The University of Missouri at Columbia
Chemistry 212 - Organic Chemistry II - Winter Semester 2003

SCHEDULE OF EXPERIMENTS

Chemistry 212 Course Web Site: http://www.missouri.edu/~chemrg/RG_T_WS03.html
Professor: Dr. Rainer Glaser, 321 Chemistry Building, (573) 882-0331, GlaserR@missouri.edu
Lab Coordinator: Dr. Phil Silverman, 53 Chemistry Building, (573) 882-8949, SilvermanP@missouri.edu


Nr. Source Analysis Description
Expt. 1 MU MP Recrystallization of Acetanilide and Melting Point Determination.
Expt. 2 MU MP Extraction.
A. Determination of the distribution coefficient for the partitioning of acetic acid and hexanoic acid between 1-octanol and water.
B. Separation of a mixture of basic, acidic and neutral organic compounds by extraction.
Expt. 3 CER 714 IR SN1 and SN2 Reactions.
A. Synthesis of n-butyl bromide.
B. Introduction to IR analysis of product.
C. Factors affecting the rates of SN1 reactions.
a. Effect of leaving group.
b. Effect of alkyl group.
c. Effect of solvent polarity.
Expt. 4 MU TLC
UV/Vis
Thin Layer Chromatography and Column Chromatography.
A. Analysis of the crude pigment extract from tomato paste by TLC.
B. Separation of lycopene and b-carotene by column chromatography.
Expt. 5 CER 716 MP
TLC
Electrophilic Aromatic Substitution.
A. Nitrating Acetanilide or Methyl Benzoate (split class, maybe share results to see both meta and ortho/para directing effects).
B. TLC analysis of crude and recrystallized products. Identify solvent system necessary. Melting point analysis.
Expt. 6 CER 715 MP
TLC
IR
NMR
Sodium Borohydride Reduction of Benzil.
A. Introduction to NMR analysis of product.
B. TLC, melting point and IR (KBr pellets) analysis.
C. The above analysis will be used to identify which stereoisomer(s) is (are) formed.
Expt. 7 MU MP
BP
Tests
Identification of an Unknown Alcohol, Aldehyde or Ketone.
A. Qualitative chemical tests.
Expt. 8 CER 713 GC
IR
NMR
Preparation of Isopentyl Acetate by the Fischer Esterification.
A. Introduction to GC analysis of product.
B. IR and/or NMR analysis.
Expt. 9 CER 726 MP
IR
NMR
Amide Synthesis of Phenacetin.
Characterization by melting point, IR and NMR
Expt. 10.1
Expt. 10.2
UCB
CER 730
IR
UV
Dyes & Dyeing I. Aldol Condensation/Indigo (Used with permission)
Dyes & Dyeing II. Synthesizing Orange II
Characterization by IR and UV/VIS
Expt. 11 MU IR
NMR
Synthesis of 1-Phenylethanol: A Grignard Reaction.
A. Preparation of the Grignard reagent (phenylmagnesium bromide).
B. Reaction of the Grignard reagent with acetaldehyde.
C. Characterization by IR, and NMR.
Expt. 12 MU MP
Tests
Analysis of an Unknown Sugar.
A. Qualitative classification tests.
B. Preparation of the osazone derivative.


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