Acetone formula: structure, preparation and properties (2023)

Acetone formula:Do you know the main component of a nail polish remover? It's Acetone \(\left( {{\rm{C}}{{\rm{H}}_3}{\rm{COC}}{{\rm{H}}_3}} \right),\) too known as \(2\)-propanone or dimethylketone. Breaks down nail polish, making it easy to remove with a cotton swab or cloth. It is the simplest and most important of the aliphatic (fat-derived) ketones. It is used as a solvent in the chemical industry and as an antiseptic in medicines. It is widely used in the textile industry for degreasing wool and degumming silk. It is also a precursor to many organic syntheses.

Acetone structure formula

The IUPAC name of acetone is \(2\)-propanone with a condensed chemical formula \({{\rm{C}}_3}{{\rm{H}}_6}{\rm{O}}.\ ) Acetone is made up of three carbon atoms, six hydrogen atoms and one oxygen atom. It is considered a ketone as it contains a carbonyl group. It is a methyl ketone composed of propane with an oxo group on the carbon atom \({\rm{C – 2}}\). The chemical formula of acetone is \(\left( {{\rm{C}}{{\rm{H}}_3}{\rm{COC}}{{\rm{H}}_3}} \right ) .\)

CLARIFIES YOUR CONCEPTUAL DOUBTS ABOUT ACETONE

molar timeof acetone

A molar mass of acetone, \(\left( {{\rm{C}}{{\rm{H}}_3}{\rm{COC}}{{\rm{H}}_3}} \right ) \)and:

\({\rm{3x}}({\rm{O}}\,{\rm{atomic}}\,{\rm{mass}}\,{\rm{de}}\,{\rm{ carbon}}){\rm{ + 6x}}({\rm{O}}\,{\rm{atomic}}\,{\rm{mass}}\,{\rm{of}}\,{ \rm{hydrogen}}){\rm{ + Atomic}}\,{\rm{mass}}\,{\rm{of}}\,{\rm{Oxygen}}\)

\(= 3(12,01) + 6\left( {\left( {1,007} \right) + 15,999 = 58,08{\mkern 1mu} \,{\rm{g}}\,{\rm{ mo}}{ {\rm{l}}^{ – 1}}} \derecha.\)

Therefore, one mole of acetone weighs \({58.08}\) grams.

hybridizationof acetone

Acetone has two terminal methyl groups attached to a \(\left( {{\rm{C = O}}} \right)\) group at the \({\rm{C – 2}}\) position. The carbons of the terminal methyl groups are\({\rm{s}}{{\rm{p}}^{\rm{3}}}\) has hybridized, while the carbon atom of the carbonyl group at \({\rm{C – 2 } } \) the position is \({\rm{s}}{{\rm{p}}^{\rm{2}}}\)hybridized.

Stereic factor of the carbonyl carbon atom \( = \) Number of bonded atoms \( + \) Lone pairs

\( = 3 + 0 = 3\)

The carbon atom of the carbonyl group is \({\rm{s}}{{\rm{p}}^{\rm{2}}}\)hybridized\(\left( {{\rm{1s + 2P = 3s}}{{\rm{p}}^{\rm{2}}}} \right)\). This means that the atomic orbitals of the carbon atom mix to form hybrid orbitals \({{\rm{3s}}{{\rm{p}}^{\rm{2}}}}\).

The \({\rm{s}}{{\rm{p}}^{\rm{2}}}\)carbon hybridized with the carbonyl group forms \(3\) sigma bonds (two \({\rm { C – C}}\) sigma bonds and a \({\rm{O – C}}\) sigma bond). The formation of \(3\) sigma bonds gives the carbonyl group a basic trigonal form. Only two of the three p orbitals participate in hybridization; therefore, a p orbital remains unhybridized. This unhybridized p orbital of the carbon atom forms a pi bond with the unhybridized p orbital of the carbonyl oxygen atom. This p orbital is directed above and below the plane of the paper. The oxygen atom of the carbonyl group has two lone pairs.

geometria molecularof acetone

The center of the acetone molecule consists of the carbonyl group. The carbon of the carbonyl group is planar-trigonal due to hybridization \({\rm{s}}{{\rm{p}}^{\rm{2}}}\), while the terminals have methyl groups with tetrahedral geometry .

Acetone bond angle

The group \(\left( {{\rm{C = O}}} \right)\) at position \({{\rm{C – 2}}}\) is \({\rm{s} { {\rm{p}}^{\rm{2}}}\)annealed, and the terminal methyl groups are \({\rm{s}}{{\rm{p}}^{\rm{ 3 } }}\)hybridized. The bond angle \({\rm{C – C – C}}\) in \({{\rm{C – 2}}}\) must be \({\rm{12}}{{\rm { 0}}^{\rm{o}}}\)but it is \({\rm{11}}{{\rm{6}}^{\rm{o}}}\) due to bonding pair repulsion of lone pairs. Since the terminal methyl groups are tetrahedral in shape, the bond angle within the methyl groups is \({\rm{109}}{\rm{.}}{{\rm{5}}^{\rm{ O} } }\).

bipolar momentof acetone

In acetone, the main component of the dipole moment is the bond \({\rm{C = O}}\). This is because-

1. The dipole moment at the terminal methyl groups is zero.
2. The dipole does not exist in similar atoms, that is, bond \({\rm{C – C – C}}\).
3. Only the bond \({\rm{C = O}}\) is polar in nature.

Therefore, no cancellation can occur and the dipole moment of the entire acetone molecule is due to the electronegativity of oxygen. The dipole moment of acetone is \(2.69\) Debye.

Lewis structureof acetone

Acetone consists of a ketone functional group present in the center of the molecule. In the Lewis structure of acetone, there are a total of \(26\) valence electrons. These electrons are distributed as shown below:

skeletal formulaof acetone

Acetone is a compound containing three carbons with the ketone functional group in the \({\rm{C – 2}}\ position). The central carbon atom is connected to neighboring carbon atoms through single bonds and to the oxygen atom through a double bond. It has nine sigma bonds and one pi bond. The skeletal structure of acetone is shown below:

three-dimensional representationof acetone

The Wedge-Dash method is used to represent the \({\rm{3 – D}}\) structure of an organic compound. The \({\rm{3 – D}}\) structure of acetone has the following features:

1. A solid wedge is used to represent a link projecting from the plane of the paper towards the viewer.
2. A dotted wedge used to represent the link projecting out of the viewer or below the plane of the paper and
3. A line is used to represent the bond that is in the plane of the paper.

Taking into account the above factors, acetone can be represented as follows:

acetone preparation

Laboratory preparation of acetone

1. By the dehydrogenation of isopropyl alcohol promoted by a copper catalyst.

2. By oxidation of isopropyl alcohol

Industrial Preparationof acetone

Acetone is largely manufactured through the oxidation of cumene. It's a two-step process.

Step 1: Cumene, also known as isopropylbenzene, is obtained by the Friedel-Crafts alkylation of benzene with propylene.

Step 2: The oxidation of cumene in air leads to the production of cumene hydroperoxide. By treating cumene hydroperoxide with dilute acid, Phenol is obtained together with Acetone.

Physical propertiesof acetone

1. Acetone is a colorless liquid with a sweet odor.
2. It is a highly volatile liquid.
3. Its melting and boiling points are \({\rm{ – 94}}.{\rm{9}}{\,^{\rm{o}}}{\rm{C}}\) and \({ \ rm{56}}.{\rm{08}}{\,^{\rm{o}}}{\rm{C}}.\)
4. Its density is \(50.785\;{\rm{g}}\;{\rm{m}}{{\rm{L}}^{ – 1}}\).
5. Acetone is miscible with water, alcohol, benzene, dimethylformamide and ether.

Chemical propertiesof Actone

Acetone is polar due to the \({\rm{ – C = O}}\) bond present in its center. Due to the presence of a positively charged center, nucleophilic molecules attack the electron-deficient carbonyl carbon.

Usosof acetone

1. It is the active ingredient in nail polish removers and paint thinners.
2. It is widely used by chemical and petroleum industries to produce adhesives and sealants, solvents, coatings, plastic and rubber, agricultural products, etc.
3. Acetone is produced and eliminated in the human body through normal metabolic processes. It is normally present in blood and urine.

Summary

Acetone is a widely used organic solvent. When our liver breaks down stored fat, it produces chemicals called ketones. Acetone is the main ketone. It is also found as a compound in food additives, food packaging and in the treatment of acne. Through this article, we learned about the formula of acetone, its structure and various properties. We also learn about its various uses in our daily lives.

Acetone formula frequently asked questions

Frequently asked questions about the acetone formula are answered here:

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