Org Chem II
Dr. Milkevitch
Assigned March 3, 2010
Due March 10, 2010
Name_______________
Problem Set 2
1) Fill in the blanks in the below with the products of the listed reaction scheme(s). Be
aware that they may be multiple products in each reaction scheme. Be sure to indicate
correct stereochemistry, where applicable. You do not have to draw any
mechanisms (3 pts each).
______________________
CH3OH, heat
NH2-
I
CH3ONa
________________
___________________
CH3CH2CH2OH
heat
___________________
2) When 2-bromo-2-methylpropane is dissolved in aqueous methanol at 25C, a mixture
of the below products is obtained. Draw mechanisms to account for each of the
products formed (4 pts each mechanism).
CH3
H3C
C
OCH3
CH3
CH3
H3C
C
OH
CH3
H3C
C
H3C
CH2
3) Predict the structure of the all the alkene products formed in the E2 reactions of the
following halides (3 pts each).
a)
Br
b)
Cl
c)
I
4) Predict all substitution and elimination products of the following reactions (4 pts
each).
a)
Br
H2O
b)
Br
c)
H2O
CH3OH
CH2Br
5) Provide the IUPAC names for the following alkenes (3 pts each).
a)
b)
c)
H3CH2C
F
e)
I
H3CH 2CH 2C
CH 2CH 3
C
H2C
g)
F
d)
CH3
CH
CH3
C
f)
CH 3
h)
CH 3
CH 2CH 3
F
I
6) Examine the structure of the following compounds and determine if they can be named
using cis-trans nomenclature or E-Z nomenclature. Draw and label the isomers, using
cis-trans or E-Z nomenclature, where applicable. If you find that cis-trans nomenclature
or the E-Z nomenclature system is not applicable, then name the alkene as normal (4 pts
each).
a) 2-pentene
b) 1,1-dicloropropene
c) hexa-2,4-diene
7) Predict the products of the following reactions. If more than one product is possible,
predict which will be the major product. You do not have to write mechanisms (3 pts
each).
a)
OH
H2SO4, heat
b)
H3PO4 , Heat
OH
c) 1-bromo-1-methylcyclohexane + triethylamine
d)
+ K+ t-butox
(CH3)3COH
Cl
e)
I
+
f)
OH
H2SO4
heat
(CH3)3COK
(CH3)3COH