Chem 215-216 HH W11 - Quiz 6: February 21, 2011
This quiz has two pages.
Lab: Mon; Tue; Wed; Fri
Name__________________________
GSI: Alex; Justin; Alina; Laura (circle the ones that apply)
I. (6 points) Treatment of allyl alcohol (1) with MnO2 in basic water results in the formation of acrolein
(2). Provide in the box below a step-by-step mechanism for the formation of the aldehyde, 2, using the
curved-arrow convention. You may start from alkoxide 3.
O
O Mn O
H
NaOH/H2O
1
O
mech. arrows: O
1 pt
need not to
show
H
2
mech. arrows:
2 pt
interm. str.:
2 pt
O
Mn
3
O
+2
O
O
O
Mn
H
H
H
2
+4
O
O
+
or
O
O
O
Mn
H
O
H
2
+ H 2O
O
Mn (+2): 1 pt
HO
+4
Mn
O
+
Mn
H
OH
6
II. (6 points) Intramolecular substitution reactions depend strongly on the stereochemical relationship
between the reacting functional groups. Which one(s) of the following reactions can undergo
intramolecular substitution to produce its (their) ether product(s)? Provide in each of the boxes below a
drawing of 3D bridge structure of the product. If no intramolecular substitution is expected, write NR in the
box and draw the 3D structure of the starting alcohol.
(1)
(2)
H
Br
NaH
Br
H
Br
H
OH
OH
NaH
H
OH
O
NR
2
2
(3)
Note:
H
Br
H
3D bridge
structure
Br
NaH
OH
NR
OH
2
Chem 215-216 HH W10 Quiz 6 – page 2
III. (8 points) Complete each of the following reactions by drawing the structure of the expected major
product in the box. Make sure to clearly indicate the stereochemistry whenever applicable.
O
HClO4-H2O
H
D 3C
H 3C
tetrahrdrofuran
(solvent)
0 °C, 1 h
D
OH
D 3C
H3C
H
OH
D
2
O
H
D 3C
H 3C
OH
CH3ONa-CH3OH
reflux, 2 h
D
D 3C
H 3C
H
D
OCH3
2
HClO4-H2O
O
H
diaxial
opening
of the
epoxide ring
tetrahrdrofuran
(solvent)
0 °C, 1 h
H
HO
H
2
HClO4-H2O
O
HO
tetrahrdrofuran
(solvent)
0 °C, 1 h
HO
HO
H
2