Sodium Cyanide

Definition

Sodium cyanide is a highly toxic chemical compound that consists of a sodium cation and a cyanide anion. It is commonly used in various industrial processes, including gold mining and chemical synthesis, and is an important precursor in the preparation of carboxylic acids.

5 Must Know Facts For Your Next Test

1. Sodium cyanide is a white, crystalline solid that is highly soluble in water and has a distinctive almond-like odor.
2. It is a powerful nucleophile and is commonly used in the formation of cyanohydrins, which are important intermediates in the synthesis of various organic compounds.
3. The cyanide ion in sodium cyanide can displace the hydroxide ion in water, forming hydrocyanic acid (HCN), which is an extremely toxic gas.
4. Sodium cyanide is also used in the preparation of carboxylic acids through the reaction of an alkyl halide with sodium cyanide, followed by hydrolysis of the resulting nitrile.
5. Due to its high toxicity, the handling and storage of sodium cyanide are strictly regulated, and it is considered a hazardous material.

Review Questions

• Explain the role of sodium cyanide in the nucleophilic addition of HCN to form cyanohydrins.
  • Sodium cyanide is a key reagent in the nucleophilic addition of hydrogen cyanide (HCN) to carbonyl compounds, such as aldehydes and ketones, to form cyanohydrins. In this reaction, the cyanide ion from sodium cyanide acts as a nucleophile, attacking the electrophilic carbon of the carbonyl group. This addition reaction results in the formation of a new carbon-carbon bond and the creation of a cyanohydrin, which is a valuable intermediate in the synthesis of various organic compounds.
• Describe how sodium cyanide can be used in the preparation of carboxylic acids.
  • Sodium cyanide can be used in the preparation of carboxylic acids through a two-step process. First, an alkyl halide (e.g., alkyl chloride or alkyl bromide) is reacted with sodium cyanide to form a nitrile compound. This nitrile is then subjected to hydrolysis, where the nitrile group is converted to a carboxylic acid group. The use of sodium cyanide in this reaction sequence allows for the introduction of a carboxylic acid functionality from a simpler alkyl halide precursor, making it a valuable synthetic tool in the preparation of carboxylic acids.
• Evaluate the safety concerns and regulations surrounding the use of sodium cyanide, and discuss the importance of proper handling and storage procedures.
  • Sodium cyanide is an extremely hazardous and toxic chemical compound that requires strict safety protocols and regulations for its handling and storage. Due to its ability to form highly toxic hydrocyanic acid when in contact with water or acids, exposure to sodium cyanide can be life-threatening, even in small quantities. As a result, the use of sodium cyanide is tightly controlled, and its transportation, storage, and disposal are subject to stringent safety guidelines. Proper personal protective equipment, containment measures, and specialized training are essential when working with sodium cyanide to minimize the risks of accidental exposure or release, which could have severe environmental and public health consequences.

Related terms

Cyanide: Cyanide is a chemical compound containing a carbon-nitrogen triple bond, which is highly toxic and can interfere with cellular respiration.

Nucleophilic Addition: A type of organic reaction where a nucleophile (electron-rich species) adds to an electrophilic carbon, typically a carbonyl carbon, to form a new product.

Carboxylic Acid: A class of organic compounds containing a carboxyl group (-COOH), which is characterized by its acidic properties and ability to undergo various chemical transformations.