Sn1, Sn2, E1, E2 Rxn

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Author:
tulipyoursweety
ID:
242321
Filename:
Sn1, Sn2, E1, E2 Rxn
Updated:
2013-10-27 05:09:28
Tags:
Sn1 Sn2 E1 E2 Rxn
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Description:
How to know if rxn is Sn1, Sn2, E1, E2.
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  1. Sn2 only
    • R-X = methyl or 1°
    • nucleophile/base = STRONG 
  2. E2 only
    • R-X with STRONG nucleophile/base
    • 1°/2° R-X with STRONG, NON-NUCLEOPHILIC (very sterically hindered) base
  3. Sn1 && E1
    2°/3° R-X with WEAK (neutral) nucleophile/base
  4. Sn2 && E2
    R-X with STRONG nucleophile/base

  5. What will this do? Why?
    • tBUO-
    • - Will not do any SN2, only E2!
    • - Really sterically hindered base!
  6. Good nucleophiles that are weak bases favor ______ over _______.
    substitution, elimination
  7. Bulky, nonnucleophilic bases favor _______ over _______.
    elimination, substitution
  8. To determin the product of a reaction with an alkyl halide: (2 steps)
    • 1. classify alkyl halide as 1°, 2° or 3°
    • 2. classify base or nucleophile as strong, weak or bulky
  9. 3° R-X with strong base
    • E2 only
    • strong base favors Sn2 or E2, but 3° R-X are too sterically hindered to undergo Sn2
  10. 3° with weak nucleophile/base
    • Sn1 and E1
    • weak base/nucleophile favors Sn1 and E1
  11. 1° with strong nucleophile
    • Sn2 only
    • Strong base/nucleophile favors Sn2 or E2, but 1° R-X are least reactive in elimination ∴ only Sn2
  12. 1° with strong sterically hindered base
    • E2 only
    • strong, sterically hindered base cannot act as nucleophile for Sn2
  13. 2° with strong bases/nucleophile
    • Sn2 and E2
    • strong base is a strong nucleophile
  14. 2° with strong, sterically hindered base
    • E2 only
    • strong, sterically hindered base cannot act as nucleophile
  15. 2° with weak nucleophile/base
    • Sn1 and E1
    • weak base or nucleophile favors both

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