Omar Bennett
Chlorination is an organic reaction involving the replacement of a loosely held hydrogen atom by a chlorine atom. When considering the monochlorination of propane, there are two possibilities: chlorination at C-1 or C-2. These two products, 1-chloropropane and 2-chloropropane, are constitutional isomers. Similarly, when determining the constitutional isomer of C6H14 that gives only two monochlorination products, the unique structural arrangement of atoms must be considered. The isomer that results in two monochlorination products is 2-methylpropane, also known as 2,2-dimethylbutane. This is because there are only two unique types of hydrogen atoms that can be replaced by chlorine atoms, resulting in different monochlorination products.
| Characteristics | Values |
|---|---|
| Constitutional isomer of C6H14 that gives only two monochlorination products | 2,2-Dimethylbutane |
| Other possible isomers | 2,3-Dimethylbutane, 2-Methylpentane, 3-Methylpentane |
| Reason for 2,2-Dimethylbutane having only two monochlorination products | Only two unique types of hydrogen atoms that can be replaced by chlorine |
| Other names for 2,2-Dimethylbutane | Neopentane, 2,2-Dimethylpropane |
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What You'll Learn
- The constitutional isomer of C6H14 that gives two monochlorination products is 2,2-dimethylbutane
- ,2-dimethylbutane has two types of hydrogen atoms that can be replaced by chlorine
- The two types of hydrogen atoms in 2,2-dimethylbutane are on the central carbon and methyl groups
- The other isomers of C6H14 have multiple types of hydrogen, resulting in more chlorination products
- Constitutional isomers have the same molecular formula but differ in the arrangement of atoms
The constitutional isomer of C6H14 that gives two monochlorination products is 2,2-dimethylbutane
The molecular formula C6H14 represents hexane and its isomers. There are five constitutional isomers with this formula, and when treated with chlorine, they yield varying numbers of monochlorination products. For instance, isomer A gives two monochlorination products, isomer B gives five, isomer C gives four, and isomer D gives three.
The constitutional isomer of C6H14 that gives only two monochlorination products is 2,2-dimethylbutane. This is because 2,2-dimethylbutane has only two unique types of hydrogen atoms that can be replaced by a chlorine atom to give different monochlorination products. One type is the hydrogen on the central carbon atom, and the other is the hydrogen on the methyl groups. Since all the methyl groups are equivalent, replacing any of these hydrogens gives the same product. Similarly, since the two central carbon atoms are equivalent, they also yield the same product upon chlorination.
Other isomers of C6H14, such as 2,3-dimethylbutane, 2-methylpentane, and 3-methylpentane, have multiple types of hydrogen atoms available for substitution, leading to several possible monochlorination products when reacted with chlorine. These isomers have three unique sets of hydrogen atoms that can participate in halogenation, resulting in three different monochlorination products.
In summary, the unique structural arrangement of atoms in 2,2-dimethylbutane, with its limited types of replaceable hydrogen atoms, is why it gives only two monochlorination products, setting it apart from other isomers of C6H14.
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2,2-dimethylbutane has two types of hydrogen atoms that can be replaced by chlorine
The monochlorination of butane typically yields two constitutional isomers: 1-chlorobutane and 2-chlorobutane. However, the constitutional isomer 2,2-dimethylbutane has a unique structure that allows for only two monochlorination products.
The molecule 2,2-dimethylbutane is a branched alkane, with a base structure of butane and two methyl (CH3) groups attached to the second carbon atom in the chain. This results in six hydrogen atoms attached to the terminal methyl groups and three hydrogen atoms attached to the central carbon atom. When heated with chlorine, 2,2-dimethylbutane undergoes a free radical substitution reaction, where the hydrogen atoms are replaced by chlorine atoms.
Due to the symmetrical structure of 2,2-dimethylbutane, there are essentially two types of hydrogen atoms that can be replaced by chlorine: those on the CH3 groups and the one on the central carbon atom. This leads to the formation of two distinct products. If a hydrogen atom from one of the terminal CH3 groups is substituted with chlorine, the product is 2-chloro-2,2-dimethylbutane. On the other hand, if the hydrogen atom from the central carbon is replaced, the product is 2-chloro-2-methylbutane.
The symmetry of 2,2-dimethylbutane reduces the number of unique structures that can be formed during the reaction. As a result, only two distinct radical substitution products are possible, showcasing the principles of radical substitution. This reaction illustrates how different reactants can lead to distinct structures, depending on which hydrogen atoms are replaced by chlorine.
In summary, 2,2-dimethylbutane has two types of hydrogen atoms that can be replaced by chlorine due to its symmetrical structure. This results in two possible monochlorination products, making it unique compared to other butane isomers.
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The two types of hydrogen atoms in 2,2-dimethylbutane are on the central carbon and methyl groups
The constitutional isomer of C6H14 that gives rise to only two monochlorination products is 2,2-dimethylbutane. This is because it has only two distinct types of hydrogen atoms that can be replaced by chlorine atoms. These two types of hydrogen atoms are found on the central carbon atom and the methyl groups.
Let's break down the structure of 2,2-dimethylbutane to understand this further. 2,2-dimethylbutane is a branched alkane, with a base structure of butane, which consists of a straight chain of four carbon atoms (C1-C2-C3-C4). To this structure, we add two methyl (CH3) groups attached to the second carbon atom (C2), resulting in the molecular formula C6H14. So, the structure looks like this: CH3 | CH3 - C2 - C3 - C4 | CH3.
Now, let's focus on the two types of hydrogen atoms in 2,2-dimethylbutane. One type is the hydrogen atom attached to the central carbon atom (C2). The other type is the hydrogen atoms found within the methyl groups (CH3) attached to the central carbon. When 2,2-dimethylbutane undergoes chlorination, these two types of hydrogen atoms can be replaced by chlorine atoms, resulting in two possible monochlorination products.
The uniqueness of 2,2-dimethylbutane compared to other isomers of C6H14, such as 2,3-dimethylbutane, lies in the equivalence of its hydrogen atoms. In 2,3-dimethylbutane, there are multiple types of hydrogen atoms available for substitution, leading to a variety of monochlorination products. However, in 2,2-dimethylbutane, the equivalence of the hydrogen atoms on the central carbon and the methyl groups results in only two distinct monochlorination products, regardless of which specific hydrogen atom is replaced within each group.
In summary, the two types of hydrogen atoms in 2,2-dimethylbutane, found on the central carbon atom and the methyl groups, are key to understanding why this isomer of C6H14 yields only two monochlorination products. This uniqueness arises from the equivalence of these hydrogen atoms, making 2,2-dimethylbutane stand out among other isomers of hexane.
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The other isomers of C6H14 have multiple types of hydrogen, resulting in more chlorination products
The molecular formula C6H14 represents hexane and its isomers. Hexane has five structural isomers: hexane, 2-methylpentane, 3-methylpentane, 2,2-dimethylbutane, and 2,3-dimethylbutane. Each of these isomers has a different arrangement of atoms, resulting in different types of hydrogen atoms available for substitution.
The number of unique monochlorination products formed is determined by the number of unique types of hydrogen atoms present in the molecule. Isomers with multiple types of hydrogen atoms will result in multiple chlorination products. For example, 2,3-dimethylbutane has three types of hydrogen atoms, leading to three distinct monochlorination products. Similarly, 2-methylpentane and 3-methylpentane also contain various hydrogen atoms that can give rise to multiple chlorination products.
On the other hand, 2,2-dimethylbutane is unique among the isomers of C6H14 because it has only two different types of hydrogen atoms. One type is the hydrogen on the central carbon atom, and the other is the hydrogen on the methyl groups. Since all the methyl groups are equivalent, replacing any of these hydrogens results in the same product. Similarly, since the two central carbon atoms are equivalent, they also yield the same product upon chlorination. Therefore, 2,2-dimethylbutane gives only two unique monochlorination products.
The relationship between the structure of an isomer and the products formed during chlorination is well-understood in organic chemistry. By analyzing the number of equivalent hydrogen sets in each isomer, we can predict the number of distinct chlorinated products that will be formed. This understanding is crucial in predicting the outcomes of substitution reactions and the chemical properties of different isomers.
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Constitutional isomers have the same molecular formula but differ in the arrangement of atoms
Isomers are two or more molecules that share the same molecular formula but differ in the arrangement of atoms. There are two types of isomers: constitutional isomers and stereoisomers. Constitutional isomers have the same molecular formula but differ in the way atoms are connected, whereas stereoisomers have the same connectivity but differ in their arrangement in space.
An example of constitutional isomers having the same molecular formula but differing in the arrangement of atoms is the case of 1-chloropropane and 2-chloropropane. These two isomers are formed when a single hydrogen on propane is replaced by chlorine. The only two possibilities for chlorination are C-1 or C-2 (chlorination at C-3 would produce the same product as C-1). These two products, 1-chloropropane and 2-chloropropane, are constitutional isomers with the same molecular formula (C3H7Cl) but a different arrangement of atoms.
Another example is the set of molecules with the molecular formula C6H12. There is only one way to connect the atoms to form cyclohexane and 1-hexene, respectively. However, there are two ways to connect the atoms to form 2-hexene and 3-methyl-1-pentene, and four ways to connect them to form 1-ethyl-2-methylcyclopropane. These molecules are all constitutional isomers of each other, with the same molecular formula but different arrangements of atoms.
Constitutional isomers can have the same or different functional groups. For instance, ethanol (C2H6O) and dimethyl ether (C2H6O) have the same molecular formula but different functional groups and physical and chemical properties. They are considered constitutional isomers because they have different atomic connectivities.
In the case of C6H14, the constitutional isomer that gives only two monochlorination products is 2,2-dimethylbutane. This is because there are only two unique types of hydrogen atoms in 2,2-dimethylbutane that can be replaced by chlorine atoms to yield distinct monochlorination products. The other isomers of C6H14 have additional types of hydrogen atoms, resulting in multiple chlorination products.
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Frequently asked questions
2,2-Dimethylbutane.
Constitutional isomers, also known as structural isomers, are organic compounds with the same molecular formula but different structural arrangements of constituent elements.
There are five constitutional isomers possible with C6H14.
