Exercicios Eliminação e Substituição Daniel Alencar

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CHM 211 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
K OC(CH3)3
(CH3)3COH, 82º C
CH3CH2CH CH2 E2
CH3CH2CH2CH2Br
Na OCH3
CH3OH, 0º C 
CH3CH2CH2CH2OCH3 SN2
(high T, 
good base)
 (low T,
good Nu or base)
Cl
Na SCH2CH3
DMF, 0º C
SCH2CH3
SN2 (low T,
good Nu)
CH3I + NaNO2 5º C
CH3NO2 SN2 (low T)
CH3 C
CH3
CH3
OTs H2O
22º C
CH3 C
CH3
CH3
OH SN1 (low T, 
weak Nu,
weak base)
CH3
Br
CH3OH
22º C
CH3
OCH3
SN1 (low T, 
weak Nu,
weak base)
CH3
Br
K OC(CH3)3
(CH3)3COH, 82º C
CH3 E2, some E1
(high T, good base)
CH3I + CH3SH 43º C
CH3SCH3 SN2 (low T)
Cl
Na OCH2CH3
CH3CH2OH, 78º C 
E2 (high T, good base)
CH3
I
H2O
22º C
CH3
OH
SN1 (low T, 
weak Nu,
weak base)
Br Na OCH3
CH3OH, 0º C 
SN2 (low T, 
allylic RX)
OCH3Br
CHM 211 Substitution and Elimination practice problem answers 
 
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
K OC(CH3)3
(CH3)3COH, 82º C
CH3CH2CH CH2 E2
CH3CH2CH2CH2Br
Na OCH3
CH3OH, 0º C 
CH3CH2CH2CH2OCH3 SN2
(1º RX, high T, 
good base)
 (1º RX, low T,
good Nu or base)Cl
Na SCH2CH3
DMF, 0º C
SCH2CH3
SN2 (2º RX, low T,
good Nu)
CH3I + NaNO2 5º C
CH3NO2 SN2 (Methyl)
CH3 C
CH3
CH3
OTs H2O
22º C
CH3 C
CH3
CH3
OH SN1 (3º RX, exc. L
low T, weak Nu
weak base)
CH3
Br
CH3OH
22º C
CH3
OCH3
SN1 (3º RX, good L
low T, weak Nu,
weak base)
CH3
Br
K OC(CH3)3
(CH3)3COH, 82º C
CH3 E2, some E1
L, high T, good base)
CH3I + CH3SH 43º C
CH3SCH3 SN2 (Methyl)
Cl
Na OCH2CH3
CH3CH2OH, 78º C 
E2 (2º RX, high T, 
good base)
CH3
I
H2O
22º C
CH3
OH
SN1 (3º RX, low T, 
v. good L, weak 
Nu, weak base)
Br Na OCH3
CH3OH, 0º C 
SN2 (allylic, low T, 
allylic RX)
OCH3
 (3º RX, good
 
 
Br OCH3