Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure

Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook

Bruice 8th Edition

Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure

Problem 55h

Chapter 4, Problem 55h

Draw a condensed structure and a skeletal structure for each of the following:
h. 5,5-dibromo-2-methyloctane

Verified step by step guidance

Step 1: Identify the parent chain. The parent chain is 'octane,' which means the molecule has 8 carbon atoms in a straight chain. Number the carbons from 1 to 8.

Step 2: Locate the substituents. The name '5,5-dibromo' indicates that there are two bromine atoms attached to the fifth carbon of the parent chain. The '2-methyl' indicates a methyl group (-CH₃) attached to the second carbon.

Step 3: Draw the condensed structure. Start with the parent chain (CH₃-(CH₂)₆-CH₃ for octane) and add the substituents. Place two bromine atoms on the fifth carbon and a methyl group on the second carbon. Use parentheses to group substituents for clarity.

Step 4: Draw the skeletal structure. Represent the parent chain as a zigzag line, where each vertex represents a carbon atom. Add the substituents: two bromine atoms on the fifth vertex and a methyl group branching off the second vertex.

Step 5: Double-check the structure. Ensure the numbering of the parent chain is correct, the substituents are placed accurately, and the structure matches the IUPAC name '5,5-dibromo-2-methyloctane.'

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Key Concepts

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

Condensed Structural Formula

A condensed structural formula is a way of representing a chemical compound that shows the arrangement of atoms in a molecule without depicting all the bonds explicitly. In this format, groups of atoms are often grouped together, and hydrogen atoms attached to carbon are usually omitted for simplicity. This representation helps in visualizing the molecular structure while maintaining clarity and conciseness.

Skeletal Structure

A skeletal structure, also known as a line-angle structure, is a simplified representation of a molecule where carbon atoms are represented by vertices and hydrogen atoms are implied. Bonds between carbon atoms are shown as lines, and functional groups or substituents are depicted as attached groups. This format is particularly useful for visualizing larger organic molecules, as it reduces clutter and emphasizes the overall framework.

Nomenclature of Organic Compounds

Nomenclature in organic chemistry refers to the systematic naming of chemical compounds based on their structure and functional groups. The name '5,5-dibromo-2-methyloctane' indicates a specific structure where 'octane' denotes an eight-carbon chain, '2-methyl' indicates a methyl group on the second carbon, and '5,5-dibromo' signifies two bromine atoms attached to the fifth carbon. Understanding nomenclature is essential for accurately drawing and interpreting chemical structures.

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