Which of the following is NOT an intermediate in the Gabriel amine synthesis?

• A.
• B.
• C.
• D.

Answer: (B)

Verified step by step guidance

1. The Gabriel synthesis is a method used to synthesize primary amines. It involves the use of phthalimide as a starting material, which is converted into a phthalimide anion.
2. The phthalimide anion is then alkylated with an alkyl halide, such as the one shown in the first image (1-bromo-3-methylbutane), to form an N-alkylphthalimide.
3. The N-alkylphthalimide is then hydrolyzed under basic conditions, often using hydrazine (H2NNH2), to release the primary amine and phthalhydrazide.
4. In the images provided, identify the structures that correspond to intermediates in the Gabriel synthesis: the phthalimide anion, the N-alkylphthalimide, and the phthalhydrazide.
5. Compare the structures in the images to the known intermediates of the Gabriel synthesis. The structure that does not match any of these intermediates is the one that is NOT an intermediate in the Gabriel amine synthesis.