Chapter 12: Problem 36
When \(n\)-butane is treated with chlorine, how man monochloro products are formed? (a) 1 (b) 2 (c) 3 (d) 4
Short Answer
Expert verified
Two unique monochloro products are formed.
Step by step solution
01
Understand the structure of n-butane
Analyze the structure of n-butane, which is a straight-chain alkane with four carbon atoms. Each carbon atom can be considered as a potential site for chlorination.
02
Determine the unique sites of chlorination
Identify the unique positions at which chlorine can attach to the carbon atoms. We have two types of hydrogen atoms in n-butane — those attached to the two end carbons (primary) and those attached to the two middle carbons (secondary).
03
Calculate the number of monochloroproducts
Chlorine can replace any of the hydrogens in n-butane, resulting in monochlorinated products. However, chlorination at any of the three primary carbon atoms (at the ends) gives the same product. Chlorination at the secondary carbon (one of the middle carbons) gives a different product.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Chlorination Reactions
In organic chemistry, chlorination reactions are a subset of halogenation processes where chlorine atoms are introduced into organic molecules. Specifically, the monochlorination of alkanes like n-butane is a type of substitution reaction where a chlorine atom replaces one hydrogen atom.
This process is typically initiated by heat or light, causing chlorine to generate radical species that can attack the hydrocarbon chain. The reactivity of different hydrogen atoms based on their position in an alkane chain varies. Primary hydrogens, attached to a carbon bonded to only one other carbon, are generally less reactive compared to secondary hydrogens, which are attached to carbons bonded to two other carbons.
Thus, in the context of n-butane, when we deal with its chlorination, the reaction can yield multiple products depending on which hydrogen atom the chlorine radical substitutes. Even though there are ten hydrogen atoms in n-butane, only a few unique chloroproducts are formed because of the symmetry and equivalent positions of certain hydrogen atoms.
This process is typically initiated by heat or light, causing chlorine to generate radical species that can attack the hydrocarbon chain. The reactivity of different hydrogen atoms based on their position in an alkane chain varies. Primary hydrogens, attached to a carbon bonded to only one other carbon, are generally less reactive compared to secondary hydrogens, which are attached to carbons bonded to two other carbons.
Thus, in the context of n-butane, when we deal with its chlorination, the reaction can yield multiple products depending on which hydrogen atom the chlorine radical substitutes. Even though there are ten hydrogen atoms in n-butane, only a few unique chloroproducts are formed because of the symmetry and equivalent positions of certain hydrogen atoms.
Structural Isomers
Structural isomers are compounds with the same molecular formula but different structural formulas. That means they have the same number of each atom, but the layout of these atoms in three-dimensional space differs, affecting the properties and reactions of the molecules.
When considering monochlorination of n-butane, structural isomerism plays a crucial role in determining the number of unique monochlorination products. In the given reaction, chlorination at the primary carbons leads to a single product because of the symmetrical structure of n-butane. The chlorination at the secondary carbon results in a structurally distinct isomer.
It is this property of structurally different but chemically related products that students need to appreciate to understand why certain reactions don't produce as many distinct products as the number of potential reaction sites might suggest. Each unique structure obtained after chlorination is an isomer, contributing to the diversity of organic compounds stemming from a seemingly simple reaction.
When considering monochlorination of n-butane, structural isomerism plays a crucial role in determining the number of unique monochlorination products. In the given reaction, chlorination at the primary carbons leads to a single product because of the symmetrical structure of n-butane. The chlorination at the secondary carbon results in a structurally distinct isomer.
It is this property of structurally different but chemically related products that students need to appreciate to understand why certain reactions don't produce as many distinct products as the number of potential reaction sites might suggest. Each unique structure obtained after chlorination is an isomer, contributing to the diversity of organic compounds stemming from a seemingly simple reaction.
Organic Chemistry
Organic chemistry is the scientific study of the structure, properties, composition, reactions, and synthesis of organic compounds primarily composed of carbon atoms. In organic reactions, such as the chlorination of n-butane, understanding the nature of the organic molecule is key.
Alkanes, such as n-butane, are saturated hydrocarbons, meaning they contain only single bonds between their carbon atoms and are fully saturated with hydrogen. Their reactivity often involves breaking one of these C-H bonds to create new compounds.
The monochlorination example from the exercise highlights the fundamental of chemical reactivity and molecular structure that organic chemistry delves into. The stability of resulting radical intermediates, the formation of products, and the dependence on the structure of the molecule are all central themes in studying organic reactions. By exploring reactions like these, students can start to predict the kinds of products that might result from a given set of reactants.
Alkanes, such as n-butane, are saturated hydrocarbons, meaning they contain only single bonds between their carbon atoms and are fully saturated with hydrogen. Their reactivity often involves breaking one of these C-H bonds to create new compounds.
The monochlorination example from the exercise highlights the fundamental of chemical reactivity and molecular structure that organic chemistry delves into. The stability of resulting radical intermediates, the formation of products, and the dependence on the structure of the molecule are all central themes in studying organic reactions. By exploring reactions like these, students can start to predict the kinds of products that might result from a given set of reactants.