Name
Chem 331, Fall 2002, PS #2, due Mon Sept 16th
for more practice, see 1991-1999 PS#2's at:
http://valhalla.chem.udel.edu/C331.html
1. Draw all of the dibromo derivatives of 1-pentene .
Note: R/S stereochemistry has not yet been considered
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
2. Give IUPAC names for the following
a
b
HS
Br
d
c
CHO
HOOC
O
COOH
NH2
6-bromo-2-octanone
(E)-6-mercapto-3-hexenal
OH
Cl
4-aminoheptanedioic acid
3-chloro-2-methyl-2-cyclohexenol
3. Draw the structures of the following
a. 3-bromo-2,5,5-trimethyl
-2-cyclohexenone
b. (Z)-6-amino-4-oxo-2-hexenal
SH
O
O
CHO
H2N
Br
c. 2-mercapto-4-penten-1-ol
OH
4. To draw the bonds clearly, we will consider each bond separately
σ -system (only bonding MO's are shown)
–
–C
CH2
–C
sp x
C
–
–C
CH2
–
C
C
CH2
sp x-sp2(xz)
sp x-spx
–C
–
H
C
H
Two bonds: sp 2(xz)—s
For the py orbitals, we need to consider
the complete MO picture
π-system
–C
–
C
H
C
H
–C
C
–
C
H
H
bonding MO
Φ3
p z-pz
Φ2
y
x
Φ1
z