ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA.

ANA 2009
ACTIVITY 5: ORGANIC DERIVATIVES OF WATER
Organic derivative of water are formed by replacing the hydrogen atom with alkyl group which results to
the formation of alcohol, phenol, or ether as illustrated in below. Alcohol is a polar compound since it is capable of
forming H-bonds with water. Phenol, an aromatic alcohol, can also form such H-bond but the presence of the
nonpolar benzene ring limits its solubility in water. Ether has net dipole moment due to its bent structure,
however, it cannot form H-bonds with water making it practically insoluble in water.

Nomenclature of Alcohols
The hydroxyl (-OH) group of alcohol is given priority as such the follow the given rules when naming alcohols.
(1) Find the longest continuous carbon chain that includes the hydroxyl group. Number the parent chain in
such a way that gives the lowest number to the carbon where OH is attached.
(2) The parent chain is named by replacing the suffix ane of the corresponding alkane with ol.
(3) Name the other substituents in alphabetical order and indicating their position on the parent chain.
(4) If the hydroxyl group is attached to a ring, the numbering always starts with the OH and continues in the
way that gives the lowest numbers to the other substituents.
(5) When multiple number of hydroxyl groups are present, the suffix -diol, triol-, -tetraol, etc. is used to
indicate their number.
(6) When the parent chain contains a double or triple bond, the hydroxyl group is still given the highest
priority. The number that indicates the position of the multiple bonds is placed in front of the hydrocarbon
root name. The number that indicates the position of the hydroxyl group is appended to the name of the
hydrocarbon chain along with the suffix ol.
Sample Exercise 1: Name the given alcohol.
5-methyl

4-propyl
4 5
3

Br
3-bromo

OH

2
1

3-bromo-5-methyl-4-propyl-2-octanol
Practice Exercise 1: Draw the structure of 6-chloro-2-isopropyl-3-ethyl-1,7-heptadiol

ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA.

ANA 2009

Sample Exercise 2: Draw the structure of 3-tert-butyl-4-cyclohexen-cis-1,2-diol.

OH
OH

Practice Exercise 2: Name the given alcohol.

OH
HO

OH

OH

Nomenclature of Phenols
The naming of phenols follows the naming system in aromatic compounds which is summarized below.
(1) The numbering on the benzene ring always starts with the hydroxyl group and continues in such a way
that gives the lowest numbers to the other substituents.
(2) The substituents are named alphabetically and the parent chain is named as phenol.
(3) For disubstituted compounds, use the prefix ortho-, meta-, or para- to indicate the position of the
substituent.
Sample Exercise 3: Name the given phenolic compound.
6

HO

1
2

Br

CH3

4-methyl

3-bromo

3-bromo-4-methylphenol
Practice Exercise 3: Resorcinol is an antiseptic and disinfectant that is used in treatment of psoriasis and
eczema. Its systematic name is meta-hydroxyphenol, draw its structure.

ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA.

ANA 2009

Nomenclature of Ethers
Ethers can either be symmetrical or asymmetrical in nature. Symmetrical ethers have the same alkyl groups
attached to either side of oxygen while asymmetrical ones have different alkyl groups. Ethers are named either
by their common or traditional names or by their systematic name according to IUPAC rules which are stated
below.
(1) For their common name, ethers are named as alkyl alkyl ethers. The name of the alkyl groups are listed
according to alphabetical order and then appending the name ether. For symmetrical ether, the prefix diis used in conjunction with the alkyl group.
(2) For their IUPAC name, ethers are named as alkoxy alkanes. The smaller alkyl group and the oxygen
atom is the one named as alkoxy, and is thus treated as substituent of the larger alkyl chain.
Sample Exercise 4: Name the given ether both in the traditional and IUPAC system.

1
6

4
5

Traditional: butyl cyclohexyl ether

IUPAC: butoxy cyclohexane
Practice Exercise 3: Draw the structure of cyclopentyl phenyl ether and give its IUPAC name.

ACTIVITY #5

ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA.

ANA 2009
ORGANIC DERIVATIVES OF WATER
NAME: __________________________________________________
SECTION:___________

SCORE: ____________

LABORATORY INSTRUCTOR:________________________________________

A. Name the following compounds (20 pts)

1.

6.

HO

HO

OH

2.

CH3O

7.

OH

OH
O

OH

3.

8.

OH

4.

9.
O
OH

OH
O

5.

10.
O

B. Draw the structure of the following organic derivatives of water. (20 pts)

ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA.

ANA 2009
1. 8-cyclohexyl-trans-6-nonen-1,2-diol

6. 2,5-dimethoxy-4-hydroxyphenol

2. trans-2-butoxy-4-isopropylcyclopentanol

7. di-3-methylcylopentyl ether

3. 10-undecaen-6-yne-2-ol

8. 2-methylpropanoxy- all trans-1,3-pentadiene

4. 1,3,5,7-cyclooctatetraen-1,3,5,7-tetraol

9. 3,5-diisopropanoxycyclohexene

5. para-1-propenoxyphenol

10. para-cyclohexanoxyphenol

ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA.

ANA 2009
EXPERIMENT #5: ORGANIC DERIVATIVES OF WATER

Alcohols can be classified based on the number of alkyl groups attached to the carbon that contains the
hydroxyl group as illustrated below.

Each type of alcohol has different reactivity towards various reagents. Primary and secondary alcohols
react with various oxidizing agents while tertiary alcohols are unreactive. On the other hand, tertiary alcohols are
most reactive to nucleophilic substitution in Lucas reagent while secondary alcohols are quite reactive and
primary alcohols are unreactive. The presence of benzene ring makes phenol more acidic than comparable cyclic
and acyclic alcohols. Phenols are oxidized only by the strongest oxidative agents. A useful chemical test for
differentiating phenols from alcohols is via ferric chloride test. Ethers are generally unreactive as it is a very stable
bond.
Objectives
In this experiment, you will be able to distinguish the difference among various organic derivatives of
water based on their characteristic solubility behavior and reactions. Using this knowledge, you will understand
how to identify unknown samples of alcohols, phenols, or ethers.
Materials and Reagent
95% Ethanol
Unknown sample 1
2-Butanol
Unknown sample 2
tert-butanol
Unknown sample 3
Phenol
Bayers reagent
Diethyl ether
1.00M Na2Cr2O7

Lucas reagent
1% Ferric chloride
Distilled water
1.00M NaOH
Conc. H2SO4

Test tubes
Pasteur pipettes

Procedures
PRECAUTIONS: Phenol, concentrated sulfuric acid, sodium dichromate, and NaOH are corrosive substances.
Avoid direct skin contact. Diethyl ether vapour is toxic, avoid inhalation.
1. Place 5 drops 1-butanol, 2-butanol, tert-butanol, phenol, diethyl ether, and each of the unknown samples on
separate dry test tubes. Prepare new set of samples for each of the test below:
a. Solubility in water add 5 drops of distilled to each sample. Shake and then observe solubility.
b. Solubility in NaOH add 5 drops of NaOH to each sample. Shake then observe solubility.
c. Bayers oxidation add 5 drops of Bayers reagent. Shake and observe the reaction.
d. Chromic acid oxidation add 5 drops of Na2Cr2O7 and 3 drops of conc. H2SO4. Observe the reaction.
e. Lucas test add 10 drops of Lucas reagent. Shake and observe the reaction for about 5-10 minutes.
f. Ferric chloride test add 5 drops of ferric chloride. Shake and observe the reaction.
2. Identify the unknown samples by comparing their solubility and reaction profile against that of the known
compounds
SCHEMATIC DIAGRAM

ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA.

ANA 2009
EXPERIMENT #5: ORGANIC DERIVATIVES OF WATER

DATA SHEET

ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA.

ANA 2009
EXPERIMENT #5: ORGANIC DERIVATIVES OF WATER
NAME:________________________________________________________________ SCORE:_________
SECTION:______ DATE PERFORMED:____________ INSTRUCTOR:_____________________________
A. Solubility and Reaction Profile (30pts)
Solubility in
H2O

Solubility
in NaOH

Bayers
oxidation

Chromic acid
oxidation

Lucas test

Ferric
chloride test

Visible + result
SAMPLES
Ethanol
2-Butanol
tert-Butanol
Phenol
Diethyl ether
Unknown 1
Unknown 2
Unknown 3
Legend: ++ fast reaction/completely soluble; + slow reaction/slightly soluble; - no reaction/insoluble
Identities of Unknown Samples
Sample 1:___________________________
Sample 2:___________________________
Sample 3:___________________________
B. Pertinent General Reactions (20 pts)
(1) Bayers oxidation:

(2) Chromic acid oxidation:

(3) Lucas test

ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA.

ANA 2009

(4) Ferric chloride test

C. Follow-up Questions and Applications (20 pts)

1. Explain why phenols are more acidic than comparable cyclic and acyclic alcohol and why is it resistant to weak
oxidizing agents? (3 pts)

2. What is the reason why tertiary alcohols cannot be oxidized? (2 pts)

3. Illustrate the mechanism for the nucleophilic substitution of tertiary alcohols with Lucas reagent. (5 pts)

4. Give some economic uses of alcohols, phenols, and ethers. (5 pts)

5. What are polyphenols and how do they protect against many degenerative disease such as cancer, Alzheimers
disease, and cardiovascular diseases? (5 pts)