An Overview of NaNH2
NaNH2 is an inorganic compound because it lacks carbon. Sodium amide is used in many organic syntheses. Sodium amide is a strong base and hence used for deprotonating the weak acid and in elimination reactions. It is formed by ammonia and sodium. It is a salt composed of positive sodium ions and negative ammonium ions. Sodium amide is a reagent that can be prepared in the laboratory. It is used for the formulation of many alkynes.
What is NaNH2?
Sodium amide is an inorganic compound made of ammonium and sodium. It is an inorganic reagent utilised in various organic syntheses. There are many methods of preparation of sodium amide (NaNH2). First, sodium amide can be prepared by reacting gaseous and liquid ammonia on sodium or any alloys of sodium. Sodium amide is formed in solid form though the colour of the solid is white.
However, it could be found in a grey colour due to the presence of iron during preparation. The commercial form is found in olive-green colour. Sodium amide quickly absorbed water and carbon dioxide from the atmosphere. As Sodium amide is made up of ammonia, it gives an ammonium odour in its end product.
NaNH2 Chemical Name and Formula
NanH2 is known as sodium amide because its chemical formula contains sodium and amide. It is sometimes also known as sodium azanide. The boiling point of NaNH2 is 752°F at 760 mm Hg and the melting point of sodium amide is 410 °F. Sodium amide is soluble in water and insoluble in alcohol. Sodium ammonium is also soluble in liquid ammonia at 20°C. The density of sodium amide is 1.39 at 68 °F.
NaNH2 Uses
Sodium amide is used in chemistry for many chemical reactions. Some of the uses are listed below:
Sodium amide is used as a strong base in liquid ammonium solution.
Sodium amide is used to dry ammonia (liquid or gaseous).
It is used as the nucleophile in many reactions.
Sodium amide is typically used for the industrial production of indigo. In indigo production, sodium amide is a component of a highly basic mixture that induces the cyclisation of N-Phenylglycine. In this reaction, ammonia is produced, which is recycled.
NaNH2 Chemical Reaction
NaNH2 reagent is used in chemical reactions. Some of the reactions are deprotonation and elimination reactions.
Deprotonation reaction
Sodium amide is used for the deprotonation of alkyne to give acetylide ions. NaNH2 is a strong base that reacts with an organic compound to form acetylide as depicted in the given image. Acetylide ion is a nucleophile and can react with alkyl halide actively forming carbon-carbon bonds.
Deprotonation reaction in the presence of NaNH2
In the above reaction, ethylene is reacting to an amide group and acetylide anion is forming.
Elimination reaction
NaNH2 acts as a strong base during the formation of alkyne from halides. Halides such as geminal dihalides (two halogens on one carbon) and vicinal dihalides (halogens on adjacent carbons) undergo an elimination reaction in the presence of NaNH2. This elimination reaction results in the formation of alkynes.
Formation of alkynes from halides
NaNH2 Safety
Since sodium amide reacts violently with water or acid. It needs to be handled carefully. Sometimes sodium amide can ignite automatically at high temperatures. While handling sodium amide, use safety glasses, protective gloves, fire retardant, and a laboratory coat. Avoid contact with direct skin and eye. It can be harmful. Inhalation and ingestion could also lead to a dangerous outcome. Ensure a fire extinguisher is nearby in the lab. Unused and unwanted leftovers of sodium amide should be immediately disposed of.
Interesting Facts about NaNH2
Sodium amide can catch fire with flame.
Sodium amide, when kept in the air, can react with air easily and diffuse itself.
Sodium cyanide can be obtained in high yield by mixing sodium amide and carbon.
Key Features of NaNH2
NaNH2 is a strong basic compound that is used in many chemical reactions as a catalyst.
NaNH2 is specially used for deprotonation reactions to form acetylide ions and in elimination, reaction to form alkyne.
NaNH2 is highly corrosive and ignitable, hence should be handled with care.
FAQs on NaNH2 Chemical Name
1. What does the NaNH2 reagent do?
As a strong base, NaNH2 will deprotonate alkynes, and alcohols to form acetylide ions and alkoxide ions.
R - OH + NaNH2 → R - O- +Na + NH3
CH3 - OH + NaNH2 → CH3 - O- +Na + NH3
In the above reaction, alcohol donate its one proton to sodium amide to form ammonia and alkoxide ions. Similarly, in place of alcohol, alkyne donates its proton to sodium amide to form ammonia and acetylide ions.
R - C ☰ C - H + NaNH2 → R - C ☰ C- +Na + NH3
H- C ☰ C - H + NaNH2 → H - C ☰ C- +Na + NH3
2. Is NaNH2 a strong reducing agent?
Yes. Sodium amide is a strong reducing agent. It forms the alkyne from halides either geminal or vicinal. It removes the halide atom and hydrogen atom, thereby forming the triple bond.
3. Why is NaNH2 a stronger base than NaOH?
NaNH2 is more basic than NaOH as the O-atom is more electronegative than N-atom. The bond between the O-H is more polar than the N-H bond, which is easy to break. Nitrogen has more tendency to donate electrons than oxygen. Therefore, NaNH2 is more basic than NaOH.
