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

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Summary applications synthesis s n 1 e1 vs s n 2 e2

Summary & Applications (Synthesis) SN1 / E1 vs. SN2 / E2


Summary applications synthesis s n 1 e1 vs s n 2 e2

E2 and E1 Reactions


Summary applications synthesis s n 1 e1 vs s n 2 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?


Summary applications synthesis s n 1 e1 vs s n 2 e2

Consider SN1/E1 vs. SN2/E2

Consider the Substrate


Summary applications synthesis s n 1 e1 vs s n 2 e2

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?


Summary applications synthesis s n 1 e1 vs s n 2 e2

Substitution and Elimination Reactions in Synthesis


Summary applications synthesis s n 1 e1 vs s n 2 e2

A hindered alkyl halide should be used if you want to synthesize an alkene


Summary applications synthesis s n 1 e1 vs s n 2 e2

Which reaction produces an ether?


Summary applications synthesis s n 1 e1 vs s n 2 e2

Consecutive E2 Elimination Reactions:

Alkynes


Summary applications synthesis s n 1 e1 vs s n 2 e2

Intermolecular vs. Intramolecular Reactions

  • A low concentration of reactant favors an intramolecular

  • reaction

  • The intramolecular reaction is also favored when a five-

  • or six-membered ring is formed


Summary applications synthesis s n 1 e1 vs s n 2 e2

Three- and four-membered rings are less easily formed

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.


Summary applications synthesis s n 1 e1 vs s n 2 e2

Designing a synthesis …


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