Ch.6 - Alkyl Halides; Nucleophilic Substitution

Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook

Wade 9th Edition

Ch.6 - Alkyl Halides; Nucleophilic Substitution

Problem 3f

Chapter 6, Problem 3f

For each of the following compounds,
1. give the IUPAC name.
2. give the common name (if possible).
3. classify the compound as a methyl, primary, secondary, or tertiary halide.
(f)

Verified step by step guidance

Step 1: Analyze the structure provided in the image. The compound is a cyclobutane ring with two halogen substituents: bromine (Br) and chlorine (Cl). The substituents are attached to adjacent carbons in the ring.

Step 2: Assign locants to the substituents for the IUPAC name. Start numbering the ring from the carbon attached to bromine (Br) to give the lowest possible numbers to the substituents. Bromine is at position 1, and chlorine is at position 2.

Step 3: Write the IUPAC name. Combine the substituents in alphabetical order (bromine before chlorine) with their locants, followed by the parent chain name 'cyclobutane'. The IUPAC name is 1-bromo-2-chlorocyclobutane.

Step 4: Determine the common name (if possible). Since the compound does not have a widely recognized common name, the IUPAC name is typically used.

Step 5: Classify the halides. Bromine is attached to a secondary carbon (a carbon bonded to two other carbons), and chlorine is also attached to a secondary carbon. Therefore, both halides are secondary halides.

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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 a set of rules to create unique names based on the structure of the molecule, including the longest carbon chain, functional groups, and substituents. Understanding these rules is essential for accurately identifying and communicating the identity of compounds.

Common Names

Common names are informal names used to identify chemical compounds, often based on historical or traditional usage rather than systematic rules. While IUPAC names are standardized, common names can vary by region and may not always reflect the compound's structure. Familiarity with common names can aid in recognizing widely used compounds in organic chemistry.

Classification of Halides

Halides are classified based on the carbon atom to which the halogen is attached. They can be categorized as methyl (attached to a methyl group), primary (attached to a primary carbon), secondary (attached to a secondary carbon), or tertiary (attached to a tertiary carbon). This classification is important for predicting reactivity and understanding the compound's behavior in chemical reactions.

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Related Practice

Textbook Question

For each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.

c. cis-2,3-dibromobut-2-ene or trans-2,3-dibromobut-2-ene

d. cis-1,2-dichlorocyclobutane or trans-1,3-dichlorocyclobutane

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Textbook Question

Kepone, aldrin, and chlordane are synthesized from hexachlorocyclopentadiene and other five-membered-ring compounds. Show how these three pesticides are composed of two five-membered rings.

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Textbook Question

For each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.

a. ethyl chloride or ethyl iodide

b. 1-bromopropane or cyclopropane

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Textbook Question

For each of the following compounds,

1. give the IUPAC name.

2. give the common name (if possible).

3. classify the compound as a methyl, primary, secondary, or tertiary halide.

b. (CH₃)₃CBr