Syllabus 26200

City College of New York

Department of Chemistry and Biochemistry

 

CHEM 26200: Organic Chemistry Lab I

 

 

Prerequisite:               Chem 10401 and Chem 26100.  Co-requisite: Chem 26300

 

Hours/Credits:             4 hours per week, 2 cr.

 

Lecture                        Once a week, 50 min

                                                           

Laboratory                   Once a week, 2 hr 50 min

 

Laboratory Manual      Chemical Education Resources: Organic Chemistry Laboratory-CHEM 26200 Experiments (ISBN: 978-0-495-30987-1, available from the Bookstore)

 

 

Course Objectives: This course is stressing the techniques involved in the preparation, isolation, purification and analysis of carbon compounds (for non-chemistry majors).

 

Topics Covered: Laboratory and analytical techniques that are taught in this course include: simple and fractional distillation; extraction; recrystallization and melting point measurement; qualitative identification of alkenes; chromatography techniques namely: gas chromatography, thin layer chromatography, liquid chromatography; IR spectroscopy.  Synthetic experiments that are performed are SN2 reaction, E1 reaction, electrophilic addition, electrophilic aromatic substitution, and condensation reaction (Aldol).

 

Lecture             Theoretical material relevant to the experiments will be discussed in the lecture and this can supplement information pertaining to the experiment itself.  Each experiment in the lab manual explains background information pertinent to that experiment.  In few cases the information pertaining to the experiment will be provided in the lecture and/or laboratory since the lab manual does not contain this.  Students are strongly encouraged to study this information prior to the lectures.

 

Laboratory Schedule The attached schedule shows the experiments that will be performed and dates for the exams.

 

Grading             There are 13 experiments, some relate to techniques, some to reactions and mechanisms, and some are aimed at synthesis of compounds.  Of the 13 experiments, the best 12 will be used in computing the final grade.

 

Laboratory reports for each experiment must be handed in no later than one week after completion of that experiment.

 

                    

Student laboratory performance will be evaluated by the TA (as well as professor) and is worth a total of 5 points. That includes your work skill, punctuality and attendance in both lecture and lab. A summary of the points assigned to each portion of the course is shown below. 

 

Experiments 13 in all, best 12/13 x 10 points each = 120 pts = 50%

Midterm exam                                                                        = 20 %

Final exam (comprehensive)                                                = 25 %

TA/instructor evaluation                                                         =   5 %

TOTAL                                                                                    = 100%

 

 

 

There are no makeup labs and no makeup exams.  Absence without a strong, verifiable, documented reason will result in zero points for the material missed.  Lab reports not submitted in a timely manner MAY also result in zero points  for that exercise.

 

Safety issues     You must wear lab goggles at all times in the lab.  Do not wear shorts or short skirts without a lab coat; this is for your safety!  Similarly, open shoes and slippers should not be worn.  YOUR workplace should be CLEAN always!

 

Breakage           Students must be aware of the fact that they will be charged for the replacement cost of any equipment that they break during the lab course.  Some of the glassware is especially expensive and so you are urged to work carefully at all times.

 

If you have questions, comments or suggestions please contact your teaching assistant or the instructor.

 

Course Learning Outcomes for Chem 26200

 

  1. To understand the physical principles underlying the techniques used for purification of compounds, separation of reaction mixtures, monitoring reactions and analyzing reaction products in organic chemistry lab.
  2. Understand the mechanistic basis of synthetic experiments.
  3. To learn and execute several fundamental organic laboratory techniques used.
  4. To perform fundamental organic reactions.
  5. To learn the safety precautions required in an organic lab.
  6. To learn the calculations associated with synthetic organic experiments.
  7. To learn how to make observations, collect data and write a lab report for an organic synthesis experiment.

 

Academic Integrity: The CCNY policy on academic integrity will be followed. A document is posted on the CCNY website (CUNY policy on academic integrity: www1.ccny.cuny.edu/facultystaff/provost/upload/academicintegrity.pdf - 2007-01-19). Make sure you have read the details regarding plagiarism and cheating, in case you are not clear about the rules of the college. Cases where academic integrity is compromised will be prosecuted according to these rules.

 

LIST OF EXPERIMENTS

 

Week 1 

Introduction, Check In, Measuring Melting Points of Compounds and Mixtures (only measure one unknown and the two known compounds with the closest m.p.)

TECH 701

Week 2  

Purifying Acetanilide by Recrystallization

(no solvent selection process--solvent is tap water, no melting point   measurement)

TECH 703

Week 3  

Separating Cyclohexane and Toluene by Distillation (run Macroscale Fractional Distillation, Use Vigreux column and shortpath distillation head)

TECH 704

Week 4  

Separating Acids and Neutral Compounds by Solvent Extraction (run Macroscale Extraction and the extraction mixtures are pre-prepared;   each student take 25 mL TBME)

TECH 705

Week 5

Separating Ferrocene and Acetylferrocene by Adsorption Column Chromatography (use dry pack method with microscale column/stationary phase—silica gel/eluent—hexane and ethyl acetate)

TECH 708

Week 6

Gas Chromatography and Thin Layer Chromatography

Handouts

Week 7 

Brominating Alkenes (Group 1); Identifying an Unknown Compound by Infrared Spectroscopy (Group 2) (semi-microscale)    

TECH 719

TECH 710

Week 8 

Brominating Alkenes (Group 2); Identifying an Unknown Compound by Infrared Spectroscopy (Group 1) (semi-microscale) (MID-TERM EXAM)

TECH 719

TECH 710

Week 9 

Qualitative Test for Alkenes and Identifying an Unknown Compound by ATR

REAC 472/Handout

Week 10

Studying SN1 and SN2 Reactions: Nucleophilic Substitution at Saturated Carbon (only synthesize 1-Bromobutane (SN2) using macroscale techniques)

REAC 714

Week 11

Dehydrating Cyclohexanol (semi-microscale)

Use traditional distillation, NOT shortpath

REAC 712

Week 12

Nitrating Methyl Benzoate

REAC 716

Week 13

The Aldol Condensation: Synthesis of Dibenzylacetone (semi-microscale)

SYNT 720

Week 14

Equipment Check Out (Lecture--FINAL EXAM)

 

 

 

-

 

 

 

Laboratory Report:

 

All your lab work should be recorded in a lab notebook and not on scraps of paper. Data recorded in the notebook must be properly dated, and neatly written.  Based on this information, you will generate a laboratory report that needs to be submitted on time for grading. You are to submit hardcopy type-written reports. Handwritten reports will not be accepted. Your TAs will provide the rubric tailored to each experiment. A general format for a synthesis-type laboratory report is provided below (total point is 10 for each lab). 

 

 

Name, ID number and section

 

 

Title of experiment

 

 

Theory and objective of the experiment

2

1

Reaction and Mechanism: Any equations chemical structures relevant to the experiment as well as any pertinent mechanisms.

1.5

2

Physical Properties: A table listing the compounds used, their molecular weights, amounts used in grams and moles, boiling points and density (for liquids), as applicable

0.5

3

Hazards: determine flammability, toxicity or corrosiveness of the compounds used in this experiment.

0.5

4

Limiting Reagent: Based on the balanced equation in section 1, calculate the limiting reagent of the reaction

 

5

Theoretical Yield: Calculate the theoretical yield of the experiment

0.5

6

Side Reactions: Try to postulate possible side reactions that might lower the yield of the reaction

0.5

7

Separation Scheme: The separation scheme is a flow chart that illustrates how the compound is isolated or separated from the reaction mixtures once the reaction is done.

1

8

Procedure and Observations: Describe exactly how you performed the experiment and exactly what observations were made (e.g., color change, if any spillage occurred etc.). The observations have to be very specific. Draw a separation scheme or a flowchart. Always write this part in the third person and in past tense.

1.5

9

Results: This part should include identification of the limiting reagent and calculation of the theoretical yield of the product. Actual yield of the product, physical properties of the compounds such as color or nature of product (e.g., colorless needles of compound X were obtained). Melting or boiling points.

1

10

Conclusion & Discussion: Did you achieve what had to be achieved? Did you have any problems? Other scientific comments on the experiments, such as suggestions if you feel you could do something differently to improve the outcome of the experiment.

1

 

Information about reagents and chemicals

            To complete items 5 and 6 of the prelab report you will need information on reagents listed in the lab procedure.  Information for these chemicals can be obtained from a number of sources.  The most common resource for this information is the CRC Handbook of Chemistry and Physics, the Material Safety Data Sheets or the Aldrich catalog.  Several sources can be found in the library.  There are also a number of sources for this information online. A page listing these sources has been assembled by the campus science librarian at the URL: 

http://resources.ccny.cuny.edu/resources/subject.jsp?sub_id=62, or http://www.fishersci.com, or http://physchem.ox.ac.uk:80/MSDS/.