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The second exam for the Organic Chemistry course CEM 251 held in Summer 2017. The exam consists of various questions related to drawing structures of organic compounds, identifying stereochemistry, and predicting reaction products. Students are required to draw the structures of given compounds, major organic products, and intermediates for different reactions. The document also includes questions on determining the stability of carbocations and olefins, and outlining an efficient synthesis of cis-2-pentene.
Typology: Lecture notes
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2 pts.
possible?
2-butene (^) 3-methyl-2-pentene
A (^) B C
2 pts.
b) phenylacetylene
c) Z -3-methyl-2-pentene
a) 3-methyl-1-butyne
2 pts.
2 pts.
2 pts.
2 pts.
e) E -2-chloro-2-hexene
d) t -butylchloride
2-methyl-2-butene
Br 2
2
d)
(2 pts.)
OsO 4
f)
show stereochemistry
(2 pts.)
3
(-)
2
3
3
Cl Cl
+^ +
3
3
2
3
2
3
a)
(2 pts.)
b) (2 pts.)
NaBH 4
Hg(OAc) 2
2
show stereochemistry
3
NaOH, H 2
2
c)
(2 pts.)
3
2
3
3
e)
(2 pts.)
2
2
4
3
d)
(2 pts.) (2 pts.)
HBr
e) (2 pts.) (2 pts.)
H 2
O, H 2
SO 4
HgSO 4
3
3
H 2
O 2
, NaOH
a)
(2 pts.) (2 pts.)
b)
(2 pts.)
(2 pts.)
HCl
(2 pts.)
Cl
(-)
(-)
3
3
2
3
3
3
3
c)
(2 pts.) (2 pts.)
Br 2
2
3
Which one ( A, B or C ) is least stable?
A B (^) C
Which one of the above carbocations ( A, B or C )
is most stable?
(2 pts.)
a)
b)
(2 pts.)
X Y
Z
Which one of the above olefins ( X, Y or Z ) has
the highest heat of hydrogenation?
Outline the steps in an efficient synthesis of cis-2-pentene from
acetylene and any desired organic halides:
2
3
3
Make: (^) From: (2 pts.)
2
3
3
2
3
3
3
3
3
2
2
(+)
CH 3 H
3
a)
c)
2
(2 pts.)
major elimination product
1
(2 pts.) (2 pts.)
NaOCH 3
d)
(2 pts.)
NaOCH 3
2
major elimination product
b)
(2 pts.)
(2 pts.)
1
CH 3
OH, H 2
O
3
Br
3
Br
3
Br
3
Br
CH 3
OH, H 2
O
(2 pts.)
9
14
Draw the structure of compound X (C 9
H 14
) in the box:
3
3
(2 pts.)
3
Zn, H 3
3
2
3
3
3
Br
2
2
2
3
3
