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Epoxides: Introduction, Structure, Synthesis of Epoxide, Uses and Applications of Epoxides, Practice Problems and Frequently Asked Questions

Epoxides: Introduction, Structure, Synthesis of Epoxide, Uses and Applications of Epoxides, Practice Problems and Frequently Asked Questions

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Table of content:

  • Introduction of Epoxide
  • Structure of epoxide
  • Synthesis of epoxides
  • Uses and applications of epoxides
  • Practice problems
  • Frequently asked questions

Introduction of Epoxide:

Epoxides have three membered ring and one oxygen atom in the center. They are associated with high ring tension, which is the basis of their reactivity towards nucleophiles, despite the lack of a sufficient leaving group.

Although oxygen is a weak leaving group, the ring strain of the epoxide aids in the reaction's completion. The ring strain is caused by the geometry of the carbons not being appropriate, as the angle between them is 60o instead of 109.5o, as it should be for sp3-hybridized tetrahedral atoms.

Larger cyclic ethers would not be susceptible to acid-catalyzed or base-catalyzed cleavage under the same conditions as the three-membered epoxide ring because the ring strain is not as great.

Structure of epoxide:

One epoxide's basic structure consists of an oxygen atom linked to two neighboring hydrocarbon carbon atoms. The general ethers, on the other hand, can be thought of as a set of chemical molecules that contain an ether group. This group is made up of two alkyl or aryl groups linked by an atom of oxygen. In general, the formula is ROR', where R and R' denote the aryl or alkyl groups respectively. As a result, it may be determined that its fundamental structure has two hydrocarbon carbon atoms connected to an oxygen atom.

The cyclic ether with a three-atom ring is known as an epoxide. Now, because this ring approximates an equilateral triangle, it is strained and thus extremely reactive in comparison to other ethers. The oxidation of ethylene over a silver catalyst produces it.

Synthesis of epoxides:

1. Epoxidation of alkenes produces a more complex type of epoxide. Peroxy acid (RCO3H) is utilized to transfer an atom of oxygen in this procedure.

2. A two-step method is required for another key industrial route to epoxides. An alkene is transformed to a chlorohydrin, which is then treated with a base to remove hydrochloric acid and yield the epoxide; this is the procedure used to create propylene oxide.

3. Epoxide is generated when ethylene combines with oxygen in the presence of a silver catalyst. It can be chemically represented as:

 7 CH2=CH2+ 6 O2+Ag → 6 C2H4O+ 2 CO2+ 2 H2O

Uses and applications of epoxides:

  • Ethylene epoxide has numerous applications, including the production of surfactants and detergents.
  • Epoxides react with amines to form epoxy glues and structural materials.
  • It serves as a stabilizer in materials such as PVC. They are also used in the production of Epoxy resists with low viscosity while maintaining strength and physical properties.
  • Insecticides, aerosols, resins, and chemical intermediates are all made with epoxides.

Practice problems:

Q.1.  Which reagent is used as a suppressing agent in direct oxidation of ethylene?

(A) Ethylene oxide
(B) Ethylene chloride
(C) Ethylene dichloride
(D) Ethylene

Answer: (C)
Ethylene dichloride is used as a suppressing agent in direct oxidation of ethylene to suppress the side reaction which produces carbon dioxide and water instead of ethylene oxide.

Q 2. What is oxirane?

(A) Ethylene oxide
(B) Diethyl ether
(C) Ethylene glycolate
(D) None of the above

Answer: (A)
The IUPAC name for ethylene oxide is oxirane, which is represented as,

Q 3. What is the formula of peroxyacetic acid?

(A) CH3COOOH
(B) CH3COOH
(C) HCOOOH
(D) C6H5COOOH

Answer: (A)
The formula of peroxy acetic acid is CH3COOOH and it is used in the preparation of epoxides.

Q 4. Epoxy is 

(A) Acidic
(B) Basic
(C) Both acidic and basic
(D) None of the above

Answer: (B)
Epoxy is basic, the family of basic components or cured end products of epoxy resins is known as epoxy. Epoxy resins, also known as polyepoxides, are epoxide-containing reactive prepolymers and polymers. Epoxide functional groups are also referred to as epoxy. An oxirane is the IUPAC name for an epoxide group.

Frequently asked questions:

Q 1. What exactly do you mean when you say regioselective reactions?
Answer: In chemistry, regioselectivity refers to the preference for chemical bonding or breaking in one direction over all other potential directions. Because one product forms preferentially over another, the reaction is selective. Because it produces one constitutional isomer rather than the other, this reaction is regioselective.

Q 2. Why are epoxides chemically more reactive than simple ethers?
Answer: Because of ring strain, epoxides are much more reactive than simple ethers. Nucleophiles attack the electrophilic C of the C-O bond, breaking it and causing a ring opening. The ring strain is relieved by opening the ring.

Q 3. What is the reagent used in an epoxidation reaction?
Answer: The chemical reaction that converts the carbon–carbon double bond into oxiranes (epoxides) using a variety of reagents such as air oxidation, hypochlorous acid, hydrogen peroxide, and organic peracid is known as epoxidation.

Q 4. What is ring strain?
Answer: Ring strain is a type of instability in organic chemistry that occurs when bonds in a molecule form abnormal angles. Small rings, such as cyclopropanes and cyclobutanes, have internal angles that are significantly smaller than the idealized value of approximately 109o.

Related Topics:

Ethanoic acid

Methanol

Ethanol

Ethers-physical and chemical properties

Lucas test

Ethers-classification and preparations

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