NAME: Faustine Caybot, Dana Pelobillo, Kate Tatad DATE: Feb.

10, 2022

Group: 3

EXPERIMENT 7 - REACTIONS OF ALCOHOLS AND PHENOLS

Objective:

● To test and compare the water solubility of samples: Ethanol, 1-Hexanol, Phenol,
Benzyl Alcohol, Glycerol and Cyclohexanol.
● To test and compare the sodium hydroxide solubility of samples: Ethanol, 1-Hexanol,
Phenol and Benzyl Alcohol.
● To test and compare the pH levels of samples: Phenol and Benzyl Alcohol.
● To test and compare the ferric chloride test of samples: Phenol, Cyclohexanol, Salicylic
Acid and Control.
● To test and compare the oxidation reactions with alkaline potassium permanganate
(KMnO4) and sodium dichromate (Na2Cr2O7) of samples: Ethanol, 1- Butanol,
2-Methyl-1-Propanol, 2-Methyl-2-Propanol and control.
● To compare the different reactions from alcohols and phenols.

PRE-LAB:

1. SDS phenol, benzyl alcohol, sodium dichromate

Phenol

Corrosive Health Hazard Acute toxic

Properties:
● Melting point of 40.9 °C
● Boiling point of 181.8 °C
● Flash point of 85 °C, (Open cup) and 175 °F; 79 °C, (Closed cup)
● Odor: distinctive phenol odor
● Color: colorless to slightly pink
● Appearance: Aqueous solution
● Solubility: 50 to 100 mg/mL at 66° F
 Benzyl Alcohol
Pictograms:

Irritant
Properties:
● Melting point of -15.2 °C
● Boiling point of 205.3 °C
● Flash point of 200 °F (93 °C) (closed cup) and 96 °C (205 °F) (Closed cup)
● Odor: Faint aromatic odor
● Color: Colorless
● Appearance: Liquid
● Solubility: 10 to 50 mg/mL at 70° F

Na2Cr2O7 (Sodium dichromate)

Pictograms:

Corrosive Irritant Health Hazard

Environmental Hazard Oxidizer Acute Toxic

Properties:
● Melting point of 356.7 °C
● Boiling point of 400 °C
● Odor: Odorless
● Color: Red or red-orange
● Appearance: Crystalline solid and liquid
● Solubility: In water, 187 g/100 g water at 25 °C
Hazard statements:
● Can intensify fire
● Toxic when ingested
● Irritant to skin
● Toxic if inhaled
● Can cause eye irritation and injury
● Carcinogenic
● Extremely dangerous to aquatic ecosystem

2. Draw diagrams showing how isopropyl alcohol, ethylene glycol and glycerol can
hydrogen bond to themselves.
3. Draw the structure of ethanol, 1-hexanol, cyclohexanol, glycerol, benzyl alcohol, phenol
and salicylic acid.

Ethanol

Glycerol

Salicylic Acid
4. Draw the resonance structure of phenoxide ions.

5. Write the equations for the oxidation reaction of the following:

A. Ethanol

B. Isopropyl alcohol
C. t-butyl alcohol / t-butanol

6. Why is sodium hydroxide used to test the solubility of phenol?

Phenol is soluble in water and aqueous sodium hydroxide; however, phenol in water
solubility is moderate and does not thoroughly mix. They ionize slightly and generate
phenoxide ion and hydronium ion products, making the solution acidic. That is why
aqueous sodium hydroxide is used to test the solubility of phenol because phenol is
an aromatic compound and sodium hydroxide only reacts to aromatics and not in
aliphatic compounds. Strong base aqueous sodium hydroxide is strong enough to
dissolve water-insoluble (Phenol). This reaction is a very weak acid (phenol) and a
strong base (aq. sodium hydroxide) reaction, and their product is a strong base (aq.
sodium phenoxide) which is soluble in water. This reaction is essential to differentiate
alcohols from phenols in this experiment because alcohol (weak acids) does not
react with aqueous sodium hydroxide.

7. What safety precautions are cited in this experiment?

Safety precautions:

● Phenol is corrosive to skin (avoid direct contact with skin)

● Wear safety laboratory equipment (gloves, lab gown and goggles).
● Flammable (No open flames)
● When mixing acid and water: Proper way- Acid to water
● Cautiously and slowly add the sulfuric acid to 3ml sodium dichromate
Flow Chart (METHODOLOGY)
Result:

Solubility in

Water (Blue pH FeCl3

food coloring) NaOH

Slightly soluble Insoluble

Ethanol Upper layer:

Light blue

Lower later:

Dark blue

Slightly soluble Insoluble

1-hexanol Upper: clear

Lower: Dark blue

Cold water: Very soluble Aq. solution: Reacts

Insoluble
Phenol Clear solution pH 4 (acidic) Final :
Hot water: Very
(Weak acid) soluble Or Purple
solution
Tap water: Colorless With NaOH:
Slightly soluble solution
pH 7 (basic)
Upper: Sol. of (Phenol
Phenol in water reacts)

Lower: Sol. of
water in Phenol
Benzyl alcohol Slightly soluble Insoluble pH 7 (neutral)

(Neutral
compound)

Glycerol Very soluble

(Slightly denser
than water)

Cyclohexanol Slightly soluble No reaction

Salicylic acid Reacts

Orange and
purple solution

Final:

Dark Purple
solution

Control Slightly
soluble
(Water / H2O)
Oxidation:

Alkaline KMnO4 Na2Cr2O7

(Strong very strong oxidizing agent) (Strong oxidizing agent)

Ethanol Purple color decolorized Light-brown or

orange-red turns into
(Primary Alcohol) Final color: Yellow-brown blue-green
solution
Odor: Sweet pungent
Products from first odor or vinegar
oxidation:
Products from first
Ethanal (Aldehyde) or oxidation:
Acetaldehyde +
2-methyl-1-propanal
Water (Aldehyde)

Product from 2nd oxidation: Product from 2nd

oxidation:
Ethanoic Acid
(Carboxylic acid) or 2-methylpropanoic acid
Acetic acid (Carboxylic acid)

1-butanol Purple color decolorizes Light-brown or

orange-red turns into
(Primary Alcohol) Final color: Yellow-brown blue-green
solution
Odor: Sweet pungent
Products from first odor or vinegar
oxidation:
Products from first
1- Butanal (Aldehyde) + oxidation:
Water
2-methyl-1-propanal
Product from 2nd oxidation: (Aldehyde)

Butanoic acid (Carboxylic Product from 2nd

acid) oxidation:
 2-methylpropanoic acid
(Carboxylic acid)

2-methyl-1-propanol Purple color decolorizes Light-brown or

orange-red turns into
(Primary Alcohol) Final color: Yellow-brown blue-green
solution
Odor: Sweet pungent
Products from first odor or vinegar
oxidation:
Products from first
2-methyl-1-propanal oxidation:
(Aldehyde)
2-methyl-1-propanal
Product from 2nd oxidation: (Aldehyde)

2-methylpropanoic acid Product from 2nd

(Carboxylic acid) oxidation:

2-methylpropanoic acid
(Carboxylic acid)

2-methyl-2-propanol No Reaction No Reaction

(Tertiary Alcohol)

Control Very Soluble Slightly Soluble

(Water / H2O) Final color: Final color:

Dark purple Light-brown or

orange-red

Equation for second oxidation using KMnO4:

Equation for second oxidation using Na2Cr2O7:
Discussion:

A. Solubility:

Water solubility test:

Most alcohol compounds are slightly soluble or moderately soluble in water. This is
because of the presence of the -OH group or hydroxyl group attached to the parent
chain in which the oxygen is capable of hydrogen bonding with the hydrogen in water
molecules. In smaller hydrocarbon chains they are very soluble in water because of the
decreasing surface tension which is a desirable factor to create hydrogen bonding with
other molecules. Ethanol, 1-hexanol, benzyl alcohol and cyclohexanol are all moderately
soluble in water. Among all the alcohols, only glycerol is very soluble in water because in
the structure, it has three hydroxyl groups unlike the other alcohols subjected to water
solubility. Furthermore, the hydrogen bonding of water and glycerol is so strong.
However phenol in this test is only slightly soluble because the products phenoxide ion
and hydronium are partially soluble to water.

Sodium hydroxide (NaOH) solubility test:

This test is used to determine and differentiate phenols from alcohols. Phenols are
weak acids and sodium hydroxide is a strong base in which it doesn’t react with
alcohol because they are weaker acids than phenols. Sodium hydroxide reacts only
with compounds containing phenol groups. This is because phenol has a sufficient
amount of hydrogen concentration and alcohols do not which makes them neutral and
less acidic. Furthermore, the Sodium or Na+ and OH- are mobile, and so is the benzene
ring in phenol. In this way alcohols do not react because they are immobile compounds
and have no benzene ring.

B. Acidity test: (0 to 5 acidic, 6 to 8 neutral; 7 as most neutral, 9 to 14 alkaline)

In this experiment, ethanol, 1-hexanol, phenol and benzyl alcohol was subjected to the
acidity test; however, only phenol and benzyl alcohol were being recorded. The data
shows that the aqueous solution of phenol is acidic while phenol with sodium hydroxide
is basic. This shows that the water typical pH is 7 and when phenol (weak acid) is added
to water, the solution is also acidic because of the addition of hydrogen or protonated
hydrogen. The proper way of mixing liquids with acid and neutral solvent is “Acid to
Water”. Otherwise, acid and water will react in a vigorous exothermic reaction. In
another method, sodium hydroxide, which is a strong base, is added to phenol and the
solution is basic because the hydrogen ion has been removed by basic hydroxide ions or
deprotonated phenol. Alcohols are very weak acids and their typical acidity is pH 7. In
this test Benzyl alcohol pH level is also 7, since it does not react with sodium hydroxide,
the acidity of the solution remains pH 7.
C. Ferric Chloride test:

Ferric Chloride test is another method to determine and indicate the presence of
phenol groups in a compound. Formation of color such as blue, violet, purple, green or
red-brown solution indicates there is phenol present. In this test, phenol, cyclohexanol,
salicylic acid and water as control were all subjected. Only phenol and salicylic acid react
because according to their chemical structure phenol and salicylic acid have a benzene
ring and phenol group they react because they have all these two factors. In solution,
the reaction is evident in color change from orange solution to dark purple. In
cyclohexanol and water, their chemical structure does not contain the benzene ring and
phenol group that is in this test they do not react thus no color change.

D. Oxidation test:

Oxidation tests determine whether an alcohol is primary, secondary or tertiary. In

general. Tertiary alcohols cannot be oxidized unless breaking the carbon-carbon bonds.
In primary alcohols, they can be oxidized into aldehydes as a product of primary
oxidation and carboxylic acids as a product of secondary oxidation. In secondary
alcohols they can be oxidized into ketones.

Potassium permanganate (KMnO4)

Potassium permanganate is a strong oxidizing agent and oftentimes the final product
when using this reagent in alcohol is usually carboxylic acids. In the experiment, ethanol,
1-butanol, and 2-methyl-1-propyl are compounds that only react to potassium
permanganate. Based on their chemical structure all three compounds are primary
alcohols and since KMnO4 is a strong oxidizing agent they all generate products with
carboxylic acid attached to their corresponding compounds. Reactions is evident in
observations of Purple color decolorizes with a final color of Yellow-brown solution

Sodium dichromate (Na2Cr2O7)

Sodium dichromate is corrosive and also a strong oxidizing agent. In the presence of
heat, odor occurs which is the chromium fuse and toxic in nature. In this experiment,
concentrated sulfuric acid is cautiously added because, if added vigorously, the
solution will lead to violent exothermic reaction and it is not desirable because it can
intensify fire if there are open flames present. Then, test subjects such as ethanol,
1-butanol, and 2-methyl-1-propyl only react with observed color change from Light-brown
or orange-red to blue-green and Sweet pungent odor or vinegar.

In this experiment, oxidation of 2-methyl-2-propanol, a tertiary alcohol (R3COH), does

not react with potassium permanganate and sodium dichromate. The reason for this is
that the carbon atom that is directly attached from the -OH group does not have any
hydrogen atoms attached.Instead it is bonded to methyl groups or any molecule that is
 not hydrogen directly attached to carbon with the -OH group. Furthermore, ketones are
also resistant due to this reason. Therefore in order for it to oxidize, breaking of
carbon-carbon bond is the option which requires too much energy or heating.
Furthermore in oxidation in water (control), the potassium permanganate completely
dissolves while sodium dichromate slightly dissolves.

Questions:

1. Explain the effect of structure on solubility and on acidity of alcohols.

Alcohols are organic compounds with a hydroxyl group attached to the aliphatic carbon
atom. Based on their structure, it affects the behavior (solubility and acidity) of the
compound. Alcohol solubility is based on hydrogen bonding of oxygen of the alcohol to
hydrogen in other compounds. That is why most alcohol is slightly soluble to water
because of the hydrogen bonding between the molecules and slightly soluble to some
alcohols. Another behavior which is acidity, alcohols are very weak acids like water but
some alcohols like methanol and ethanol are most simply as acidic as water. In this
case, using strong base acid can deprotonate an alcohol and generate an alkoxide ion
which is a conjugate base of an acid. Moreover, like water, alcohols are both weak base
and acidic and using strong acid can protonate ions while using strong base can
deprotonate the compound.

2. Explain why pentane is less soluble in water than isopropyl alcohol. Use drawings.

Pentane Isopropyl alcohol

Pentane is less soluble in water because pentane is not capable of hydrogen bonding
due to absence of functional group alcohol or absent hydroxyl group. Whereas, isopropyl
alcohol is soluble to water because of the presence of hydroxyl group attached to the
second carbon in the chain. Furthermore, pentane intermolecular force is dispersion and
due to the carbon-hydrogen bonds the molecule is not stable enough. Thus, pentane
cannot hold water and dissolve due to the temporary breaking and bonding of carbon
and hydrogen.
 3. Using tests performed in this experiment, tell how you would distinguish between the
following compounds.

a) cyclohexanol and phenol

Using the tests in this experiment, we can identify and distinguish cyclohexanol and
phenol properties, functional groups whether a compound is either alcohol or phenol and
their behavior towards each test. In water solubility, cyclohexanol and phenol are
slightly miscible to water. In sodium hydroxide solubility only phenol reacts to phenol
because cyclohexanol is not acidic and in acidity test in order to create reaction, the
compounds must be at least acidic so that sodium hydroxide (strong base) can react by
deprotonation of ions resulting to basic solution. In this example, reaction of acid-base
only occurs in phenols. In ferric chloride test, only phenol reacts because cyclohexanol
doesn’t have phenol group in which a hydroxyl group is attached to a benzene ring or
aromatic whereas cyclohexanol has hydroxyl group is attached to an aliphatic ring. In
oxidation reactions, cyclohexanol (secondary alcohol) oxidizes into ketone
cyclohexanone while phenol oxidizes into benzoquinone.

b) 1-butanol and 4-chlorophenol

Using the tests in this experiment, we can identify and distinguish 1-butanol and
4-chlorophenol, properties, functional groups whether a compound is either alcohol or
phenol and their behavior towards each test. In water solubility, 1-butanol and
4-chlorophenol are both soluble in water. 4-Chlorophenol and water generates products
of hydroquinone and hydrochloride. In sodium hydroxide solubility, only
4-chlorophenol reacts due to the presence of phenol group while 1–butanol doesn’t
react. In the acidity test, 1- butanol has a pH of 16 which belongs to alkaline and not
acid, while 4-chlorophenol is acidic. In the ferric chloride test, only 4-Chlorophenol
reacts and forms blue, violet, purple, green or red-brown because of the presence of
phenol group. In oxidation reaction, 1-butanol is a primary alcohol and oxidized into
aldehyde (product of first oxidation) and carboxylic acid (product of secondary oxidation).
While 4-Chlorophenol oxidizes into hydroquinone.

Conclusion:

In this experiment, solubility tests (water and sodium hydroxide) determine and differentiate
alcohols and phenols through the physical properties such as color changing, and formation of
layers. In which alcohols are slightly soluble to water and insoluble to sodium hydroxide while
phenols are also slightly soluble to water and very soluble to sodium hydroxide. In acidity tests,
alcohols are very weak acids similar to water and phenols are also weak acids but stronger than
alcohols. In the ferric chloride test, color changing from orange to purple,or green indicates that
a phenol in the compound is present. Lastly, in the oxidation test, it determines compounds
whether primary, secondary tertiary or phenol. Therefore, all of this test is essential for
understanding the behavior of alcohol and phenols based on their structure (presence of hydroxyl
groups and benzene rings or aromatic rings, acidity and intermolecular forces such as dispersion
and hydrogen bonding.
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