Biol 112L ORGANIC MOLECULES LABORATORY

ACTIVITY 3: Solubility and Reactions of Alcohols

Introduction:
Alcohols are organic compounds containing the hydroxyl (-OH) group. The hydroxyl group (OH) is
connected to an sp3-hybridized carbon atom, and is characterized by names ending in “ol”. Alcohols can be
classified as monohydric, dihydric and trihydric depending on the number of hydroxyl groups attached to the
compound. They can also be classified as primary, secondary, or tertiary, according to which carbon of the alkyl
group is bonded to the hydroxyl (-OH) group.
Alcohols are among the most common organic compounds. They are used as sweeteners and in making
perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly
produced organic chemicals in industry.

Materials and Equipment:

Ethyl alcohol 1% iodine solution
Benzyl alcohol Sodium hydroxide (dilute)
Glycerol Sec-butyl alcohol
5% sodium hydroxide solution Tert-butyl alcohol
Cold water Lucas reagent
Calcium sulphate (anhydrous) disposable gloves
Sodium metal test tubes
Glacial acetic acid medicine droppers
Sulfuric acid (concentrated) small graduated cylinder
Ceric ammonium nitrate (CAN) reagent hot plate
2- Propanol filter papers

Aims:
At the end of the activity, the students should be able to:
1. describe the solubility of alcohols in water and in alkaline solutions;
2.
Correctly perform the different tests to identify alcohols; and
3. write the equations involved in the different tests.

Procedure:

Note: Use disposable latex or nitrile gloves when performing the procedures.

A. Solubility in water and in alkaline solutions

1. Into 3 separate test tubes, place small samples (10 drops each) of the following: ethyl alcohol, benzyl alcohol
and glycerol.
2. Using the small graduated cylinder, add 3 ml of water to each sample, shake well and observe. Record your
observations on the answer sheet (column A).
3. Place all test tubes in a water bath and warm to 65 degrees Celsius for 3 minutes.
4. Remove all samples from the water bath and allow them to cool at room temperature. Record your
observations (column B).
5. Repeat no.1 and no.2 procedure but instead of water use 3 ml of 5% sodium hydroxide (NaOH) solution. Mix
by shaking each solution as before but DO NOT HEAT. Record your observations (column C).

B. Reaction with sodium

1. Measure 5 ml of ethyl alcohol and put this in a test tube.

2. To this, add a small amount of anhydrous calcium sulphate using a spatula. Shake the test tube well.
3. Filter the contents into another dry clean test tube using a funnel and filter paper. Set this aside on the test
tube rack.

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4. Take a small piece of sodium metal using forceps and place it into a clean filter paper. Dry the sodium metal
using the filter paper. (CAUTION: HANDLE THE SODIUM METAL WITH CARE; CAN BE HIGHLY
REACTIVE.)
5. Using the forceps, carefully put the dry piece of sodium metal into the test tube with filtrate. Record your
observations.

C. Formation of ester

1. Measure 2 ml of ethyl alcohol and put this in a test tube. To this, add 1 ml of glacial acetic acid and 2-3 drops
of sulfuric acid (CAUTION!).
2. Warm the mixture into a water bath for 5 minutes.
3. Prepare cold water in a small beaker. Pour out the mixture into the cold water and smell it by wafting.
(CAUTION: DO NOT SMELL THE MIXTURE DIRECTLY.) Record your observations.

D. Ceric Ammonium Nitrate test

1. Measure 2 ml of glycerol and put this in a test tube. Add 5 drops of ceric ammonium nitrate to this and shake
the solution well.
2. Record your observations.

E. Iodoform test

1. Measure 2 ml of 2-propanol and put this in a test tube. To this add 5 drops of 1% iodine solution using a
dropper. (CAUTION:DO NOT INHALE THE IODINE.)
2. Using another dropper, add dilute sodium hydroxide to the solution until the violet color of iodine disappears.
3. Warm the mixture gently in the water bath. Observe the changes and record your observations.

F. Lucas test

1. Measure 1 ml of ethyl alcohol, sec-butyl alcohol and tert-butyl alcohol in three different test tubes.
2. Using a dropper, add 10 drops of Lucas reagent to the tert-butyl alcohol. Shake the mixture well. Record your
observations. Take note of the time it takes to observe a reaction.
3. Repeat procedure 2 with the sec-butyl alcohol.
4. Repeat procedure 2 with the ethyl alcohol. This time, warm the mixture in a water bath. Record your
observations.

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 ANSWER SHEET
Biol 112L ORGANIC MOLECULES LABORATORY
ACTIVITY 3: Solubility and Reactions of Alcohols

Group Number: 05 Schedule: 1:30-3:30 Code: 0714L Date/s performed: 10-06-2022

Date submitted: 10-08-2022

Members Participation
1 Ancheta, Monalhie ● Assists other members during the experiment
● Rewriting the answers
● Answered observation B and C
● Documentation
● Helps in writing the equations for chemical reaction
2 Cruz, Lex Anneken ● Take notes during the experiment.
● Assists other members during the experiment
● Documentation
● Writing equations for the chemical reactions
3 Gonzales, Mon Anthony ● Rechecking and answering of answers for the results
and observations
● Conducted experiment A, C, D, E, F
● Answered chemical reactions/equations for B, C, D, E &
F
● Assisted other members during experiment
4 Munar, Khristine ● Printing
● Documentation
● Assists other members during the experiment
● In charge in water bath and time checking
5 Toreno, Mark Alexis ● Conducted experiment B and D
● Answered results and observations A, D, E, F based on
the notes of Cruz and Gonzales.
● Input the answers in the google docs
● Assists other members during the experiment
● Writing equations for chemical reactions.

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Results and observations:

A. Solubility in water and in alkaline solutions

Alcohol A B C
Alcohol and cold Alcohol and hot Alcohol and 5%
water water NaOH
1. Ethyl alcohol
● No separation of ● No separation of ● No separation of
the two liquids in the two liquids in the two liquids in
two different two different two different
layers. layers. layers.
● The ethyl alcohol ● The ethyl alcohol ● The ethyl alcohol
mixed well with mixed well with mixed well with
the cold water. the hot water. the water.

2. Benzyl alcohol
● There is a ● There is a ● The benzyl
separation of the separation of the alcohol did not
two liquids. two liquids. fully mix with the
● The benzyl ● The benzyl NaOH.
alcohol did not alcohol did not ● There are tiny
mix with the cold mix with the hot bubbles formed in
water. water. the solution.
● The benzyl ● The benzyl
alcohol sank in alcohol sank in
the water forming the water forming
like a bubble with like a bubble with
a whitish color. a transparent
color.

3. Glycerol
● There is no ● There is a little ● There is a
separation of the separation of the separation of the
two liquids. two liquids. two liquids.
● The glycerol mix ● The glycerol did ● The glycerol did
with the cold not mix throughly not mix with the
water. with the hot water. NaOH.
● The glycerol ● The glycerol ● The glycerol
dissolves with forms bubbles at forms a layer at
water. However, the bottom of the the top of the
some tiny bubbles test tubes. NaOH.
can be found on However, it
the bottom of the somehow mixes
test tube. with the hot water
but not totally.

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B. Reaction with sodium
1. Describe what
happens when ethyl alcohol
reacts with the sodium metal.
2. Write the equation
for the chemical reaction of
ethyl alcohol with sodium.
C. Formation of ester
1. Describe the smell of
the final mixture formed.
What is an ester?
The ethyl alcohol dissolves the sodium metal, the longer as it gets, the
faster the sodium metal breaks down. The color changes from transparent
to yellow-ish ethyl alcohol. Moreover, the results of the experiments done
for letter B shows that it’s the hydroxide (OH -) part of sodium hydroxide
(NaOH) reacting with the alcohol, not the sodium ions present in the
reactant. This is due in part because of the miniscule free energy difference
found between the reactant and product side of the equation, meaning that
the solution will have a concentration in which the reactants in the form of
hydroxide ions (OH-) and alkoxide ions (R-O-) are constant.
The scent of the final product was akin to that of ethyl acetate with a hint of
vinegar. This is due to the fact that when the glacial acetic acid (CH 3COOH)
reacted with the ethyl alcohol (C2H5OH), we added sulphuric acid (H2SO4) as
a dehydrating agent, which is a substance that removes water from a
compound. This process is called esterification. Esters are a group of
chemical compounds that are formed by the chemical bonding of a group of
organic acids and an alcohol group by losing water molecules present in
the solution. These are chemical compounds that are derived from the
presence of an inorganic or organic acid which contains at least 1 hydroxyl
(OH-) group that is replaced by an alkoxy group.
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 2. Write the equation
for the formation of ester
from ethyl alcohol.

D. Ceric Ammonium Nitrate test

1. Describe what A change in color is the most apparent reaction in the solution. The
happens when glycerol glycerol changes its color from transparent to dark orange/reddish. The
reacts with ceric ammonium ceric ammonium nitrate mostly dissolves with the glycerol. However, there
nitrate. are some tiny particles formed in the solution.

2. Write the equation

for the chemical reaction of
glycerol to ceric ammonium
nitrate.

E. Iodoform test
1. Describe your As the sodium hydroxide is being poured to the solution, a gradual change
observations. What is in color is happening. There is a formation of very pale yellow precipitate
iodoform? with an antiseptic smell. This pale yellow precipitate of iodoform or
triiodomethane is created when iodine and sodium hydroxide is introduced
to a substance that contains either a methyl ketone or a secondary alcohol
with a methyl group in the alpha position. It can be used to detect ketones
or aldehydes.

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 2. Write the equation
for the formation of iodoform
from 2-propanol.
F. Lucas test
1. How long did it take
for each of the different
alcohols to react with the
Lucas reagent? What is the
Lucas reagent used for?
For the ethyl alcohol, there were little bubbles that occurred right after the
addition of the Lucas reagent, although they disappeared faster. So, no
visible reaction was observed, no precipitate formed, and the solution
remained colorless even if it was heated. For the sec-butyl alcohol, when it
was added by Lucas reagent, at first, there was no precipitate formed in the
mixture. However, when it was put in the water bath, the solution turned
turbid after 5 minutes of waiting, and an oily layer could be seen. As for the
tert-butyl alcohol, as soon as the Lucas reagent was poured into the tert-
butyl alcohol, the solution turned turbid and formed an oily layer rapidly.
The Lucas test is used to differentiate and categorize tertiary, secondary
and primary alcohols using a Lucas reagent which is a solution composed
of anhydrous zinc chloride in concentrated hydrochloric acid (ZnCl + HCl).
The reaction present in the Lucas test is classified as a nucleophilic
substitution reaction in which the chloride in the zinc-chloride bond is
replaced by the hydroxyl group present in the alcohols. The alcohols
whether they be primary, secondary or tertiary are then classified based on
their reactivity with the Lucas reagent. The test displays the difference
between the carbocations present in the different types of alcohol as well as
the reactivity difference between them. An example of this would be the
ethyl alcohol, which is a primary alcohol, used in the experiment. Primary
alcohols do not readily react at room temperature with the added Lucas
reagent whereas the tertiary alcohol (tert-butyl) used in the experiment
reacted immediately due to the fact that organic chloride has relatively low
solubility in the aqueous mixture. A positive reaction for the Lucas test is
the observation of change where the clear and colourless characteristics
present in the alcohol solutions change to a turbid, cloud or hazy one. This
implies the formation of a chloroalkane in the solution.
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3. Write the equation
for the chemical reaction of
1°, 2°, and 3° alcohols with
Lucas reagent.