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Problems and exercisesSN2-SN1 Competition

1. Order of reactivity

Give a reasoned order of SN1/SN2 reactivity for the following compounds towards: 1) NaSMe/DMF; 2) dilute H3O+.

Seven chlorides: (S)-3-chlorocyclohexene (1), benzyl chloride (2), 1,1-dichloro-2-methylpropene (3), 1-(chloromethyl)-3-methylcyclopentane (4), (R)-cis-1-chloro-3-methylcyclopentane (5), tert-butyl chloride (6) and chlorobenzene (7)

2. SN1 or SN2?

Predict the main mechanism of each reaction:

  1. (CH3)3CBr in methanol.
  2. CH3CH2Br with NaCN in DMSO.
  3. (R)-2-bromobutane with NaN3 in DMF.
  4. Benzyl bromide in water.

3. Benzylic halides

Why does benzyl bromide react quickly by both SN1 and SN2?

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