Experiment 1, page1

EXPERIMENT 1:
ADVANCED COMPOUND IDENTIFICATION

Aims of the experiment

To identify the structures of an unknown compound from a given set of spectral data.

Techniques used/learned:

Analysis of collated spectral/physical data to deduce structures.

Introduction and Experimental

The identification of unknown compounds is a vital skill for practising organic chemists.

The

deduction of the structure of, for example, a by-product in an industrial process can lead to

improved processes and important savings.

Many pharmaceuticals are natural products or semi-

synthetic derivatives thereof (egpenicillin, erythromycin and vancomycin antibiotics) and the

determination of the structure of the active components isolated from a fermentation broth is a key

step in the development of these entities as drugs.

This experiment will give you experience in the determination of the structure of materials prepared

in the research labs here at Imperial College.

These compounds may be known intermediates

(prepared as part of a synthetic route) or may be compounds as yet unpublished in the literature.

You are provided with copies of spectral data on a compound. Use these to deduce the structure of

your unknown.

In cases where your compound can exist as stereoisomers, you must attempt to

identify the relative stereochemistry using either the spectroscopic data or by comparison to known

compounds in the literature where possible. To confirm your proposals, you may wish to use the

Beilstein Crossfire service to retrieve data for the authentic compound. Full details of how to carry

out this search are located at http://www.ch.ic.ac.uk/local/organic/cf.html. Please note that some of

the unknown compounds are unpublished, and hence not (yet) abstracted by Beilstein or CAS.

Write Up

Write a succinctaccount of your observations and deductions for the structures.

The write up

should conform to the RSC Org. Biomol. Chem.style (see Issue 1, 2003 or the RSC web page

( http://www.rsc.org/pdf/obc/ifa.pdf) for further instructions) and include all literature references.

Credit will be given for successful identifications, but just as importantly for the manner in which

you reach your conclusions.

A logically argued deduction of the structure based upon your data

will gain most marks - simply guessing from one or two pieces of poorly interpreted data will not

impress the judges!

Do not mark the spectra provided – you may copy them but the
originals must be returned for re-use by other students!!!

Department of Chemistry, Imperial College

Third Year Advanced Practical Organic Chemistry