Solubility of Organic Compounds in Water

Three groups of compounds, I, II & III, are designated below. Structural formulas for these compounds will be displayed by clicking the appropriate button. In each group the compounds have roughly the same molecular weight. Some of the compounds in each group are completely miscible with (soluble in) water. Other compounds in each group are immiscible with (insoluble in) water. Using your knowledge of polar functional groups and hydrogen bonding of functional groups, try to assign a majority of the compounds to the appropriate category. Some compounds in each group are only partially soluble in water (4 to 15%). You will be given the number of these compounds, and asked to identify them.
The questions posed below require you to enter appropriate letters in the answer box for each question. Do not enter superfluous characters, since they will be counted as incorrect answers.


I.
A
  benzene
B
  butanoic acid
C
  pyridine
D
  1,2-dimethoxyethane
E
  cyclohexane
F
  ethyl acetate
G
  piperidine
H
  dioxane
I
  γ-butyrolactone
J
  methylene chloride
  (1) Which compounds are completely water soluble? .. 
(2) Which compounds are insoluble in water? ..............  
(3) Which compound is partially soluble in water? .......  


II.
A
  1-butanol
B
  butyl amine
C
  tetrahydrofuran
D
  diethyl ether
E
  pentane
F
  1,3-propanediol
G
  furan
H
  2-methyl-2-propanol
I
  butanal
J
  1-chloropropane
  (1) Which compounds are completely water soluble? ...... 
(2) Which compounds are insoluble in water? .................  
(3) Which three compounds are partially water soluble? ...


III.
A
  cyclohexanol
B
  toluene
C
  triethylamine
D
  3-methylbutanoic acid
E
  phenol
F
  2,4-dimethylpentane
G
  aniline
H
  cyclohexylamine
I
  diethanolamine
J
  diethylene glycol
  (1) Which compounds are completely water soluble? ..... 
(2) Which compounds are insoluble in water? ...............  
(3) Which five compounds are partially water soluble? ..  


         

  

  

This script written by William Reusch, Dept. of Chemistry, Michigan State University. Please send comments and corrections to whreusch@pilot.msu.edu.