June Nicoli H.

Cerbas

Discussions

Alcohols are compounds containing the hydroxyl (-OH) functional group bonded to an alkyl, R
and thus maybe presented by the formula R-OH.

The reactivity of alcohols is mainly attributed to the OH group. This functional group has an
inherent acid character shown when hydrogen is released from the O-H bond. The case of
removal is dependent upon the relative polarization of the O-H bond. The-OH group may also
be protonated at the oxygen, which weakens the C-O bond so that the whole group maybe
cleaved off as water and subsequently replaced in the molecule.

Based on the alkyl group, the alcohol maybe classified into:

R-CH2OH primary

R 2 . CH - OH secondary

Some examples of these classes of alcohols are:

C*H_{3} .CH 2 .CH 2 .OH n-propyl alcohol

CH 3 .CH 2 . CH - OH

CH

sec(- b * utylalcohol)

R3.C-OH tertiary

CH3

C*H_{3} - C - OH

C*H_{3}

tert-butyl alcohol

The most commonly known primary alcohol is ethyl alcohol. It is the alcohol present in alcoholic
beveragesEthyl alcohol or ethanol is obtained from the fermentation of sugars and starches.
The reaction is catalyzed by the enzyme, zymase which is found in yeast.

C_{6}*H_{12}*O_{6}
Yeast

zymase

2. C*H_{3} .CH 2 .OH ethyl alcohol

2C*O_{2}

Primary and secondary alcohols may be distinguished from tertiary alcohols by the chromic acid test.
Primary alcohols are oxidized to aldehydes while the secondary alcohols are oxidized to ketones. This is
indicated by the change in color of the solution from orange to green. Tertiary alcohols are not readily
oxidized by the chromic acid because of the absence of an alpha hydrogen

To further distinguish then different classes of alcohols, Lucas test is employed. Tertiary

alcohol react immediately to form an immiscible layer of alkyl chloride. The alkyl chloride is

insoluble in the medium and causes the solution to become cloudy before it separates as a distinct
layer. With the secondary alcohols the cloudiness appears after 5 minutes, while the primary
alcohols do not react under these conditions.

Alcohols may be classified according to the number of OH group as monohydroxy polyhydroxy

alcohols. Examples of polyhydroxy alcohols are:

CH₂.OH

CH-OH

CH₂OH

CH-OH

CH-OH

glycerol

Ethylene glycol

The most important triol is glycerol. It is obtained as a by-product from the manufacture of soap. It is
used as a moisturizing agent in cosmetic formation, in tobacco products, and in foods. Glycerol is
detected by the acrolein test. Glycerol is dehydrated when heated with KHSO4 to form propenal
(acrolein), which is pungent.
Reagents and Materials:

ethyl alcohol

n-butyl alcohol

medicine dropper

beaker(water bath) Bunsen burner copper wire 10% NaOH

benzyl alcohol

sec-butyl alcohol Tert-butyl alcohol isoprophyl alcohol 5% H₂SO ₁ Lucas reagent (HCL-ZnCL ₂)

methyl alcohol

test tube holder

thermometer

distilled water 0.5% resorcinol

5% K2Cr2O7

acetic acid conc. H2SO4

test tube

lodine solution

Procedure:

1. Chromic Acid Test.

a. Into 4 separate dry test tubes, place 20 drops each of the ff: ethyl alcohol, n-butyl alcohol, sec-
butyl alcohol and tert-butyl alcohol and label the test tubes

correspondingly. b. To each. test tube, add 10 drops of 5% potassium dichromate and 10 drops of
5% sulfuric acid.

c. Place all the test tube in a boiling water bath at the same time. Record the time required for each
solution to change color. Note the change in color and odor of the product formed.
2. Lucas Test.
a. Into 4 separate test tubes, place 20 drops each of the ff: Tert-butyl alcohol, sec- butyl alcohol, n-
butyl alcohol and benzyl alcohols. b. To each test tube, add 20 drops of freshly prepared Lucas
reagent. Shake only

once and let stand. c. Record the time required for the formation of an insoluble layer or emulsion in
each of the test tubes indicating the production of the alkyl halide.

3. Esterification.

a. Put 20 drops of ethyl alcohol in a dry test tube. Add 10 drops of acetic acid and-5 drops of conc.
Sulfuric acid to it. (Atetic)

develop.

b. Warm in boiling water bath. Note the odor and the time required for the odor to c. Repeat the test
with tert-butyl alcohol alcohol in place of ethyl alcohol.

the results.

4. Test for Methyl Alcohol (Reaction with Copper).

Compare

a. Mix 10 drops of methyl alcohol with 10 drops of distilled water in a vial. b. Heat a copper spiral in
the Bunsen flame and dip into the methyl alcohol-water

mixture. Repeat this test 10 times. c. Carefully add I drop of 0.5% resorcinol and 10 drops of conc.
sulfuric acid allowing them to flow down along the side of the test tube. Note: Do not shake. Observe
the color produced of the junction of the two layers.

5.Iodoform Test.

a. To 4 drops of ethyl alcohol, add 4 ml of iodine solution.

Then add drop by drop 10% NaOH until the iodine is decolorized. b. Place the test tube in a warm
bath (60°). .

Note the odor of the vapors and the color of the precipitate formed c. Repeat the test with: 1)
isopropyl, and 2) methyl alcohol in place of ethyl alcohol.

Questions:
1. Compare the relative ease of oxidation of primary, secondary, and tertiary butyl alcohol
toward acid dichromate based on the time required for the solution to change color.
-Based on the data and observations provided, it is not possible to compare the relative ease of
oxidation of primary, secondary, and tertiary butyl alcohols towards acid dichromate as the
results for the chromic acid test are missing.

2. What is the significance of Lucas Test? Account for the re-activity of benzyl alcohol.
-The Lucas test is a qualitative test used to differentiate primary, secondary, and tertiary
alcohols based on their reactivity with Lucas reagent, which is a mixture of zinc chloride and
concentrated hydrochloric acid. The test is based on the formation of an insoluble layer or
emulsion when the alcohol is treated with the reagent, indicating the formation of an alkyl
chloride.

DATA AND OBSERVATION

1. Chromic Acid Test

SAMPLES OBSERVATIONS

Ethyl alcohol The color change observed in the solution

from orange to green or blue-green
indicates the formation of the
chromium(III) ion.

n-butyl alcohol n-butyl alcohol is oxidized by acid

dichromate to form n-butyl aldehyde and
chromium(III) sulfate. The orange color of
the dichromate ion (Cr2O7^-2) is reduced
to green chromium(III) ion (Cr3+),
indicating the completion of the reaction.

Sec-butyl alcohol sec-butyl alcohol is oxidized to give the

corresponding ketone, acetone, while the
chromium ion is reduced from Cr(VI) to
Cr(III). The change in color of the solution
from orange to green indicates the
reduction of chromium ion.

Tert-butyl alcohol tert-butyl alcohol is oxidized to form

acetone and chromium trioxide (CrO3),
which gives a characteristic green color to
the solution.

1. Lucas Test
 SAMPLES OBSERVATIONS

Tert-butyl alcohol tert-butyl alcohol react rapidly with

Lucas reagent to form an alkyl
chloride, resulting in an immediate
and vigorous formation of a cloudy
precipitate.

Sec-butyl alcohol sec-butyl alcohol) react slowly with

Lucas reagent to form an alkyl
chloride, resulting in a cloudy
precipitate that forms after a few
minutes of mixing.

n-butyl alcohol do not react with Lucas reagent under

normal conditions, and hence no
precipitate is formed.

Ethyl alcohol no immediate reaction is observed

2. Esterification

SAMPLES OBSERVATIONS

Ethyl alcohol the ester formed from ethyl alcohol

would be ethyl acetate,

Tert- alcohol the ester formed from tert-alcohol

would depend on the specific
carboxylic acid used in the reaction.

3. Test for Methyl Alcohol (reaction with copper)

Observations: The test for methyl alcohol using copper involves the reaction of
methyl alcohol with copper metal to produce copper(I) oxide and hydrogen gas. If
the test is positive, a red-brown precipitate of copper(I) oxide (Cu2O) is formed,
and hydrogen gas is evolved.

4. Iodoform Test

SAMPLES Observations

Ethyl alcohol it does not undergo oxidation and

decarboxylation in the presence of
iodine and sodium hydroxide to form
iodoform (CHI3) as a yellow
 precipitate.

Isopropyl alcohol a yellow precipitate is observed,

indicating the presence of a methyl
group (-CH3) adjacent to a carbonyl
group (-CO-).

Methyl Alcohol Methyl alcohol (methanol) does not

give a positive result in the iodoform
test because it does not have a methyl
group adjacent to a carbonyl group,
which is necessary for the reaction to
occur. Therefore, it does not undergo
oxidation and does not form a yellow
precipitate.

QUESTIONS:
1. Compare the relative ease of oxidation of primary, secondary, and tertiary
butyl alcohol toward acid dichromate based on solution toward acid
dichromate based on time required for the solution to change color.
-Based on the observations from the Chromic Acid Test, tertiary butyl
alcohol shows the slowest oxidation rate towards acid dichromate
compared to primary, secondary and n-butyl alcohol, which oxidize
relatively faster. This is because the reaction rate depends on the ease of
breaking the C-O bond in the alcohol molecule. Tertiary butyl alcohol has
a more substituted carbon center which makes the carbon-oxygen bond
stronger and more challenging to break, resulting in a slower reaction
rate.

2. What is the significance of Lucas Test? Account for the reactivity of benzyl
alcohol?
-The Lucas Test is significant because it distinguishes between primary,
secondary, and tertiary alcohols based on their reactivity with the Lucas
reagent (a mixture of zinc chloride and concentrated hydrochloric acid).
Primary alcohols do not react with the Lucas reagent, while secondary
alcohols produce a cloudy emulsion after a few minutes, and tertiary
alcohols form an insoluble layer almost immediately. Benzyl alcohol,
which is not a simple alcohol but rather an aromatic alcohol, reacts with
the Lucas reagent due to the electron-withdrawing effect of the benzene
ring, which makes the alcohol more acidic and thus more reactive
towards the Lewis acid (zinc chloride) in the Lucas reagent.