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Ch.3 - Structure and Stereochemistry of Alkanes
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
Chapter 3, Problem 2b

Name the following alkanes and haloalkanes. When two or more substituents are present, list them in alphabetical order.
(b)

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1
Step 1: Identify the longest continuous carbon chain in the molecule. In this case, the longest chain contains 4 carbon atoms, making it a butane backbone.
Step 2: Number the carbon atoms in the main chain starting from the end closest to the substituents (Br and CH2CH3) to ensure the lowest possible numbers for the substituents.
Step 3: Identify and name the substituents attached to the main chain. The substituents are a bromine atom (Br) and an ethyl group (CH2CH3).
Step 4: Assign the correct position numbers to the substituents based on the numbering of the main chain. Bromine is attached to carbon 2, and the ethyl group is attached to carbon 3.
Step 5: Combine the names of the substituents in alphabetical order followed by the name of the main chain. The final name will include the positions of the substituents and the name of the main chain (butane).

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Key Concepts

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

Nomenclature of Alkanes

Alkanes are hydrocarbons with single bonds and follow specific naming conventions based on the number of carbon atoms. The longest continuous carbon chain is identified, and the corresponding prefix (e.g., 'but-' for four carbons) is used, followed by the suffix '-ane'. If substituents are present, they are named and numbered according to their position on the main chain.
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Nomenclature of Haloalkanes

Haloalkanes, or alkyl halides, are alkanes that contain one or more halogen atoms (e.g., Br, Cl, I, F) as substituents. The halogen is treated as a substituent in the naming process, and its position is indicated by a number corresponding to the carbon atom it is attached to. The name of the haloalkane is formed by combining the alkane name with the halogen prefix (e.g., 'bromo-' for bromine).
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Alphabetical Order of Substituents

When naming compounds with multiple substituents, the substituents must be listed in alphabetical order, regardless of their position on the carbon chain. This rule applies to all substituents, including alkyl groups and halogens. For example, if both a bromo and an ethyl group are present, the name would start with 'bromo' followed by 'ethyl', even if the ethyl group is located at a lower-numbered carbon.
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