Welcome to Chem 36!
Organic Chem Lab
Dr. Katie Masters
Chem 36 Info
Section 1:
Section 2:
Section 3:
M/W at 1:25 to 4:25 pm in 205/215 Whitmore Lab
M/W at 1:25 to 4:25 pm in 205/215 Whitmore Lab
T/R at 6:30 to 9:30 pm in 205/215 Whitmore Lab
Faculty
in
Charge
Dr. Katie Masters
Director, Organic Labs
218 Whitmore Lab
Phone: 863-3319
kmasters@psu.edu
Dr. Jackie Bortiatynski
Director, Instrumentation
211D Whitmore Lab
Phone: 865-2772
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:
Second Half of Semester:
5 Technique Experiments
• Recrystallization & Melting Point
• Distillation & Boiling Point
• Liquid/Liquid Extraction
• Thin-Layer Chromatography (TLC)
• Column Chromatography
5 Synthetic Experiments
Assigned experiments; Download
from the course website.
Throughout the Semester:
Spectral Unknown Experiment
Determine 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)
Breakdown of the Chem 36 Points
Chapter 1
5 Technique Experiment PreLabs
120 points*
5 Technique Experiment Final Reports
400 points*
5 Synthetic Experiment Prelabs
150 points
5 Synthetic Experiment Final Reports
500 points
Spectral Unknown Determination
100 points
TA Evaluation
100 points
Quizzes
300 points
Final Exam
100 points
Maximum 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.
The Lab Experiments: The Techniques
Chapter 4: Recrystallization and Melting Point: Two day lab
Recrystallization & MP of an Unknown
Recrystallization of Phthalic Acid
MP of Spectral Unknown (Ch 10 experiment)
Decolorization with Norit
Chapter 5: Distillation & BP: Two day lab
Simple or Fractional Distillation of a Known Mixture
Microscale Fractional Distillation of an Unknown Mixture
Chapter 6: Liquid/Liquid Extraction: Two day lab
Separation of a Solid Mixture (acid/base chemistry)
Extraction of Caffeine from Tea
The Technique Experiments
Chapter 7: Thin-Layer Chromatography: One day lab
Finding a TLC Mobile Phase
Identifying Compounds in an Analgesic Tablet
Chapter 8: Column Chromatography: Two day lab
Oxidation of Fluorene to Fluorenone
Column Chromatography of Reaction Mixture
Chapter 10: Spectral Unknown Experiment: Ongoing lab
Acquire mp, IR and 1H NMR spectra
Determine 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 through
and understands the theory and procedures of each experiment.
PreLab Format (Described in Chapter 3)
Sections:
1. Purpose of Experiment
2. Diagrams of Special Apparatus/Reactions
3. Chemical Data Table
4. PreLab Exercise
5. Chromatographic & Spectral Features Comparisons (only for Ch 8 & 9)
PreLabs are hand-written into the Lab Notebook. White pages
are handed in for grading. The yellow copies are kept within the
notebook.
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 of
the purified unknown to determine its identity.
Bad Example:
I will take a melting point.
PreLab Sections: Diagrams of Special Apparatus and/or
Reaction 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.
O
O
CH2CH3
Oxidation by KMnO4
in base, heat for 1/2 hr
Cl
4-chloropropiophenone
Limiting Reagent
OH
Cl
4-chlorobenzoic acid
Theoretical 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 Common
Shelf 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 the
table. Use the “least pure” entry for the price.
PreLab Sections: Chemical Data Table
There are two main different editions of The Aldrich catalog.
Chapter 3 for details about your edition!
Please see
Columns of the Chemical Data Table:
Chemical Name
Chemical 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/mL
Quantity: 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 experiments
Flammability: if flammable, write “yes”; if not, write “no”; this info given in
Aldrich
Toxicity: if toxic, write “yes”; if not, write “no”; info given in Aldrich
Price: given in Aldrich; give price for 100 g or 100 mL
Waste category: info given in Chapter 2; some categories include HO, NHO, D,
WB, HM
Comment: 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 Comparison
Relative Rf comparison between main organic starting material and main
product of reaction.
Example:
OH
Cyclohexanol
Starting material
Cyclohexene
Product
(Draw out structures)
Cyclohexanol would have a lower Rf value due to the OH functionality, which
is more polar than the alkene of cyclohexene.
PreLab Sections: Chromatographic & Spectral
Features Comparisons
For Chapter 8 and Chapter 9 experiments only!
Spectral Features Comparison
Consider diagnostic 1H NMR & IR signals for the starting material and product
that would be used to distinguish the two from one another.
Example:
OH
(Draw out structures)
Cyclohexanol
Starting material
Cyclohexene
Product
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 cm1
Lab Quizzes
Purpose: To test your understanding of theory and your preparedness for
the experiments.
Quiz 1: Chapter 4
Quiz 2: Chapter 5
Quiz 3: Chapter 6
Quiz 4: Chapter 7
Quiz 5: Chapter 8
Quiz 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.
II.
III.
IV.
V.
Introduction
Procedure and Data/Observations
Results/Discussion/Conclusions
PostLab Exercise
Reference
Attach the white in-lab notebook pages. You must have your TA
initial all pages used during each lab session. Attach annotated
spectral data when appropriate. Attach grade sheet to the front.
Final reports are computer-generated. Reaction schemes can be
hand 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/or
compound 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 to
Camphor, Experiment 125”
Final Report Sections
New for this edition:
Each experiment/chapter (Chapters 4 through 9) has detailed “consideration
lists” 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 side
shelves or in the refrigerator immediately!
• Keep your area clean. Your TA will assign one person to do a general
lab 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 the
Instrument Room as soon as you acquire them.**
Next Lab
• Chapter 4 PreLab Due
• Quiz 1 - read Chapter 4 thoroughly!!