Summary applications synthesis s n 1 e1 vs s n 2 e2
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Summary & Applications (Synthesis) S N 1 / E1 vs. S N 2 / E2. E2 and E1 Reactions. Substitution vs. Elimination. Alkyl halides can undergo S N 2, S N 1, E2 and E1 Reactions. 1) Which reaction conditions favor S N 2/E2 or S N 1/E1? S N 2/E2 reactions are favored by a high

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Summary applications synthesis s n 1 e1 vs s n 2 e2
Summary & Applications (Synthesis) SN1 / E1 vs. SN2 / E2



Substitution vs. Elimination

Alkyl halides can undergo SN2, SN1, E2 and E1 Reactions

  • 1) Which reaction conditions favor SN2/E2 or SN1/E1?

    • SN2/E2 reactions are favored by a high

  • concentration of nucleophile/strong base

    • SN1/E1 reactions are favored by a poor

  • nucleophile/weak base

2) What will be the relative distribution of substitution product

vs. elimination product?


Consider SN1/E1 vs. SN2/E2

Consider the Substrate


NOTE: a bulky base encourages elimination over substitution


Returning to sn2 and e2 considering the differences
Returning to Sn2 and E2:Considering the differences

Can you predict the products?

Can you explain the products?




Which reaction produces an ether? synthesize an alkene


Consecutive E2 Elimination Reactions: synthesize an alkene

Alkynes


Intermolecular vs. Intramolecular Reactions synthesize an alkene

  • A low concentration of reactant favors an intramolecular

  • reaction

  • The intramolecular reaction is also favored when a five-

  • or six-membered ring is formed


Three- and four-membered rings are less easily formed synthesize an alkene

Three-membered ring compounds are formed more

easily than four-membered ring compounds

The likelihood of the reacting groups finding each other

decreases sharply when the groups are in compounds

that would form seven-membered and larger rings.


Designing a synthesis … synthesize an alkene


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