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APPLIED CHEM. Module 4

2ND QUARTER

Department of Education
Region XII
KIDAPAWAN CITY DIVISION
JP Laurel St. Kidapawan City
 KIDAPAWAN CITY NATIONAL HIGH SCHOOL- STE PROGRAM

Self-Learning Module in Applied Chemistry

Quarter 2/ Module 4

Name: ________________________ Grade and Section______________

Subject Teacher: _____________________ LRN_____________________

I. OBJECTIVES:
1. Define ethers.
2. Classify ethers as simple or mixed.
3. Give the common and IUPAC name of some ethers.
4. Describe the processes used in the preparation of erhers.

II. SUBJECT MATTER/ TOPIC

➢ The Ethers

III. LEARNING RESOURCES

Compiled Organic Chemistry book
Media/ Internet Sources (www.google.com)

IV. PROCEDURE

Lesson 1

DEFINITION
Ethers are a class of organic compounds that contain an oxygen between two alkyl groups.
They have the formula R-O-R', with R's being the alkyl groups. They are considered as alkyl
oxides or anhydrides of alcohols.

Lesson 2
CLASSIFICATION OF ETHERS

Ethers can be classified into two varieties: if the alkyl groups are the same on both sides of
the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers
are called mixed or unsymmetrical ethers.

Examples:
A. Simple or symmetrical ether
O
or
H5C2 C2H5
Dimethyl ether Diethyl ether

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 B. Mixed or unsymmetrical ether
O
O
or or H3C C6H5
H3C C2H5
Ethyl methyl ether Methyl phenyl ether

Lesson 3
NOMENCLATURE OF ETHERS

The nomenclature of ethers rotates around two standard ways of naming, which are given
below.
• Common nomenclature of ethers
• IUPAC nomenclature of ethers

RULES IN NAMING ETHERS

• The common ether nomenclature follows the rule of naming different alkyl/aryl groups that
are attached in alphabetical order to the oxygen atom on either side and adding the word
ether to it finally.
For example, naming CH3OC6H5 is given by “Methyl phenyl ether.”
• The oxygen atoms of ethers attached to the same group on either side are named using
Greek numerical prefixes like “di.” Ethers of these kinds are named by adding the suffix “di”
before the aryl/alkyl groups, attached to the oxygen atom.
For example, CH3OCH3 is named as “Dimethyl ether.”
• IUPAC nomenclature of ethers follows various guidelines. As per the IUPAC naming, a
substituent group having more carbon atoms is chosen as parent hydrocarbon. Whereas,
the other substituent group attached to the same oxygen atom is named by using a prefix
“oxy.”
For example, CH3OC2H5 is named as “1-methoxy ethane.”

IUPAC NOMENLATURE OF ETHERS

ALKYL GROUP NAME ALKOXY GROUP NAME

CH3 Methyl CH3O Methoxy
CH3CH2 Ethyl CH3CH2O Ethoxy
CH3CH Isopropyl CH3CHO Isopropoxy
(CH3)3C tert-butyl (CH3)3CO Tert-Butoxy
C6H5 Phenyl C6H5O Phenoxy

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EXAMPLES:

FORMULA COMMON NAME IUPAC NAME

CH3-O-CH3 Methyl ether or dimethyl ether Methoxy methane

CH3-O-C2H5 Ethyl methyl ether Methoxy ethane
C2H5-O-C2H5 Ethyl ether or diethyl ether Ethoxy ethane

Lesson 4
PREPARATION OF ETHERS

1. For Simple Ethers

➢ Dehydration of Alcohols – this is sometime called continuous etherification process.
Ethyl ether or sulfuric ether or simply ether is prepared in the laboratory by dehydration
of ethyl alcohol by concentrated sulfuric acid at 1400C. The temperature must be carefully
controlled as ethylene might be formed at higher temperature. This reaction takes place in
the presence of excess ethyl alcohol.
1400C
Equation: 2 C2H5OH C2H5-O-C2H5 + H2O
Ethyl alcohol Conc. H2SO4 Ethyl ether

2. For Mixed ethers

➢ Williamson Synthesis – This is the reaction between an alkyl halide and an alkoxide forming
an ether.

Equation: R-X + R-ONa R-O-R + Na-X

Alkyl halide Alkoxide Mixed ether

Example: C2H5-Br + CH3-ONa CH3-O-C2H5 + NaBr

Bromoethane Sodium methoxide Ethyl methyl ether Sodium, bromide

Lesson 5
PROPERTIES OF ETHERS

A few low molecular-weight ethers are gases, like methyl ether, and the rest are colorless
liquids or solids with characteristic odor or pleasant odor in many instances. They have boiling points
close to those of hydrocarbons of comparable molecular weight and lower than the values of the
alcohols. Ethers have greater solubility in water than hydrocarbons.

Ethyl ether is a clear, colorless mobile liquid with a pleasant characteristic odor and a burning
sweetish taste. It is slightly miscible in water but soluble in alcohol and other organic solvents. Ether
and its vapors are highly inflammable. Its boiling point is 34.50C which is lower than the boiling point

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of alcohols with similar molecular mass. It is extremely volatile. When dropped in the hand it
produces a cooling sensation due to its rapid evaporation.

Lesson 6
USES OF SOME ETHERS

1. Diethyl ether is the most commonly used general anesthetic. It causes excellent relaxation of
muscles and has little depressing effect on blood pressure, pulse or respiration. The main
objection to its use is the nauseating after-effects and the irritating effects on respiratory passages.
Because its vapors are very flammable, great care must be taken in operating rooms to eliminate
all possibilities of sparks.
Ethyl ether is an excellent solvent for fats, resins, oils, waxes and alkaloids. It is also used for
removing adhesive tape because of its solvent power. It is also used as a carminative in medicine.
2. Divinyl ether or vinethene is a new ether rapidly coming into prominence as an excellent general
anesthetic for short anesthesia. It is often used in bone setting. Its advantages are the pleasant,
rapid induction and recovery and the good relaxation it produces. Its disadvantages are the
marked stimulation of secretion of mucous and saliva and the possibility of liver damage in
prolonged cases.
3. Methyl propyl ether or metopryl, CH3-O-C3H7, has been found to be more potent and less irritating
anesthetic than ethyl ether.

ACTIVITIES:

Activity 1:
Classify the following ethers as simple or mixed.

STRUCTURAL FORMULA CLASSIFICATION

(Simple or Mixed)

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Activity 2

Give the common name and IUPAC name of the ethers on Table 2. Choose your answer from
table 1 below.

Table 1
COMMON NAME IUPAC NAME
• Cyclopentyl methyl ether • 2-methyl-2-methylpropane
• Ethyl methyl ether • Methyl cyclohexane
• Diethyl ether • Methoxy cyclopentane
• Cyclohexyl methyl ether • Methoxy ethane
• Methyl-tert-butyl ether • Ethoxy ethane

Table 2
STRUCTURAL FORMULA OF COMMON NAME IUPAC NAME
ETHERS

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Activity 3

Complete the following equations for Williamson Ether Synthesis by giving the products.

1. C2H5-ONa + C2H5-Cl +
Sodium ethoxide Chloroethane Name: Name:

2.
C2H5-ONa + C3H7-F +
f
Sodium ethoxide Fluoropropane Name: Name:

ASSESSMENT

Multiple Choice.

Each item has four (4) choices A, B C and D. Choose the letter of the correct answer and
write it on your answer sheet.

1. Which of the following molecules react in Williamson Ether Synthesis?

A. ether and alkoxide C. alkyl halide and alkoxide
B. alkyl halide and alcohol D. alcohol and alkoxide

2. Which of the following is the formula type of ether?

A. R-OH B. R-O-R C. R-CHO D. R-CO-R

3. Dimethyl ether is classified as simple or symmetrical ether. Which of the following formulas
represent Dimethyl ether?
A. CH3-O-CH2 B. CH3-O-C2H5 C. CH3-O-CH3 D. C2H5-O-C3H7

4. Which of the following is an example of mixed or unsymmetrical ether?

A. Dimethyl ether B. Ethyl ether C. ethyl methyl ether D. methoxy methane

5. What substance serves as catalyst in the dehydration of alcohols to produce simple ether?
A. Sulfuric acid B. Sulfur dioxide C. Hydrochloric acid D. acid-dichromate

6. What is the name of this ether? CH3 CH2 CH2 O CH3

A. ethyl methyl ether C. ethyl propyl ether

B. methyl propyl ether D. methyl pentyl ether

7. What substance reacts with chloroethane to form diethyl ether?

A. H2SO4 B. NaOH C. Na2SO4 D. C2H5Ona

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8. Which of the following statements is true?
A. The boiling point of ethers is lower than the boiling point of alcohols of comparable
molecular mass.
B. The boiling point of ethers is similar to the boiling point of alcohols of comparable
molecular mass.
C. The boiling point of ethers is little higher than the boiling point of alcohols of comparable
molecular mass.
D. The boiling point of ethers is much higher than the boiling point of alcohols of comparable
molecular mass.

9. What is the IUPAC name of ethyl methyl ether?

A. ethoxy ethane C. methoxy propane
B. methoxy ethane D. ethoxy propane

10. Which of the following statements about ethers is incorrect?

A. Ethers are flammable
B. Ethers form peroxides by free radical oxidation
C. Ethers are widely used as extraction solvents
D. An ether oxygen can only be found within an acyclic carbon chain