chm2211ps18sol - CHM 2211 Problem Set 18 Solutions Alpha...

COO
+ CHI
3
COO
+ CHI
3
CHM 2211
Problem Set 18 Solutions
Alpha Substitution and Aldol Reactions
Complete the Reactions. If No Reaction Occurs, Write N.R.
1.
2. This is a Cannizarro
reaction. One molecule
gets oxidized and the
other gets reduced.
3.
4.
5.
6.
7.
8.
9.
10.
CH CH
3
O
OH
-
warm
OH
-
warm
CHO
2
OH
-
Br
2
CH
3
C CH
3
O
C
O
CH
3
I
2
NaOH / H
2
O / heat
CH
O
+
CH CH
3
O
OH
-
CH
OH
CH
3
I
2
NaOH / H
2
O / heat
H
2
C O
CH
3
C CH
3
O
+
OH
-
OH
-
CH
CH
2
CH
2
CH
2
CH
2
C
CH
3
O O
OH
-
CH O
C CH
3
O
+
C
CH
3
O
O
CH
2
CH
3
NaOEt
CH CH
2
CH CH
3
O OH
COOH
CH
2
OH
+
CH Br Br
Br
C CH
3
O
O
+
CH
OH
CH
2
CHO
CH
3
C CH
2
CH
2
O
HO
O
OH
-H
2
O
O
H
CH CH C
O
C CH
2
C O
O
CH
2
CH
3
O
H
3
C

O
OH
O
C CH CH
2
CH
2
CH
3
OH
O CH
2
CH
3
C C
CH
2
CH
2
CH
3
OEt
O CH
2
CH
3
COOEt
C CH
2
CH
2
CH
3
OH
O
O
CH
3
CH
3
OH
CH
3
CH
3
Br
CH
3
CH
3
O
OCH
2
CH
3
O
+ EtOH
CH
3
C CH
3
O
11.
12.
13.
14.
15.
16.
17.
18.
C
CH
CH
CH
H
2
C
H
2
C
O
CH
3
1. (CH
3
)
2
CuLi
2. H
2
O
NaBH
4
EtOH / H
2
O
PBr
3
3,3-dimethylbutanone
I
2
/ NaOH
H
2
O / EtOH / heat
C CH
3
O
O
CH
2
CH
3
NaOEt
OH
-
/ H
2
O / reflux
H
+
heat
C CH
2
C
CH
3
O
O
O
CH
2
CH
3
1 mole NaOEt
1 mole CH
3
CH
2
Cl
1. OH
-
/ H
2
O / reflux
2. H
+
3. heat
NaOEt
1. OH
-
/ H
2
O / reflux
2. H
+
3. heat
C CH
2
CH
2
CH
2
CH
2
C OEt EtO
O O
C CH
2
C OEt EtO
O O
1. NaOEt
1. NaOEt
2. CH
3