Discussion

These experiments were conducted to study the reaction of alcohols and phenols. This
experiment covers 5 parts of alcohol. They were solubility, reaction with alkali, reaction with
sodium metal, alcohol tests and reaction of phenol.

Solubility:

Alcohols are soluble in water. This is due to the hydroxyl group in alcohol which is able to
form hydrogen bonds with water molecules. Alcohols with smaller hydrocarbon chain are
very soluble. As the length of the hydrocarbon chain increase, the solubility in water
decreases. With four carbon in the hydrocarbon chain and higher, the decrease in solubility
become visible as the mixture forms two immiscible layers of liquid. The reason why the
solubility decreases as the length of hydrocarbon chain increases is because it is required
more energy to overcome the hydrogen bonds between the alcohol molecules as the
molecules are more tightly packed together as the size and mass increases. Ethanol is
easy to dissolve. On case of tert-butyl alcohol, the alkyl group is branched and have less
surface area i.e. less hydrophobic ad hence more soluble in water. Phenol is insoluble in
water because of the presence of benzene ring. The phenyl group in phenol is nonpolar and
hydrophobic so it is insoluble in water.

Reaction with alkali:

Phenol is a strong acid enough to react with sodium hydroxide solution to produce sodium
phenoxide and water. This reaction will produce sodium salts. Since alcohols will not react
with sodium hydroxide, this can be used as a test to distinguish alcohols from phenols.

Reaction with metallic sodium:

Both alcohol and phenol react with a reactive metal i.e. phenol react with metallic sodium to
give sodium phenoxide and hydrogen gas. Acids react with the more reactive metals to give
hydrogen gas. Phenol is no exception - the only difference is the slow reaction because
phenol is such a weak acid. A small piece of sodium is added into a phenol solution. There is
some fizzing as hydrogen gas is given off. The mixture left in the tube will contain sodium
phenoxide. This reaction is more vigorous than the one with alcohol because phenol is more
acidic.

Lucas Reagent:

Lucas Reagent is a solution of saturated and anhydrous zinc chloride in concentrated

hydrochloric acid. This test is used o distinguish between water soluble primary, secondary,
and tertiary alcohols. Some alcohols react with ZnCl2 in an acidic aqueous solution to give
an alkyl chloride. The Lucas test involves a substitution reaction, where the –OH group of
alcohol is replaced by a Cl atom. The Lucas reagent consists of a mixture of HCl and ZnCl2
that are dissolved in water. The mechanism of this reaction involves a carbocation
intermediate: first n OH- ion is removed from the alcohol, leaving the carbon atom in the
molecule positively charged carbon atom. Then a Cl- ion adds to the positively charged
carbon atom. The result is the alcohol is converted to a chlorinated alkane, with the Cl
occupying the spot that the –OH was in. since tertiary carbocation are much more stable
than primary and secondary carbocation, tertiary alcohols will react readily with the Lucas
reagent. Secondary alcohols will react slowly (usually in 5-10 minutes) primary alcohols will
not react much at all, since a primary carbocation is so unstable. Therefore, tertiary alcohols
(t-butyl alcohol) react immediately. The test tube will get hot, and because the chloride is
Insoluble two layers may be apparent, or a cloudy dispersion forms. Secondary alcohols (2-
butanol) will become cloudy in 5 to 10 minutes. After heating slightly, gives the white layer
within 10 min. Primary alcohols (1-butanol) give no reaction at all.

Oxidation:

primary alcohol can be oxidized to either aldehydes or carboxylic acids depending on the
reaction conditions. Secondary alcohols are oxidized to ketones. Tertiary alcohols are not
oxidized by acidified sodium or potassium dichromate (VI) solution. There is no reaction
whatsoever. This is because tertiary alcohols don’t have hydrogen attached to that carbon
for the oxygen to remove. In this experiment, potassium dichromate is added as a oxidizing
agent to determine whether the alcohol will, undergo oxidation or not. Potassium dichromate
is an orange-yellow solution. The orange colour is due to the Cr O ion. The 2 oxidation
number of chromium is 6+. This reagent will oxidize primary and secondary alcohols and in
turn, becomes reduced. The chromium in dichromate is reduces to chromic ion, Cr. A
greenish colour solution results. This colour change from orange-yellow to green to serves
as an indicator for the presence of a primary or secondary alcohol. A primary alcohol is
oxidized first to an aldehyde, which will be further oxidized to an acid. Through the
experiment, all of the compound show positive result and undergoes changes of colour.

Reaction with bromine in water:

The reaction of phenol with bromine is known as bromination of phenol. Solvent has great
influence on the reaction.In different solvents, different products are obtained. Phenol reacts
with bromine water to give 2,4,6-tribromophenol.
In water, ionisation is facilitated. Phenol gets ionised to form phenoxide ion, which is even
better ortho-para directing. Bromine also gets ionised to a larger extent to form a large
number of bromonium ions. And Bromine ions are highly stabilized in ionic solvents. So the
formation of strong o/p directing group and stabilization of Br+ enhances the formation of
tribromophenol. The bromine water is decolourised and a white precipitate is formed which
smells of antiseptic .

Ferric chloride (III) test:

Ferric chloride (III) is used to identify the presence of phenol. When ferric chloride (III) added
into phenol solution, it will form a light violet solution.
Reference:

1. Identification and reaction of alcohols and phenol; LIM JOE JEAN,

https://www.academia.edu/14250669/Identification_and_reaction_of_alcohols_and_phenol_l
ab_report

2.Chemistry, LibreTexts ; Sep 30, 2018;

https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Map%3A_Organic_Chemistry_(
McMurry)/Chapter_17%3A_Alcohols_and_Phenols/17.02_Properties_of_Alcohols_and_Phe
nols

3. Experiment 5 CHM207 Intermediate Organic Chemistry Reactions of Aliphatic Alcohols

and Phenol; https://www.scribd.com/document/266239277/Experiment-5-CHM207-
Intermediate-Organic-Chemistry-Reactions-of-Aliphatic-Alcohols-and-Phenol

4. Reactions of Phenols - Reactions of Phenols Reaction with...; Course hero;

https://www.coursehero.com/file/16098739/Reactions-of-Phenols/

5. https://clay6.com/qa/87777/what-happens-when-phenol-react-with-bromine-water-