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Problems and exercisesNucleophilic Substitution

1. Gabriel synthesis

Write the steps of the Gabriel synthesis of 2-phenylethylamine from (2-bromoethyl)benzene.

2. Does it work?

State whether these reactions are useful to prepare the amine and why:

  1. Potassium phthalimide + 2-bromo-2-methylpropane
  2. NaN3 + cyclohexyl bromide, then LiAlH4
  3. Potassium phthalimide + bromobenzene

3. Cyclization

What product is formed when 4-chloro-1-butanamine, Cl(CH2)4NH2, is treated with triethylamine? Why is it favourable?

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