What is the Difference Between Sandmeyer Reaction and Gattermann Reaction?
🆚 Go to Comparative Table 🆚The Sandmeyer reaction and Gattermann reaction are both organic reactions, but they differ in the type of reaction and the reactants involved.
Sandmeyer Reaction:
- It is a type of organic substitution reaction.
- Synthesizes aryl halides from aryl diazonium salts.
- Uses copper salts as a catalyst.
- Involves a single electron transfer from copper to diazonium.
- Useful in halogenation, cyanation, trifluoromethylation, and hydroxylation of benzene.
Gattermann Reaction:
- Refers to the formylation of aromatic compounds.
- Involves the use of a Lewis acid.
- Reactant is a cuprous halide and a halogen acid (e.g., CuCl/HCl or CuBr/HBr).
- Important in introducing aldehyde groups to the benzene ring.
In summary, the key difference between the Sandmeyer reaction and the Gattermann reaction is that the Sandmeyer reaction synthesizes aryl halides from aryl diazonium salts in the presence of copper salts as a catalyst, whereas the Gattermann reaction refers to the formylation of aromatic compounds in the presence of a Lewis acid.
Comparative Table: Sandmeyer Reaction vs Gattermann Reaction
The Sandmeyer Reaction and Gattermann Reaction are both used in organic chemistry for converting aryl diazonium salts into other functional groups. Here are the main differences between the two reactions:
| Reaction | Catalyst | Reactants | Reaction Type | Applications |
|---|---|---|---|---|
| Sandmeyer Reaction | Copper(I) salts (CuCl, CuBr, or CuI) | Aryl diazonium salts and hydrochloric acid (HCl) or hydrobromic acid (HBr) | Organic substitution reaction (radical-nucleophilic aromatic substitution) | Synthesis of aryl halides, useful for halogenation, cyanation, trifluoromethylation, and hydroxylation of benzene |
| Gattermann Reaction | Copper powder with CuCl or CuBr | Aryl diazonium salts | Organic substitution reaction | Introduction of aldehyde groups to the benzene ring |
The Sandmeyer reaction uses copper(I) salts as catalysts and reacts aryl diazonium salts with hydrochloric or hydrobromic acid to form aryl halides. This reaction is useful for various transformations on benzene, such as hydroxylation, trifluoromethylation, cyanation, and halogenation.
On the other hand, the Gattermann reaction is a modification of the Sandmeyer reaction and uses copper powder with CuCl or CuBr as reactants to introduce aldehyde groups to the benzene ring. This reaction is particularly important for synthesizing aryl bromides and iodides, but it is less effective for synthesizing aryl chlorides.
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