BICOL UNIVERSITY

Laboratory Plan
Organic Derivatives of Water
Group Members
Annjanet M. Ayson
Danna EinaBitara
Zane Arden Namora
Nikko Mar
Rommel san Luis
Eric Maglente
Jim Paolo Dioneda

Subject Instructor
Engr. Claribelle L. Pempea

MATERIALS
15 Dropper

Microbeakers

40 Test Tube (10 mL)

10 Spatula

Test Tube Brush

7 Beaker (50 mL)

20 Cork

1 Beaker (100 mL)

2 Test Tube Stand

Tripod

3 Stirring Rod

Wire Mesh

7 Graduated Cylinder (10 mL)

Bunsen Burner

3 Pipet (5 mL)

Test Tube Holder

Aspirator

REAGENTS
Water

KMnO4

1-butanol (n-butyl alcohol)

AgNO3

2-Propanol (sec-propyl alcohol)

NH4OH

2-metyl-2-propanol
alcohol)

HCl

(tert-butyl

phenol
NaOH
H2SO4

PROTECTIVE GADGETS
Lab Gown
Lab Gloves
Goggles
Gas Mask

ZnCl2
FeCl3
I2

OBJECTIVES
a. To be acquainted with the e chemical properties of the organic derivatives
of water
b. To observe the differences in chemical reactivity of primary and tertiary
alcohol, phenols and ethers towards selected chemical reagents.

PREPARATION OF REAGENTS
10 g 10 % NaOH
1. Measure 1 g of pure NaOH.
2. Dissolve the NaOH in 9 mL of
water.
3. Shake well.
4. Set aside.

x
=.1
10
x = 1 gram of NaOH
10=w+x
w=9 g of water

21 mL Acidic Potassium Permanganate

1. Dissolve 0.3200 g of Potassium Permanganate in 20 mL water.
2. Acidify by adding 1 mL of 1 M H2S04.
3. Shake well.
4. Set aside.

20 mL Ammonical Silver Nitrate [Silver Nitrate in excess of

Ammonium Hydroxide]
1.
2.
3. Shake well.
4. Set aside.

5g 2.5 % FeCl3
1. Measure 0.1250 g of FeCl3.
2. Dissolve the FeCl3 in 4.8750 mL water
3. Shake well.
4. Set aside.

I2
1.
2.
3. Shake well.
4. Set aside.

PROCEDURE
The following representative compounds will be used in this experiment:
a. 1-butanol (n-butyl alcohol)
b. 2-propanol (sec-propyl alcohol)
c. 2-metyl-2-propanol (tert-butyl alcohol)

d. phenol

CAUTION:
Phenol crystals slowly liquefy in hot humid air. The yellow color of the
samples is due to phenol oxidation products. The sample is suitable for the
chemical test, except where anhydrous samples are required. HANDLE
PHENOL WITH CARE AS IT CAN CAUSE PEAINFUL BURNS. IF SPILLED ON THE
SKIN, WASH FREELY WITH 95% ETHANOL, THEN WITH SOAP AND WATER.
Diisopropyl ether is highly volatile and flammable. Its vapor has a high
tendency to form explosive hydroxides. Fire is therefore a hazed is to be
guided against. SAY AWAY FROM ANY OPEN FLAME WHEN WORKING WITH
ETHER AND MINIMIZES ITS EXSPOSURE TO AIR.

A. SOLUBILITY BEHAVIOUR
1. Place 2 mL water in a test tube.
2. Add 15 drops of sample.
3. Cover the tube with a cork stopper.
4. Shake to mix.
5. Examine the mixture.
6. Repeat steps 1-5 using 1 mL of 10%NaOH as solvent.
7. For the compounds insoluble in bas, repeat steps 1-5 using 1 mL
concentrated H2SO4 as solvent.
BE CAREFUL IN HANDLING CONCENTRATED SULFURIC ACID AS IT IS
CORROSIVE.

B. CHEMICAL REACTIVITY
1. Reaction with Potassium Permanganate (KMnO4)
1.1. Place 3 mL dilute, slightly acidic permanganate in a clean test tube.
1.2. Add 5 drops of the sample.
1.3. Warm the tube gently in a water bath.
1.4. Examine the mixture after 5 mins.

2. Reactions with Tollens reagent (ammonical silver nitrate) [silver nitrate

in excess of ammonium hydroxide]
Note: This test should be done using attest tube with smooth walls and
is scrupulously clean. Otherwise, the mirror will not deposit on the tube.
2.1. Place 3 mL Tollens reagent in a test tube.
2.2. Add 4 drops of sample.
2.3. Shake then heat gently in a water bath.
2.4. Examine the mixture.
3. Reaction with ferric chloride (FeCl3)
4.1. Place two drops of sample in 2 mL water.
4.2. Add several drops of 2.5 % aqueous FeCl3.
4.3. Examine the mixture
4.4. Compare the results with a blank using water.
4. Iodoform test: reaction with I2, NaOH
5.1. Place about 1 mL of the sample in a test tube.
5.2. Add 2 mL water.
5.3. Add about 1 mL of I2/KI solution.
5.4. Add 10% NaOH solution dropwise with shaking until the iodine color
disappears and the solution is faintly yellow.
5.5. Examine the contents of the tube and note the odor.
5.6. If the test seems negative, shake the tube.
5.7. Heat gently in a water bath for 1-2 minutes.
5.8. Examine the mixture again.

SET-UP
Diagram

STRATEGIES AND TECHNIQUES USED

All the test tubes and reagents were labeled prior to use.
The test being done is also labeled by placing the test name in the test tube
rack where the test is being done.

We maintained an arrangement of 1 alcohol, 2 alcohol, 3 alcohol and

phenol from left to right in every test to prevent confusion of results and in
testing.
Tests were done simultaneously to save time but care was done to prevent
mix-up in data gathering or testing.
Pictures were taken of each test to ensure that the observed and recorded
data match.

DATA TABULATION
Derivative of
Water

Solubility Behavior
H2O

NaOH

H2SO4

Insoluble

Insoluble

Soluble

Soluble

Insoluble

Soluble

Soluble

Insoluble

Partially Insoluble

Strongly Insoluble

Soluble

Insoluble

1-butanol

2-propanol

Tert-butanol

Phenol

Derivative

Chemical Reactivity

of Water

1-butanol

2-propanol

Tert-butanol

Phenol

Reaction with
potassium
permanganat
e (KMnO4)
Strong
Oxidizing
Agent
Positive of
Brown
Precipitate
Formation in
clear solution
after Heating
Positive of
Brown
Precipitate
Formation in
clear solution
after Heating
Negative No
Change from
being a Dark
Purple
Solution
Positive of
Brown
Precipitate in
clear solution
that forms an
extremely
thick mixture
after Heating

Reactions
with Tollens
reagent
Ag ( NH 3 )2 OH
Weak
oxidizing
Agent

Reaction with
Iodoform test:
ferric chloride
reaction with
(FeCl3)
I2, NaOH
Phenol Test

Pale Yellow
Solution
Insoluble
Layer
Acetone
Scent
Pale Yellow
Precipitate in
a Light Yellow
Solution
formation
Vinegar

Negative of
silver mirror
formation

Negative No
Change from
being Pale
Yellow
Solution

Negative of
silver mirror
formation

Negative No
Change from
being Pale
Yellow
Solution

Negative of
silver mirror
formation

Negative No
Change from
being Pale
Yellow
Solution

Yellow
Solution
Acetone
Scent that is
Nauseous

Positive Pale
Purple
Solution

White
Solution with
Insoluble
Layer
Acetone
Scent

Silver Mirror
Formation

ANALYSIS AND INTERPRETATION OF DATA

Solubility
1-butanol is partially insoluble in water, soluble in basic solution but insoluble
in acidic solution.

2-propanol is soluble in water and acidic solution but insoluble in basic

solutions.
2-metyl-2-propanol is soluble in water, insoluble in basic solution and slightly
insoluble in acidic solution.
Phenol is strongly insoluble in water, soluble in basic solution and insoluble in
acidic solution.

Chemical Reactivity
Using 1-butanol as a representative compound of Primary Alcohols, 2propanol as a representative compound of Secondary Alcohols, 2-metyl-2propanol as a representative compound of Tertiary Alcohols, and Phenol as
the representative compound of Phenols we can infer that following
properties.
Primary Alcohols are oxidizable but it is not strongly oxidizable, free of
Phenolsand does not form Iodoform. It isoxidizable because the C bonded to
OH has 2 H bonded to it that can be replaced by O.
Secondary Alcohols are also oxidizable but it is not strongly oxidizable,
free of phenol and form Iodoform is one of the R attached to COH is methyl.
It is less oxidizable than Primary Alcohols because the C bonded to OH has
only one H bonded to it that can be replaced by O.
Tertiary Alcohols are not oxidizable, free of Phenol and do not form
Iodoform. It is not oxidizable because the C bonded to OH does not have H
bonded to it that can be replaced by O.
Phenol is strongly oxidizable, contains phenol and does not form
Iodoform.It is strongly oxidizable because even if Ammonical Silver Nitrate is
only a weak Oxidizing Agent it is still oxidized.

CONCLUSION
The organic derivatives of water have different properties no matter
their similarity in structure. This is either a difference in solubility or chemical
property. Such properties are vital in testing the compound present in
different mixtures.
Alcohols with large number of Carbon atoms are largely insoluble in
water need either a basic or acidic solution as the solvent. Phenols are only
soluble in basic solutions.

Alcohols of first and secondary degree are oxidizable the latter being
less so than the first but both are less oxidizable than phenol. Third degree
alcohols are effectively resistant to oxidizable due to the lack of C-H bonds to
the C attached to OH.
FeCl3 Test is perfect in testing whether a sample contains Phenols as it
is unreactive to other derivatives of water. This is very important especially
in industrial companies to determine the components of such samples.
Iodoform Test which identifies the CH3CHO group is also perfect for
testing Alcohol to find out if they are Secondary Degree but only if they have
a methyl group attached to the COH group.

QUESTIONS AND ANSWERS

1. Explain the solubility behavior of the representative compounds in water
as a function of
a. branching in the molecules
The branching in the molecules of the representative compounds
affects the solubility behavior of a compound by affecting the resulting
arrangement of molecules during its bonding with water to form a chain
network if this network is composed of more interlocking representative
compound instead of water then it only shows that the compounds is not
soluble in water. The longer the branching of the molecules also affects it
solubility by creating more hydrophobic sites in the compound therefore
decreasing the chances of it being dispersed in water but instead
increasing it chances of bonding with itself.
b. relative proportions of hydrophilic bonds to hydrophobic bonds
The relative proportions of hydrophilic bonds to hydrophobic bonds
affect the solubility behavior of a compound by affecting the amount of
water molecules able to bond with the compound. The high proportion
hydrophobic bonds to hydrophilic bonds lower the solubility of the
compounds while the high proportion of hydrophilic bonds to hydrophobic
bonds increases the solubility of the compounds by increasing the amount
of water molecules bonded to the compound making it miscible. This is
because the more hydrophilic bonds available to the compounds the more
water is able to form an interlocking chain to form a soluble solution while
the more hydrophobic bonds the more those compounds will bonds with

each other instead of water and form an insoluble layer in the solution
instead of dispersing into a solution.
2. Explain the acidity differences observed for the compounds used in this
exercise in terms of stability of the corresponding conjugate bases.
Phenols have a greater acidity than alcohols due to the stabilization of
the conjugate base formed through resonance in the aromatic ring. Alcohols
forms conjugate bases that are less stable than Phenols because of the lack
of stabilization the ring brings therefore these conjugate bases are unstable
therefore the given number of conjugate bases of alcohols is less than that of
phenol because at any given time these conjugate bases of alcohol arent in
conjugate base form.

3.Bases on the results of the oxidation test, classify he compounds tested as

easily oxidizable or resistant to oxidation.
Phenol ( C 6 H 5 OH ) > 1butanol ( 1 alcohol )> 2 propanol ( 2 alcohol )> 2metyl2 propanol(3 alcohol)
Phenol
1 alcohol

(C 6 H 5 OH )

is the most easily oxidizable while 1-butanol a

isalso easily oxidizable but less so than Phenol (C 6 H 5 OH ) .2-

metyl-2-propanol a 2 alcohol

is the least oxidizable of all the tested

compounds less than 1-butanol a

1 alcohol

because it only has one H

attached to the main carbon atom or the Carbon atom attached to the
Hydroxyl group (OH).2-metyl-2-propanol a 3 alcohol
is not oxidizable
because of the lack of C-H bonds to remove in the central Carbon atom that
is attached to the Hydroxyl group (OH).
4. Suggest a simple chemical test that will differentiate between the
following pairs of compounds. Write equations for the reactions involved.
a. Phenol and isopentyl alcohol
Tollens Reagent Test
C6 H 5 OH (aq)+ 2 Ag(NH 3)2 OH (aq) 2 Ag(s) + H 2 O(l) +3 NH 3(aq) +C 6 H 5 O2 NH 4(aq)

Phenol reacts with ammonical silver nitrate to form solid silver that
creates the silver mirror in the reaction test tube while isopentyl alcohol
does not.
b. Tert-butyl alcohol and isobutyl alcohol
Reaction with Potassium Permanganate (KMnO4)

Isobutyl Alcohol is oxidized to form a solid precipitate Manganese

Oxide in clear solution while Tert-butyl Alcohol is not and retains a dark
purple coloration.

c. Neopentyl Alcohol
Reaction with Potassium Permanganate (KMnO4)

Neopentyl Alcohol is oxidizable by Potassium Permanganate (KMnO 4)

and forms a solid precipitate Manganese Oxide in clear solution.
d. Sec-butyl Alcohol and Neopentyl Alcohol
Iodoform Test

Sec-butyl alcohol forms a solid precipitate called Iodoform during

Iodoform test while neopentyl alcohol does not.
e. Propene and 2-butanol
Bromine Test
CH 3 CH =CH 2+ Br 2 CH 3 CHBr CH 2 Br
Propene decolorizes bromine while 2-butanol does not.

RECOMMENDATIONS
Wider time frame for testing
More test to determine the more properties and more details about these
properties of derivatives of water
Doing duplicates or triplicates of test for greater accuracy

COMMENTS
Hard to observe in bad lighting

DOCUMENTATION
Solubility Test

Chemical Reactivity

Reaction with Ferric Chloride

(FeCl3) added

Iodoform Test: Reaction with I2,

NaOH

From Left to right

1-butanol (n-butyl
alcohol) 1-ol
2-propanol (secpropyl alcohol) 2ol
2-metyl-2propanol (tertbutyl alcohol) 3ol
Phenol

From Left to right

1-butanol (n-butyl
alcohol) 1-ol
2-propanol (secpropyl alcohol) 2ol
2-metyl-2propanol (tertbutyl alcohol) 3ol
Phenol

Leaders Report
Members

Laboratory
Safety (40)

Participation
(40)

Teamwork
(20)

Total

Danna Eina
Bitara
Zane
Namorra
Nikko Mar
Rommel san
Luis
Eric Maglente
Jim Dioneda

35
35
35
35
35
35

35
38
38
38
38
30

15
20
20
20
20
10

85
93
93
93
93
75