How to figure out substitution reactions- SN2 versus SN1

Substitution Reactions In Organic Chemistry

Questions about substitution reactions show up very often on organic chemistry exams. So far, we have talked about SN2 versus E2…but what about SN2 versus SN1? Here is a quick overview…

Let’s look at 3 main points to help us determine whether it is SN1 or SN2.

The type of carbon that contains the leaving group

  • Methyl
  • Primary
  • Secondary
  • tertiary

The type of nucleophile

  • Strong
  • weak

The type of solvent

  • Polar protic
  • Polar aprotic

From this, you will be able to determine the correct mechanism to write on your homework or exam. Let’s use the following diagram:

Here are some examples of strong and weak nucleophiles:

Finally, here are some examples of polar aprotic and polar protic slovents:

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