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Acetamide which is also known as Acetic Acid or Ethanamide is an inorganic compound. Derived from acetic acid, Acetamide is a little acidic in nature and is considered to be one of the simplest amides. It is extensively used as a plasticizer and industrial solvents. Also, if measured on a pH scale it can be observed that the pH reading of Acetamide is higher than acetone. Ethanamide originates from the class of acetamides and it formally leads to the condensation of the acetic acid (CH3COOH) with ammonia (NH3). The natural form of acetamide can be found in red beetroot.
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Key Terms: Acetamide, Ammonolysis, methyl group, amides, carboxylic acid, carbonyl, Ethanamide, acetic acid, acetone, inorganic compound, organic compound
Acetamide Structure & Formula
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The chemical formula used for acetamide is C2H5NO or CH3CONH2 with a molar mass of 59.07 g/mol. A methyl group (-Ch3) of the acetamide is attached to a carbonyl (CO) and Amine (NH2). Moreover, the acetamide components include a functional group of carboxylic acid amides with a general structure RC (=O)NH2. Also, it is related to the primary carboxylic acid amides group and exists as a natural compound in nature. The chemical structure is given below:
Chemical Structure of Acetamide
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Properties of Acetamide
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| C2H5NO | Acetamide |
|---|---|
| Molecular weight/molar mass of C2H5NO | 59.068 g/mol |
| Density of Acetamide | 1.159 g/cm3 |
| Boiling Point of Acetamide | 221.2 oC |
| Melting Point of Acetamide | 79 to 81 oC |
Acetamide Occurrence
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Usually, burning waste coal piles at a temperature ranging between 50 and 150 oC (122-302 oF) results in the formation of acetamide. It occurs only during dry weather. Additionally, the presence of acetamide has been discovered close to the center of the Milky Way galaxy by scientists.
This discovery proves to be fairly critical for amino acids in proteins. It also establishes the theory as per which organic molecules that can contribute towards life can originate in space.
Production of Acetamide
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Acetamide can be produced in chemical laboratories by dehydration of ammonium acetate. The chemical reaction for the same is:
[NH4][CH3CO2] → CH3C(O)NH2 + H2O
Ammonolysis of acetylacetone within conditions that are mostly used in reductive amination, produces a generous quantity of acetamide.
Besides, the production of acetamide can also occur from anhydrous acetic acid (CH3COOH), dried hydrogen chloride gas, and acetonitrile within an ice bath accompanied with reagent acetyl chloride. Generally, the product is considered to be low (till 35%) and the acetamide is produced in the form of a salt with HCL.
However, dehydration of ammonium acetate or hydrolyzing acetonitrile can result in producing acetamide on an industrial level. This method is similar to the one used by scientists
CH3CN + H2O → CH3C(O)NH2
Solubility of Acetamide in HCL
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Various researches have proved that acetamide and ammonia are water and HCL soluble compounds due to their small molecular size. However, aniline, triethylamine, and N, N-dimethylaniline compounds are not regarded as water and HCL soluble. These compounds are MTBE soluble (Methyl Tert-Butyl Ether) which is also non-soluble in acetamide and ammonia.
Uses of Acetamide
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- For several organic and inorganic compounds, it is used as a solvent.
- It is used while making explosives.
- It is widely used for making plasticizers.
- It is used in the form of a hygroscopic agent.
- It is used for producing methylamine.
- It is used in the form of a stabilizer.
- It is used in the form of a penetrating agent.
- It is used as a fire controller.
Health & Safety Hazards of Acetamide
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The low toxicity level of acetamide leads to weight loss which is possible only through a high oral dose exposure. Also, the mucous membranes, eyes, and skin may develop minor irritations. Corneal damage is quite likely in such a situation. Moreover, due to its combustible nature, it produces toxic gases or fumes when heated. Serious diseases like liver tumors and lymphoma might result due to multiple oral exposures to acetamide over a period of time.
Things to Remember
- Acetamide is obtained from acetic acid and is known to be the simplest form of amide.
- The other names of acetamide are Acetic acid amide, Ethanamide, Acetic acid.
- It is an inorganic compound its chemical formula is C2H5NO
- It has been observed that acetamide can occur in burning waste coal piles at 50 to 150o C temperature, during dry weather and also near the center of the Milky Way.
- Ammonolysis of acetylacetone can produce a sufficient quantity of acetamide under conditions that are generally used during reductive amination.
- Acetamide can also be produced in industries acetonitrile hydration or through dehydration of ammonium acetate.
- Acetamide has ammonia or vinegar-like odor.
- It is primarily used as a plasticizer and hygroscopic agent.
- Prolonged usage of acetamide can cause irritation of mucous membrane, skin and eyes. It can also cause corneal damage, liver tumors and lymphoma.
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Sample Questions
Ques 1. What is the purpose of using acetamide? (2 marks)
Ans. Acetamide is an organic compound and is considered to be the simplest form of amide belonging to the class of acetic acid derivatives. It has a formula CH3CONH2. Acetamide has several usages like manufacturing polymeric products. One such example is polyvinyl acetamide which is a polymeric commodity and used in the form of an absorbent and co-monomer.
Ques 2. What is the reason for acetamide being soluble in water? (2 marks)
Ans. The basic amide is produced from NH2 which is the amino group that replaces the carboxyl hydroxyl group. A working example of this group is acetamide (acetic acid + amide). Amides with a lower molecular weight that are caused when hydrogen bonds are formed are considered water-soluble.
Ques 3. What is the odor of acetamides? (1 mark)
Ans. Since acetamide is produced from the chemical acetic acid, its odor is identified as similar to vinegar or ammonia. It holds on to inactive musculus regions and also to places from where it looks for food.
Ques 4. Is acetamide HCL soluble? (2 marks)
Ans. Due to their small molecular size, ammonia and acetamide are water and HCL soluble compounds. The MTBE soluble compounds like triethylamine, aniline, and N, N-dimethylaniline are considered non-water and non-HCL soluble. Hence, MTBE is also considered non-ammonia and acetamide soluble.
Ques 5. Why is acetamide considered a weaker base than ethylamine? (2 marks)
Ans. The presence of a single pair of electrons on a base confirms its intensity. It is due to the fact that these electrons are supposed to “mop up” H+ ions in the solution. This increases the pH level for more alkaline conditions. Phenylamine is also a weaker base than ethylamine due to fewer single pairs of electrons.
Ques 6. How is acetamide produced in laboratories by scientists? (1 mark)
Ans. Acetamide is produced by scientists in laboratories by the process of ammonium acetate hydration. The process is mentioned below:
[NH4][CH3CO2] → CH3C(O)NH2 + H2O
Ques 7. Which one of the following is/are the most basic compound? Give reasons. (1 mark)
a.C6H5 - NH2
b.C6H5 - NHCH3
c.C6H5 - N(CH3)2
d.C6H5N (C2H5)2
Ans. The correct answer is option “4” C6H5N (C2H5)2 and the reason is:
The ethyl group has a greater +ve inductive effect compared to methyl and hydrogen. Thus, it is the most basic compound.
Ques 8. Which of the following is the most basic compound in nature? Give reasons. (3 marks)
a.NH3
b.CH3NH2
c.(CH3)2NH
d.C6H5N(CH3)2
Ans. The correct answer is option “3” (CH3)2NH and the reason is:
The availability of lone pairs of electrons that are ready for donation decides the basicity of amines. The groups releasing electrons such as CH3 expand the basicity of amines with higher electron density than nitrogen through which donation of lone pairs of electrons is established.
pH is a type of electron-withdrawing group that lowers the basicity of amines.
Ques 9. Acetamide is treated separately with the following reagents. Which one of these would give methylamine? (2 marks)
a.PCl5
b.Soda-lime
c.NaOH + Br2
d.Hot concentrated H2SO4
Ans. The correct answer is option “3” NaOH + Br2
Acetamide when treated with bromine and NaOH produces methylamine. The Hoffmann bromamide degradation reaction is a type of reaction through which an amide is converted to an amine with one less carbon atom.
CH3CONH2 + Br2 + 4NaOH + CH3NH2 + 2KBr + Na2CO3 + 2H2O
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