**Prepared by Nimona**

### Ethers: Structure, Properties, and Preparation

#### Structure of Ethers

- **Definition**: Ethers are organic compounds where an oxygen atom is bonded to
two alkyl or aryl groups (R−O−R’).
- **Symmetrical Ethers**: When both substituents (R and R’) are the same.
- **Unsymmetrical Ethers**: When the substituents are different.

#### Nomenclature of Ethers

- **Common Names**: Consist of the names of the alkyl substituents (in alphabetical
order), followed by "ether".
- Examples: diethyl ether, ethylisopropyl ether, ethylmethyl ether.
- **IUPAC Names**: Ethers are named as alkanes with an RO− substituent.
- The substituent is named by replacing the “yl” ending of the alkyl group with
“oxy”.

#### Physical Properties of Ethers

- **Polarity**: Ethers are polar compounds due to the partial negative charge on
the oxygen and partial positive charges on the carbons bonded to oxygen.
- **Boiling Points**: Ethers have lower boiling points than alcohols of comparable
molecular weight due to the lack of intermolecular hydrogen bonding.
- Example: Ethanol (78 °C) vs. Dimethyl ether (-24 °C).
- **Comparison with Hydrocarbons**: Ethers have higher boiling points and greater
solubility in water than hydrocarbons of similar molecular weight and shape due to
their ability to form hydrogen bonds with water.

#### Preparation of Ethers

1. **Dehydration of Alcohols**
- **Process**: Alcohols are dehydrated in the presence of protic acids (e.g.,
sulfuric acid or phosphoric acid) to form ethers.
- **Example**: Ethanol is dehydrated to ethene at 170 °C with sulfuric acid, or
to ethoxyethane (diethyl ether) at 140 °C.
- **Limitations**: This method is mainly effective with primary alcohols.
Secondary and tertiary alcohols tend to undergo elimination reactions leading to
alkenes.
- **Symmetry Consideration**: The method works well for symmetrical ethers;
unsymmetrical ethers are more challenging to synthesize due to possible side
reactions.

2. **Williamson Ether Synthesis**

- **Process**: An alkyl halide reacts with an alkoxide ion to form an ether.
- **Versatility**: This method is suitable for both symmetrical and
unsymmetrical ethers.
- **Equation**: RO⁻ + R'X → ROR' + X⁻

#### Chemical Properties of Ethers

- **Inertness**: Ethers are generally resistant to reactions with oxidizing agents
(e.g., K₂Cr₂O₇ or KMnO₄) and bases.
- **Reactions with Acids**: Ethers can react with strong acids (HI, HBr, H₂SO₄) to
cleave the ether linkage, forming alkyl halides or alcohols.
- **Oxonium Salts Formation**: Ethers can form oxonium salts when reacting with
proton donors.
- **Solvent Properties**: Due to their chemical inertness and good solvent
properties, ethers are commonly used as solvents in organic reactions.

#### Common Uses of Ethers

1. **Medicine**: Ethers are used as anesthetics (e.g., diethyl ether) due to their
volatility and effectiveness in inducing unconsciousness.
2. **Industry**: Ethers serve as solvents in various chemical reactions,
extractions, and formulations due to their non-reactivity with many reagents.

#### Preparation of Alkoxide Ions for Williamson Ether Synthesis

- **Chemical Equation**: An alkoxide ion is typically prepared by reacting an
alcohol with a strong base (e.g., sodium or potassium).
- Example: ROH + Na → RO⁻Na⁺ + 1/2 H₂

#### Exercise 6.5

1. **Common Uses of Ethers**:
- **Medicine**: Anesthetics, antiseptics.
- **Industry**: Solvents in organic synthesis, extraction solvents, fuel
additives.
2. **Preparation of Alkoxide Ion**:
- **Equation**: \( ROH + Na \rightarrow RO^-Na^+ + 1/2 H_2 \)
- This reaction involves the deprotonation of an alcohol by a metal like sodium
to form the corresponding alkoxide ion and hydrogen gas.

### Final Test Questions on Ethers

#### Part A: Multiple Choice Questions

1. **Which of the following is a symmetrical ether?**

- a) Diethyl ether
- b) Ethyl methyl ether
- c) Ethyl isopropyl ether
- d) None of the above

2. **What is the IUPAC name for the compound commonly known as ethyl methyl ether?
**
- a) Methoxyethane
- b) Ethoxymethane
- c) Methylethyl ether
- d) Ethylmethoxy

3. **Why do ethers generally have lower boiling points compared to alcohols of

similar molecular weight?**
- a) Ethers are nonpolar compounds.
- b) Ethers cannot form hydrogen bonds with each other.
- c) Ethers have higher molecular weights.
- d) Ethers have stronger intermolecular forces.

4. **Which method can be used to synthesize both symmetrical and unsymmetrical

ethers?**
- a) Dehydration of alcohols
- b) Williamson ether synthesis
- c) Both a and b
- d) Neither a nor b

#### Part B: Short Answer Questions

1. **Explain the main difference in boiling points between ethanol and dimethyl
ether.**

2. **Describe the general structure of ethers and explain how symmetrical and
unsymmetrical ethers differ.**
3. **Outline the preparation of ethoxyethane using ethanol, including the reaction
conditions required.**

4. **Discuss the role of ethers as solvents in organic reactions and why they are
preferred over other solvents.**

#### Part C: Long Answer Questions

1. **Compare and contrast the dehydration of alcohols and Williamson ether

synthesis as methods for preparing ethers. Include a discussion on the limitations
of each method.**

2. **Provide a detailed explanation of the preparation of an alkoxide ion for the

Williamson ether synthesis. Include the chemical equation and describe the type of
reaction that occurs.**

3. **Ethers are described as inert compounds. Discuss the chemical reactions they
can undergo, particularly with strong acids, and explain the implications of these
reactions in practical applications.**

### Answer Key

#### Part A: Multiple Choice Questions

1. **a) Diethyl ether**

2. **a) Methoxyethane**
3. **b) Ethers cannot form hydrogen bonds with each other.**
4. **b) Williamson ether synthesis**

#### Part B: Short Answer Questions

1. **Ethanol has a higher boiling point than dimethyl ether due to the presence of
a polar O−H group in ethanol, which allows for intermolecular hydrogen bonding.
Dimethyl ether lacks this O−H group and cannot form hydrogen bonds, resulting in a
significantly lower boiling point.**

2. **Ethers have a general structure of R−O−R’, where an oxygen atom is bonded to

two alkyl or aryl groups. In symmetrical ethers, both groups (R and R’) are the
same, while in unsymmetrical ethers, the groups are different.**

3. **Ethoxyethane (diethyl ether) can be prepared by dehydrating ethanol in the

presence of sulfuric acid at 140 °C. The reaction is as follows:**
\[ 2 CH_3CH_2OH \xrightarrow{H_2SO_4, 140°C} CH_3CH_2OCH_2CH_3 + H_2O \]

4. **Ethers are preferred as solvents in organic reactions due to their inertness,

meaning they do not react with most reagents at moderate temperatures. This
property allows them to dissolve reactants without participating in the reactions,
ensuring that the desired chemical transformations proceed without interference.**

#### Part C: Long Answer Questions

1. **Dehydration of alcohols involves heating an alcohol with a protic acid to form

an ether. This method is limited to primary alcohols and often results in
symmetrical ethers. Secondary and tertiary alcohols tend to form alkenes under
these conditions. The Williamson ether synthesis, on the other hand, involves the
reaction of an alkyl halide with an alkoxide ion and can be used to form both
symmetrical and unsymmetrical ethers. However, it requires careful selection of
reactants to avoid side reactions.**
2. **An alkoxide ion for the Williamson ether
an alcohol with a strong base such as sodium.
\[ ROH + Na \rightarrow RO^-Na^+ + 1/2 H_2
**This reaction involves the deprotonation
alkoxide ion and hydrogen gas.**
synthesis can be prepared by reacting
The reaction proceeds as follows:**
\]
of the alcohol by sodium, forming the

3. **Ethers are generally inert and do not react with most reagents, including
oxidizing agents and bases. However, they can react with strong acids such as HI,
HBr, and H₂SO₄, leading to cleavage of the ether linkage and formation of alkyl
halides or alcohols. This reactivity with strong acids can be exploited in certain
synthetic applications but also means that ethers must be handled carefully to
avoid unwanted reactions in the presence of these acids.**