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.

K OC(CH3)3
CH3CH2CH2CH2Br CH3CH2CH CH2 E2 (high T,
(CH3)3COH, 82º C good base)

Na OCH3
CH3CH2CH2CH2Br CH3CH2CH2CH2OCH3 SN2 (low T,
CH3OH, 0º C
good Nu or base)
Cl
SCH2CH3
Na SCH2CH3
SN2 (low T,
DMF, 0º C good Nu)

CH3I + NaNO 2 CH3NO 2 SN2 (low T)

5º C

CH3 CH3
CH3 C OTs H2O SN1 (low T,
CH3 C OH
22º C weak Nu,
CH3 CH3 weak base)

CH3 CH3
CH3OH SN1 (low T,
Br 22º C OCH3 weak Nu,
weak base)

CH3 K OC(CH3)3 CH3

E2, some E1
Br (CH3)3COH, 82º C (high T, good base)

CH3I + CH3SH CH3SCH3 SN 2 (low T)

43º C

Cl
Na OCH2CH3
E2 (high T, good base)
CH3CH2OH, 78º C

CH3 CH3 SN 1 (low T,

H2O weak Nu,
I OH weak base)
22º C

BrBr Na OCH3 OCH3 SN2 (low T,

CH3OH, 0º C allylic RX)
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.
K OC(CH3)3
CH3CH2CH2CH2Br CH3CH2CH CH2 E2 (1º RX, high T,
(CH3)3COH, 82º C good base)

Na OCH3
CH3CH2CH2CH2Br CH3CH2CH2CH2OCH3 SN2 (1º RX, low T,
CH3OH, 0º C
good Nu or base)
Cl
SCH2CH3
Na SCH2CH3
SN2 (2º RX, low T,
DMF, 0º C good Nu)

CH3I + NaNO2 CH3NO2 SN2 (Methyl)

5º C

CH3 CH3
H2O SN1 (3º RX, exc. L
CH3 C OTs CH3 C OH
22º C low T, weak Nu
CH3 CH3 weak base)

CH3 CH3
CH3OH SN1 (3º RX, good L
Br 22º C OCH3 low T, weak Nu,
weak base)

CH3 K OC(CH3)3 CH3

E2, some E1 (3º RX, good
Br (CH3)3COH, 82º C L, high T, good base)

CH3I + CH3SH CH3SCH3 SN2 (Methyl)

43º C

Cl
Na OCH2CH3 E2 (2º RX, high T,
CH3CH2OH, 78º C good base)

CH3 CH3
H2O SN1 (3º RX, low T,
I OH v. good L, weak
22º C
Nu, weak base)

BrBr Na OCH3 OCH33

OCH SN2 (allylic, low T,
CH3OH, 0º C allylic RX)