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SOLUBILITY OF
ORGANIC COMPOUNDS
Objectives
to describe the structural features common to compounds that
belong to a specific functional grouping
Physical Properties
can be determined without changing the chemical identity of a substance
examples are physical color, odor, physical state, solubility and density
Acid-Base properties
Acids Bases
sour in taste taste bitter and feel soapy
increase H+ concentration increase OH- concentration
Reference Standards
Physical Properties
Amyl acetate
physical state
Cyclohexane
Ethylamine
5 drops or color
Ethanol microspatula
Benzoic acid
odor
Phenol
Solubility/Miscibility Test
1. Amyl acetate
+ 1 mL 1M HCl
1 2 3 4 5 6
2. Cyclhexane Observe
and record
3. Ethylamine the
solubility of
4. Ethanol each
+ 1 mL 1M NaOH compound
1 2 3 4 5 6
5. Benzoic acid
6. Phenol
23
Before
After heating:
heating:
With
Ethanol Liquid Alcohol-like odor; Colorless miscible miscible
NaHCO3*
-
Benzoic Acid Solid Odorless; White, fine powder insoluble soluble
With effervescence
-
Phenol Liquid Formalin-like odor; Light red immiscible miscible Without
effervescence
24
Amyl Acetate
neutral compound
ester molecules cannot hydrogen-bond to each other
immiscible in both HCl and NaOH
25
Cyclohexane
neutral compound
cannot form H bonds because of its non-polarity
immiscible in both HCl and NaOH
26
Ethanol
can form H-bond
considered neutral compound but may act as acid or base
can dissolve in both polar and non-polar substances
miscible with HCl and NaOH
27
Ethylamine
can form H-bond
act as a base
basicity depends on the availability of the lone pair of electrons of N and on
the electronic properties of the substituents
miscible with HCl and NaOH
28
Benzoic acid
can form H-bond
act as an acid
soluble in NaOH
insoluble in HCl and forms effervescence with NaHCO3
Reaction of Benzoic acid with NaOH
C6H5COOH + NaOH C6H5COO-Na+ + H2O
29
Phenol
can form H-bond
slightly acidic
miscible in NaOH
immiscible in HCl and does not form effervescence with NaHCO3
30
A B C D E F G H