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Jalalon
Performed:
Lab Partner:
Date
Experiment 1
Solubility of Organic Compounds
I. Objectives(s)
To determine the solubility class of organic compounds using solvent systems in order
to determine their main functional group
+ H2O
S1
S2 (highly
polar
+ 5% NaOH
+ 5% HCl
+ 5%
NaHCO3
Water-soluble compounds
B
Reagent
or
Product
Acetone
A2
(weak)
A1
(strong)
Basic
Physical
Hazards
Waste
Acidic
compounds
Properties
Disposal
compounds
M
+ conc
(MP, BP, Density,
H2SO4
Appearance, etc)
Miscellaneous
(CH3)2CO neutral Melting Point:
skin and
non-95C (-139F)
eye irritant,
halogenated
compounds
BoilingI Point:
organic waste
N carcinogeni
56.5C
(133F)
c,
Inert compounds
Neutral compounds
hazardous
when
ingested.
Structure
Density: 0.7845
Appearance:
Clear, colorless,
volatile liquid.
Aniline
C6H5NH2
Melting Point:
-6.2C (21F)
Boiling Point:
184C (363F)
Density: 1.022
Appearance:
Colorless, oily
liquid. Darkens on
exposure to light or
air.
combustible
,
carcinogeni
c, irritant,
permeator,
hazardous
when
ingested
nonhalogenated
organic waste
Benzaldeh
yde
C7H6O
Melting Point:
-26C
Boiling Point:
179C
Density:
1.04
Appearance:
slightly soluble in
water
eye and
skin irritant,
permeator,
hazardous
when
ingested
nonhalogenated
organic waste
Benzamid
e
C7H7NO
Melting Point:
127 - 130C (261 266F)
Boiling Point:
288C (550F)
Density: 1.314
Appearance:
Colorless crystals.
irritant,
permeator,
very
hazardous
in case of
ingestion
nonhalogenated
organic waste
Benzoic
Acid
C6H5COOH
Melting Point:
122C (252F)
Boiling Point:
249C (480F)
Density:
1.2659
Appearance:
White, needle-like
crystals.
eye and
skin irritant,
permeator,
hazardous
when
ingested
nonhalogenated
organic waste
Benzyl
Alcohol
C6H5CH2OH
Melting Point:
-15C (5F)
Boiling Point:
205C (401F)
slightly
hazardous
when
nonhalogenated
organic
Density:
1.04
Appearance:
Clear, colorless
liquid.
ingested,
skin and
eye irritant
waste
Ethanol
C2H6O
Melting Point:
-114
Boiling Point:
78C
Density: 0.789
Appearance:
Clear, reddish
brown liquid.
sensitizer,
skin and
eye
irritant,
permeator,
do not
inhale
nonhalogenated
organic
waste
Hexane
C6H14
skin and
eye
irritant,
permeator,
flammable
nonhalogenated
organic
waste
Phenol
C6H6O
Melting Point:
ca. -95C (ca. -139F)
Boiling Point:
ca. 68C (ca. 154F)
Density:
0.66
Appearance:
Clear, colorless
liquid.
Melting Point:
43C (109F)
Boiling Point:
182C (360F)
Density:
1.07
Appearance:
Colorless to light
pink crystals.
corrosive,
irritant,
sensitizer,
permeator,
may
produce
blistering,
nonhalogenated
organic
waste
Sucrose
C12H22O11
Melting Point:
160 - 186C (320 367F)
Density:
1.587
Appearance:
Monoclinic
sphenoidal crystals.
eye
irritant,
slightly
hazardous
in case of
contact
nonhalogenated
organic
waste
Tert-butyl
chloride
C4H9Cl
Melting Point:
-26C
Boiling Point:
127.0 - 129.0 deg C
@ 760.00m
Density:
0.84
Appearance: Clear
flammable,
do not
induce
vomiting,
hazardous
when
halogenated
organic
waste
liquid
ingested
Toluene
C7H8
Melting Point:
-95C (-139F)
Boiling Point:
111C (232F)
Density:
0.867
Appearance:
Clear, colorless
liquid.
flammable,
irritant,
hazardous
when
ingested
nonhalogenated
organic
waste
Diethyl
ether
C4H10O
Melting Point:
-123C (-189F)
Boiling Point:
35C (95F)
Density:
0.7137
Appearance:
Clear, colorless
liquid.
irritant,
permeator,
flammable
nonhalogenated
organic
waste
5% NaOH
NaOH
Melting Point:
318C (604F)
Boiling Point:
1390C (2534F)
Density:
2.13
Appearance:
White, deliquescent
pellets or flakes.
corrosive,
permeator,
do not
induce
vomiting
base waste
5%
NaHCO3
NaHCO3
Melting Point:
60C (140F)
Boiling Point:
851C
Density:
2.159
Appearance:
White crystalline
slightly
hazardous
when
ingested,
skin and
eye irritant
base waste
powder.
5% HCl
HCl
Conc.
H2SO4
H2SO4
Melting Point:
-74C (-101F)
Boiling Point:
53C (127F)
Azeotrope (20.2%)
boils at 109C (228F)
Density:
1.19
Appearance:
Colorless, fuming
liquid
Melting Point:
3C (100%), -32C
(93%), -38C (78%),
-64C (65%).
Density:
1.84
Appearance:
Clear, colorless
solution.
corrosive,
permeator,
irritant,
sensitizer
acid waste
very
corrosive,
irritant,
may
produce
tissue
damage
acid waste
Waste Disposal
Dilute all aqueous solutions and pour to the sink with copious running water. Dispose the
undissolved solids to the SOLID WASTE container.
Transfer all heterogenous solutions to a separatory funnel. Collect the awueous layer and
pour to the sink with copious running water. Dispose the organic layer to the NONHALOGENATED ORGANIC WASTE jar.
V. Data
Guide Questions
1. For solutes that are dissolved because of intermolecular attractions with the
solvent, state the intermolecular forces of attraction involved.
a.
b.
c.
d.
e.
2. For solutes that are dissolved because of reaction with the solvent, write the
balanced equations involved.
a Benzoic acid 5% NaOH
C6H5COOH(s) + NaOH(aq) C6H5COO-Na+(aq) + H2O(l)
b Benzoic acid 5% NaHCO3
C6H5COOH(s) + NaHCO3(aq) C6H5COO-Na+(aq) + H2CO3(g)
c Benzyl alcohol concentrated H2SO4
C6H5CH2OH(l) + H2SO4(aq) C6H5CH2OH2+(aq) + HSO4-(aq)
d Benzaldehyde concentrated H2SO4
C6H5CHO(l) + H2SO4(aq) C6H5COH+(aq) + HSO4-(aq)
e Phenol 5% NaOH
C6H5OH(s) + NaOH(aq) C6H5ONa(aq) + H2O(l)
f Aniline 5% HCl
C6H6NH2(l) + HCl C6H6NH3+Cl-(aq) + H2O(l)
3. On the basis of solubility behavior, determine the best solvent to
differentiate the following pairs of compounds.
a. CH3COOH and CH3(CH2)5COOH (H2O)
b. CH3CH2OCH2CH3 and CH3CH2OH (diethylether)
c. Toluene and benzaldehyde (H2SO4)
d. Tert-butyl chloride and tert-butanol (H2SO4)
a CH3COOH and CH3(CH2)5COOH
Water: CH3COOH is soluble in water while CH3(CH2)5COOH is not
because it has more than 5 carbons in its parent chain
b CH3CH2OCH2CH3 and CH3CH2OH
Water: CH3CH2OH is soluble in water while CH3CH2OCH2CH3 is not
because it is a non polar molecule
c toluene and benzaldehyde
concentrated H2SO4: benzaldehyde is soluble in concentrated
H2SO4 while toluene is not because it will not react with the
solvent
d tert-butyl chloride and tert-butanol
water: tert-butanol is soluble in water while tert-butyl
chloridebecause they do not have the same intermolecular force
References
1 M. Jones and S.A. Fleming, "Organic Chemistry", Norton, 4th edn., pp1416.
2 Chemistry Online. (n.d.). Solubility. Retrieved January 28, 2015 from
http://webapps.utsc.utoronto.ca/chemistryonline/solubility.php
3 Clayden, J (2001). Organic Chemistry. OxfordUniversity Press