All mechanisms

Nucleophilic substitution — excess ammonia

Year 1
AQA 3.3.3

Nucleophilic substitution & elimination · excess NH3 in ethanol · heated in a sealed tube

Reagents: excess NH3 in ethanol · Conditions: heated in a sealed tube

Step 1 of 2

δ+δ−CH3CHHBrH3N
  1. 1.The nitrogen lone pair attacks the δ+ carbon.
  2. 2.The C–Br bond breaks heterolytically towards bromine.

An ethylammonium ion (CH3CH2NH3⁺) forms — note the + on nitrogen — plus Br⁻.

Step 2 of 2

CH3CHHN+HHHH3N
  1. 1.A second ammonia acts as a base, using its lone pair to remove a proton from N⁺.
  2. 2.The N–H bonding pair collapses back onto nitrogen, neutralising the positive charge.

Ethylamine forms; NH4⁺ (with Br⁻, ammonium bromide) is the by-product.

Product: ethylamine

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