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 67h

Chapter 4, Problem 67h

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed.
h. 5-ethyl-2-methylhexane

Verified step by step guidance

Step 1: Begin by identifying the longest continuous carbon chain in the given structure. This chain will serve as the parent chain and determine the base name of the compound. Count the number of carbons in this chain to assign the correct alkane name.

Step 2: Number the parent chain starting from the end closest to the first substituent group. This ensures that the substituents are assigned the lowest possible locants (numbers).

Step 3: Identify and name all substituents attached to the parent chain. Substituents are named based on the number of carbons they contain, with the suffix '-yl' added to the alkane name (e.g., methyl, ethyl).

Step 4: Combine the substituent names with their respective locants and arrange them alphabetically. Ensure that the locants are correctly assigned based on the numbering of the parent chain. If the numbering results in a tie, the substituent that comes first alphabetically gets the lower number.

Step 5: Check the given name '5-ethyl-2-methylhexane' against the systematic naming rules. If the numbering of the substituents does not follow the lowest-locant rule, correct the name accordingly. For example, if the parent chain was misnumbered, renumber it and adjust the substituent locants to reflect the correct systematic name.

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Key Concepts

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

IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming organic chemical compounds. It provides rules for identifying the longest carbon chain, naming substituents, and determining the correct order of naming based on the position of functional groups. Understanding these rules is essential for accurately naming compounds and avoiding misnomers.

Alkane Structure

Alkanes are saturated hydrocarbons consisting only of carbon and hydrogen atoms, connected by single bonds. Their general formula is CnH2n+2, where 'n' is the number of carbon atoms. Recognizing the structure of alkanes helps in identifying the correct parent chain and substituents when naming compounds.

Substituent Naming and Positioning

Substituents are groups attached to the main carbon chain and are named based on their structure. The position of each substituent is indicated by a number corresponding to the carbon atom it is attached to. Correctly identifying and numbering these substituents is crucial for accurate systematic naming.

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Name the longest carbon chain and substituents

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