alleryWhy can aromatic primary amines not be made by the Gabriel synthesis?
AAryl halides resist purification
BAmide anions resist substitution
CAmide anions resist purification
DAryl halides resist substitution
Answer & Solution
Correct answer: D. Aryl halides resist substitution
1. Gabriel synthesis needs the phthalimide anion to attack a halide.
2. That attack is a nucleophilic substitution.
3. Aryl halides do not undergo nucleophilic substitution with the anion formed by phthalimide.
4. So aromatic primary amines cannot be prepared this way.
_Source: syllabus Chemistry Part II, Ch 9 'Amines'_
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