Chapter 11: Problem 11
Draw all possible structural isomers for this alkane: \(\mathrm{C}_{7} \mathrm{H}_{16}\)
Short Answer
Expert verified
The alkane C7H16 has 9 structural isomers: Heptane, 2-Methylhexane, 3-Methylhexane, 2,2-Dimethylpentane, 2,3-Dimethylpentane, 2,4-Dimethylpentane, 3,3-Dimethylpentane, 2,2,3-Trimethylbutane, and 2,3,3-Trimethylbutane.
Step by step solution
01
Start with an Unbranched Chain
Beginning with an unbranched, straight chain alkane: Draw a chain of seven-carbon (heptane). It is the simplest straight-chain alkane with the formula C7H16.
02
Start Making Structural Changes
Now begin the process of creating isomers by making structural changes one step at a time. First, make one carbon branch off the six-carbon chain (hexane) which gives us a methyl hexane.
03
Change the Location of the Branch
There are five different locations to put the methyl group on the six-carbon chain. We can place it in either positions 2, 3 or 4 (the positions are counted from both ends, and by the IUPAC rules, the methyl group must be attached to the carbon with the lowest number). We cannot place it on carbon 1 or 6 since it would then be a straight seven-carbon chain, which we already drew.
04
Create Two Branches
Two structural changes can be made to create two branched isomers: either split the six-carbon chain into a five-carbon chain (pentane) and create two branches (a methyl and an ethyl group) or create two methyl groups on the five-carbon chain. Both will result in different isomers.
05
Create Three Branches
It is possible also to split the seven-carbon chain into a four-carbon chain (butane) and create three branches (three methyl groups), resulting in another different isomer.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Structural Isomerism
Structural isomerism occurs when molecules with the same molecular formula have different physical structures. In organic chemistry, this phenomenon is quite common due to the versatility of carbon atoms. These atoms can form chains and rings of various sizes, which can be arranged in different ways to create distinct structures known as isomers.
Take, for example, the alkane with the molecular formula \( \mathrm{C}_{7}\mathrm{H}_{16} \). Alkanes are a type of hydrocarbon where carbon atoms are connected only by single bonds and are saturated with hydrogen atoms. The simplest structural form of this molecule is heptane, which is an unbranched, or 'straight-chain', alkane. However, by rearranging the carbon atoms to create branches, we can form different structural isomers, each with unique properties.
By understanding structural isomerism, students can better visualize the diversity of organic compounds. For the \( \mathrm{C}_{7}\mathrm{H}_{16} \) alkane, identifying all its structural isomers involves a systematic approach; change the length of the main carbon chain and the position of the branches. Each different arrangement gives a new structural isomer, providing a beautiful illustration of organic chemistry's complexity and variety.
Take, for example, the alkane with the molecular formula \( \mathrm{C}_{7}\mathrm{H}_{16} \). Alkanes are a type of hydrocarbon where carbon atoms are connected only by single bonds and are saturated with hydrogen atoms. The simplest structural form of this molecule is heptane, which is an unbranched, or 'straight-chain', alkane. However, by rearranging the carbon atoms to create branches, we can form different structural isomers, each with unique properties.
By understanding structural isomerism, students can better visualize the diversity of organic compounds. For the \( \mathrm{C}_{7}\mathrm{H}_{16} \) alkane, identifying all its structural isomers involves a systematic approach; change the length of the main carbon chain and the position of the branches. Each different arrangement gives a new structural isomer, providing a beautiful illustration of organic chemistry's complexity and variety.
Organic Chemistry
Organic chemistry is the branch of chemistry that deals with the structure, properties, composition, reactions, and synthesis of organic compounds, which contain carbon. It's a vast field that covers molecules simple enough to be gases at room temperature to large, complex structures found in materials like DNA or proteins.
The study of organic molecules extends from understanding essential hydrocarbons, such as alkanes, to much more complex molecules involving functional groups with oxygen, nitrogen, or other elements. Hydrocarbons like alkanes are fundamental, primarily consisting of carbon and hydrogen atoms. In the context of isomerism, learning about the structure of alkanes lays the groundwork for grasping more complex molecules.
The study of organic molecules extends from understanding essential hydrocarbons, such as alkanes, to much more complex molecules involving functional groups with oxygen, nitrogen, or other elements. Hydrocarbons like alkanes are fundamental, primarily consisting of carbon and hydrogen atoms. In the context of isomerism, learning about the structure of alkanes lays the groundwork for grasping more complex molecules.
Importance of Hydrocarbons
Alkanes, as one of the simplest forms of hydrocarbons, are crucial for students to understand because they form the basis for more complex structures. They are also significant in various applications, including fuels and as a starting point for synthesizing other organic compounds. By exploring the structural variations of alkanes, students get a glimpse into the vast and intricate world of organic compounds and their transformations.IUPAC Nomenclature
IUPAC, or the International Union of Pure and Applied Chemistry, establishes a system of rules to name chemical compounds uniformly, known as IUPAC nomenclature. This system is essential for organic chemistry students to learn because it allows chemists worldwide to communicate about compounds unambiguously.
By understanding IUPAC nomenclature, students can name various organic compounds systematically, which is crucial for studying reactions and discussing organic chemistry effectively. This naming process helps in identifying structural differences, as seen with the isomers of \( \mathrm{C}_{7}\mathrm{H}_{16} \), describing precisely which atoms are connected and where, aiding in visualizing the molecule's three-dimensional structure.
Basic Principles
The base name for an alkane chain depends on the number of carbon atoms in the longest, continuous chain. This chain is known as the 'parent' hydrocarbon. From there, we add prefixes and suffixes to indicate the presence and position of branches or functional groups. In our exercise example, the base molecule is called 'heptane'.Branches and Substituents
When branches occur, we use numbers to indicate the carbon's position in the chain where the branch, or 'substituent,' attaches. The position numbers are assigned to give the lowest possible numbers to the substituents. For instance, if a methyl group is on the second carbon, it's called '2-methyl'.By understanding IUPAC nomenclature, students can name various organic compounds systematically, which is crucial for studying reactions and discussing organic chemistry effectively. This naming process helps in identifying structural differences, as seen with the isomers of \( \mathrm{C}_{7}\mathrm{H}_{16} \), describing precisely which atoms are connected and where, aiding in visualizing the molecule's three-dimensional structure.