Alcohol reactions

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What happens when a tertiary alcohol reacts with HX (HCl or HBr)? What kind of reaction is this?

  • The tertiary alcohol undergoes a substitution reaction where the hydroxyl group is replaced by a halide ion, forming a tertiary alkyl halide and water (X+H2O).

  • This reaction typically proceeds through a carbocation intermediate.

  • Sn1


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What happens when a primary/secondary alcohol reacts with SOCl2 ? What kind of reaction is this?

  • A primary/secondary alkyl chloride (RCl) is formed, the hydroxyl group is replaced by a chlorine atom, forming alkyl chlorides and sulfur dioxide.

  • Often an Sn2 reaction


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What happens when a primary/secondary alcohol reacts with PBr3 ? What kind of reaction is this?

  • A primary/secondary alkyl bromide is formed by replacing the hydroxyl group with a bromine atom, resulting in alkyl bromides and phosphoric acid.

  • This is typically an Sn2 reaction.


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