Advices For Studying Organic Chemistry

(Wang) #1

  1. The boiling point of a liquid is the temperature at which the vapor pressure of the
    liquid equals the pressure of the atmosphere above it.



  1. Boiling points of liquids are pressure dependent.

  2. The normal bp given for a liquid is its bp at 1 atm (760 torr).

  3. The intermolecular van der Waals attractions increase as the size of the molecule
    increases because the surface areas of heavier molecules are usually much
    greater.

  4. For example: the bp of methane (–162 °C), ethane (–88.2 °C), and decane (174
    °C) becomes higher as the molecules grows larger.


Table 2.5 Attractive Energies in Simple Covalent Compounds

Attractive energies
(kJ mol–^1 )
Molecule moment (D) Dipole Dipole-Dipole van der Waals Melting point (°C) Boiling point (°C)
H 2 O 1.85 36 a 88 0 100
NH 3 1.47 14 a 15 –78 –33
HCl 1.08 3 a 17 –115 –85
HBr 0.80 0.8 22 –88 –67
HI 0.42 0.03 28 –51 –35
a These dipole-dipole attractions are called hydrogen bonds.



  1. Fluorocarbons have extraordinarily low boiling points when compared to
    hydrocarbons of the same molecular weight.



  1. 1,1,1,2,2,3,3,4,4,5,5,5-Dodecafluoropentane (C 5 F 12 , m.w. 288.03, bp 28.85 °C)
    has a slightly lower bp than pentane (C 5 H 12 , m.w. 72.15, bp 36.07 °C).

  2. Fluorine atom has very low polarizability resulting in very small van der Waals
    forces.

  3. Teflon has self-lubricating properties which are utilized in making “nonstick”
    frying pans and lightweight bearings.

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