Textbook Question
The following names are all incorrect or incomplete, but they represent real structures. Draw each structure and name it correctly.
a. 2-ethylpentane
b. 3-isopropylhexane
2
views
Ch.3 - Structure and Stereochemistry of Alkanes
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Not the one you use?Change textbookSelect a different textbook
Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 3, Problem 41e,f
The following names are all incorrect or incomplete, but they represent real structures. Draw each structure and name it correctly.
e. 2-cyclohexylbutane
f. 2,3-diethylcyclopentane
Verified step by step guidance1
Step 1: Understand the naming conventions for cycloalkanes. Cycloalkanes are named by identifying the ring size and then adding substituents as prefixes with their position numbers.
Step 2: For 2-cyclohexylbutane, recognize that the name suggests a cyclohexyl group attached to a butane chain. However, the name is incomplete because it does not specify the position of the cyclohexyl group on the butane chain.
Step 3: Draw the structure for 2-cyclohexylbutane. Start with a butane chain (CH₃-CH₂-CH₂-CH₃) and attach a cyclohexyl group (a six-membered ring) to the second carbon of the butane chain.
Step 4: Correct the name for 2-cyclohexylbutane. The correct name should reflect the position of the cyclohexyl group on the butane chain, ensuring the longest carbon chain is identified and numbered correctly.
Step 5: For 2,3-diethylcyclopentane, recognize that the name suggests two ethyl groups attached to a cyclopentane ring. However, the name is incorrect because it does not follow the proper numbering system for substituents on a cycloalkane ring. Draw the structure with ethyl groups on the second and third carbons of the cyclopentane ring, then rename it using the lowest possible numbers for substituents.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
1mWas this helpful?
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 of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry. It provides a standardized way to name chemical compounds, ensuring that each name is unique and descriptive of the compound's structure. Understanding IUPAC rules is essential for correctly naming and interpreting the names of organic molecules.
Recommended video:
Guided course
03:43
The different parts of an IUPAC name
Cycloalkane Structure
Cycloalkanes are types of hydrocarbons that contain carbon atoms arranged in a ring structure, with the general formula CnH2n. They are saturated, meaning they have single bonds only. Recognizing the structure of cycloalkanes is crucial for understanding how substituents are attached and how to correctly name compounds with cyclic components.
Recommended video:
Guided course
01:11How to find the root name for cycloalkanes
Substituent Positioning
In organic chemistry, the position of substituents on a carbon chain or ring is indicated by numbers, which are assigned based on the lowest possible locants rule. This ensures clarity in the structure's description. Correctly identifying and numbering substituents is vital for accurate naming and understanding of molecular structures, especially in complex molecules.
Recommended video:
4:06Reactions at the Allylic Position Example 3
Related Practice
Textbook Question
Construct a graph, similar to Figure 3-11, of the torsional energy of 3-methylpentane along the C2―C3 bond.
e. Indicate which conformations are the most stable (lowest energy) and the least stable (highest energy).
2
views
Textbook Question
In each pair of compounds, which compound has the higher boiling point? Explain your reasoning.
c. 2,2,5-trimethylhexane or nonane
1
views
Textbook Question
In each pair of compounds, which compound has the higher boiling point? Explain your reasoning.
b. nonane or 2-methylheptane
2
views
Textbook Question
The following names are all incorrect or incomplete, but they represent real structures. Draw each structure and name it correctly.
c. 5-chloro-4-methylhexane
d. 2-dimethylbutane
1
views
Textbook Question
In each pair of compounds, which compound has the higher boiling point? Explain your reasoning.
a. octane or 2,2,3-trimethylpentane