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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Alkyl halides can undergo SN2, SN1, E2 and E1 Reactions
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
Can you predict the products?
Can you explain the products?
A hindered alkyl halide should be used if you want to synthesize an alkene
Which reaction produces an ether? synthesize an alkene
Consecutive E2 Elimination Reactions: synthesize an alkene
Intermolecular vs. Intramolecular Reactions synthesize an alkene
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