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Abstract
The experiment was aimed to differentiate the three types of alcohols and distinguish the
reactions of alcohols and phenols. Qualitative tests were done such as solubility of alcohols and
phenols; reaction of alcohols with sodium metal, potassium dichromate, hypohalite, Lucas test
and reaction of phenols with ferric chloride. According to the results, it was shown that alcohols
with below 8 carbon chain and less compact alcohol compound were soluble in water, also, it
was shown that saturated alcohols were soluble in concentrated H 3PO3 while unsaturated were
insoluble. In solubility of phenols, it was found to be that phenols with to benzene ring or greater
molecular weight were insoluble with water such as 2-naphtol while p-chlorophenol, resorcinol
and salicylic acid were soluble in water. In test of sodium metal, it was found out that all types of
alcohols would show exothermic reaction upon addition of sodium metal. In determining the
type of alcohols Lucas reagent was used and based on the results, tertiary alcohol would react
first followed by a secondary alcohol and so forth. In test with oxidizing agent such potassium
dichromate, primary alcohol was found to be easily oxidized to aldehyde and over oxidized to
form carboxylic acid, likewise, the secondary alcohol was able oxidized to form a ketone
compound while the tertiary did not undergo oxidation due to its lack H atom to react with the
reagent. The addition of Iodine in NaOH solution in the Iodoform test also detected the presence
of a methyl ketone in isopropyl alcohol and reacted with ethanol to form a yellow precipitate
which was called iodoform. In ferric chloride test, the p-chlorophenol, 2-naphtol, resorcinol,
salicylic acid shown positive reaction which exhibited different characteristics of colors upon
addition of ferric chloride. The experiment was done due to help the author being a chemistry
major student fully discern the characteristics and types of the alcohol and phenols.
Introduction
Alcohols and phenols can be thought of as organic derivatives of water in which one of
the water’s hydrogens is replaced by an organic group: H - O - H versus R - O - H and Ar - O -
H. In practice, the group name alcohol is restricted to compounds that have their -OH group
bonded to a saturated, sp3-hybridized carbon atom. Alcohols are classified as primary (1°),
secondary (2°), or tertiary (3°), depending on the number of organic groups bonded to the
hydroxyl-bearing carbon (McMurry, 2016). Representative examples of a phenol, and three types
of alcohols are shown below.
These four classes of compounds contain the functional group OH, the unique differences
in their reaction chemistry allows one to easily differentiate one from the other. The solubility of
alcohol is determined by the hydroxyl group present. The hydroxyl group in alcohol is involved
in the formation of intermolecular hydrogen bonding. Thus, hydrogen bonds are formed between
water and alcohol molecule which makes alcohol soluble in water. However, the alkyl group
attached to the hydroxyl group is hydrophobic in nature. Hence, the solubility of alcohol
decreases as the size of alkyl group increases (Robert and Caserio, 1977). Lucas reagent is made
up of zinc chloride in concentrated hydrochloric acid. Testing using this reagent depends on the
different rate of conversion of primary, secondary and tertiary alcohol to their chloride forms.
Phenols are more characterized by a hydroxyl group attached to a carbon atom that is part
of an aromatic ring. Phenols are more soluble than alcohol since it can form stronger hydrogen
bonds and more acidic than alcohols (Robert and Caserio, 1977). The hydroxyl group of a phenol
compound attached to unsaturated carbon atoms will react with ferric chloride to give red,
purple, coloration depending on the phenol’s structures.
The experiment was done due to help the author being a chemistry major student fully
discern the characteristics and types of the alcohol and phenols. Furthermore, the experiment was
conducted to differentiate the three types of alcohols and distinguish the reactions of alcohols
and phenols.
In the course of the experiment, the instructor explained the theoretical reactions of the
different types of alcohol and phenols which can be found on the laboratory manual “Chemistry
127.2- Organic Chemistry I- Lab” (Villar, 2019). The materials used in the experiment were 10
mL n-butyl alcohol, 10 mL sec-butyl alcohol, 10 mL Ethyl alcohol, I2 in KI solution, 10 mL
isopropyl alcohol, 10 ml tert-butyl alcohol, cyclohexanol, 3% FeCl3 solution, 5% K2Cr3O7, 2-
naphthol, 100 mL Lucas reagent, 2M H2SO4, catechol, 10 % NaOH, Resorcinol, 15 M Test
tubes, 10 Med droppers, Test tube rack, water bath, screen for test tubes, hot plate and wash
bottle. The experiment was divided into two: the properties and reactions of alcohols and lastly,
the properties and reactions of phenols.
Iodoform test was used to test the presence of alcohols with the structure RCH(OH)CH 3.
A solution of I2 was added to small amount of an alcohol followed by NaOH to remove the color
of the iodine. Iodoform was distinctively identified as the yellow precipitate and had a faintly
medical smell. Based on the results, isopropyl alcohol and ethanol was the only to form a yellow
precipitate of iodoform, CHI3. Since, When the alcohol is combined with sodium hydroxide
(NaOH) and Iodine, the resulting sodium hypoiodite (NaOI) will cause the oxidation like the
primary and a secondary alcohol which are shown below. Then, the intermediate ketone and
aldehyde is further oxidized to give a carboxylic and iodoform (Clark, 2014).
On the other hand, tert-butyl alcohol did not react at all since it is a tertiary alcohol and it
does not have available hydrogen to give up. Hence, no intermediate ketone was formed.
In table 6, it shown that only p-chlorophenol and resorcinol were soluble in room
temperature. Since, they are polar compounds and has a hydroxy group which would form
hydrogen bonding with water. Furthermore, it due to it weak acidic nature which make soluble
with water. On the other hand, salicylic acid and 2-napthol were insoluble since salicylic acid
contains 7 carbon atoms in its molecule, 6 of which are in a carbon ring along with hydrogen and
oxygen. Its substance is more closely related to oil that resists bonding with water, however its
solubility is influenced by temperature (Shalmashi and Eliassi, 2008). Hence, when the salicylic
acid was subjected to water bath it became soluble. The 2-napthol was insoluble due its
molecular weight, as the size of the chain increase the solubility decreases.
In ferric chloride test, all samples shown different characteristic of colors. For the reason
that compounds with a phenol group will form a complex ion which causes the color blue, violet,
purple, green, or red-brown color upon addition of aqueous ferric chloride (Clark, 2004).
Conclusion
Based on the result of the experiment, the students were able to differentiate the three
types of alcohols through Lucas test and understand the reactions of alcohols such as primary
alcohol can undergo oxidation to produced aldehyde and carboxylic acid while secondary
alcohol can oxidize to produced ketone. Furthermore, the students were able to distinguish the
reaction of phenols like when treated with ferric chloride, it produces complex ion that exhibit
intense colors.
Reference
Festin, A.J. and Raquepo, V.V. (2014). Solubility Classification Using Water, 5% NaOH, 5%
HCl, 5% NaHCO3 , Ether, Concentrated H2SO4 and 85% H3PO4 . Retrieved from,
https://www.academia.edu/6416813/Solubility_Classification_Using_Water_5_NaOH_5_HCL_
5_NAHCO3_Ether_Concentrated_H2SO4_and_85_H3PO4.
Kjonaas, R. A and Riedford, B. A. (1991). "A Study of the Lucas Test". Journal of Chemical
Education. 68 (8): 704.
Shalmashi, A. and Eliassi, A. (2008). Solubility of Salicylic Acid in Water, Ethanol, Carbon
Tetrachloride, Ethyl Acetate, and Xylene. Journal of Chemical & Engineering Data. 53 (1): 199-
200 DOI: 10.1021/je7004962