ORGANIC EXPERIMENT SCHEDULE
CH2421, SPRING 2008
SUPERVISOR: Andrew Galerneau, Chem Sci 601, :ajgalern@mtu.edu
ADVISOR: Dr. Marshall W. Logue, ChemSci 610, 487-2910, mwlogue@mtu.edu
INTERNET ACCESS: http://www.chemistry.mtu.edu/~kmsmith/Organic/
LAB 1 (JANUARY 15 & 17): Check-in, Safety Review, and Introduction to The Chemical Abstract Author Index
ASSIGNMENT: Read/review sections 1-4 of The Organic Chem Lab Survival Manual by James W. Zubrick 1)
Read/review Lab Notes
LAB 2 (JANUARY 22 & 24): Selective Oxidation of Alcohols with Pyridinium Chlorochromate & SPECTRA
PREPARATION: Read experiment, review techniques, and prepare preliminary lab notebook (for 2 weeks).
TECHNIQUES (found in Zubrick): Reflux, reflux and addition, gravity filtration, thin-layer chromatography, nuclear
magnetic resonance interpretation, and infrared spectroscopy.
NOTE: The CA Author Index exercise is due in lab during Lab 3.
LAB 3 (JANUARY 29 & JANUARY31): Continuation of Selective Oxidation of Alcohols with Pyridinium
Chlorochromate
PREPARATION: Review experiment and techniques.
Reminder: The CA Author Index due.
(FEBRUARY 5 & 7): CARNIVAL BREAK- NO LABS WILL MEET DURING THE WEEK OF WINTER CARNIVAL.
LAB 4 (FEBRUARY 12 & 14): QUALITATIVE TESTS FOR IDENTIFICATION OF CARBON-CARBON
UNSATURATION AND ALCOHOL FUNCTIONS
PREPARATION: Read experiment, review techniques and prepare a preliminary lab notebook according to the
following: EXAMPLE PRELIMINARY NOTEBOOK
LAB 5 (FEBRUARY 19 & 21): The Grignard Reaction
PREPARATION: Read experiment, review techniques, and prepare preliminary lab notebook.
TECHNIQUES (found in Zubrick): drying glassware, reflux, boiling stones, heating, separation/washing,
recrystallization, vacuum filtration, melting point, products, wet column chromatography.
ADDITIONAL ASSIGNMENT: Read the Lab 8, Part II, experiment, "Borohydride Reduction of Vanillin" and
develop a procedure. An outline of your procedure for this assignment is due during Lab 6.
This will give teaching assistants an opportunity to grade and return the procedure before the experiment is
scheduled.
LAB 6 (FEBRUARY 26 & FEBRUARY 28): Continuation of the Grignard Reaction: Column Chromatography
PREPARATION: Review experiment and techniques.
Reminder: Outline for procedure of Lab 8, experiment, "Borohydride Reduction of Vanillin" due.
NOTE: A flow diagram of the procedure for the final experiment, "Separation and Identification of an Unknown
Binary Mixture" is due during the lab 7. This will give teaching assistants an opportunity to grade and return the flow
diagrams before the experiment.
LAB 7 (MARCH 4 & 6): Friedel Crafts Acylation; 4-Methoxybenzophenone & SPECTRA
PREPARATION: Read experiment, review techniques, and prepare preliminary lab notebook.
TECHNIQUES (found in Zubrick): Reflux, separation/washing, drying agent2, recrystallization, vacuum filtration,
melting point determination, products, and infrared.
Reminder: A flow diagram of the procedure for the experiment "Separation and Identification of an Unknown Binary
Mixture" is due.
(MARCH 11 & 13): SPRING BREAK- NO LABS WILL MEET DURING THE WEEK OF SPRING BREAK.
LAB 8 (MARCH 18 & 20): Part I & II
Part I: Continuation of Friedel Crafts Acylation; 4-Methoxybenzophenone
PREPARATION: Review experiment and techniques: melting point determination, IR.
Part II: Borohydride Reduction of Vanillin
PREPARATION: Read experimental theory, review procedure (self-prepared) & techniques, and prepare preliminary
lab notebook (according to the procedure for this experiment).
TECHNIQUES (found in Zubrick): Products, melting point, recrystallization, & vacuum filtration.
LAB 9 (MARCH 25 & 27): Part I and Part II
Part I: Identification of an Alcohol or Carbonyl Compound by Means of Three Reagents
PREPARATION: Read experiment, review techniques, and prepare preliminary lab notebook with tables similar to:
Example Table for Preliminary Notebook.
Part II: Separation and Identification of an Unknown Binary Mixture
PREPARATION: Read experiment introduction, review techniques, and prepare a flow diagram of the procedure (2
weeks prior).
TECHNIQUES (found in Zubrick): extraction and washing, drying agent2, simple distillation, recrystallization, vacuum
filtration, melting point.
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LAB 10 (APRIL 1 & 3): Continuation of Separation and Identification of an Unknown Binary Mixture
PREPARATION: Review procedure performed, prepare/outline procedures needed to finish, and review techniques.
TECHNIQUES (found in Zubrick): Numerous, most or all performed previously!
LAB 11 (APRIL 8 & 10): Continuation of Separation and Identification of an Unknown Binary Mixture
PREPARATION: Review procedure (self-written), techniques, and prepare preliminary lab notebook. TECHNIQUES
(found in Zubrick): infrared, sample preparation, nuclear magnetic resonance.
LAB 12 (APRIL 15 & 17): Part I and Part II
Part I: Continuation and Completion of Separation and Identification of an Unknown Binary Mixture
PREPARATION: Review procedure (self-written), techniques, and prepare preliminary lab notebook.
TECHNIQUES (found in Zubrick): infrared, sample preparation, nuclear magnetic resonance.
Part II: Introduction to The Science Citation Index (library assignment)
LAB 13 (APRIL 22 & 24): Lab Check-out, Clean-up, and Evaluations
NOTE: Any student enrolled in this course must check out before the last lab. For further instructions,
please see early check-out. Students who do not make arrangements to check out of their drawer will be
fined $25.00 in addition to the cost of replacement equipment.
CORRECTIONS TO TEXT (ZUBRICK ONLY, 7th Edition):
pp. 31-34: Much of the Lange's Handbook of Chemistry information on nomenclature is only true for the 1st -12th
editions.
2 p. 92, 3.: Since it is a fine powder, lots of your water product can become trapped on the surface.
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Mattson FTIR is scheduled during this expeirment.