SUPPLEMENTAL PROBLEMS
ARMSTRONG
CHEM 12A
SN1/SN2/E1/E2
1) Circle any of the following that are strong Nucleophiles:
CH3SH, CH3OH, CH3NH2, NH3, LiN[CH(CH3)2]2, PH3, Cl–, CH3O-, OH–, H2O,
NaOCOCH3
2) Which of the following are strong bases? ( pKa of their conjugate acid ≥ 11)
CH3S–, CH3OH, CH3NH2, NH3, LiN[CH(CH3)2]2, Cl–, CH3O-, OH–, CH3CH2CH2CH2Li
3) Which of the compounds listed above are weak bases but moderate or strong
Nucleophiles? What will be their dominant reaction with 2-bromopropane?
4) Predict the product and the dominant mechanism by which each of the following
alkyl bromides react under the reaction conditions shown (ie SN1, SN2, E1 or E2).
Include stereochemistry using wedge-dash formalism if stereoselectivity is expected.
ONa
+
A)
Br
Br
+
NaOCH2CH3
B)
+
C)
Br
CH3OH
EtOH
SUPPLEMENTAL PROBLEMS
ARMSTRONG
CHEM 12A
+
D)
NaOCH2CH3
EtOH
Br
E)
+
NaCN
+
NaSH
DMSO
Br
Br
DMSO
F)
5) Identify the starting materials from which each of the following ethers can be
prepared in high yield:
O
O
O
O
O
6) Tell which of each pair is likely the Faster reaction. Explain why.
A
O
O
+
NaI
I
+
O
ONa
Br
A'
+
NaI
I
+
NaBr
SUPPLEMENTAL PROBLEMS
ARMSTRONG
CHEM 12A
A
A'
N3
EtOH
Br
+
NaN3
Br
+
NaN3
+
NaBr
+
NaBr
N3
DMF
OCH3
OSO2CH3
+
CH3OH
+
HOSO2CH3
A
OSO2CH3
OCH3
+
A'
CH3OH
+
HOSO2CH3