All mechanisms

Nucleophilic substitution — hydroxide ions

Year 1
AQA 3.3.3

Nucleophilic substitution & elimination · NaOH or KOH (aqueous) · warm, aqueous

Reagents: NaOH or KOH (aqueous) · Conditions: warm, aqueous

Step 1 of 1

δ+δ−CH3CHHBrOH
  1. 1.The lone pair on the hydroxide oxygen attacks the δ+ carbon — OH⁻ is the nucleophile.
  2. 2.The polar C–Br bond breaks heterolytically: both electrons go to the more electronegative bromine.

OH⁻ bonds to the carbon as the C–Br bond breaks: ethanol forms and a bromide ion leaves.

Product: ethanol

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