All mechanisms

Electrophilic addition — concentrated H2SO4

Year 1
AQA 3.3.4

Electrophilic addition · concentrated H2SO4 · cold

Reagents: concentrated H2SO4 · Conditions: cold

Step 1 of 2

CCHHHHδ+δ−HOSO2OH
  1. 1.The π electrons attack the δ+ hydrogen of the O–H bond.
  2. 2.The O–H bond breaks heterolytically towards oxygen, releasing the hydrogensulfate ion.

A carbocation and a hydrogensulfate ion form.

Step 2 of 2

CH3C+HHOSO2OH
  1. 1.A lone pair on the hydrogensulfate oxygen bonds to the positive carbon.

Ethyl hydrogensulfate forms.

Product: ethyl hydrogensulfate

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