Substitution and Elimination Practice Problems
Substitution and Elimination Practice Problems
Substitution and Elimination Practice Problems
Analyze the reactant(s) and reaction conditions, then predict the structure of the major organic
product and indicate the predominant mechanism (SN1, SN2, E1, or E2) of each reaction.
CH3CH2CH2CH2Br
CH3CH2CH2CH2Br
K OC(CH3)3
(CH3)3COH, 82 C
Na OCH3
CH3OH, 0 C
CH3CH2CH CH2
E2 (high T,
good base)
CH3CH2CH2CH2OCH3
SN2 (low T,
good Nu or base)
Cl
Na SCH2CH3
SCH2CH3
SN2 (low T,
good Nu)
DMF, 0 C
CH3I
NaNO 2
CH3
CH3
SN2 (low T)
CH3NO 2
5 C
H2O
C OTs
22 C
CH3
CH3
C OH
CH3
CH3
Br
CH3I
CH3
CH3OH
CH3
22 C
OCH3
CH3
K OC(CH3)3
Br
(CH3)3COH, 82 C
CH3SH
CH3
CH3SCH3
SN1 (low T,
weak Nu,
weak base)
SN1 (low T,
weak Nu,
weak base)
E2, some E1
(high T, good base)
SN 2 (low T)
43 C
Cl
Na OCH2CH3
E2 (high T, good base)
CH3CH2OH, 78 C
CH3
I
H2O
22 C
BrBr
Na OCH3
CH3OH, 0 C
CH3
OH
OCH3
SN 1 (low T,
weak Nu,
weak base)
SN2 (low T,
allylic RX)
CHM 211
Analyze the reactant(s) and reaction conditions, then predict the structure of the major organic
product and indicate the predominant mechanism (SN1, SN2, E1, or E2) of each reaction.
CH3CH2CH2CH2Br
CH3CH2CH2CH2Br
K OC(CH3)3
(CH3)3COH, 82 C
Na OCH3
CH3OH, 0 C
CH3CH2CH CH2
E2 (1 RX, high T,
good base)
CH3CH2CH2CH2OCH3
Cl
Na SCH2CH3
SCH2CH3
SN2 (2 RX, low T,
good Nu)
DMF, 0 C
CH3I
5 C
CH3
CH3
SN2 (Methyl)
CH3NO2
NaNO2
H2O
C OTs
22 C
CH3
CH3
C OH
CH3
CH3
Br
CH3I
CH3
CH3OH
CH3
22 C
OCH3
CH3
K OC(CH3)3
Br
(CH3)3COH, 82 C
CH3SH
CH3
CH3SCH3
SN2 (Methyl)
43 C
Cl
Na OCH2CH3
E2 (2 RX, high T,
good base)
CH3CH2OH, 78 C
CH3
I
H2O
22 C
BrBr
Na OCH3
CH3OH, 0 C
CH3
OH
OCH33
OCH