Cyanide

Definition

Cyanide is a chemical compound containing a carbon-nitrogen triple bond. It is a highly toxic substance that can interfere with cellular respiration and is found in various forms, including potassium cyanide and hydrogen cyanide. Cyanide is relevant in the context of SN2 reactions, hydration reactions, and the chemistry of nitriles.

5 Must Know Facts For Your Next Test

1. Cyanide is a strong nucleophile that can participate in SN2 reactions, displacing other nucleophiles at a saturated carbon center.
2. In the context of hydration reactions, cyanide can act as a nucleophile, adding to the carbon-nitrogen triple bond of a nitrile to form an imidate intermediate.
3. The hydrolysis of nitriles, such as those containing a cyanide group, can produce carboxylic acids or amides depending on the reaction conditions.
4. Cyanide is a highly toxic substance that inhibits cellular respiration by binding to the iron in cytochrome c oxidase, preventing the transfer of electrons in the electron transport chain.
5. The use of cyanide-containing compounds, such as potassium cyanide, in organic synthesis requires strict safety precautions due to the inherent hazards associated with cyanide exposure.

Review Questions

• Explain how the nucleophilic nature of cyanide affects its behavior in SN2 reactions.
  • As a strong nucleophile, cyanide can participate in SN2 reactions by attacking the electrophilic carbon center and displacing the existing nucleophile. The high electron density of the carbon-nitrogen triple bond in cyanide allows it to readily form a new covalent bond, leading to the substitution of the leaving group and the formation of a new carbon-cyanide bond.
• Describe the role of cyanide in the hydration of nitriles and the subsequent formation of imidate intermediates.
  • In the nucleophilic addition of water to nitriles, cyanide can act as a nucleophile, attacking the carbon of the nitrile and forming an imidate intermediate. This intermediate can then undergo further hydrolysis to produce either a carboxylic acid or an amide, depending on the reaction conditions. The ability of cyanide to participate in this hydration process is a key aspect of the chemistry of nitriles.
• Analyze the potential hazards associated with the use of cyanide-containing compounds in organic synthesis and discuss the safety precautions that must be taken.
  • Cyanide is an extremely toxic substance that can inhibit cellular respiration by binding to the iron in cytochrome c oxidase, preventing the transfer of electrons in the electron transport chain. The use of cyanide-containing compounds, such as potassium cyanide, in organic synthesis requires strict safety precautions to minimize the risk of exposure. These precautions may include working in a well-ventilated area, using appropriate personal protective equipment, and having access to antidotes in case of accidental exposure. Proper handling, storage, and disposal of cyanide-containing waste are also crucial to ensure the safety of both the researcher and the environment.

Related terms

Nucleophile: A nucleophile is a species that donates an electron pair to form a new covalent bond, often attacking an electrophilic carbon atom.

Nitrile: A nitrile is a functional group containing a carbon-nitrogen triple bond, which can undergo various chemical transformations.

Hydrolysis: Hydrolysis is a chemical reaction where a compound is cleaved by the addition of water, often resulting in the formation of new products.