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....

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.

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 H can de deduced once A is obtained.

(6) No carbocation rearrangements since B and D are already tertiary

(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 H can de deduced once A is obtained.

(6) No carbocation rearrangements since B and D are already tertiary