---
title: "Catalytic hydrogenation on a metal surface Template | MolDraw"
url: https://www.moldraw.com/templates/catalytic-hydrogenation-syn-surface/
description: "Catalytic hydrogenation on a metal surface template: 1,2-Dimethylcyclohexene with H₂ over Pd gives cis-1,2-dimethylcyclohexane. In the Horiuti–Polanyi scheme…"
lang: en
publisher: Scidart Academy
generated: 2026-11-13
---
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# Catalytic hydrogenation on a metal surface template

![Catalytic hydrogenation on a metal surface template: 1,2-Dimethylcyclohexene with H₂ over Pd gives cis-1,2-dimethylcyclohexane. In the Horiuti–Polanyi scheme (simplified here: surface atoms drawn as Pd) H₂ dissociates to surface H atoms, one H adds to give a half-hydrogenated alkyl, then the second H adds from the same face and the alkane leaves.](https://www.moldraw.com/templates/catalytic-hydrogenation-syn-surface.webp)

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1,2-Dimethylcyclohexene with H₂ over Pd gives cis-1,2-dimethylcyclohexane. In the Horiuti–Polanyi scheme (simplified here: surface atoms drawn as Pd) H₂ dissociates to surface H atoms, one H adds to give a half-hydrogenated alkyl, then the second H adds from the same face and the alkane leaves.

## Mechanism step by step

H₂ and the alkene bind to the metal, and both H atoms add from the metal side: syn addition

1. **H₂ adsorbs** – Schematic: H₂ binds to the metal and the H–H bond breaks to give surface Pd–H
2. **First H (half-hydrogenated)** – The alkene lies flat on the surface by one face; Pd–H adds across C=C (four-centre, syn): H to one carbon, the other bonds to the metal
3. **Second H, desorption** – The second H comes from the same (metal) face: both new C–H bonds are cis

## Key points

- Syn addition: both H atoms come from the metal surface, so 1,2-dimethylcyclohexene gives cis-1,2-dimethylcyclohexane.
- Heterogeneous catalysts (Pd/C, PtO₂, Raney Ni) lower the barrier; without a catalyst H₂ and alkenes do not react. Heats of hydrogenation (about −120 kJ mol⁻¹ for a disubstituted C=C) measure alkene stability.
- Horiuti–Polanyi steps are reversible: the half-hydrogenated alkyl can lose an H again, which explains H/D scrambling and some C=C migration (the accepted mechanism, simplified here).
- C=O, aromatic rings and esters are untouched under mild conditions; alkynes go to alkanes unless the catalyst is poisoned (Lindlar).

Drawn with 62 atoms, 6 arrows, 432 shapes – every one editable in MolDraw.

## Sources

- [Wade, Organic Chemistry, 8th ed., Pearson 2013, ch. 8](https://openlibrary.org/isbn/9780321768414) Textbook
- [Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012, ch. 23](https://openlibrary.org/isbn/9780199270293) Textbook
- [Smith, March's Advanced Organic Chemistry, 8th ed., Wiley 2020, ch. 15](https://openlibrary.org/isbn/9781119371809) Textbook

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