Chem 353 W 2007 Final: Structure Det.
Part 10: STRUCTURE DETERMINATION
A schematic of the solution is shown below. The information
from the question is given in black. Deductions directly from this
information are given in red. Points that provide potential key information
are shown in green which leads to the structures which are linked via
the blue arrows to show the path required to work them all out. There
are, of course, other possible thought pathways.
Note that A-D do not contain chirality centers, whereas
E-G do.
The crux of this problem is reaction recognition..... ozonolysis, esterification,
intramolecular Claisen condensation, alkylation and decarboxylation are all
there.
Alternatively, once you get that B is a cyclic alkene, if you know it
is C6 then there is only one possible structure with a total of 3C types but
only 1 type of vinyl C.
From B then C and D are obtained.
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