CYCLOHEXENE - (110-83-8)

Introduction

Name: cyclohexene; cyclohex-1-ene; 1,2,3,4-tetrahydrobenzene
* IUPAC
CAS Number: 110-83-8
Chemical Formula: C6H10
Molar Mass: 82.1436 g
State of Matter: colorless liquid
Mass Percent: C 87.729 %; H 12.270 % 
Isomers:  1-hexyne  •  3-hexyne

Classification

• organic • alkene • aromatic

Uses/Function

• "Alkylation component. In the manuf[acture] of adipic acid, maleic acid, hexahydrobenzoic acid and aldehyde. To prepare butadiene in the laboratory. Has been suggested for the synthesis of maleic acid and as a stabilizer for high octane gasoline." 1

Physical Properties

Melting Point:*
-103.5°C 1 = 169.65 K = -154.3°F
-103.5°C 2 = 169.65 K = -154.3°F
-103.7°C 3 = 169.45 K = -154.66°F
Boiling Point:*
83°C 1 = 356.15 K = 181.4°F
82.9°C 2 = 356.05 K = 181.22°F
83.3°C 3 = 356.45 K = 181.94°F
Density (g/cm3):
0.8110 at 20°C 2
* - 1 atm pressure

Solubility

Qualitative:
insoluble:  3
miscible:  • • 3

Bonding

Double Bonds: 1
Triple Bonds: 0
Sigma Bonds: 16
Pi Bonds: 1
Total: 17
Carboxyl Groups: 0
Hydroxyl Groups: 0
Hybridization: single bonded carbons are sp3; double bonded carbons are sp2
Bonding: polar covalent
Ionic Character: 10.61 %

Thermochemistry

ΔHf° (ℓ): -9.28 kcal/mol 4 = -38.83 kJ/mol
ΔHf° (g): -1.28 kcal/mol 4 = -5.36 kJ/mol
ΔHf° (ℓ): -9.20 kcal/mol = -38.5 kJ/mol 5
ΔHf° (g): -1.20 kcal/mol = -5.0 kJ/mol 5
S° (ℓ): 51.67 cal/(mol•K) 6 = 216.19 J/(mol•K)
S° (g): 74.27 cal/(mol•K) 6 = 310.75 J/(mol•K)
S° (ℓ): 51.29 cal/(mol•K) = 214.6 J/(mol•K) 7
ΔGf° (ℓ): 24.28 kcal/mol 8 = 101.59 kJ/mol
ΔGf° (g): 25.54 kcal/mol 8 = 106.86 kJ/mol
The heat of combustion is the amount of heat released when one mole of a substance undergoes combustion according to the general reaction equation:
CxHyOz + 0.25(4x+y-2z) O2 (g) → x CO2 (g) + 0.5y H2O (ℓ)

ΔHcomb° (ℓ): -896.595 kcal = -3751.38248 kJ
ΔHcomb° (g): -904.595 kcal = -3784.85448 kJ
ΔHcomb° (ℓ): -896.6732791587 kcal = -3751.71 kJ
ΔHcomb° (g): -904.679971319312 kcal = -3785.21 kJ

Reactions

Elimination of cyclohexanol to cyclohexane:


Safety Information

NFPA 704 Ratings:
Health: 1 - Exposure would cause irritation with only minor residual injury.
Flammability: 3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Liquids having a flash point below 23°C (73°F) and having a boiling point at or above 38°C (100°F) or having a flash point between 23°C (73°F) and 38°C (100°F).
Reactivity: 0 - Normally stable, even under fire exposure conditions, and is not reactive with water.
Special Hazard: OX - Oxidizer.

For More Information

Wikipedia
Journals:
Coleman, Johnstone, Org. Syn. 5, 33 (1925)
Wagner, J. Chem. Ed. 10, 113 (1933)
Hershberg, Ruhoff, Org. Syn. 17, 25 (1937)
Purvis, Proc. Cambridge Phil. Soc. 23, 588 (1927)
Hartley, Dobbie, J. Chem. Soc. 77, 846 (1900)

Sources

(1) - The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 13th ed.; Budavari, S.; O'Neil, M.J.; Smith, A.; Heckelman, P. E.; Kinneary, J. F., Eds.; Merck & Co.: Whitehouse Station, NJ, 2001; entry 2756.
(2) - Lide, David R. CRC Handbook of Chemistry and Physics, 83rd ed.; CRC Press: Boca Raton, FL, 2002; p 3-128.
(3) - Dean, John A. Lange's Handbook of Chemistry, 12th ed.; McGraw-Hill Book Company: New York, NY, 1979; p 7-143.
(4) - Dean, John A. Lange's Handbook of Chemistry, 12th ed.; McGraw-Hill Book Company: New York, NY, 1979; p 9:71.
(5) - Lide, David R. CRC Handbook of Chemistry and Physics, 83rd ed.; CRC Press: Boca Raton, FL, 2002; p 5-45.
(6) - Dean, John A. Lange's Handbook of Chemistry, 12th ed.; McGraw-Hill Book Company: New York, NY, 1979; p 9:71.
(7) - Lide, David R. CRC Handbook of Chemistry and Physics, 83rd ed.; CRC Press: Boca Raton, FL, 2002; p 5-45.
(8) - Dean, John A. Lange's Handbook of Chemistry, 12th ed.; McGraw-Hill Book Company: New York, NY, 1979; p 9:71.
(9) - Lide, David R. CRC Handbook of Chemistry and Physics, 83rd ed.; CRC Press: Boca Raton, FL, 2002; p 5-45.