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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
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