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SC226 Quiz
20 Jan 2016
Prof. Urban
1. Predict the major product(s) ofthe reaction below and provide a complete mechanism. If
multiple regioisomers are possible, explain which, if any, are expected to predominate in the
()~fI
reaction mixture. If multiple stereoisomers are possible, explain which, if any, are expected to
predominate in the reaction mixture. Justify your answers in terms of the mechanism. (4 x::;ts) ,J, (..fII"\g"b
n {lJ....\O··
H20
~..
y-
H2S04 ,.n
!
U
o~')...- ----""'~(V\ s J,
-)
I.
I
~
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<»IJe o" ,.~ r ... c}l4 vr
~+(6V' ~Io~
r
@/~
~H-'~--L-\
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\.
\.;!:I
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'-----....-
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n c::
y1-\,v.(
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)
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l1-0CAAf.oo~f\DI'- \s
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S·tHl"e6ciAt"",,51vO· ..
+,
S'1'" ( ..... 6\dd,+,OV'
OC(.Wl- ~)( dl ~ft,oCtJ,n'.M
\3crft...
(11».
r, tkJ/t'ttJ. vJJ.
2. Predict the major product{s) of the reaction below and provide a complete mechanism. If
I>" multiple regioisomers are possible, explain which, if any, are expected to predominate in the reaction mixture. If multiple stereoisomers are possible, explain which, if any, are expected to predominate in the reaction mixture. Justify your answers in terms of the mechanism. (4 points) 1t q(b d.t "'" ,s~'1: tJ IA­ ,""
J
-ft..l ew
~ ..J..e,y.eo ~v¥\. -:, M~:
o.JJ ;-hQv\ Vv~
3.
e
Show the products of these reactions. (2 points)
y 6'M \J'I\ ; II N'­
H3C
H3C~CH3
3".+ HBr I
c.-c 1-1;
32-\
CA"\ - Cl..\. -
Cl-t,
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