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The identification of the structure of chemical substances is an activity fundamental to
all varieties of research in organic chemistry. In some instances, the chemist may wish to
establish that an unknown substance is identical to a previously reported compound. In
other cases, the structure of an entirely new unknown compound must be deduced. This
experiment is designed to simulate these common research situations.
The aim of the experiment is to separate and identify the components of a binary
organic mixture. Unknown samples will consist of approximately 2 g of a mixture of two
organic compounds. One unknown in each sample is an organic acid (e.g. carboxylic acid,
phenol or sulfonic acid). The other unknown in each sample is a neutral organic compound
(e.g., ketone, ester, amide etc.).
¡¤  The unknowns will be separated by extraction (monitored by thin layer
chromatography). The separated compounds will then be purified by
recrystallization.
¡¤  The structure of the neutral unknown will be deduced by analysis of the 1D NMR
(1H NMR, 13C NMR, DEPT1), 2D NMR (gCOSY,2 HETCOR3 or HMQC4), FT-IR
and GC/MS spectral data together with analytical and data supplied by the
teaching staff. UV-Vis analysis is optional.
¡¤  The acid unknown will be identified by infrared, 1H NMR, 13C NMR spectral data
and comparison of its spectral characteristics with those of previously reported
compounds, and by the preparation of a suitable derivative (amide).
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