Textbook Question
Draw skeletal structures for the following:
c. 2,3,3,4-tetramethylheptane
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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 70f
Bruice 8th EditionCh. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and StructureProblem 70fChapter 4, Problem 70f
Draw skeletal structures for the following:
f. 2,6-dimethyl-4-(2-methylpropyl)decane
Verified step by step guidance1
Step 1: Start by identifying the parent chain. The parent chain is 'decane,' which means it contains 10 carbon atoms in a straight chain. Draw a straight chain of 10 carbons.
Step 2: Number the parent chain from one end to the other to ensure the substituents are assigned the lowest possible numbers. In this case, number the chain from left to right.
Step 3: Add the substituents to the parent chain. The name '2,6-dimethyl' indicates that there are methyl groups (-CH₃) attached to carbons 2 and 6 of the parent chain. Draw these methyl groups branching off from the respective carbons.
Step 4: Add the next substituent, '4-(2-methylpropyl).' This indicates that at carbon 4 of the parent chain, there is a 2-methylpropyl group attached. A 2-methylpropyl group consists of a three-carbon chain with a methyl group attached to the second carbon. Draw this group branching off from carbon 4.
Step 5: Double-check the structure to ensure all substituents are correctly placed and the parent chain remains intact. Verify that the numbering matches the IUPAC name and that all bonds are correctly drawn.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Skeletal Structures
Skeletal structures, or line-angle formulas, are a simplified way of representing organic molecules. In these diagrams, carbon atoms are represented by vertices or ends of lines, while hydrogen atoms are implied and not explicitly drawn. This method allows chemists to visualize complex molecules more easily, focusing on the connectivity and functional groups rather than individual atoms.
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How bondline is different from Lewis Structures.
IUPAC Nomenclature
IUPAC nomenclature is a systematic method for naming organic chemical compounds. It provides rules for identifying the longest carbon chain, substituents, and their positions. Understanding IUPAC naming conventions is essential for interpreting the names of compounds and translating them into their corresponding skeletal structures, as seen in the example of 2,6-dimethyl-4-(2-methylpropyl)decane.
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03:43The different parts of an IUPAC name
Substituents and Branching
Substituents are groups of atoms that replace hydrogen atoms in a hydrocarbon chain, affecting the molecule's properties and reactivity. In the case of 2,6-dimethyl-4-(2-methylpropyl)decane, the 'dimethyl' and '2-methylpropyl' groups indicate branching off the main carbon chain. Recognizing how to depict these branches in skeletal structures is crucial for accurately representing the compound's structure.
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03:07How to identify and locate branches (substituents)
Related Practice
Textbook Question
Draw skeletal structures for the following:
e. 2-methyl-4-(1-methylethyl)octane
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Textbook Question
Draw skeletal structures for the following:
d. propylcyclopentane
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Textbook Question
For rotation about the C-3---C-4 bond of 2-methylhexane, do the following:
c. About which other carbon–carbon bonds may rotation occur?
d. How many of the carbon–carbon bonds in the compound have staggered conformers that are all equally stable?
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Textbook Question
Draw all the isomers that have molecular formula C5H11Br. (Hint: There are eight.)
a. Give the systematic name for each of the isomers.
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Textbook Question
For rotation about the C-3---C-4 bond of 2-methylhexane, do the following:
a. Draw the Newman projection of the most stable conformer.
b. Draw the Newman projection of the least stable conformer.
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