Part 9 : STRUCTURE DETERMINATION

First, the flow chart of the basic information from the question.... use this to try to answer the question before just looking at the answers....

question flow chart

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 by green arrows 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.

complete solution flow chart

Important points:
(1)  D gives 1-methylcyclopentene ... hence we have a methylcyclopentane framework.
(2)  A has 4 types of C and H, one of which is tertiary.
(2)  B is a tertiary bromide - evident from synthesis from A and reactions with AgNO3 and NaI
(3)  Elimination of B with a hindered base gives the less substituted alkene as the major product
(4)  Dehydration of alcohol D gives the more stable, more highly substituted alkene as the major product
(5)  F, G and can de deduced once A is obtained.
(6) No carbocation rearrangements since B and D are already tertiary