Enthalpies of hydration of alkenes. 1. The n-hexenes

Journal Article · Wed Nov 04 04:00:00 EST 1981 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00412a005· OSTI ID:5845569

Wiberg, K B; Wasserman, D J

Alkenes undergo a rapid reaction with trifluoroacetic acid containing 0.25 M trifluoroacetic anhydride in the presence of a strong acid catalyst. The enthalpies of trifluoroacetolysis of the five n-hexenes were determined and were corrected to the enthalpies corresponding to the formation of the equilibrium mixture of 2-hexyl trifluoroacetate and 3-hexyl trifluoroacetate. The enthalpy difference between the latter was determined by measuring the equilibrium constant as a function of temperature. The trifluoroacetolysis data may be combined with the measured enthalpies of formation of the alkenes to derive more precise values for the latter. The enthalpies of reaction of water, 2-hexanol, and 3-hexanol with the reaction solvent were determined, and when combined with the other data lead to enthalpies of hydration of the alkenes and the enthalpies of formation of the alcohols.

• Research Organization: Yale Univ., New Haven, CT
• OSTI ID: 5845569
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 103:22; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ACETIC ACID
ALKANES
ALKENES
ANHYDRIDES
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
DATA
ENTHALPY
EXPERIMENTAL DATA
HEXANE
HYDRATION
HYDROCARBONS
INFORMATION
MONOCARBOXYLIC ACIDS
NUMERICAL DATA
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
PHYSICAL PROPERTIES
SOLVATION
THERMODYNAMIC PROPERTIES