© 2000, MU Department of Chemistry

The University of Missouri at Columbia
Chemistry 212 - Organic Chemistry II - Winter Semester 2000


Instructor Professor Rainer Glaser
Office 321 Chemistry Building
Telephone (573) 882-0331
E-Mail GlaserR@missouri.edu
Chemistry 212 Course Web Site http://www.missouri.edu/~chemrg/RG_T_WS00.html

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
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
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
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
Identification of an Unknown Alcohol, Aldehyde or Ketone.
A. Qualitative chemical tests.
Expt. 8 CER 713 GC
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
Amide Synthesis of Phenacetin.
Characterization by melting point, IR and NMR
Expt. 10 CER 721 MP
Wittig Reaction: Synthesis of trans-9-(2-Phenylethenyl) anthracene.
A. Characterization by melting point, TLC, IR and NMR.
B. Perhaps monitor the reaction by TLC.
Expt. 11 MU IR
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
Analysis of an Unknown Sugar.
A. Qualitative classification tests.
B. Preparation of the osazone derivative.

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