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) C is obtained from 2-methylbutane with Br_{2} / uv tells you that C is 2-bromo-2-methylbutane (3^{o}
H most reactive).

(2) Formation of C from B with HBr results in a rearrangement because reaction with PBr_{3} gives A.

(3) t-butoxide eliminations (tBuO-) often disobey Zaitsev's rule - remove least hindered H, hence C to D.

(4) Alcohol dehydration obeys Zaitsev's rule - hence B to E (more substituted = more stable alkene).

(5) As D, E and F react to give the same alkane, F is deduced (only other alkene variant).

(6) A can be deduced from knowing B or F or based on the chirality information.

(1) C is obtained from 2-methylbutane with Br

(2) Formation of C from B with HBr results in a rearrangement because reaction with PBr

(3) t-butoxide eliminations (tBuO-) often disobey Zaitsev's rule - remove least hindered H, hence C to D.

(4) Alcohol dehydration obeys Zaitsev's rule - hence B to E (more substituted = more stable alkene).

(5) As D, E and F react to give the same alkane, F is deduced (only other alkene variant).

(6) A can be deduced from knowing B or F or based on the chirality information.