Name: Bation, Michael John G.

Course & Yr: BS Chemistry-II

Offering Number: R204

Chem 127.2 Organic Chemistry I Laboratory

Experiment No. 9
Alcohols and Phenols

Instructions: You can copy and paste the structures from the internet. Make sure to cite the link source. Every positive reaction should be given the
chemical reaction that happened.

Part I. Properties and Reactions of Alcohols

A. Solubility in water and in acidic solutions.

Compound Structural Formula Solubility with water (Show IMFA) Reaction with H3PO4
It reacts with H3PO4 in the presence of heat to
form 1-butene.
Partially soluble in water because of
the ability of the hydroxyl group to (i) C4H9OH + H3PO4  C4H9(OH2)+ + H2PO4-
n-butyl alcohol form hydrogen bonds with water but
altered with the alkyl chain which is (ii) C4H9(OH2)+ + H2PO4-  C4H8 + H3PO4 + H2O
non-polar.
- n-butyl alcohol is miscible in phosphoric acid.
(a)
Tert-butyl alcohol is dehydrated in the presence of
H3PO4 to form isobutylene (2-methylpropene).
Tert-butyl alcohol is highly miscible in
Tert-butyl alcohol water. The branching increases the
surface area of the non-polar H3PO4
→
hydrocarbon as well as its ability to
form H-bonds with water.
(b)
 If cyclohexanol is heated with a catalytic amount
of phosphoric acid, elimination of water results in
Sparingly soluble in water because the cyclohexene as the product.
formation of hydrogen bonds with
Cyclohexanol water does not compensate for the loss
of the London forces of the hydrophobic H3PO4
→ + H 2O
part.

(c)

Also sparingly soluble in water because

Benzyl alcohol the large part of the molecule is No reaction
hydrophobic with London dispersion
forces and H-bonding with water is
apprehended.

(d)
B. Reaction with Sodium Metal

Alcohol Structural Formula, Type of alcohol (1o,2o,3o) Reaction with Sodium Metal

Ethanol rapidly reacts with Na(s) to produce sodium ethoxide and H2

Ethyl alcohol gas.
(1o)________
2 + 2Na(s) → 2 Na+ + H2(g)
--

Isopropanol minimally reacts with Na(s) to produce sodium

isoropoxide and H2 gas.
--
Na+
Isopropyl Alcohol (2o)_______ 2 + 2Na(s) → 2 + H2(g)

Tert-butyl alcohol very slowly reacts with Na(s) to produce sodium

tert-butoxide and H2 gas.

Tert-butyl alcohol (3o)

2 + 2Na(s) → 2 + H2(g)
--
Na+

C. Reaction with Lucas Reagent:

Composition of Lucas Reagent: Zinc chloride in concentrated hydrochloric acid

Alcohol Structural Formula, Type of alcohol (1o,2o,3o) Reaction with Lucas Reagent

Ethanol reacts very slowly unto the reagent and cloudiness only
Ethyl alcohol appears after several hours or on heating
 (1o)________ ZnCl2
+ HCl → Cl + H 2O

Isopropanol reacts with the Lucas reagent to give an insoluble alkyl

chloride but turbidity only appears after 5 minutes
Isopropyl Alcohol (2o)_______ Cl
ZnCl2
+ HCl → + H 2O

Tert-butyl alcohol rapidly reacts with Lucas reagent to give an

insoluble alkyl chloride which appears as a cloudy dispersion
Tert-butyl alcohol (3o)
ZnCl2
+ HCl → + H 2O
Cl

D. Reaction with Potassium Dichromate

Alcohol Structural Formula, Type of alcohol (1o,2o,3o) Reaction with Potassium Dichromate (Indicate Color Change)

Ethyl alcohol reacts with K2Cr2O7 which give first aldehydes and
finally carboxylic acids as oxidation products.
Color Change: colour of the solution turns from orange to green
(1o)________
Ethyl alcohol
Oxidation- Reaction:
3 + 2Cr2O72- + 16H+ → 3 + 4Cr3+ + 11H2O
orange green
 Isopropyl alcohol reacts with K2Cr2O7 to produce acetone.
Color Change: colour of the solution turns from orange to green
(2o)_______
Isopropyl Alcohol
9 + Cr2O72- + 8H+ → 12 + 2Cr3+ + 4H2O
orange green

(3o)
Tert-butyl alcohol
Tertiary alcohols are inert toward most mild oxidizing agents. Hence,
no reaction occurs.

E. Reaction with hypohalite (I2,KI, NaOH)

Alcohol Structural Formula, Type of alcohol (1o,2o,3o) Reaction with Hypohalite Sol’n (Indicate Color Change)

When ethanol is warmed (60oC) with iodine in the presence of an alkali

Ethyl alcohol (NaOH), iodoform is obtained
(1o)________ Color change: orange-brown to Cloudy-yellow (precipitate)
Summarize Reaction:

+ 4I2 + 6NaOH → CHI3 + HCOONa + 5NaI + 5H2O

Orange-brown Cloudy-yellow
 Propane-2-ol on reacts with iodine and sodium hydroxide to give
Iodoform

Color change: orange-brown to Cloudy-yellow (precipitate)

Isopropyl Alcohol Series of reaction:

(2 )_______
o
2NaOH + I2 → NAI + NaOH
C3H8O + NaOI → C3H6O + NaI + H2O
C3H6O + 3NaOI → CH3COCI3 + 3NaOH
CH3COCI3 + NaOH → CHCl3 + CH3COONa
Cloudy-yellow

The carbon atom of tertiary alcohol do not have any available

Tert-butyl alcohol (3o) hydrogen to give up so that an intermediary ketone will be created.
Hence, no reaction occurs.

II. Properties and Reactions of Phenols

A. Solubility in water

Phenol Structural Formula, Type of alcohol (1o,2o,3o) Solubility in water Color Change with Litmus Paper

p-chlorophenol
(2o) Slightly soluble in water Blue LP to Red LP
Red LP remained Red
 (e)

2-naphthol Insoluble in water Blue LP to Red LP

(2o) Red LP remained Red

(f)

Blue LP to Red LP
Resorcinol Soluble in water Red LP remained Red
(2o)

(g)

Salicylic acid Blue LP to Red LP

(2o) Sparingly soluble in water Red LP remained Red

(h)

B. Ferric Chloride Test

Phenol Structural Formula, Type of alcohol (1o,2o,3o) Reaction with FeCl3(Indicate Color Change)
 It reacts with FeCl3 to form a colored complex with Fe3+.
Color Change: Dark Purple

p-chlorophenol
---
(2o) 3 + FeCl 3 → [ ]3Fe
Yellow
Dark Purple + 3HCl__

It catalyzes in the presence of FeCl3 to form 2,2-

binaphthol and reduce Fe3+ to Fe2+.
Color change: green
2-naphthol
(2o)
2 + FeCl3 → + 2FeCl2 +2HCl
Yellow Green

Resorcinol with FeCl3 to form colored complex.

Color Change: purplish-blue
---
Resorcinol
(2o) 3 + FeCl3 → [ ]3 Fe + 3HCl
Yellow
Purplish-blue

Salicylic acid with FeCl3 also forms colored complexes of

Fe3+.
Salicylic acid Color Change: Violet
(2o)
---
3 + FeCl3 → [ ]3 Fe + 3HCl
Yellow

Violet
C. Bromine Water Test

Phenol Structural Formula, Type of alcohol (1o,2o,3o) Reaction with Bromine Water(Indicate Color Change)

It reacts with bromine water to form 2,6-dibromo-4-

chlorophenol.
p-chlorophenol Color Change: the solution decolorizes
(2o)
Br2
→

This reacts with bromine water to produce a

halogenated napthol.
Color Change: the solution decolorizes
2-naphthol (2o)

Resorcinol reacts with bromine water and precipitates

tribromoresorcinol.
Color Change: the solution decolorizes

(2o)
Resorcinol
+ 3Br2 → + 3HBr
 Salicylic acid react with bromine water to form
tribromophenol.
Color Change: the solution decolorizes

(2o)
Salicylic acid Br2
→

Reference Links on the Chemical Structures:

a. https://www.indiamart.com/proddetail/n-butyl-alcohol-11162635848.html
b. https://commons.wikimedia.org/wiki/File:Tert-butyl-alcohol-2D-skeletal.svg
c. https://study.com/academy/lesson/cyclohexanol-structure-hazards-physical-properties.html
d. https://en.wikipedia.org/wiki/Benzyl_alcohol
e. https://www.chemsynthesis.com/base/chemical-structure-4015.html
f. merckmillipore.com/INTL/en/product/2-Naphthol,MDA_CHEM-822290
g. https://en.wikipedia.org/wiki/Resorcinol
h. https://www.researchgate.net/figure/Structure-of-salicylic-acid_fig1_328596319