Final_SG_1 - Final_Study_Guide_1 SN1 SN2 E1 and E2 Summary of Substitution vs Elimination Reactions of Haloalkanes SN1 and E1 carbocation

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Final_Study_Guide_1 S N 1, S N 2, E1 and E2
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Summary of Substitution vs Elimination Reactions of Haloalkanes S N 1 and E1: carbocation intermediate two transition states, the activation energy required to go through the first transition state is reflecting the stability of the cabocation intermediate rate determining step is the formation of the c arbocation S N 2 and E2: no intermediate one transition state S N 2 -less crowded carbon center undergoes S N 2 reaction E2 - transition state structure is similar to the product alkene. Alkene stability contributes to the
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Summary of Substitution vs Elimination Reactions of Haloalkanes RCH 2 X CH 3 X S N 1 and E1 reactions of primary halides are never observed. S N 2 S N 1 reactions of methyl halides are never observed. The methyl cation is so unstable that it is never  formed in solution. S N 2 E2 The main reaction with strong, bulky bases, such as  potassium  tert- butoxide. Primary cations are never formed in solution; therefore, Methyl Primary S N 1 / E1 S N 1 The only substitution reactions observed The main reaction with strong bases such as OH -   and EtO - . Also, the main reaction with good  nucleophiles/weak bases, such as I -  and CH 3 COO - .
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carbocation intermediate S N 1 and E1: go through carbocation intermediate. S N 2 and E2: do not form intermediate. S N 1 E1 The stability of carbocation intermediate formed from alkyl halide (starting material) determines whether the reaction go through SN1 and E1 or not.
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CH 3 X: methyl halide C H H H X C H H H + X • CH 3 X undergoes only S N 2 reaction. 1. S
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This test prep was uploaded on 04/17/2008 for the course CHEMISTRY 624 taught by Professor Mure during the Spring '08 term at Kansas.

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Final_SG_1 - Final_Study_Guide_1 SN1 SN2 E1 and E2 Summary of Substitution vs Elimination Reactions of Haloalkanes SN1 and E1 carbocation

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