Homework Set
Chem 315
Beauchamp
1. This collection of RX compounds and reagents will generate 40 SN/E problems. You should be able to predict reasonable products (major and minor) for each of them. Use structure C to write reasonable mechanisms for the SN/E reactions of reagents 2, 4, 5 and 6. RX Compounds H
T C
C
H D
H
A
H
D
4
O
make
H Li H
Na
Al
H
H
make
Li
C
Na
Na
Na
buy
make
make
CH2
S
Na
H buy
O
7
10
9
N
Br
O O
make
O
6 N
K
make
8
D
D
5
O
O
Na
Na buy
H3C
Br
C
B
O
H
Br
Nucleophile/Base Compounds 3 2 1 H
D
C
H3C
Br
H
D
buy
2. Write out detailed mechanisms for the tautomer reactions below. Hint: How many protons have changed positions? a
H O O
O
C H3C
C H
H
H
H O
H
H
O O
C H H3C
H
b
O
O
C
C
H3C
H
H H
NH2 O
O
O
SH
O
OH O
C
OH O
N
Z:\classes\315\Daily Homework Sets\315_hw5.doc
H
H
O
C H3C
3. Nomenclature problem
H
O
C H
H
H
O
O
H
C H
H H
Homework Set
Chem 315
Beauchamp
The elimination products are the same for all the strong nucleophile/bases and are shown below. H
T C
None, only SN2 is possible.
Br
H D
C H
H
Br
H
C
C
C
H
H
H3 C
H
D
H
A Only SN2
buy
SN2
Na
HO
C
O
Na
make
O
H3C
Br
D
Br
D
E2 > SN2 H
OH
D Only E2
D
H
HO
D
SN2 > E2
T
H
C H
Only SN2
D
H
E2 > SN2 O
H
D
C H3C
H
SN2
C
D
Only E2
C H
D
H D
O
H
T
3 O
O
K
C
SN2
H
O
4
Na O
make
O
Only SN2 O
C
S N2
O
C
H3C C
SN2 > E2
T SN2
N
C
C
make
C
H
D
Only E2 N
D
SN2 > E2
Only SN2 H3C
C
D
H H
S N2
H
C
H 3C
H D
Na
SN2 > E2
C
C
buy
6
Only E2
H
O
D N
Only SN2 C
D
D
H
5
H
O
H D
H
Na
Only E2
SN2 > E2
SN2 > E2
T
O
N
Only E2
mainly E2
D
make
CH3
T C
H H
D
CH3 C
C
D
C H
C C D
Z:\classes\315\Daily Homework Sets\315_hw5.doc
mainly E2
C CH2
H3C
H 3C
C
C
D
2
H
D
H3C
H
H 3C
CH2 CH3
H
C
D
C
Br
SN2 > E2
T
C H3 C
DHC
B
Nucleophile/Base Compounds O
H
C C
H
H
CH3
C
D
H3C
CH2 CH3
C
H
CH3
C
H 3C
CH3
Br
C H
H3 C
DHC
T C
CH3
C
H 3C
RX Compounds
1
C
CH2
D
Br
C
H 3C
H H 3C
H D
CH2
CH3
CHD
C
C
DHC
CH3 H 2C
Only E2
H
H
C
DHC
D
D
C
CH3
CH3 H
C H 3C
H3C
B
D
D
C
H 3C
C
H3 C
D
Br
H
D
H
C
C
H3C
A H
H
D
Only E2
CH3
Homework Set
Chem 315
7
Only SN2
O
Li make
C
SN2 > E2
O
S N2
N
H
H
H
H
Al
D
SN2 > E2
H
H
H3 C
C
H
SN2 > E2
SN 2
Na
HS
H
SN2 > E2
D
H
Only E2 D
H
D
H
C C
H
buy
H
SH
H3 C
C
not covered in our course
D
SN2 > E2
T
D
D
H H
Only SN2 S
H
C C
D
10
a
O
T SN2
Only E2
H
N
D
Only SN2
H
H
O
C O
H buy
N
C H
O
Li
D
CH3
C D
9
H
SN2 > E2
O
Na O
O
D
T
make
D
H
Only SN2
O
Only E2
H
C
H3C H
N
D
H D O
8
H
SN2 > E2
C
SN 2
CH2
O
SN2 > E2
T
Beauchamp
HS
D
H
O O C
O
O
H3 C
C
H C
H
C
O
H3 C H
H
O
H C
H
H H
O
O
H
O
H3 C
C
resonance
H
H
O
C
H
H3C
O C
H
H
H
O
Requires two tautomeric cycles. H
H H
O
O
O
Acid reaction not shown.
resonance C O
C H3C
H
C
O
H
H3C
C
O H3C
C
H
H
H H
5
4
2 3
1
4 3 2 1
NH2 H
12
10 11
O
5 6
9
O
8 7
6
OH
4 3
5 O
O 2
1
SH
O
1
2
C
4 3 OH
O
H
N 3R-mercapto-4S-hydroxy-4-phenylbutyl (2R,3R,10R,11S)-2-formyl-3-propoxy-4-cyano-6,12-dioxo9-(3-pentyl-6,6-dimethylcyclohex-3-enyl)-10-hydroxy-11-aminododec-4E-en-7-ynoate
Z:\classes\315\Daily Homework Sets\315_hw5.doc
O C
H