Simone Lawson
Butane is a highly flammable gas with the molecular formula C₄H₁₀. It has two structural isomers, also known as constitutional isomers: n-butane and isobutane (2-methylpropane). These isomers have the same molecular formula but different structural arrangements of atoms, which results in distinct chemical and physical properties. The phenomenon of isomerism is an important concept in organic chemistry, with two main types: structural isomerism and stereoisomerism or spatial isomerism. This question specifically focuses on identifying the constitutional isomer of butane from a list of options, highlighting the importance of understanding isomerism in chemistry.
| Characteristics | Values |
|---|---|
| Constitutional isomer of butane | 2-methylpropane (also known as isobutane) |
| Molecular formula of butane | C₄H₁₀ |
| Molecular formula of 2-methylpropane | C₄H₁₀ |
| Structural difference | Butane is unbranched, 2-methylpropane is branched with a central carbon atom connected to three other carbon atoms |
| Number of covalent bonds | 13 |
| Types of isomerism | Structural or constitutional isomerism, stereoisomerism or spatial isomerism |
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What You'll Learn
What is a constitutional isomer?
Constitutional isomers are compounds that have the same molecular formula but different structural arrangements of atoms. In other words, they are molecules with the same molecular formula but different structural formulas or connectivity of atoms. For example, n-butane and isobutane (2-methylpropane) are constitutional isomers of butane. N-butane is a straight-chain compound with four carbon atoms bonded with single covalent bonds, while isobutane has three carbon atoms from the parent chain and one carbon atom placed as the side chain at C-2 of the parent chain. This structural difference leads to varying properties despite having the same molecular formula (C4H10).
Constitutional isomers can also be referred to as chain isomers or skeletal isomers, as they involve different arrangements of the skeleton of the molecule. This type of isomerism commonly arises in organic compounds containing long carbon chains. For example, pentane can be rearranged in three different ways, resulting in three different chain isomers: N-pentane, isopentane, and neopentane. N-pentane has a five-membered carbon chain with no branching, isopentane has a four-membered parent chain that branches in the second position, and neopentane has a three-membered parent chain that branches twice from the second position.
Another example of constitutional isomerism is functional isomerism, which occurs when the atoms are connected differently. For instance, 1-hexene and cyclohexane share the same molecular formula, but 1-hexene has a straight-chain structure with one carbon-carbon double bond, while cyclohexane has a cyclic structure with no carbon-carbon double bonds.
Constitutional isomerism is a fundamental concept in organic chemistry, and it is important to distinguish it from stereoisomerism or spatial isomerism. While constitutional isomers have different bonding arrangements between atoms, stereoisomers have the same bonds but differ in the relative positions of the atoms. Stereoisomers can be further classified into conformational isomers, which differ in their conformation or spatial configuration of atoms due to rotation around a sigma bond. For example, butane can exhibit conformational isomerism through rotation around the C-C single bond, resulting in eclipsed, gauche, and anti conformations.
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What is butane?
Butane is a hydrocarbon and a highly flammable, colourless, odourless, easily liquefied gas. It has the molecular formula C₄H₁₀. Butane was identified as a component of gasoline in the 1910s by W. Snelling, who found that it could be stored in a volume-reduced liquified state in pressurized containers. It is one of the most produced industrial chemicals, with around 80-90 billion lbs produced by the United States annually.
Butane has several applications across various industries. It is commonly used as a fuel for cigarette lighters, portable stoves, and cooking, barbecues, and camping stoves. Butane is also utilized as a propellant in aerosols, a heating fuel, and a refrigerant. Additionally, it plays a crucial role in the manufacture of a diverse array of products, including synthetic rubber and fragrances.
In organic chemistry, the concept of isomerism is significant. Isomerism occurs when two or more compounds share the same molecular formula but exhibit different properties due to variations in the arrangement of atoms. Butane has several isomers, including n-butane and isobutane or 2-methylpropane. N-butane, or normal butane, is a straight-chain compound with four carbon atoms bonded by single covalent bonds. On the other hand, isobutane, or 2-methylpropane, has three carbon atoms from the parent chain and one carbon atom as a side chain at the C-2 position. These isomers of butane differ in their structural arrangement, resulting in distinct physical and chemical properties.
The harmful effects of butane inhalation have been well-documented. Butane gas can lead to "sudden sniffing death," caused by cardiac arrhythmia or cardiac arrest, especially if the person is stressed or engages in heavy exercise during or shortly after exposure. Additionally, high levels of butane inhalation within a short period can lead to depressed breathing and loss of consciousness. Butane misuse has been associated with accidents, injuries, and risks taken while intoxicated.
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What are the isomers of butane?
Butane has the molecular formula C₄H₁₀. It has two isomers: n-butane and isobutane (2-methylpropane).
N-butane is a straight-chain compound with four carbon atoms bonded by single covalent bonds. Isobutane, on the other hand, has three carbon atoms from the parent chain and one carbon atom placed as a side chain at C-2 of the parent chain. This structural difference leads to varying properties despite having the same molecular formula.
Conformational isomers are isomers that differ in their conformation or spatial arrangement. Butane has four conformational isomers: eclipsed, gauche, skew, and anti. The eclipsed conformation is unstable because identical groups are directly in line with one another. The gauche conformation is more stable than the eclipsed conformation due to less steric hindrance between the same molecules. The anti conformation is the most stable form, where identical groups are 180 degrees from one another.
Constitutional isomers, also known as structural isomers, are compounds that have the same molecular formula but different structural formulas. In the context of butane, 2-methylpropane is its constitutional isomer. This is because 2-methylpropane has a branched chain, with one carbon atom in the centre bonded to three other carbon atoms, whereas butane contains an unbranched chain.
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How do you identify constitutional isomers?
Constitutional isomers, also known as structural isomers, are compounds that have the same molecular formula but different structural formulas or bonding arrangements. In other words, they have the same number and type of atoms but differ in how these atoms are connected. To identify constitutional isomers, follow these steps:
First, determine the molecular formula of the compound in question. This will ensure that you are only dealing with potential isomers, as constitutional isomers must have identical molecular formulas. For example, butane has the molecular formula C₄H₁₀.
Next, examine the structural formula, which illustrates how the atoms are bonded and arranged in the molecule. This will allow you to identify differences in the connectivity of atoms and determine if the compounds are indeed constitutional isomers. For instance, in n-butane, all carbon atoms are in a straight chain, whereas isobutane, or 2-methylpropane, has a side chain attached to the parent chain. This structural difference results in distinct properties, despite the shared molecular formula.
Additionally, you can calculate the HDI (unsaturation index) value, which is based on the combination of cycles and double or triple bonds in the molecule. Constitutional isomers with the same molecular formula will also have identical HDI values. This can be a useful tool for predicting structural motifs and drawing various constitutional isomers.
It is important to note that the number of possible constitutional isomers increases exponentially with the number of atoms in the molecule. Therefore, larger molecules may have numerous isomers, adding complexity to the identification process.
In summary, to identify constitutional isomers, begin by confirming that the compounds share the same molecular formula. Then, analyze their structural formulas, paying close attention to the bonding arrangements and connectivity of atoms. Finally, you can utilize the HDI value to further support your identification of constitutional isomers.
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What are conformational isomers?
Conformational isomers, also known as rotamers or conformers, are different spatial arrangements of atoms within a molecule that can be converted into one another by rotation around a single bond. In other words, conformational isomers are different shapes or conformations of the same molecule. This phenomenon is known as conformational isomerism or conformerism.
Conformational isomers have the same molecular formula and bond connectivity but differ in their energy levels and spatial arrangement of atoms. The energy barriers required to change one conformational isomer to another are usually low, allowing for the interconversion of conformational isomers at room temperature. This rotation is due to the free rotation about C-C single bonds in alkanes, which results in different spatial arrangements of carbon and hydrogen atoms.
For example, in ethane ($CH_3-CH_3$), rotating one carbon atom while keeping the other stationary results in an infinite number of spatial arrangements of hydrogen atoms. These arrangements are known as conformational isomers. Two extreme orientations are the eclipsed and staggered conformations. In the eclipsed conformation, the hydrogens on the forward carbon are directly in front of those on the back carbon, resulting in higher instability due to repulsive forces between electron clouds. In the staggered conformation, the hydrogens on the forward carbon are positioned between the hydrogens on the back carbon, resulting in greater stability due to the maximum separation between electron clouds.
Another example is butane, which has eclipsed, gauche, and anti conformational isomers. In the anti form, both methyl groups of butane are in the anti position, making it one of the most stable forms. The gauche form, also known as the skew conformation, is another possible isomer.
Conformational isomerism is a fundamental concept in organic chemistry, particularly in the study of alkanes, which frequently exhibit conformational isomerism due to the presence of C-C bonds.
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Frequently asked questions
Constitutional isomers, also known as structural isomers, are compounds that have the same molecular formula but different structural formulas.
Butane isomers include n-butane and isobutane.
In n-butane, all carbon atoms are in a straight chain, whereas isobutane has a side chain in the molecule.
2-methylpropane is a constitutional isomer of butane.
