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 69
Bruice 8th EditionCh. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and StructureProblem 69Chapter 4, Problem 69
Give the systematic names for all alkanes with molecular formula C7H16 that do not have any secondary hydrogens.
Verified step by step guidance1
Step 1: Understand the problem. The molecular formula C7H16 corresponds to an alkane with 7 carbon atoms and 16 hydrogen atoms. The problem specifies that the alkanes must not have any secondary hydrogens. A secondary hydrogen is a hydrogen atom attached to a secondary carbon, which is a carbon bonded to two other carbons.
Step 2: Recall the structural requirements. To avoid secondary hydrogens, the structure must consist only of primary carbons (bonded to one other carbon) and/or tertiary carbons (bonded to three other carbons). This means the alkane must be highly branched.
Step 3: Begin constructing possible structures. Start with the most branched structure for C7H16. A highly branched structure ensures that no carbon is secondary. For example, consider a structure where all carbons are either primary or tertiary.
Step 4: Verify the structure. Check that the total number of carbons is 7 and the total number of hydrogens is 16. Additionally, confirm that no carbon has a secondary hydrogen by ensuring no carbon is bonded to exactly two other carbons.
Step 5: Assign the systematic name. Use IUPAC nomenclature rules to name the structure. Identify the longest continuous carbon chain, name the substituents, and number the chain to give the substituents the lowest possible numbers. Combine these elements to write the systematic name for the alkane.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alkanes
Alkanes are saturated hydrocarbons consisting only of carbon and hydrogen atoms, connected by single bonds. They follow the general formula CnH2n+2, where 'n' is the number of carbon atoms. In the case of C7H16, the structure must adhere to this formula, indicating it is a straight-chain or branched alkane.
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Functionalizing Alkanes
Hydrogen Types
Hydrogens in organic compounds can be classified as primary, secondary, or tertiary based on the carbon atom to which they are attached. A primary hydrogen is attached to a primary carbon (one carbon neighbor), while a secondary hydrogen is attached to a secondary carbon (two carbon neighbors). The question specifies alkanes without secondary hydrogens, meaning all hydrogens must be attached to primary or tertiary carbons.
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00:48The definition of hydrogenation.
Systematic Naming (IUPAC)
The International Union of Pure and Applied Chemistry (IUPAC) provides a systematic method for naming organic compounds. For alkanes, names are derived from the longest continuous carbon chain, with prefixes indicating the number of carbons (e.g., hept- for seven). Branches and substituents are named and numbered according to their position on the main chain, ensuring clarity and consistency in chemical communication.
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Related Practice
Textbook Question
Draw skeletal structures for the following:
a. 5-ethyl-2-methyloctane
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Textbook Question
Draw skeletal structures for the following:
b. 1,3-dimethylcyclohexane
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Textbook Question
A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed.
k. 2-methyl-2-isopropylheptane
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Textbook Question
A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed.
l. 2-methyl-N,N-dimethyl-4-hexanamine
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Textbook Question
Which of the following conformers has the highest energy (is the least stable)?
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