Textbook Question
Convert the following condensed structures into skeletal structures:
e. CH3CH2NHCH2CH2CH3
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Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and StructureProblem 19a
Bruice 8th EditionCh. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and StructureProblem 19aChapter 4, Problem 19a
Draw a condensed and a skeletal structure for each of the following:
a. 3,4-diethyl-2-methylheptane
Verified step by step guidance1
Step 1: Understand the IUPAC name '3,4-diethyl-2-methylheptane'. The parent chain is 'heptane', which means it is a seven-carbon straight chain alkane. The substituents are located at carbons 2, 3, and 4, as indicated by the name.
Step 2: Identify the substituents. The '2-methyl' indicates a methyl group (-CH₃) attached to the second carbon of the heptane chain. The '3,4-diethyl' indicates two ethyl groups (-CH₂CH₃), one attached to the third carbon and the other to the fourth carbon.
Step 3: Draw the condensed structure. Start with the seven-carbon chain (heptane) and add the substituents at the appropriate positions. For example, at carbon 2, add a -CH₃ group, and at carbons 3 and 4, add -CH₂CH₃ groups.
Step 4: Draw the skeletal structure. Represent the seven-carbon chain as a zigzag line, with each vertex representing a carbon atom. Add the substituents as lines branching off the main chain at the appropriate positions. Use shorter lines for methyl groups and longer lines for ethyl groups.
Step 5: Double-check the structure to ensure all carbons have four bonds and the substituents are placed correctly according to the IUPAC name. Verify that the condensed and skeletal structures are consistent with each other.
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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 implied rather than shown. This method provides a clear and concise way to visualize the molecular structure while maintaining essential information about connectivity.
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Skeletal Structure
A skeletal structure, also known as a line-angle formula, is a simplified representation of a molecule where carbon atoms are represented by vertices or ends of lines, and hydrogen atoms are omitted for clarity. Each vertex represents a carbon atom, and the implicit hydrogen atoms are assumed to satisfy carbon's tetravalency. This format is particularly useful for visualizing larger organic molecules, as it reduces clutter and highlights the overall framework of the compound.
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IUPAC Nomenclature
IUPAC nomenclature is a systematic method for naming organic chemical compounds based on their structure. It provides rules for identifying the longest carbon chain, substituents, and their positions, which is essential for accurately interpreting and drawing chemical structures. In the case of 3,4-diethyl-2-methylheptane, understanding the nomenclature helps in determining the correct arrangement of carbon chains and substituents in both condensed and skeletal forms.
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Related Practice
Textbook Question
Give two names for each of the following alkyl halides and indicate whether each is primary, secondary, or tertiary:
a.
Textbook Question
Convert the following condensed structures into skeletal structures:
c.
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Textbook Question
Draw a condensed and a skeletal structure for each of the following:
b. 2,2,5-trimethylhexane
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Textbook Question
Convert the following condensed structures into skeletal structures:
f.
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Textbook Question
Give two names for each of the following alkyl halides and indicate whether each is primary, secondary, or tertiary:
b.
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