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Gabriel synthesis template
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Phthalimide is deprotonated and alkylated with benzyl bromide; hydrazine then releases benzylamine.
Mechanism step by step
Phthalimide as a protected NH₂: primary amines without over-alkylation
- Deprotonation – The N–H between two C=O is acidic (pKa 8.3)
- N-Alkylation (SN2) – The imide anion displaces bromide
- Hydrazine attacks – First of two addition–elimination steps (Ing–Manske)
Key points
- The N-alkyl phthalimide is no longer nucleophilic: only one alkyl group adds.
- Hydrazine attacks both C=O groups in turn, releasing the amine and phthalhydrazide.
- Acid or base hydrolysis also works but needs harsher conditions.
- Only for primary alkyl halides (SN2); aryl halides do not react.
Drawn with 122 atoms, 10 arrows, 5 shapes – every one editable in MolDraw.
Sources
How to use this template
- Press Edit in MolDraw. The template opens on the canvas of the free MolDraw editor.
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Frequently asked questions
Is the Gabriel synthesis template free?
You can preview the Gabriel synthesis template here and open and edit it in MolDraw for free. Downloading or exporting it is part of MolDraw Pro, together with the other premium templates.
Can I edit the Gabriel synthesis template?
Yes. It opens as an ordinary MolDraw drawing, so every structure, arrow, label and colour can be changed, and you can add your own content around it.
Is the chemistry checked?
Every structure is checked with RDKit and every curly arrow passes MolDraw’s electron-flow audit. The sources used are listed on this page.
Which name reactions are included?
Over seventy, covering the reactions most often asked in school-leaving exams (A-level, IB, CBSE, JEE and NEET) and first-year university courses, including condensations, rearrangements, oxidations, reductions and aromatic substitutions.