Advices For Studying Organic Chemistry

6.2 PHYSICAL PROPERTIES OF ORGANIC HALIDES

Table 6.2 Organic Halides

Fluoride Chloride Bromide Iodide

Group bp (°C) Density

(g mL–1) bp (°C)

Density

(g mL–1) bp (°C)

Density

(g mL–1) bp (°C)

Density
(g mL–1)
Methyl –78.4 0.84–60 –23.8 0.92^20 3.6 1.73^0 42.5 2.28^20
Ethyl –37.7 0.72^20 13.1 0.91^15 38.4 1.46^2072 1.95^20
Propyl –2.5 0.78–3 46.6 0.89^20 70.8 1.35^20102 1.74^20
Isopropyl –9.4 0.72^2034 0.86^20 59.4 1.31^20 89.4 1.70^20
Butyl 32 0.78^20 78.4 0.89^20101 1.27^20130 1.61^20
sec-Butyl 68 0.87^20 91.2 1.26^20120 1.60^20
Isobutyl 69 0.87^2091 1.26^20119 1.60^20
tert-Butyl 12 0.75^1251 0.84^20 73.3 1.22^20 100 deca 1.57^0
Pentyl 62 0.79^20 108.2 0.88^20 129.6 1.22^20155 740 1.52^20
Neopentyl 84.4 0.87^20105 1.20^20 127 deca 1.53^13
CH 2 =CH– –72 0.68^26 –13.9 0.91^2016 1.52^1456 2.04^20
CH 2 =CHCH 2 – –3 45 0.94^2070 1.40^20 102-103 1.84^22
C 6 H 5 – 85 1.02^20132 1.10^20155 1.52^20189 1.82^20
C 6 H 5 CH 2 – 140 1.02^25179 1.10^25201 1.44^2293 10 1.73^25
a Decomposes is abbreviated dec.

1. Solubilities:
   
   
   1. Many alkyl and aryl halides have very low solubilities in water, but they are
      miscible with each other and with other relatively nonpolar solvents.
   
   
   2. Dichloromethane (CH 2 Cl 2 , methylene chloride), trichloromethane (CHCl 3 ,
      chloroform), and tetrachloromethane (CCl 4 , carbon tetrachloride) are often
      used as solvents for nonpolar and moderately polar compounds.
   
   
   
   


2. Many chloroalkanes, including CHCl 3 and CCl 4 , have a cumulative toxicity and
   are carcinogenic.


3. Boiling points:
   
   
   1. Methyl iodide (bp 42 °C) is the only monohalomethane that is a liquid at room