Chloranil

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Chloranil is an organic compound with the formula C6Cl4O2. It is a yellow solid that is soluble in organic solvents. Chloranil is used as a reagent in organic synthesis and as a fungicide.

Structure and Properties

Chloranil is a quinone, specifically a tetrachloroquinone. It consists of a benzene ring with four chlorine atoms and two ketone groups at the para positions. The molecular structure of chloranil is planar, and it exhibits a high degree of electron deficiency due to the presence of the electron-withdrawing chlorine atoms and carbonyl groups.

Synthesis

Chloranil can be synthesized by the chlorination of hydroquinone or p-benzoquinone. The reaction typically involves the use of chlorine gas in the presence of a catalyst such as iron(III) chloride.

Applications

Organic Synthesis

In organic synthesis, chloranil is used as an oxidizing agent. It is particularly useful in the dehydrogenation of hydroquinones to quinones and in the oxidation of amines to imines.

Fungicide

Chloranil has been used as a fungicide in agriculture. It is effective against a variety of fungal pathogens that affect crops.

Safety and Handling

Chloranil is a hazardous substance and should be handled with care. It is toxic if ingested or inhaled and can cause skin and eye irritation. Proper protective equipment, such as gloves and goggles, should be used when handling chloranil.

Related Compounds

• Quinone
• Hydroquinone
• Benzoquinone
• Tetrachlorohydroquinone

See Also

• Organic synthesis
• Oxidizing agent
• Fungicide