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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
- 1.The nitrogen lone pair attacks the δ+ carbon.
- 2.The C–Br bond breaks heterolytically towards bromine.
An ethylammonium ion (CH3CH2NH3⁺) forms — note the + on nitrogen — plus Br⁻.
Step 2 of 2
- 1.A second ammonia acts as a base, using its lone pair to remove a proton from N⁺.
- 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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