Acetone

1.0Introduction to Acetone

Acetone, also known as propanone (CH₃COCH₃​), is the simplest and most well-known example of a symmetrical ketone. In a symmetrical ketone, the carbonyl group (C=O) is flanked by two identical alkyl groups. In the case of acetone, these groups are methyl groups (-CH₃​). General Properties of acetone are-

Chemical Formula: CH₃COCH₃

IUPAC Name: Propan-2-one
Common Name: Acetone

2.0Structure of Acetone

3.0Properties of Acetone

1. Physical Properties of Acetone

2. Chemical Properties of Acetone

3. Polarity and Solvent Properties:

• Acetone is a polar molecule due to the electronegative oxygen atom in the carbonyl group.
• It is an excellent solvent for organic and some inorganic compounds, dissolving polar and nonpolar substances.

4.0Chemical Reactions of Acetone

1. Oxidation: Strong oxidizing agents can oxidize acetone to form acetic acid (CH3COOH), carbon dioxide, and water. 

CH₃COCH₃  +  [O]  → CH₃COOH 

2. Reduction: Acetone undergoes reduction to form isopropanol when treated with reducing agents like sodium borohydride (NaBH₄​) or hydrogen in the presence of a nickel catalyst. 

CH₃COCH₃ + 2[H] → CH₃CHOHCH₃

3. Aldol Condensation: In the presence of a base or acid, acetone undergoes aldol condensation to form β-hydroxy ketones, which dehydrate to α,β-unsaturated carbonyl compounds. 

$2C{H}_{3}COC{H}_3\stackrel{NaOH}{\to }C{H}_{3}C(OH)C{H}_{2}COC{H}_3\stackrel{heat}{\to }C{H}_{3}C=CHCOC{H}_3+H_{2}O$

4. Reaction with Grignard Reagents: Acetone reacts with Grignard reagents (RMgX) to form tertiary alcohols. 

$C{H}_{3}COC{H}_3+RMgX\to (C{H}_3{)}_{2}C(OH)R$

5. Reaction with Ammonia Derivatives: Acetone reacts with ammonia derivatives (e.g., hydrazine, hydroxylamine) to form corresponding imines, hydrazones, or oximes.

• Oxime Formation: $C{H}_{3}COC{H}_3+N{H}_{2}OH\to C{H}_{3}C=NOHC{H}_3$

6. Reaction with Halogens: In the presence of a base, acetone reacts with halogens like bromine or iodine to form halogenated compounds.

• Haloform Reaction:

7. Reaction with Alcohols (Hemiacetal and Acetal Formation): Acetone reacts with alcohols in the presence of acid catalysts to form hemiacetals and acetals. 

5.0Preparation of Acetone

Acetone (CH₃COCH₃CH​) can be prepared by various methods. Important industrial and laboratory techniques are:

1. By Dehydrogenation of Isopropanol:

2. By Oxidation of Propylene:
   ${\text{CH}}_3\text{CH}={\text{CH}}_2+{\text{Pd(II)Cl}}_2+{\text{H}}_2\text{O}\to {\text{CH}}_3\text{C(O)}{\text{CH}}_3+\text{Pd(O)}+2\text{HCl}$
3. Industrially (Cumene Process): Acetone is produced as a by-product during the manufacture of phenol.

6.0Uses of Acetone

1. Solvent: Widely used as a solvent for paints, coatings, varnishes, and adhesives due to its ability to dissolve organic compounds.
2. Chemical Intermediate: Used in the production of methyl methacrylate (for plastics) and bisphenol A (for polycarbonate plastics).
3. In Pharmaceuticals: Utilized as a solvent in drug formulations.
4. Cleaning Agent: Commonly used in laboratory and household cleaning for removing grease, oil, and adhesives.
5. Nail Polish Remover: A primary ingredient in many nail polish removers.

7.0Health and Safety

Toxicity: Acetone is moderately toxic; prolonged exposure can cause irritation to the eyes, skin, and respiratory system.

Safety Measures:

• Use in well-ventilated areas.
• Avoid contact with open flames as it is highly flammable.