Bioorg Chem
Dr. Milkevitch
Assigned: Oct 21, 2009
Due Oct 28, 2009
Name_______________
Problem Set 3
Note: Working in groups is encouraged. If you choose to work in groups, indicate
who the group members were on the top of the page.
1) Name the following compounds using the IUPAC nomenclature system (4 pts each).
a)
CH3CH
CHCH 2CH2CH2CH2CH2CH2CH3
CH3 CH(CH 3)2
b)
CH3CH2CH
CHCH2CCH 2CHCH 2CH3
CH3
c)
CH3
Cl
CH2CH3
1
d)
2) Draw the correct structural formula for the following compounds. (4 pts each).
a) 3-methyl-1-pentene
b) cis-1-chloro-1-butene
c) 2,3-dimethyl-1-cyclopentene
d) 4-isopropyl-2,6-dimethyl-2-heptene
2
3) For each of the following pairs of structural formulas, indicate whether the pair
represents: (3 pts each).
1) The same compound
2) Different compounds that are constitutional isomers
3) Different compounds that are cis-trans isomers
4) Different compounds that are not isomers
a)
H3C
C
H3C
H
H
C
H3C
H
H3C
and
C
C
CH3
C
CH 3
C
Cl
and
H
H3C
C
H3C
CH3
C
H
H3C
H
C
c)
and
C
H
b)
H
CH3
C
Cl
CH 3
3
Cl
C
CH 3
4) Name the following compounds using the IUPAC system of nomenclature (3 pts
each).
a)
H 3C
C
C
CH 3
C
C
Br
b)
H3C
C
CH3
Br
CH3
CH3
c)
CH3
C
CH2
CH2
C
C
CH2
CH
CH3
CH3
5) Complete the following reactions. If multiple products can be formed, be sure to draw
both products and indicate which product is the major product and which is the minor
product (5 pts each).
a)
+ HBr
4
b)
H2, Pt
c)
H+
+ H2O
d)
+ Cl2
e)
H+
+ H2O
5
6) Draw the structure of the following compounds from their IUPAC names (3 pts each).
a) 5-methyl-3-octyne
b) 1,3-cyclohexadiene
c) trans-3-bromo-4-chloro-3-hexene
7) Name the following compounds using the IUPAC system of nomenclature (4 pts
each).
a)
6
b)
F
c)
d)
NH2
OH
7