Part 9 : 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 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 Br2 / uv tells you that C is 2-bromo-2-methylbutane (3o
H most reactive).
(2) Formation of C from B with HBr results in a
rearrangement because reaction with PBr3 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.