SOL 1

SOLUBILITY OF ORGANIC COMPOUNDS

Date:

Name
: ____________________
TA
: ____________________
Section : ____________________

RESULTS
Record the results of you and your partners experimental work in the table provided on the
following page. For each compound, make sure you complete each the following:
(1) Draw the structure.
(2) Identify the functional groups present.
(3) Record your observations on the solubility in each solvent system and designate each
compound as either soluble or insoluble in each of the solvent systems (by circling the
appropriate word in the table provided).

QUESTIONS
1. Write a balanced equation for the reaction of benzoic acid with 5% aq. NaOH

2. Write a balanced equation for the reaction of sodium benzoate with 5% aq. HCl

SOL 2

naphthalene

glycine

benzoic
acid

sodium
benzoate

thymol

benzamide

p-toluidine

Structure & Name

Of Functional Group(s)

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

5% HCl

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

5% NaOH

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

5% NaHCO3

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Water

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Soluble Insoluble

Diethyl ether

Recorded observations and conclusion about solubility (circle either soluble or insoluble)
in the solvent systems:

Soluble Insoluble

SOL 3

QUESTIONS (continued)
3. A solution of p-toluidine in 5% aqueous HCl is placed in a flask. An equal volume of the
solvent diethyl ether is then added and the mixture is stoppered, shaken and then allowed to
stand to reach equilibrium. Diethyl ether is immiscible with aqueous solvents, and the
mixture forms two layers: a diethyl ether layer and an aqueous layer.

(a) Which solvent forms the upper layer ? Briefly explain your choice.

(b) What does the aqueous layer contain ? Briefly explain your choice.

5% aqueous NaOH is now carefully added in order to neutralise the mixture, then the flask is
stoppered, shaken and then allowed to stand to reach equilibrium again.

(c) Now, which solvent contains the p-toluidine ? Briefly explain your choice

Outline a procedure for separating a mixture of p-toluidine and naphthalene by exploiting

their different solubilities (use the back of this sheet if necessary).