Question

Give the isomers of \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\) that are ethers.

Short answer

The possible isomers of \(C_{4}H_{10}O\) that are ethers are Methoxypropane and Ethoxyethane.

Step-by-step solution

Knowing the structure of ethers

Ethers are organic compounds containing an oxygen atom bonded to two alkyl or aryl groups. They have the general formula \(R-O-R'\). Methyl, ethyl, propyl, and butyl are common alkyl groups. Here, R and R' could be the same or different.

Identifying possible structures

With the molecular formula \(C_{4}H_{10}O\), ethers can be arranged in the following ways: \n1. Methoxypropane (\(CH_{3}OCH_{2}CH_{2}CH_{3}\)) : This is a structure where methyl group (\(CH_{3}\)) is attached to a propane chain through an oxygen atom.\n2. Ethoxyethane (\(CH_{3}CH_{2}OCH_{2}CH_{3}\)): This structure consists of two ethyl groups (\(CH_{3}CH_{2}\)) attached through an oxygen atom.

Drawing and Naming the Isomers

Draw the structural formula for each possible isomer and assign proper IUPAC names. \n1. Methoxypropane: The IUPAC name is obtained from the alkyl group (Methoxy) and the number of carbon atoms in the longest carbon chain (Propane). \n2. Ethoxyethane: The name is derived from the two ethyl groups (Ethoxy) involved, connected by an oxygen atom.

Key concepts

Ether Structure

Understanding the structure of ethers is crucial in organic chemistry, as these compounds feature prominently in chemical synthesis and various applications. An ether is characterized by an oxygen atom connected to two alkyl groups. This functional group follows the general formula \( R-O-R' \), where \( R \) and \( R' \) represent alkyl or aryl chains which can be identical or different.

For example, in the molecular formula \( C_{4}H_{10}O \), different arrangements of carbon chains can lead to the formation of different ether structures. In methoxypropane, a single methyl group \( CH_{3} \) is bonded to a three-carbon chain through an oxygen atom, whereas, in ethoxyethane, two ethyl groups \( CH_{3}CH_{2} \) are bonded together by an oxygen atom. These structures demonstrate the variety of ways ether linkages can organize alkyl groups.

IUPAC Nomenclature

The IUPAC nomenclature of organic compounds is a systematic method of naming that provides unique and universally accepted names. For ethers, the name usually involves the alkyl groups attached to the oxygen atom followed by the term 'ether'.

The alkyl groups are named in ascending order of complexity, and the corresponding alkoxy group is determined by replacing the -yl ending of the alkyl group with -oxy. For instance, \( CH_{3}O- \) is named methoxy, and \( CH_{3}CH_{2}O- \) is called ethoxy. The IUPAC name of methoxypropane is derived from methoxy \( CH_{3}O- \) and propane \( CH_{2}CH_{2}CH_{3} \), while ethoxyethane is named from ethoxy \( CH_{3}CH_{2}O- \) and ethane \( CH_{3}CH_{3} \). These names not only specify the compounds’ structures but also help in predicting their chemical properties and reactivity.

Organic Chemistry

Organic chemistry is the branch of chemistry that deals with the study of carbon-containing compounds and their reactions. It encompasses a vast array of substances including hydrocarbons, alcohols, acids, and ethers. The versatility of carbon atoms to form stable bonds with other carbon atoms and elements like hydrogen, oxygen, and nitrogen leads to the formation of a diverse range of organic molecules.

Understanding isomerism, such as that observed in the different arrangements of \( C_{4}H_{10}O \) ethers, is a fundamental concept within organic chemistry. Isomers are compounds with the same molecular formula but different structures, and thus different properties. The ability to discern and name these isomers correctly is essential for students to grasp the complexity and beauty of organic molecules.

Alkyl Groups

Alkyl groups are fundamental constituents of organic molecules. An alkyl group is a hydrocarbon group that has had one hydrogen atom removed, allowing it to bond to other atoms. Some common examples are methyl \( CH_{3}- \) and ethyl \( CH_{3}CH_{2}- \).

In the context of ethers, these groups are attached to an oxygen atom. The variety of alkyl group combinations affects the physical and chemical properties of the resulting ether. For instance, methoxypropane and ethoxyethane have different boiling points and solubilities due to their differing alkyl groups. Recognizing these subtleties aids students in understanding larger concepts in organic chemistry, such as reactivity and molecular interactions.