SN and E reactions

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10 Terms

1
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SN2 reaction rate factors

  1. alpha carbon substitution level

  2. strength of n-phile (strong vs weak)

  3. reaction solvent (protic vs polar aprotic)


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strength of n-phile factors

  1. negative charge> neutral n-phile

  2. greater polarizability=> greater n-phile strength

    1. polarizability means bigger atom size


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strong n-philes to know

  1. S- (HS-, RS-)

  2. neutral S (H2S, RSH)

  3. O- (HO-, RO- )

  4. non-fluorine halogens (I-, Br-, Cl-)

  5. F- when in Polar Aprotic Solvents

  6. Cyanide Ion (C- = N)


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weak n-philes to know

  1. neutral O (H2O, ROH)

  2. F- in protic solvents


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types of solvents

  1. nonpolar solvent: no δ- or δ+

  2. polar aprotic solvent:

    1. cannot easily generate H+ or act like (Lewis acid)

    2. has > 1 δ-/ δ+ pairs

    3. no O-H or N-H bonds

  3. protic solvent:

    1. acidic H+s

    2. must be polar by definition

    3. has O-H or N-H bonds


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Bulky Bases to know

  1. t-BuOK

  2. Diisopropylamine (DIPA)

  3. triethylamine (TEA)


<ol><li><p>t-BuOK </p></li><li><p>Diisopropylamine (DIPA) </p></li><li><p>triethylamine (TEA) </p></li></ol><p></p>
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Non-Bulky Bases to know

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Bulky Bases definition

“crowded” bases, control reaction outcomes via steric crowding

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Non-bulky bases definition

allows “natural” reaction outcomes (ie. makes more stable products) by NOT steric crowding

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reaction trends


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