Mission Statement: Los Angeles Harbor College promotes ... · alkenes, reaction of alkenes and...

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CHEMISTRY 211: ORGANIC CHEMISTRY. SYLLABUS INSTRUCTOR: BASIL O. IBE, Ph.D. PHONE: (310) 233-4160 OFFICE HRS: SCC 257; M/W, 3:00 – 5:00 pm. E-mail: [email protected] or [email protected]

Mission Statement: Los Angeles Harbor College promotes access and

student success through associate and transfer degrees, certificates, economic

and workforce development, and basic skills instruction. Our educational

programs and support services meet the needs of diverse communities as

measured by campus institutional learning outcomes.

Textbooks Lecture: Organic Chemistry, 9th Ed; L.G Wade, Prentice Hall, 2017. Laboratory: Macroscale and Microscale Organic Experiments. Williamson, KL and

Masters KM, 7th Ed. Cengage, 2017. Course Structure A. Lecture: Three hours per week; Tue/Thu 5:20-6:45 p.m. SCC 142 Cell phones, must be turned off or maintained in non-ring mode during class or lab times. Ten (10) points (out of total semester score of 1100) will be lost for each noncompliance. 1. Four (4) regular exams to be given at lecture time and each normalized to 100%.

THERE WILL BE NO MAKE UP EXAMS. IF YOU MISS ONE EXAM, THE NEXT EXAM COUNTS DOUBLE, HOWEVER, I MUST KNOW BEFORE HAND AND A DOCTOR’S NOTE MAY BE REQUIRED IF IT IS AN EMERGENCY. Not more than one occurrence per semester. This does not apply to exam #4 or the final exam and you cannot do this retroactive.

2. Regular in-class 10-20 min multiple choice test, given at end of each chapter and/or materials common to chapters that have been discussed. All are normalized to 100% at end of semester. THERE WILL BE NO MAKE UP QUIZZES. Conditions are as for regular class exams. 3. Take-Home Quiz will be given during the semester. These tests involve deeper knowledge and application of course materials. These take-home tests must be handed in for grading on the stipulated day. Late turn-ins will not be accepted. All take-home tests will be normalized to100% at end of semester. 4. The final exam is worth 100 points, to be given in the finals’ week. 5. Recitation: Students will be assigned recitation topics for presentation during lab

mailto:[email protected]

mailto:[email protected]

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period (It becomes a dry lab). This is a PowerPoint presentation by the student. Student’s work is handed in for grading before presentation. Students are graded on clarity of answers and on clarity of PowerPoint presentation. These recitation problems are mechanism-based questions. (NO MAKE UP RECITATIONS). (Recitation problems are treated as a 20-point Take-Home Quiz 6. Reading assignment(s) will be given and written reports turned in for grading. (Reading assignments are treated as a 50-point Take Home Quiz) Note: No bathroom breaks during in-class exams. B. Laboratory Laboratory hours are Tue/Thu, at 6:50-10:05 p.m. SCC 311, i.e., immediately following lecture time. THERE WILL BE NO MAKE UP LABS. Why? Each student will need the following supplies: Hardcover, bound notebook for lab data. Black/blue pen for lab records (please no purple, pink, red, green, yellow or orange colored pens or pencils for writing lab. Pencils may be used for exams). Lab coats and gloves are strongly recommended, but not provided.

Each student will also need: Approved type safety goggles, closed-toe shoes and no loose outfits for lab. Students should have combination type padlocks for lab lockers. Instructions will be given in lab and lab techniques will be demonstrated if necessary. Methods of scoring laboratory works 1. Laboratory quiz: There will be pre-lab tests to be given before each lab. Pre-lab tests cover theory and lab procedures and will be normalized to 100 points at end of semester. (NO MAKE UP pre-lab tests.) Conditions will apply as in regular exams. 2. Laboratory reports: Lab reports will be turned in for grading on the designated day. (Late turn-in of reports are not allowed. Laboratory reports are not returned to students. The student hands in the original copy and keeps the carbon copy. Laboratory reports are worth 100 points at the end of the semester. 3. Assigned laboratory problems (AKA post-lab problems): Some problems relevant to the laboratory exercise are assigned. These problems are to be turned-in on a separate sheet of paper for grading. This answer sheet must have the students full name, date that the lab was done, title of the lab, and the problem identified by the problem number on the lab manual. If more than one sheet of paper was used, they must be stapled at the top left hand corner. The lab problems are worth 100 points at the end of the semester.

4. End-of-semester laboratory exam: To be given in about the last week of labs. This involves identifying selected laboratory equipment used in the course, setting up and/or describing a given experimental method that was done in the course. The end-of-semester laboratory examination is worth 100 point.

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Please note that this course does not drop any exam or test scores SCHEDULE OF EXAMS: There will be no make-up exams Exams cover materials discussed in class, sections of textbook chapters which students are required to read, and laboratory materials. EXAM 1, Thursday September 26, 2019.

Chapters 1, 2, 3, and related laboratory sessions: Review of physical organic chemistry, structure and properties of organic compounds, chemical bonding, alkanes, structure and stereochemistry of alkanes, chemical reactions

EXAM 2, Thursday October 31, 2019.

Chapters 4, 5, 6, and related laboratory sessions: Study of chemical reactions, stereochemistry of organic compounds, alkyl halides and types or reaction: Sn1 vs Sn2, E1 vs E2 reactions

EXAM 3, Tuesday November 19, 2019.

Chapters 7, 8, 9, and related laboratory sessions: Structure and synthesis of alkenes, reaction of alkenes and alkynes

EXAM 4, Tuesday December 5, 2019.

Chapters 10, 11, 25 related laboratory sessions: structure and synthesis of alcohol, reactions of alcohols, lipids and reactions of lipids Final examination: Tuesday December 10, 2019. (Comprehensive) POINTS SUMMARY: 4 Exams x 100% each 400 points Final exam 100 points Total end-of-chapter tests 100 points Total take-home tests 100 points Pre-lab tests 100 points End-of-semester lab exam 100 points Laboratory questions 100 points Laboratory report 100 points (if Requirement is satisfied) Total points possible 1100 points

The letter grade scale GRADE ASSIGNMENT: 1012 - 1100 A 880 - 1011 B 770 - 879 C 660 - 769 D 000 - 659 F

No bathroom breaks are allowed during in-class exams. Students should

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visit the bathroom before sitting for exam. Chemistry 211, Lecture Syllabus [Please note: School weeks begin on Mondays]

WEEK LECTURE TOPIC AND TEXTBOOK CHAPTER

Week 1, 8/26 Chapter 1: Bonds and bond characters, Lewis structure electronegativity, polarity of organic compounds, hybridization and geometry, etc.

Week 2, 9/2 Chapter 2: Acids, bases, functional groups, Organic molecules, hybridization, empirical formula, molecular weight, etc.

Week 3, 9/9 Chapter 3: Alkanes, reactions of alkanes, conformational analysis, cycloalkanes, alkane nomenclature, mechanism of halogenation, structures, etc. More lecture during lab time; Check into lab lockers.

Week 4, 9/16 Chapter 4: Study of chemical reactions. More lecture during lab time (if necessary).

Week 5, 9/23 Chapter 4 continued, More Lecture, Tuesday 9/24, Ex 1 review and Recitation problems during lab period.

Exam 1: Thursday 9/26, 2019 @ 5:20 -6:45 p.m.

Week 6, 9/30 Chapter 5 Stereochemistry

Week 7, 10/7 Chapter 5: Stereochemistry continued. chirality of organic molecules. Solved problems

Week 8, 10/14 Chapter 6: Alkyl halides, nucleophiles, nucleophilic reactions, mechanisms and reaction kinetics, etc. Thursday, more lecture during lab sessions.

Week 9, 10/21 Chapters 7: Structure and synthesis of alkenes, Thursday 9/24, rev Exam 2 and recitation during lab period.

Week 10, 10/28 Chapter 8: Reaction of alkenes. Exam: Thursday 10/31, 2019 @ 5:20 -6:45 p.m.

Week 11, 11/4 Chapter 8: Alkenes continued. Unsaturation in organic chemistry. Introduce chapter 9, alkynes

Week 12, 11/11 Chapter 9: alkynes continued. Reactions of alkynes. Introduce chapter 10.

Week 13, 11/18 Chapters 10, 11: Structure and synthesis of alcohols. Reaction of alcohols Thursday 11/21 review Ex 3 and recitation during lab period.

Week 14, 11/25 Exam #3, Tuesday November 22, 2019 @ 5:20-6:45 pm

Thursday 11/28/18, Thanksgiving Day, Holiday no class

Week 15, 12/2 Chapter 11 continued, Reactions of alcohols. Thursday 12/5 Review Ex 4 ; Exam 4:

Thursday December 11, 2019 @ 5:20-6:45 p.m. Week 16, 12/9,

Final Exam: Tuesday December 10, 2019 @ 5:30-7:30 p.m. Venue to be determined. [Most likely SCC 142]

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LAB EXPERIMENTS for CHEMISTRY 211 Note: Laboratory reports are due on the stated dates. (10 points will be deducted for lateness, each occurrence from the total points at end of semester. Assigned problems in each lab should be done on a separate sheet of paper. Week & Date

Tuesday

Thursday

Week 1, 8/26

Lecture: Chapter 1 continued. Discuss syllabus and course requirements, need padlock by next class.

Lecture cont’d Chapter 2.

Review lab text book (Assign lab lockers)

Week 2, 9/2

Expt. #1: Interpreting and presenting physical constants of organic compounds. Using reference books. [see handout and Elements of chap 3 of lab manual, pg 41-48]

Expt. #2: Determination of melting points: Chapter 3 of Lab manual pages 48-60. Melting Point Experiment Pages 53-55. Solubility of organic compounds. Do Parts A to E. [Do questions #2, 4 and 9 on page 60]

Week 3, 9/19

Lecture.

Lab report of experiment #1 is due today.

Expt. #3: Recrystallization and solubility Chapter 4 of Lab manual pages 62-85, We are using macroscale techniques for #5 and 7 page 82 and 84.[Do questions 2 , 3 and 11 on page 86]

Lab report and problems of experiment #2 are due today.

Wek 4, 9/16

Expt. #4, Chapter 7, Lab manual pages 132- 143. Follow scheme in Part 2: page 142-146, Do experiment 1 on pages 146-148. Extraction based on acid base properties of a mixture. [Do Qs. #2, 4, and 7 on page 164].

Assign recitation problems

Lecture Lab repot and problems of experiment #3 are due today.

Week 5, 9/23

Lecture, then student recitation for Review of Exam #1

Lab report of experiment #4 lab problems are due today.

Expt. #5: Chromatography, lab manual page 165-176.TLC of analgesic drugs Expt. 1 Analgesics, pages 176-178 ([Do Q2, 7, and 12 on pg184-185]

Week 6, 9/30

Expt. #6: Chromatography, lab manual page 165-176.TLC of plant pigments, Expt. 2 on page 178-182 ([Do Q3, 8, and 10, pages 184-185].

Expt. #7, Lab manual p156-162 {Expt. 8 of lab manual p161 use macroscale technique}. Isolation of caffeine from Coca Cola with methylene chloride. [Do Q8, Q9 and Q11, page 164]

Lab report and problems of experiment #5 are due today.

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Week 7, 10/7

Expt. 8: Extraction and purification of components of an analgesic tablet. Experiment 5 of lab manual pages 151-156, use

macroscale technique. [Do Q #10 page 164] Lab report and problems for experiment #6 are due today.

Expt.9: Terpenes and phenylpropanolamines. Lab manual p103-107; 112- 115. Expt. 5, {lab manual pages 112-116}: Isolation of Eugenol from cloves, macroscale. [Do Q 4, 11, and 12, pages 130-131]

Lab report and problems for experiment #7 are due today

Week 8, 10/14

Lecture

Lab report and problems for experiment #8 are due today.

Expt. 10: Lab manual Chapter 26, page 392-394; Conformational Analysis. No post-lab problems. Assign recitation problems to exam #2


Week 9, 10/21

Student recitation #2, Exam 2 review and Discussion:

Expt. 11: Synthesis of 4-methylcyclohexene. Lab manual p209-pg214 of Pavia et al. {Expt. 24B of lab manual, pg212. Use fig 19.2 of Williamson and Masters lab manual and set 339}. [Do Q1, and Q2 (a, b ,c, d) page 214 of Pavia et al.]


Week10,

10/28

Expt. 12: Oxidation of cyclohexanol to cyclohexanone. Lab manual chapter 22, page 358-363; experiment #2 using macroscale procedure page 361-363 (post-lab problems will be handed out on experiment day.

Expt. 13. Local anesthetics: Preparation of benzocaine Lab manual p364-371 of Pavia et al. {Expt. 24B of lab manual, pg212. {lab manual Expt. 42, Preparation of benzocaine page 368} [Do Q2, Q3, and Q5, p371].

Complete Exp11. [Do Q1, Q2, Q4, and Q6] “Make copies for students”

Lab report and problems for experiment 11 are due today.

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Week 11, 11/4

Expt. 14, Ethanol from sucrose. Lab manual Pavia et al p151-p158, {Expt. 18 of lab manual}.


Lecture

Lab report and problems for experiment 13 are due today.

Disclaimer Regarding Offensive Material: There may be videos or other materials presented that may be construed in some way to be offensive to someone. Enrollment in the class means

Week 13, 11/18

Exam #3 during lecture

Expt. 14, Complete experiment 14. Lab manual p151-p158, {Expt. 18

of lab manual}. Please save the alcohol (ethanol) you distilled for testing on Thursday during lab.


Thanksgiving Day, no class/no lab

Week 14, 11/25

Expt. 15, Test for alcohols. Lab manual Pavia et al p491-495 {Expt. 52H}. Omit sections on spectroscopy p495 and 498 (infrared and nuclear magnetic resonance).

Assign Exam #4 recitation problems

Lecture is necessary

Week 15, 12/2

Review Ex 4 problems (students’ recitation).

Lab report and problems for experiment #14 are due today.

Laboratory examination

Check out of lab lockers

Lab report and problems for experiment #15 report are due today.

Week 16, 12/9

Exam #4 12/10/19 @ 5:20-6:45 p.m.

Comprehensive semester final Exam, Thursday 12/12/19 at 5:30-7:30 p.m. Venue to be announced

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the student accepts all responsibilities pertaining to the course materials. Honesty Policies: This class follows all honesty (dishonesty) and other college policies as described in the College catalog. Most assignments will be processed through a plagiarism checking program. Plagiarism results in lost points for that item. Special Needs: If a student has special needs, the student should contact the Special Programs and Services (SPS) office at the college so they may notify the instructor of any adaptations that are appropriate. All Los Angeles Harbor College policies are observed. Serious infractions will be reported to the administration. “Los Angeles Harbor College complies with the Americans with Disabilities Act (ADA) and Section 504 of the Rehabilitation Act of 1973. Any student with a documented or suspected disability (physical, learning, or psychological) needing academic accommodations should contact the instructor and the Special Programs and Services Office at (310) 233 – 4629, which is located in Café 108.” Title IX

"No person in the United States shall, on the basis of sex, be excluded from participation in, be denied the benefits of, or be subjected to discrimination under any education program or activity receiving Federal financial assistance." –If you feel that you have experienced this type of behavior or you have witnessed this type of behavior immediately contact the campus Title IX Coordinator: Ms. Claudette McClenney at (310)233-4346.

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SLO Objectives

Course Intended Outcomes Means of Assessment and Criteria for

Success

1. Use Chemistry handbooks to assign physical and

chemical properties to a given compound.

Students will use standard chemistry reference books

such as the Chemical Abstracts and the CRC

Handbook to locate the physical and chemical

properties of a given set of compounds.

70% of the students will be expected to correctly

locate the compounds in the reference books and

identify the corresponding physical and chemical

properties.

2. Perform given synthesis as assigned from the

laboratory manual.

Students are asked to synthesize benzoic acid as

described in the laboratory manual, including

purification processes, differentiate between salt and

free acid and accurately determine the melting point of

the purified product.

80%of the students should synthesize purified

benzoic acid to get above 50% yield, 70% of

students should get over 70% yield of purified

product and assign correct NMR spectral

characteristics.

3. Purify, identify, and recover organic or biological

compounds using the techniques of column or thin

layer chromatography (TLC).

Students will be asked to isolate caffeine from a given

volume of a caffeinated soft drink and then to purify

the isolated product by liquid extraction using a

separatory funnel and then compare the purified isolate

qualitatively to reference standard by TLC .

70% of the students should be able to perform this

laboratory exercise.

4. Identify pieces of equipment used in chemical

reactions and processes during the semester.

Students will be asked to identify by name the different

types of equipment that have been used during

laboratory sessions within the semester. Such

equipment include; condensers, flasks, Erlenmyer

flask, spatula, spectrophotometer and funnels, etc.

70% of the student should be able to name all

displayed equipment and what they are used for.

MERRY CHRISTMAS And a HAPPY NEW YEAR

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ORGANIC CHEMISTRY FOR SCIENCE MAJORS

(Chemistry 211 and 212)

FORMAT FOR WRITING THE LABORATORY NOTEBOOK AND LAB

PROBLEMS

Laboratory reports are scored on a PASS/FAIL basis. One has to make70% on the

lab report to earn a “PASS” on the lab report. Each lab is worth 100 points. At the

end of the semester, the scores will be normalized to 100%, (e.g., assuming a total

of 11 labs were done each worth 100 points, total points possible will be 1100

points. If a student earns 850 points, the student will earn 77% for the laboratory

grade which is calculated as follows: (850/1100 x 100 =77%), WHICH WILL

BE A PASS AND WILL EARN 100 POINTS AS FINAL SCORE.

Note: Laboratory reports are not returned to students therefore student must be

sure to save own carbon copy (in case a discrepancy arises).

Writing the laboratory report

Laboratory notebook headings

Full name [First name followed by last name as it in official class roster] (2 points)

Date of experiment (2points) Experiment # (2 points)

Full name of lab partner or partners if applicable (4 points)

Title of experiment

The title of the experiment must be reasonable, descriptive and complete.

For example, student should write “Determination of the melting points of organic

of organic compounds” instead of “melting point of compounds”. (5 points)

The introduction

Give a very brief description of the purpose of the experiment, about 3-5 complete

sentences containing verbs, of course. This can be summarized from the

description of the experiment given in the laboratory manual (5 points)

List the major pieces of equipment used for the experiment (a beaker, an

Erlenmyer flask or graduated cylinder are not major equipment). In the example

given above, a capillary tube used for the melting point determination will be

relevant equipment to mention. (5 points)

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A sketch of the experimental set up (This is optional)

List of relevant chemicals used in the experiment.

Assume that all the chemicals used in the experiment are relevant and worth

listing. Give the structure of the compound if it will help your chain of thought.

Note: You will not be penalized for giving an exhaustive list, but points will be lost

for not listing a relevant chemical. (5 points)

The body of the report

Give a brief description of the experimental procedure. (10 points)

Give the equation of the reaction when applicable. Remember that an organic

chemist works with chemical reactions and equations. Therefore use of chemical

structures in answering questions is very important. (10 points)

Data: Weights and measures; weights are presented in the appropriate metric

system value and unit (grams or milligrams and volume in milliliters as used or

obtained. When necessary, present the data in a table format. Please note that any

weight or measure without the relevant units is meaningless and earns no

points. (10 points)

Calculations: For example, calculation of theoretical yield, actual, %yield, all

steps in the calculations must be shown in dimensional analysis format (also

known as the cofactor method), and answers must be shown in correct units or

significand digits (25 points)

When applicable, side reactions must be shown with reasonable chemical equation

or equations. (5 points)

Experimental summary

This involves discussion of reaction results and data collected. In this section, you

should discuss why you think your result, for instance why the yield of your

reaction is high or low. (10 points)

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Problems are assigned to some labs.

These related laboratory work must be submitted on a separate sheet of paper for

grading. These lab problems (often called post laboratory problems) have their

own scores in the final grading scale.

The first page of the lab problem answer sheet must have the student’s name

centralized on the top of the page; Title of the experiment; Date the experiment

was done and the due date of the problem set should be stated below the student’s

name.

Rules for presenting answers/solutions to assigned laboratory problems

1. Do not staple this sheet of paper to your laboratory report. Please do not use

pages from your lab notebook to do these problems.

2. The first page of the answer sheet to the lab problems must have the student’s

name (first and last names) centralized on the top of this first page.

3. The answer sheet to the problems must be on standard 8.5x11 inch white paper.

It’s ok to be a ruled paper and colored paper will be allowed as long as the color

does not create a problem with reading the document at night.

4. The title of the lab experiment with the problems assigned must be clearly

written at the top, below the student’s name. Then the number of the assigned

problems must be given. Date the experiment was done and the due date of the

problem set must be shown.

5. If more than one page was used in the problem solution, the pages must be

stapled together at the top left hand corner of the submission.

These 5 point instructions are worth 10 points. Thus a 20-point post-lab

problems will be worth a total of 30 points.

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