1. CHEM 213
Organic Laboratory

2. CHEM 213 – Organic Lab Important Information:
Lab Section
001 T (2:30 – 5:00 PM)
002 W (1:25 – 3:55 PM)
003 R (9:30 AM – 12:00 PM)
004 R (2:30 – 5:00 PM)
Instructor
Dr. Martin Kociolek
Mrs. Tracy Halmi
Dr. Michael Justik
Office
37 Hammermill
35 Hammermill
32 Hammermill
Phone
Web Page
chemistry.bd.psu.edu/kociolek/
chemistry.bd.psu.edu/halmi/
chemistry.bd.psu.edu/justik/
Office Hrs
T 9:30 –11:00 AM
W 1:30 – 3:00 PM
M 1:25 – 3:15 PM
W 9:30 – 10:45 AM
F 1:25 – 2:15 PM & by appt
M 8:00 –11:00 AM
Recitation: All students will attend mandatory lab recitation on Mondays 3:35 PM.
Recitation will NOT meet every week, see attached schedule for recitation dates.

3. Thanksgiving Week – No Lab
Laboratory Schedule
Week of
Recitation Readings
EXPERIMENT
ASSIGNMENT
DUE DATES
8/27*
Techniques
1, 2, & 3
Check-in
Safety Quiz
9/3
6, 9, & 10
Experiment #1:
Purification of Solid Organic Compounds -
9/10*
11, 13, 16, & 18
Experiment #2:
Purification of Liquids by Distillation
9/17
Experiment #2: continued
Exp #1 Short Report
9/24*
Technique 8 & 11.7
Experiment #3: Steam Distillation
10/1
Experiment #3: continued
Exp #2 Short Report
& Notebook
10/8*
Handout
Experiment #4: Acid/Base Extraction
10/15
Experiment #4: continued
Exp #3 Short Report
10/22*
Technique 15
Experiment #5:
Thin-Layer Chromatography
10/29
Experiment #5: continued
Exp #4 Full Report
11/5*
Technique 17
Experiment #6: Benzoylation of Ferrocene
11/12
Experiment #6 continued
Exp #5 Full Report
11/19
Thanksgiving Week – No Lab
11/26*
Experiment #7: Synthetic Puzzle
Exp #6 Full Report
12/3*
Final exam
Experiment #7: continued
12/10
No Lab
Exp #7 Full Report
* NOTE: Lab recitation will only meet on these Mondays.

4. Required Materials: Text: Techniques in Organic Chemistry, 2nd edition
Jerry R. Mohrig et al, W. H. Freeman and Company, 2006
Handouts: Downloaded from instructor’s web site prior to recitation
for each new experiment
Notebook: A bound notebook is required
unacceptable - spiral or three-ring bound notebooks
most convenient - composition notebook
Goggles: Any goggles or safety glasses with side-shields
Software:

5. Assignments: Notebook (35 pts) Quizzes (50 pts) Lab Reports (275 pts):
PreLab
Quizzes (50 pts)
recitation includes a short (10 pt) quiz on the readings
six quizzes - no make-up quizzes – but one quiz may be dropped
Lab Reports (275 pts):
First 3 experiments a short report (25 pts each), emphasizing a particular section
Final 4 experiments require a full report (50 pts each)
Late reports will be penalized at two points per day up until they are one week late when they will not longer be accepted.
Final Exam (75 pts):
A comprehensive final exam will be given during the recitation. (see schedule)
General Lab Courtesy:
Failure to collaborate, cooperate and abide by the safety rules will result in an automatic deduction of points from that lab, at the discretion of the instructor. Students who do not checkout their desk equipment will be charged a $25 checkout fee.

6. Grades: Total 435 pts The minimum grade you will receive :
Notebook
35 pts
Quizzes (5 x 10 pts)
50 pts
Lab Reports (3 x 25 pts, 4 x 50 pts)
275 pts
Final Exam
75 pts
Total
435 pts
The minimum grade you will receive :
A (100-93%), A- (92-90 %), B+ (89-87%), B (86-83%), B- (82-80%), C+(79-75%), C (74-70), D (69-60%), F (<60%).

7. Notes:
Academic Integrity: It is expected that each student will do his/her own work on all assignments including quizzes and laboratory reports.
This includes but is not limited to …
stealing, purchasing or copying quizzes and/or laboratory reports from present or previous students.
even the possession of other student’s notebook, laboratory reports, or quizzes constitutes a violation of the academic integrity polity at Penn State.
For more information see the Academic Integrity & Academic Dishonesty (Senate Policy 49-20) at or Behrend’s Academic Integrity policy at
Students with disabilities: If you have a disability-related need for modifications or reasonable accommodations in this course, contact the Disability Specialist in the Office of Student Affairs, Room 115 Reed Union Building,

8. WELCOME to CHEM 213

9. Experimental Objectives
Purification of Organic Solids
Identification using Melting Point Determination
Experiment 1
Experimental Objectives
become familiar with common heating & cooling methods (Technique 6)
purify organic unknown using recrystallization (Technique 9)
identify unknown by melting point & solubility data (Technique 10)

10. Recrystallization
crystalline material (solute) is dissolved in a hot solvent then returns to solid when cooled
important to understand “dissolving”
solid
solvent
choice & amount of solvent is critical

11. Solubility solvent temperature - solubility increases with temperature
solvent volume - amount of solute vs. volume of solvent
solvent properties - solute/solvent interactions “like dissolves like”
- polar H2O dissolves most (polar) inorganic compounds
- nonpolar organic solvents dissolve most (nonpolar) organics

12. Recrystallization Solvents

13. 7 Steps to Recrystallization
find “best” solvent
dissolve bulk sample in solvent
decolorize (if necessary)
remove insoluble impurities (if necessary)
cool solute/solvent mixture
collect crystals
dry & analyze crystals

14. Step 1 find “best” solvent small (test tube) size using a sand bath
dissolves went hot – not when cold
limited to six initial solvent choices
water
ethanol
ethyl acetate
methylene chloride (dichloromethane)
toluene
hexane

15. Steps 2 - 4 dissolve bulk sample in solvent decolorize (if necessary)
minimum amount of solvent to dissolved solute with heat
this will be unique to solute & solvent choice
use boiling chips or sticks
decolorize (if necessary)
charcoal adheres to colored impurities
remove insoluble impurities (if necessary)
hot gravity filtration

16. Hot Filtration
Hot Plate

17. Step 5 cool solute/solvent mixture
cool slowly to eliminate soluble impurities from crystallizing
If crystals do not form try…
scratching with glass stir rod
add a seed crystal
evaporate some excess solvent

18. Step 6 collect crystals vacuum filtration using Buchner Funnel
to vacuum

19. Step 7 dry Review Steps 2 – 6: video leave on vacuum filter
leave crystals in funnel open in desk
heat under a heat lamp – take care
Review Steps 2 – 6: video

20. Percent Recovery evaluates recrystallization quantitatively
do not forget to record weight of unknown
not the same as a percent yield
% =
amount of solid recovered
amount of initial solid
X 100

21. Melting Points temperature where solid & liquid phases in equilibrium
characteristic physical property of solid
the identity of an organic solid
the purity of an organic solid
most organic solids melt oC
A. Sublimation
B. Melting
C. Evaporation

22. Melting Points Organic molecules within the solid are held together
by intermolecular forces
Hydrogen bonding 2 – 10 kcal/mol
Dipole-dipole interactions kcal/mol
Van Der Waals forces (temporary dipole) kcal/mol
compare to a intramolecular covalent bond ~100 kcal/mol

23. Melting Points
Consider the effects of intermolecular forces on the melting point of three organic compounds of similar mass:

24. Hydrogen Bonding
Benzoic acid
melting point oC

25. Dipole-Dipole Ethyl benzoate, melting point -23 oC
Dipole-dipole interactions are weaker. Ethyl benzoate is heavier than benzoic acid, yet its melting point is below room temperature, almost 150o below benzoic acid.

26. Van Der Waals Ethyl benzene, melting Point -95 oC
Temporary dipoles are the weakest form of intermolecular force.
Solids held together by these forces have low melting points.

27. Melting Point Determination
The energy (heat) required to break these intermolecular interactions is the same for any two molecules within the solid
pure organic compounds have a distinct melting point that can be used for identification
melting point should also occur over a very narrow range of temperatures
impurity in the solid disrupts intermolecular forces – takes less energy to melt solid – therefore lowering and broadening melting point range

28. Pure Solid The Van Der Waals forces that hold the
solid together are regular
are the same from
molecule to molecule
Pure naphthalene
melts at 82-83oC

29. Impure Solid
cyclohexane contaminated
naphthalene, mp 62-69oC

30. Melting Point Determination
Problem:
Suppose you are cleaning the chemical stockroom and you encounter a reagent bottle whose label has decomposed. You suspect that the compound could be either benzoic acid (mp oC) or succinimide (mp oC). You take a melting point, and sure enough the unknown melts at 123 oC.
How would you use what you have learned to determine the true identity of the contents of the bottle?

31. Mixed Melting Point Solution:
obtain known samples of benzoic acid & succinimide
mix each of the known samples with a portion of the unknown
determine the melting point for each mixed sample
Temp (◦C)
MP Pure A
MP Pure B
100% A % B
Mole % Composition

32. Thomas-Hoover silicone oil bath five samples simultaneously
oil slow to respond to temperature changes – so a slower, better melting point can be obtained
silicone oil has a temp limit 200 °C
good choice for organics that melt between °C

33. Mel-Temp uses a heated aluminum block three samples simultaneously
aluminum is quick to respond to temperature changes – higher temps can be achieved more quickly
advantage in determining high melting points
good choice for organics that melt over 200 °C

34. MP Sample Size
Use the minimum amount of sample & slowest heating rate to obtain the sharpest, most accurate melting point.
Sample size: samples placed in a mp
capillary tube. Use the minimum amount
seen through the magnifier (1-2 mm)
Heating Rate: quickly go to
20 °C below the expected MP,
then slow to 1-2 °C per minute
to observe the correct MP
Melting Point Video

35. Introduction Brief Paragraph (2-5 sentences) Do not include:
interesting background information
goals/objective
reaction (if applicable)
proper reference
Do not include:
explanation
procedure

36. Conclusion Brief Paragraph (2-3 sentences)
statement summarizing discussion
must include conclusion
Typed, 12 point black font, double spaced
grammar, spelling, etc.

37. Notebook Chapter 3 in Mohrig Prelab Observations
table of contents (leave room)
numbered pages (no pages torn out)
Prelab
title, date
purpose including balanced reaction (if applicable)
chemical data table
do not write out the procedure (outline if helpful)
Observations
in class notes recorded in ink
calculations

38. Questions?
Comments?