? Question 12
10 pts
Suggest a sequence of 4 reactions that will transform Compound A into Compound B. Input the answer as follows. Write the
lower case letter for the first reaction that you would use, then the letter for the second reaction employed, then the letter for
the third reaction, followed by the letter for the last reaction. There should be nothing between the letters (no spaces, dashes,
colons, etc). If you wanted to use reaction a, then reaction b, then reaction c, then reaction b, the answer would be abcd (this
would be the wrong answer by the way). NOTE THAT THE I BETWEEN h & j LOOKS LIKE AN I DUE TO A RESOLUTION
ISSUE. HINT: The bromines are anti and use the reaction that installs two bromines in an anti-addition as the last step of the
reaction.
$CH_3$
A
Br
B
a\ Br$_2$ (no light or heat)
h $H_2$/Pt
b NBS/hv
i Na/NH$_3$/EtOH
c $H_2SO_4$/Heat
j $NaNH_2$ then $CH_2CH_3$
d 2 moles HBr
k $NaC?C-CH_2CH_3$ ($C?CCH_2CH_3$)
e $H_2O/H_2SO_4/HgSO_4$
l KO-$t$-Bu/t-BuOH (for E2)
f $O_3$ then $H_2O$
m Aq. $KMnO_4$/Heat
g $H_2$/Lindlar's catalyst