--- title: "Kiliani–Fischer synthesis Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/sugar-kiliani-fischer/ description: "Kiliani–Fischer synthesis template: Cyanide adds to the aldehyde of D-arabinose and protonation gives the cyanohydrins, epimeric at the new C2; hydrolysis to…" lang: en publisher: Scidart Academy generated: 2026-11-13 --- [MolDraw](https://www.moldraw.com/) › [Templates](https://www.moldraw.com/templates/) › [Biochemistry](https://www.moldraw.com/templates/biochemistry/) › Kiliani–Fischer synthesis [Biochemistry](https://www.moldraw.com/templates/biochemistry/)Premium # Kiliani–Fischer synthesis template ![Kiliani–Fischer synthesis template: Cyanide adds to the aldehyde of D-arabinose and protonation gives the cyanohydrins, epimeric at the new C2; hydrolysis to the aldonic acids, lactonisation and Na(Hg) reduction of the lactones give the two aldohexoses D-glucose and D-mannose, which differ only at C2.](https://www.moldraw.com/templates/sugar-kiliani-fischer.webp) [Edit in MolDraw](https://www.moldraw.com/)Download with Pro Premium template. Preview and edit it free in MolDraw; downloading and exporting it is part of [MolDraw Pro](https://www.moldraw.com/pricing). Cyanide adds to the aldehyde of D-arabinose and protonation gives the cyanohydrins, epimeric at the new C2; hydrolysis to the aldonic acids, lactonisation and Na(Hg) reduction of the lactones give the two aldohexoses D-glucose and D-mannose, which differ only at C2. ## Mechanism step by step An aldose gains one carbon at C1 through a cyanohydrin: D-arabinose gives D-glucose and D-mannose 1. **Cyanide adds** – CN⁻ attacks C1 from either face: two configurations at the new stereocentre 2. **Protonation** – HCN protonates the alkoxide: the cyanohydrins (gluco drawn; the manno epimer forms too) 3. **Hydrolysis** – Hot water hydrolyses the nitrile to the aldonic acid, D-gluconic acid (summarised) 4. **Lactone** – The acid closes to the γ-lactone (1,4-lactone), which can be separated from its epimer (summarised) 5. **Reduction** – Sodium amalgam in weak acid reduces the lactone to the aldose: D-glucose (D-mannose from the other epimer; summarised) ## Key points - The chain grows at C1: the old C1 becomes C2, a new stereocentre, so two C2 epimers form (usually not 1 : 1). - The old stereocentres are untouched, so a D-aldopentose gives two D-aldohexoses: D-arabinose → D-glucose + D-mannose. - Fischer used this route to relate the aldoses; the improved version reduces the nitriles directly to imines (H₂, Pd/BaSO₄), which hydrolyse to the aldoses. - The reverse, removing C1, is the Ruff (or Wohl) degradation. Drawn with 171 atoms, 10 arrows, 10 shapes – every one editable in MolDraw. ## Sources - [Wade, Organic Chemistry, 8th ed., Pearson 2013, ch. 23](https://openlibrary.org/isbn/9780321768414) Textbook ## How to use this template 1. Press **Edit in MolDraw**. The template opens on the canvas of the free MolDraw editor. 2. Change anything: move structures, edit atoms and labels, recolour highlights or delete what you do not need. 3. Add your own structures, arrows and text next to it, or combine several templates on one page. 4. Export the drawing as PNG, SVG or PDF for slides, worksheets, theses and papers. ## Frequently asked questions ### Is the Kiliani–Fischer synthesis template free? You can preview the Kiliani–Fischer 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 Kiliani–Fischer 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. ### Are the biochemical pathways drawn with structures? Yes. Pathway templates show the intermediates as structures, with enzymes and cofactors (NAD⁺, FAD, ATP) on the arrows. ## More biochemistry templates [**Urea cycle**Free · Biochemistry](https://www.moldraw.com/templates/biopath-urea-cycle/)[**Fatty acid β-oxidation**Free · Biochemistry](https://www.moldraw.com/templates/biopath-beta-oxidation/)[**Electron transport chain and ATP synthase**Free · Biochemistry](https://www.moldraw.com/templates/biopath-electron-transport/)[**Light reactions of photosynthesis**Premium · Biochemistry](https://www.moldraw.com/templates/biopath-light-reactions/)[**Calvin cycle**Premium · Biochemistry](https://www.moldraw.com/templates/biopath-calvin-cycle/)[**Pentose phosphate pathway**Premium · Biochemistry](https://www.moldraw.com/templates/biopath-pentose-phosphate/)[**Peptide bond formation**Premium · Biochemistry](https://www.moldraw.com/templates/biopath-peptide-bond/)[**Polymerase chain reaction (PCR)**Premium · Biochemistry](https://www.moldraw.com/templates/biopath-pcr/) ## Related pages [**All Biochemistry templates**59 templates](https://www.moldraw.com/templates/biochemistry/)[**All chemistry templates**525 templates in 31 categories](https://www.moldraw.com/templates/) MolDraw Pro Download all 525 templates - Export the 437 premium templates as PNG, SVG or PDF - AI chemistry assistant - Structure scanning from images - Cloud save and teaching slides [See Pro plans](https://www.moldraw.com/pricing) Free templates stay free. Every template can be opened and edited in MolDraw.