Experiment 4- Reactions of Alcohols and Phenols

Hanieh Yousef
Laboratory Partner: Holly Rossignol
Organic Chemistry II 202-CWD-05
Experiment Performed: Thursday March 31st, 2016
Laboratory Report Submitted: Friday March 22nd, 2016
Dr. Anushuyadevi Saravanamuthu

Introduction:

Alcohols are organic compounds consisting of a hydroxyl functional group.

This is a compound made up of an Oxygen-Hydrogen molecule, bonded to a Carbon.
Alcohols can be primary, secondary or tertiary depending on the number of beta
carbons attached to the functional carbon. Meaning, a Carbon with two Carbons,
one Hydroxyl group, and one Hydrogen as substituents would make the alcohol
secondary. Phenols refer to an aromatic ring with an OH substituent on it. Alcohols
are compounds where the hydroxyl group is attached to a saturated carbon atom,
whereas phenols are compounds which can have one or more hydroxyl groups
attached to the benzene or arene ring.
The reactivity of alcohols depends on the structure of the alcohol and the
reagent. Primary and secondary alcohols are fairly reactive because they are not
very bulky. Tertiary alcohols will never oxidize because they are too bulky. Phenols
are very reactive. The hydroxyl group attached to the benzene ring is an activating
group; therefore, it increases the reactivity of the ring.
Methanol:

Tertiary butyl alcohol:

Results & Discussion:

Isopropyl alcohol:

Phenol:

Table 1: Tests performed on Alcohols

Alcohols
Tests
Chromic Acid Iodoform Test Ferric
Test
Chloride Test
Methanol
-Initially,
-Amber color, -Yellow
orangeafter some
yellow & over time, lighter
time a darker yellow
yellowish
color.
- Appears oily
Isopropyl
-Dark
-Amber
-Dark yellow
alcohol
brown/red
-Solid formed - With water
-When
turned bright
shaken,
yellow
yellow
appearance
on side of
test tube
Tertiary butyl -Darker
-Amber
N/A
alcohol
orangeyyellow
Phenol
-Black
N/A
-Dark
blue/black
Unknown
-Dark yellow, -Yellow
over time
Heterogeneo
cleared up
us mixture:
yellow
precipitate at
the bottom,
clear liquid
on top

Bromo
Derivatives
-Darker
yellow

-Remains
yellow

N/A
-Remains
cloudy
-Dark yellow

Positively tested equations:

Chromic Acid Test
Methanol:

CH3OH + CrO3 + H2+ HCOOH + Cr+3 + 2H2O

Isopropyl Alcohol:

(CH3)2CHOH + H2CrO3 (CH3)2CO + Cr+3 + 2H2O

Iodoform Reaction Test

Isopropyl Alcohol:
+ 2OH + H2O

(CH3)2CHOH + 4NaOI CH3COO- + CHI3 + Na+ +I-

Ferric Chloride Test

Phenol:

C6H5OH + FeCl3 C6H5OFeCl2 + HCl

Bromine Water Test

Phenol:

C6H5OH + 3Br2 C6H5OHBr3 + 3HBr

The methanol, t-butanol and isopropyl all have the same attached groups; CH, C-C, C-O & O-H. Phenol however also has a C=C group. The positions for
the O-H and C-O groups were similar for all four alcohols with slightly varying
intensities. The C-H group however differed for phenol in contrast to the
other 3 alcohols because it is aromatic.
The unknown alcohol tested in the lab is suspected to be methanol. This
prediction can be confrmed by comparing the tests between methanol and
the unknown. The chromic acid test, ferric chloride test and bromo derivative
tests all have the same results for both methanol and the unknown. The
iodoform test results for the unknown differ slightly due to contaminations in
the lab.
Conclusion:
In conclusion, the purpose of this laboratory was to observe the differentiate
reactivity of alcohols based on their properties. Based on the properties of
alcohols, they will be oxidized by different reagents. Through observation, it
was proven that: Chromic Acid reagent oxidize primary and secondary
alcohols, Iodoform reagent oxidizes alcohols with a CH2CH3 group, and both
Ferric Chloride and Bromine Water are reagents that oxidize phenols. After
completing all four tests with the 4 known alcohols it can be concluded that
the unknown sample is methanol.