Cyclohexanone

Overview

A cyclic ketone that reduces to cyclohexanol.

Its carbonyl carbon forms part of the six-membered ring. Nucleophilic addition converts that planar site into a tetrahedral carbon while retaining the ring skeleton. Simple reduction gives cyclohexanol; it does not open the ring or add a carbon atom.

Identifiers

Formula

C6H10O

Functional group

Ketones

Molar mass

98.14 g/mol

Also known as

Ketohexamethylene, Pimelic ketone, Sextone, Nadone, Anone, Anon

Properties

Melting Point

-31 °C

Boiling Point

155.6 °C @ 760 MM HG

Relative density (water = 1)

Relative density (water = 1): 0.95

Water solubility

Solubility in water, g/100ml at 20 °C: 8.7

Related compounds

• Ketones

  A cyclic ketone that reduces to cyclohexanol.

Connected reactions

• Secondary alcohol oxidation: Cyclohexanol → Cyclohexanone

  Oxidation removes hydrogen from the O-H group and its attached carbon, creating a C=O bond. Because that carbon already bonds to two other carbons, the product is a ketone and the six-membered ring is retained.

• Ketone reduction: Cyclohexanone → Cyclohexanol

  Hydride adds to the planar carbonyl carbon while the pi electrons move onto oxygen. Subsequent protonation gives cyclohexanol; the existing carbon ring remains intact.

References

1. PubChem Compound Summary: Cyclohexanone (CID 7967)National Center for Biotechnology Information · PubChem

   Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.

2. OpenStax Organic Chemistry: Nucleophilic addition reactions of aldehydes and ketonesJohn McMurry · OpenStax · 2023

   Supports the qualitative structure and reactivity context; identity and numerical measurements retain their original references.

3. OpenStax Organic Chemistry: Nucleophilic addition of hydride and Grignard reagents: alcohol formationJohn McMurry · OpenStax · 2023

   Supports the qualitative structural interpretation of the recorded molecular structure; no new physical measurement or verified preparative yield is claimed.

4. Hazardous Substances Data Bank (HSDB): Cyclohexanone — melting pointHazardous Substances Data Bank (HSDB)

   Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/7967#section=Melting-Point. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 75th ed. Boca Raton, Fl: CRC Press Inc., 1994-1995., p. 3-127

5. Hazardous Substances Data Bank (HSDB): Cyclohexanone — boiling pointHazardous Substances Data Bank (HSDB)

   Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/7967#section=Boiling-Point. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 426

6. ILO-WHO International Chemical Safety Cards (ICSCs): Cyclohexanone — densityILO-WHO International Chemical Safety Cards (ICSCs)

   Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/7967#section=Density. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred.

7. ILO-WHO International Chemical Safety Cards (ICSCs): Cyclohexanone — solubilityILO-WHO International Chemical Safety Cards (ICSCs)

   Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/7967#section=Solubility. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred.