Report#8
Report#8
Report#8
Alcohol (R-OH) and Phenols (Ar-OH ) are organic compounds comparable to water(H-OH).
Phenols are stronger acid of both alcohol and water so they are able to be converted to their salts.
In the following , properties of alcohol and phenols were determined using 4 different
experiments.
Experimental:
Glassware:
Test tubes
Beaker
Cylinder
Equipment:
Heating apparatus
Plastic transfer pipet
Spatula
Chemicals:
Organic Formula Structure Molecular Safety hazardous
Compounds weight(g/mol)
1-Butanol C4H9OH 74.12
Cyclohexanol 100.158
2-methyl-2- 74.12
propanol
Acetic Acid 60.05
Ethanol C2H5OH 46.07
Resorcinol
Phenol
FeCl3 162.2
Results:
Alcohol Very soluble Moderately soluble Slightly soluble insoluble
Ethanol ×
1-butanol ×
t-butanol ×
Cyclohexanol ×
Discussion:
Ethanol replaced water molecules due to its low molecular weight, leading to a very high
solubility. However, t-butanol and 1-butanol were less soluble in water than ethanol due to their
large molecular weight. Knowing that these two compounds have the same empirical formula,
the slight difference in their solubility is due to the fact that t-butanol has a more branched
structure and can be more easily dissolved in water. Cyclohexanol, on the other hand, is cyclic,
therefore insoluble.
Reaction:
Results:
Alcohol Observation
1-butanol Clear
2-butanol Cloudiness after a while
t-butanol Cloudiness on the spot
Cyclohexano cloudiness after a while
l
Discussion:
Lucas(catalyst) is used to convert alcohols into alkyl chlorides. The cloudiness of the solution
revealed which is the fastest compound. If the cloudiness directly was observed, then the
compound is a tertiary alcohol insoluble in the mixture. Therefore, the rate of the reaction
determines the class of alcohols which have the following reactivity :
tertiary>secondary>primary. The test tube containing t-butanol was immediately observed to be
cloudy, supporting our claim that tertiary alcohols are the fastest in forming the cloudiness with
Lucas reagent due to formation of the stable tertiary carbocation. However, primary carbocations
are way too unstable to be formed leading to a clear test tube and no reaction occurring. In the
case of cyclohexanol and 2-butanol, which are both secondary alcohols and less reactive than the
tertiary ones, cloudiness appeared but took some time to be clearly shown.
Experiment 3: Esterification
Aim: Test the formation of ester
Method: In the same test tube, 1 ml of acetic acid and 1 ml of ethanol were placed in the same
test tube and shaken. While shaking ,1 ml of H2 SO4 was also added and then the test tube was
placed in beaker of warm water (50°C) for 5 mins. The contents were then poured in a beaker
containing 5g of ice.
Mechanism:
Results:
A distinguished smell resulted from the esterification after addition of test tube in ice.
Discussion:
This weird smell was the resultant of mixing an acid with an alcohol to produce ester (ethyl
acetate) the heating and sulfuric acid were catalysts in order to push the esterification reaction
forward. The mixture was placed in ice in order for it to be stopped to identify the smell of
commercial glue.
Experiment 4: Reaction of phenols and Enols with the ferric acid ( FeCl3)
Aim : Distinguish the phenol from enol and alcohol
Method: In 3 separated test tubes, 5ml of distilled water and 5 drops of ferric chloride were
placed. Then, in each tube, different organic compound was added: 5 drops of 2-propanol,few
crystals of phenol and Resorcinol were added to tubes 1,2 and 3 respectively. The colors were
observed and compared.
Results:
Tube Result (color)
2-propanol yellow
phenol purple
resorcinol Purple
Discussion:
phenol and resorcinol(enol) resulted in a purple solution after their reaction with ferric chloride
due to the formation of coordination complexes with iron, indicating that a reaction took place.
However, alcohols(2-propanol) do not react with ferric chloride and therefore showed a yellow
color (reaction didn’t occur).
Conclusion:
the solubility test of alcohols in water revealed that the lower the molecular weight and the more
branched is the structure of an alcohol, the more soluble it is in water.
Lucas test revealed that the fastest alcohol to react with the lucas reagent is the tertiary alcohol
followed by the secondary followed by the primary.
Esterification was detected and proven to occur when mixing an alcohol with a carboxylic acid
due to the presence of a certain smell.
Phenols, enols and alcohols were distinguished from each other by the unreactivity of the latter
with ferric chloride(yellow solution), while the first two formed a purple solution proving the
occurrence of a reaction.
References:
Organic Chemistry, laboratory manual, by H. Hart and L.E. Craine, D.Hart and
T.K.Vinod, 13th edition, 2012
MSDS
Alcohol and Phonol Compounds Handouts, Ghada Naous
www.erowid.org
Questions:
Page 223:
2. Only primary and secondary alcohols give positive results with the Bordwell-wellman test. So
the alcohols are: 2-pentanol,3-pentanol and 2-methyl-2-butanol.
3. 2-methyl-2-butanol react at the fastest rate with Lucas reagent because it is a tertiary alcohol
so a cloudiness will be formed rapidly since the formation of its relative carbocation is the
fastest.
4. Phenols and enols are compounds with a hydroxyl group attached to an unsaturated carbon.
and they give coloration with ferric chloride due to the formation of coordination complexes with
iron. Therefore, the first compound does not react with ferric chloride.
Page227 :
2. 1-heptanol is less soluble in water than 1-pentanol due to the longer chain; the more
hydrophobic effect dominates and the less soluble the alcohol will be.
Page 228
b. Cyclopentanol is a secondary alcohol so, Lucas test will be positive .However, the
cloudiness will take time to be shown.
10. + Na+OH- +
H2O
11. Phenol is more acidic than 1-heptanol because the phenoxide ion formed is stabilized by the
delocalization of the negative charge around the carbon ring.