Home > Community > How would propargyl bromide react with triethylamine under room temperature, an SN2-reaction or an acid-base reaction?
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Adrian Poaca

How would propargyl bromide react with triethylamine under room temperature, an SN2-reaction or an acid-base reaction?

CT Berchem  Follow

Characteristics of SN¹ reactions: -

  1. Two step reaction.
  2. Rate of reaction = K [R — L]
  3. It is a first order reaction.
  4. Carbocation intermediate is formed. rearrangement of carbocation is possible.
  5. Rate is dependent on stability of carbocation. [3°>2°>1°]
  6. Rate of reaction also depends on stability of cation and anion.
  7. Polar Protic Solvent favours SN¹ reaction. (As PPS dissolves both cation and anion in it)
  8. Leaving group should be strong i.e. weak base (same as SN²).
  9. Weak nucleophile performs SN¹ reaction. (Strong nucleophile will directly attack substrate resulting in E¹ reaction)
  10. Rate of reaction is independent of concentration and strength of nucleophile.
  11. Products formed will be both R- and S- form i.e. mirror image.
  12. Low temperature favours SN¹ reactions.

Characteristics of SN² reactions: -

  • Single step reaction.
  • Rate of reaction = K [R — L] [Nu(:)]
  • It is a second order reaction.
  • Rate is dependent on concentration and strength of Nucleophile.
  • Transition state is formed which is sp² hybridized, planar structure. (Not sp³d as Carbon doesn't have d orbital.)
  • No carbocation intermediate formation.
  • Leaving group should be strong i.e. weak base.
  • Rate of reaction is inversely proportional to bulkiness of groups attached to C atom. [CH3Cl > CH3CH2Cl > CH3CH(CH3)Cl > CH3C(CH3)²Cl]
  • Rate of reaction 1° > 2° > 3° substrates.
  • Strong nucleophile performs SN² reactions. Nucleophile attacks substrate directly from backside.
  • Polar Aprotic Solvent like DMSO, DMF, DMA favours SN² reactions. (Because PAS doesn't dissolves/solvent cations and it dissolves only anions in solution, so by taking PAS cations are removed and only Nu(:) is only anion present to attack substrate.]
  • Walden inversion occurs.
  • Reaction is favored by low temperature. High temperature leads to E² reaction.

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Anbuselvan Sellamuthu   Follow

Well, I suppose either of these two reactions could occur though it will be the SN2-reaction that occurs, not the acid-base. Shown below are both reactions. The upper reaction is the SN2 and this will go just fine - a nice, not too hindered, nitrogen base will happily react with a very reactive bromide to give the quat salt.

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