Welcome to Chem 36!Organic Chem Lab

Dr. Katie Masters

Chem 36 Info

Section 1: M/W at 1:25 to 4:25 pm in 205/215 Whitmore LabSection 2: M/W at 1:25 to 4:25 pm in 205/215 Whitmore LabSection 3: T/R at 6:30 to 9:30 pm in 205/215 Whitmore Lab

Faculty Dr. Katie Masters Dr. Jackie Bortiatynskiin Director, Organic Labs Director, InstrumentationCharge 218 Whitmore Lab 211D Whitmore Lab Phone: 863-3319 Phone: 865-2772

kmasters@psu.edu jackie@chem.psu.edu

Office Hours Wednesdays, 3 to 5 pm

Website http://courses.chem.psu.edu/chem36

Course Materials

Lab Guide for Chemistry 36: Introductory Organic Laboratory Minard, Masters, Halmi & Williamson, 2006-2007 Edition, Hayden McNeil

Organic Chemistry Laboratory Notebook, 2nd Edition, Hayden McNeil

Eye Protection - Eye Protection is required at all times in lab!

Organic Lab Equipment Kit

Combination or key lock - for next week

Lab apron and rubber gloves (optional)

Lab Assignments

First Half of Semester:

5 Technique Experiments• Recrystallization & Melting Point• Distillation & Boiling Point• Liquid/Liquid Extraction• Thin-Layer Chromatography (TLC)• Column Chromatography

Second Half of Semester:

5 Synthetic ExperimentsAssigned experiments; Downloadfrom the course website.

Throughout the Semester:

Spectral Unknown ExperimentDetermine an unknown’s structure

Assessment: PreLabs (30 pts) and Final Reports (100 pts)For each experiment you run. Ch 10 has no

PreLab.6 Lab Quizzes (50 pts)Final Exam (100 pts)

5 Technique Experiment PreLabs 120 points*5 Technique Experiment Final Reports 400 points*5 Synthetic Experiment Prelabs 150 points5 Synthetic Experiment Final Reports 500 pointsSpectral Unknown Determination 100 pointsTA Evaluation 100 pointsQuizzes 300 pointsFinal Exam 100 pointsMaximum Lab Points 1770 points

*Chapter 4 PreLab and Final Report do not count towards the final grade. These assignments are NOT an option! Failure to do either assignment will

result in a 20 point deduction off your final grade for each missing assignment.

Breakdown of the Chem 36 PointsChapter 1

The Lab Experiments: The Techniques

Chapter 4: Recrystallization and Melting Point: Two day labRecrystallization & MP of an UnknownRecrystallization of Phthalic AcidMP of Spectral Unknown (Ch 10 experiment)Decolorization with Norit

Chapter 5: Distillation & BP: Two day labSimple or Fractional Distillation of a Known MixtureMicroscale Fractional Distillation of an Unknown

Mixture

Chapter 6: Liquid/Liquid Extraction: Two day labSeparation of a Solid Mixture (acid/base chemistry)Extraction of Caffeine from Tea

The Technique Experiments

Chapter 7: Thin-Layer Chromatography: One day labFinding a TLC Mobile PhaseIdentifying Compounds in an Analgesic Tablet

Chapter 8: Column Chromatography: Two day labOxidation of Fluorene to FluorenoneColumn Chromatography of Reaction Mixture

Chapter 10: Spectral Unknown Experiment: Ongoing labAcquire mp, IR and 1H NMR spectraDetermine the structure of an unknown

The Synthetic Experiments

Chapter 9: The Synthetic Experiments:

• 5 Synthetic Experiments - downloaded from web

• Assigned based on major!

• Up to 20 different experiments in each TA’s section

• Work independently

• Curriculum is a work-in-progress

PreLab Assignments

Purpose of PreLabs & Lab Quizzes: To ensure that each student has read throughand understands the theory and procedures of each experiment.

PreLab Format (Described in Chapter 3)

Sections:1. Purpose of Experiment2. Diagrams of Special Apparatus/Reactions3. Chemical Data Table4. PreLab Exercise5. Chromatographic & Spectral Features Comparisons (only for Ch 8 & 9)

PreLabs are hand-written into the Lab Notebook. White pagesare handed in for grading. The yellow copies are kept within thenotebook.

Grade sheets for the PreLabs are located at the end of the chapters.

PreLab Sections: Purpose of Experiment

• A concise, brief statement that describes the purpose of the complete experiment.• Never use the first person!• Do not include set-up of apparatus in this section.

Good Example:To sublime (purify) an unknown solid and to take a melting point ofthe purified unknown to determine its identity.

Bad Example:I will take a melting point.

PreLab Sections: Diagrams of Special Apparatus and/orReaction Equations

Diagrams of Special Apparatus:• Hand-draw and label any piece of glassware/equipment or reaction set-up that has not been used in previous experiments.• Please draw neatly!

Reaction Equations:• Hand drawn.• You will start including reaction equations with Chapter 8.• Indicate limiting reagent and include the theoretical yield of the product.

Cl

CH2CH3

O

4-chloropropiophenoneLimiting Reagent

Oxidation by KMnO4

in base, heat for 1/2 hrCl

OH

O

4-chlorobenzoic acidTheoretical yield = 0.67 g

PreLab Sections: Chemical Data Table

1.Common Shelf Chemical Data Table:•Located in notebook•Fill out completely and hand in with Chapter 5 PreLab

2.Blank Chemical Data Tables:•Located in notebook•Include chemicals for the experiment that do not appear on CommonShelf Chemical Data Table•Fill out all information about each chemical (see examples in Ch 3).•Waste disposal information can be found in chapter 2 of the lab guide.

Use the Aldrich Catalog to find information about chemicals. When using Aldrich, pick the chemical entry that does NOT have isotopic labeling, e.g, d, 15N, 13C. These are more expensive and will have different FWs. Aldrich will also tell you if a chemical is flammable or toxic or an irritant.

Typically, use the last entry that gives all necessary data for thetable. Use the “least pure” entry for the price.

PreLab Sections: Chemical Data TableThere are two main different editions of The Aldrich catalog. Please see Chapter 3 for details about your edition!

Columns of the Chemical Data Table:Chemical NameChemical Structure (draw out structure)Physical state: s (solid) or l (liquid)BP/MP: If solid, list melting point; if liquid list boiling point (in °C)Liquid density: in catalog, density is represented by “d”; units in g/mLQuantity: the amount you’ll use in the procedure (mg, mL, or g)MW: molecular weight of compound; units in g/mol (given in catalog)mmol: millimole amount; calculate by using the quantity and MW; fill in only for Chapter 8 and 9 experimentsFlammability: if flammable, write “yes”; if not, write “no”; this info given in

AldrichToxicity: if toxic, write “yes”; if not, write “no”; info given in AldrichPrice: given in Aldrich; give price for 100 g or 100 mLWaste category: info given in Chapter 2; some categories include HO, NHO, D,

WB, HMComment: if compound is an irritant, hydroscopic, corrosive, etc, write it here; info given in Aldrich

PreLab Sections: PreLab Exercise

Answer the three assigned questions located in the lab guide.

Assignment sheet is attached to the course syllabus.

PreLab Sections: Chromatographic & Spectral Features Comparisons

For Chapter 8 and Chapter 9 experiments only!

Chromatographic ComparisonRelative Rf comparison between main organic starting material and main product of reaction.

Example:

OH

CyclohexanolStarting material

CyclohexeneProduct

Cyclohexanol would have a lower Rf value due to the OH functionality, whichis more polar than the alkene of cyclohexene.

(Draw out structures)

PreLab Sections: Chromatographic & Spectral Features Comparisons

For Chapter 8 and Chapter 9 experiments only!

Spectral Features ComparisonConsider diagnostic 1H NMR & IR signals for the starting material and product that would be used to distinguish the two from one another.

Example: OH

CyclohexanolStarting material

CyclohexeneProduct

(Draw out structures)

Cyclohexanol Cyclohexene

Diagnostic 1H NMR Signals

OH proton at 2-6 ppm, singlet

=C-H (alkene) proton at 5-6.5 ppm, quartet or multiplet (due to complex splitting)

Diagnostic IR Signals O-H stretch (broad) at 3600-3200 cm-1

C=C stretch at 1658 cm-1

Lab Quizzes

Purpose: To test your understanding of theory and your preparedness forthe experiments.

Quiz 1: Chapter 4Quiz 2: Chapter 5Quiz 3: Chapter 6Quiz 4: Chapter 7Quiz 5: Chapter 8Quiz 6: Chapter 9 and 10 (spectral interpretation)

Please note schedule for dates of quizzes. They will be given at the beginning of lab and will take 10-15 minutes to complete.

Each is worth 50 points. Graded quizzes are not allowed to leave the lab.

Quizzes 1-5 will include questions on the specific procedures of the chapters’experiments and safety considerations.

Sample quiz questions are given in Chapters 4-8.

Final Report Assignments

5 Sections (Described in Chapter 3):

I. IntroductionII. Procedure and Data/ObservationsIII. Results/Discussion/ConclusionsIV. PostLab ExerciseV. Reference

Attach the white in-lab notebook pages. You must have your TAinitial all pages used during each lab session. Attach annotatedspectral data when appropriate. Attach grade sheet to the front.

Final reports are computer-generated. Reaction schemes can behand drawn. Use the passive voice.

Graded final reports cannot be taken out of the lab (except Ch 4).

Final Report Sections: Introduction

• For the technique experiments (Chapters 4 through 8), include a description of each technique used (there may be more than one), of what the technique is, the theory that makes it work, and why chemists use it. Take care to be concise and to avoid repetition.

• For the synthetic reactions, state the significance of the reaction and/orcompound made or isolated. Include a hand-drawn scheme of the reaction mechanism and briefly discuss it.

General Comments about the Introduction Section:

DO NOT include experimental, procedural detail in the Introduction!! For instance, do not describe how you add a reagent to a flask or mention the size flask you will use. Do not include specific measurements made. Save this procedural detail for the Procedure and Data/Observations section of your Final Report.

Final Report Sections: Procedure and Data/Observations

• Paragraph format• Use your in-lab notebook pages (carbonless copy pages)

to write this section• Type up the procedure and include data and observations when

appropriate

General Comments:• Never start a sentence with a number.• For synthetic experiments, provide mmol amount with mass

amount• Use leading zeroes: 0.080 g rather than .080 g• Include units with every measurement• Use abbreviations where appropriate (g for grams, etc)• Use the proper number of significant figures• Old techniques need not be described in detail again• Use sub-headings as appropriate to organize this section• Report, but do not analyze data

Final Report Sections: Results/Discussion/Conclusion

Results & Discussion:• Data analysis• Introduce the data or calculations before presenting them• Explain deviations from expected results• Use grade sheet as a guide!• Most important section of report!

Conclusions:• Was the purpose achieved?• Were the expected results obtained?• Was the desired product made?• Did the analysis support/confirm predicted results?• Do not include new information here.

Final Report Sections: Reference

Referencing the Lab Guide:

Minard, B.; Masters, K. M.; Halmi, T. O.; Williamson, K. L. Lab Guide for Chemistry 36, 2004-2005, pp. 30-42.

Referencing a Synthetic Experiment Handout:

http://courses.chem.psu.edu/chem36, “Oxidation of Borenol toCamphor, Experiment 125”

Final Report Sections

New for this edition:

Each experiment/chapter (Chapters 4 through 9) has detailed “considerationlists” for each section of a final report that will help guide you through writing the Final Reports for these experiments! Thanks to Denise Conner, a former Chem 35 TA.

For example in Chapter 4, Recrystallization Introduction Section (page 111),Items to consider:

• What is recrystallization, physically?• How/why does recrystallization work?• What constitutes a good solvent?• What is recrystallization good for? Why do chemists use it?• What does melting point reveal about a compound?• What factors affect melting point? How?• How would recrystallizing a compound affect its melting point?• What were the main activities of this chapter’s experiment?

TAs will use these lists as a guide when grading.

Lab Assignments: PreLabs and Final Reports

• PreLabs must be handed in BEFORE running the experiment. Please write them neatly!

• Late work is subject to a 10-point deduction the first day late and a 5-point deduction each additional day.

• See Chapter 3 (Lab Guide) for complete details on PreLabs and Final Reports.

• Grade sheets are to be attached to the front of the PreLabs and Final Reports; use them as a guide to include all important items. PreLab and Final Report grade sheets are located at the end of the chapters.

• Graded final reports and quizzes are not to be taken out of the lab. They will be kept in a secure location until the end of the semester when they will be shredded.

• Please see the syllabus and Lab Guide discussion on Academic Dishonesty.

Academic Dishonesty

Academic dishonesty includes, but is not limited to, the following situations:

Giving your electronic file of your final report to another current student or future student via e-mail, flash drive, CD, etc. Using a current or former student’s e-file of a final report. Using someone else’s data unless instructed to do so. Not citing other students when instructed to collect other student’s data. Fabricating data. Using phrases or sentences directly from the lab guide or any other source (book, journal, or website) and not referencing that source or not using quotation marks. Using phrases or sentences directly from this lab guide or any other source (book, journal, or website), referencing that source, but not using quotation marks.

If you are found to be involved with academic dishonesty on a final report, you will be given a zero for that report. The second offense will involve receiving an F or an XF for the course.Please see Chapter 1, Section 1.6 for a detailed discussion on academic dishonesty.

Final Exam

• Worth 100 pts; cumulative

• Not so much theory, but application.

• Example question: Two layers form in a separatory funnel during extraction. You are unsure as to which layer is the organic and which layer is the aqueous. Without using densities, what can you do to determine which layer is aqueous?

Important Safety Rules

• Always wear eye protection when in the lab!

• Use gloves when appropriate; wash hands often.

• All chemistry must be done in the fume hoods.

• Your TA must be present when you are in the lab.

• If you wear shorts that are above the knee, you must wear a lab apron.

• No bare midriffs or open-toed sandals.

• No iPods or cell phones in lab.

• Report accidents immediately to your TA.

• Keep coats and book bags on the shelves above your desk - keep them out of the aisles!

• If fire alarm goes off, exit the building and walk at least 100 yards away.

Courtesy in the Lab

• Return all reagent and solvent bottles to their proper place on the sideshelves or in the refrigerator immediately!

• Keep your area clean. Your TA will assign one person to do a generallab clean-up after each lab session.

• Show up prepared and on time.

• Keep the Instrument Room clean (room 206 Whitmore).

• Avoid floods.

• Keep balances clean!

• Treat everyone with respect.

Instrument Room

• NMR Spectrometer• IR• UV/Vis• RI (refractive index)• Polarimeter• GC• GC-MS

Chem 36 TAs will hold their office hours in this room.Instrument Room hours will be posted on the door.

Note: Monday evenings (5:35 to 7:30 pm) will be walk-on time.

**You are required to get all spectra signed and dated by a TA in theInstrument Room as soon as you acquire them.**

Next Lab

• Chapter 4 PreLab Due

• Quiz 1 - read Chapter 4 thoroughly!!