Jeanette Vivien R.

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

II. Schematic Diagram of the Procedure

Add 5 drops solvent to micro test
tubes

Add 1-2 drops/pinch test

compound, shake; fresh sample

+ H2O

III. Table of Reagents/Products (MSDS)

+ diethyl ether

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

IV. Set-ups (if any)

Materials and Apparatus

Micro test tubes, Pasteur pipette, spatula

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.

Sucrose - water: Hydrogen bond

Ethanol - water: Hydrogen bond
Ethanol - diethyl ether: London dispersion forces
Acetone - water: Hydrogen bond & Dipole-dipole forces
Acetone - diethyl ether: London dispersion forces

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

4 Gilbert, J. (2011).Experimental Organic Chemistry: A Miniscale and

Microscale Approach. Boston, MA: Cengage Learning
5 Lehman, J. (2008) Operational Organic Chemistry: A Problem-Solving
Approach to theLaboratory Course.
Prentice HallShriner, R. (2004).The Systematic Identification of Organic
Compounds. Canada: John Wiley &Sons.