence or assigned work due for that class.

 

Withdrawals and Incompletes

 

If you are considering to withdraw from the course, consult with your instructor first.  Also, be sure you understand the college's policies on withdrawals and incompletes (refer to class schedule for the semester).  The instructor hopes that no student will have to withdraw from the course.  A student withdrawing from the course must first checkout of the laboratory lockers.

 

 

 

Laboratory

 

In Chemistry 211B, the laboratory is an integral part of the course.  Failure to complete the experiments and hand in the reports will result in unsatisfactory grades for the course.  Laboratory reports should be written in ink.  White-out should not be used in laboratory reports.  Part of the laboratory training is to develop neat working habits.  Students also learn how to budget their time in performing their experiments.

 

Laboratory Safety Procedures (SHP)

 

Safety must be a primary consideration for all persons entering a chemical laboratory.  Experiments have been selected for their relevance to the lecture class materials as well as their expected safety for students learning new techniques.  Students have the responsibility for learning and understanding appropriate safety for each experiment.  Further, each student has an obligation to consult the instructor for help when safety procedures are not clear.  The following general procedures must be observed.

 

                        1.      Before beginning the first experiment, familiarize yourself with the location of the fire extinguishers, safety shower and eye wash fountain in the laboratory.  Consult with your instructor regarding the proper operation of this equipment.  Also, read the information on laboratory safety which can be found in the text.  Always note any safety which are mentioned for specific experiments.

                        2.      Approved safety glasses or goggles must be worn at all times while you or others are working in the laboratory.

                        3.      Wear appropriate clothing.  This includes closed-toe shoes and some type of protective apron or lab coat.

                        4.      Work is not permitted in the laboratory except during regular class periods when an instructor is present.  Performance of unauthorized experiments is not allowed.

                        5.      Smoking and eating are not permitted at any time in the laboratory.

                        6.      Waste chemicals must not be poured down the drain without proper treatment or neutralization.  Consult your instructor before excess chemicals are disposed of.

                        7.      Report any accident, even the most minor, to your laboratory instructor.

                                 In case of a chemical splash, flush the area thoroughly with water.  Use the eye wash for at least 15 minutes for chemicals in the eyes.  Fires can usually be extinguished by smothering.  Use the fire extinguisher with care.

8.      Read and follow the 23-point Laboratory Safety Recommendations in the Lab Safety Packet.

9.      If you miss the first day laboratory session, you must watch the safety video online before you come to the next lab meeting. The website is at http://www.oid.ucla.edu/webcast/chemistry/chemistry body.html

 


 

 

 

Laboratory Notebook:

 

             The laboratory notebook has two main purposes.  First, it is intended to teach you how to keep a detailed record of what you actually did in the laboratory.  The overriding question you should answer in deciding what and how to write in the notebook should be "Can someone else pick up my notebook, and without any other outside information, repeat what I have done?"  If the answer to this questions "yes" then your notebook is properly written.  Secondly, the keeping of a notebook will teach you how to record, summarize and report your work to others.  That will include research reports to supervisors, to journals for publication, and before technical and scientific audiences.  This skill is a vital part of your successful performance in any field of science.  Communication of your findings is an essential ingredient to successful performance.  Your notebook must have a current Table of Contents.  Some other ideas are cited below.

 

The prewriteup - before coming to class the following information should be entered in ink in a bound hard cover notebook with crosshatched lines and with consecutively numbered pages that are perforated and have carbon copy pages.

 

                                 1.      Title of the Experiment: Write the full title of the experiment

 

                                 2.      Date

 

                                 3.      Reaction Equation: Write the reaction equation (when appropriate)                           showing the structural formulas and names of substances involved in the                                reaction.  If the experiment involves only techniques, sketch the apparatus                                  and write the structures of substances used in this particular experiment.

 

                                 4.      Side Reactions: Show any possible side reactions (when necessary) and                               the steps that may be used to avoid them.

 

                                 5.      Purpose: Write the objectives of this experiment clearly, keeping in mind what you intend to accomplish in this experiment.

 

                                 6.      Physical Properties: Enter the physical constants and quantities of                             reactants, products and reagents, as appropriate (e.g. molecular weights,                           densities, 6p, mp solubility and any precautions).  Refer to Handbook of                          Chemistry and Physics for some of this information.  This section of your prewrite-up can be presented in a table format as shown below.

 

Compound

MW                                                MW

Mass                                                Mass

Volume                                                Volume

Density                                                Density

Moles                                                Moles

BP                                               bp

MP                                                MP

Solubility                                                Solubility

Precautions                                              Precaution

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

                                 7. Introduction (Theory): Refer to your laboratory textbook, lecture textbook and other relevant organic chemistry books and write a background (theoretical) information about the experiment.  Include information on the reactions, concepts and techniques involved.


 

The writeup - While the experiment is in progress write all data and relevant observations directly in your notebook.  Be observant, noting precipitation, color change, gas evolution, heating, or any other change which occurs.  Do not record information on odd scraps of paper which may be lost.  Do not “white out” or erase material in your notebook. 

 

                                 8.      Procedure: Write what you did and observed in a paragraph format using the third person singular and the past tense.

 

                                 9.      Results: Attach firmly in your notebook and analyze all spectra and                     chromatograms.  Calculate the theoretical maximum and determine the                           percent yield.  Discuss results in terms of reaction objectives and                              conditions, and comment on the theoretical chromatograms. Calculate the theoretical maximum and determine the percent yield. Discuss the results in terms of reaction objectives and conditions, and comment on the theoretical foundation of the results.

 

                                 10.    Mechanism: Write a mechanism for any reaction which has occurred, when appropriate.

 

                                 11.    Conclusion: Include a brief conclusion which summarizes the results, and comment on unexpected results or any problems encountered.                

 

                                 12.    References: All references should be cited as follows:

                                          Author last name, first name, name of the book, pages, year published.

                                

 

 

STUDENTS ARE TO BE AWARE AND ABIDE BY THE COLLEGE'S REGULATIONS CONCERNING STUDENT CONDUCT.  A POLICY GUIDELINE ON ACADEMIC HONESTY IS ATTACHED.

 

 

 

 

 

 

 

 

 

 

 

 

 

 


 

 

 

 

 

 

 

 

 

 

 


 

 

 

 

 

 

 

 

 

 

 

 

CHEMISTRY 211BL (Laboratory)

Fall 2009

Fullerton College

 

Dates                      Topics                                                                                                                                     Chapters

MW                                                                                         

8/17                         Check-in, Laboratory Safety,                                                                            

8/19                         Oxidation Reactions - Discussion                                                                    

8/24                         Oxidation of Cyclohexanol to Cyclohexanone (3)                                                           22

8/26                         Grignard Synthesis of Triphenylmethanol – Discussion and Preparation                 38

8/31                         continue Grignard

9/2                           Identification of Unknown Aldehydes and Ketones, (1,2,3,4,5 & 6)                           36

9/7                           LABOR DAY

9/9                           continue Unknown

9/14                         Hydrolysis of Methyl Salicylate                                                                                        Handout

9/16                         continue Hydrolysis, continue unknown

9/21                         Mass Spectroscopy                                                                                                            13

9/23                         continue Mass Spectroscopy

9/28                         Dibenzalacetone by the Aldol Condensation                                                                 37

9/30                         continue Aldol

10/5                         N-Butyl Acetate by Azeotropic Distillation of Water (1)                                              40

10/7                         N-Butyl Acetate continued

10/12                       Catalytic Hydrogenation of Oleyl Alcohol (2)                                                                25

 10/14                      continue Hydrogenation

10/19                       Ultraviolet Spectroscopy                                                                                                    14

10/21                       Synthesis of Benzpinacol (Start Experiment) - Photo Chem - Part 1                            62

10/26                       Computers in Molecular structure drawings-CHEM DRAW                                       Handout

10/28                       continue Photochemistry

11/2                         Nitration of Methyl Benzoate                                                                                            28                           

11/4                         Acetylferrocene                                                                                                                   32

11/9                         Veteran’s Day

11/11                       Diels-Alder Reactions - Discussion                                                                                  48

11/16                       Diels-Alder Reaction, Experiments 1 and 2 (Micro)                                       

11/18                       Polymers (Experiment 1 - modified)                                                                                   67

11/23                       Sugars (1,2,3,4, & 5)                                                                                                             63

 11/25                      Continue Sugars

11/30                       Check-out