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Ch.4 Introduction to Organic Compounds
Chapter 1, Problem 4.25a

Draw the skeletal structure for each of the following compounds:


(a) 2,3-dimethylpentane

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1
Identify the parent chain: The parent chain is the longest continuous chain of carbon atoms. In this case, it is 'pentane', which means the parent chain has 5 carbon atoms.
Number the carbon atoms in the parent chain: Start numbering from the end closest to the substituents to give them the lowest possible numbers. For 2,3-dimethylpentane, number the chain from left to right or right to left to ensure the methyl groups are on carbons 2 and 3.
Identify and place the substituents: The compound has two methyl groups (CH₃) as substituents. Place one methyl group on carbon 2 and another on carbon 3 of the parent chain.
Draw the skeletal structure: Represent each carbon atom as a vertex (or end) of a line. Draw a straight line for the 5-carbon parent chain, and add lines branching off from carbons 2 and 3 to represent the methyl groups.
Verify the structure: Ensure that each carbon atom forms four bonds, and the structure accurately represents 2,3-dimethylpentane.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Skeletal Structures

Skeletal structures, or line-angle formulas, are simplified representations of organic molecules where carbon atoms are represented by vertices and hydrogen atoms are implied. This notation omits the explicit depiction of hydrogen atoms attached to carbons, making it easier to visualize complex organic compounds. Understanding how to read and draw these structures is essential for accurately representing molecular connectivity.
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Alkanes

Alkanes are saturated hydrocarbons consisting only of carbon and hydrogen atoms, connected by single bonds. They follow the general formula CnH2n+2, where 'n' is the number of carbon atoms. Recognizing the characteristics of alkanes, such as their structural variations and nomenclature, is crucial for drawing their skeletal structures correctly.
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IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming organic chemical compounds based on their structure. It provides rules for identifying the longest carbon chain, substituents, and their positions, which is essential for accurately interpreting compound names like 2,3-dimethylpentane. Familiarity with these naming conventions is vital for translating chemical names into their corresponding skeletal structures.
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