Textbook Question
Draw the structure that corresponds with each name.
i. tert-butylcyclohexane
j. pentylcyclohexane
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Ch.3 - Structure and Stereochemistry of Alkanes
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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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 36c,d
Draw the structure that corresponds with each name.
c. sec-butylcycloheptane
d. 2,3-dimethyl-4-propylnonane
Verified step by step guidance1
Step 1: Understand the naming conventions in IUPAC nomenclature. 'sec-butylcycloheptane' indicates a cycloheptane ring with a sec-butyl group attached. '2,3-dimethyl-4-propylnonane' indicates a nonane chain with methyl groups on carbons 2 and 3, and a propyl group on carbon 4.
Step 2: For 'sec-butylcycloheptane', start by drawing a cycloheptane ring, which is a seven-membered carbon ring. Then, identify the 'sec-butyl' group, which is a four-carbon group where the second carbon is attached to the main structure. Attach this group to one of the carbons in the cycloheptane ring.
Step 3: For '2,3-dimethyl-4-propylnonane', begin by drawing a straight chain of nine carbon atoms, representing nonane. Number the carbon atoms from 1 to 9 to keep track of substituent positions.
Step 4: Add the substituents to the nonane chain. Place a methyl group (CH₃) on the second and third carbon atoms. Then, add a propyl group (CH₂CH₂CH₃) to the fourth carbon atom.
Step 5: Ensure that all valencies are satisfied by adding hydrogen atoms where necessary. Each carbon should have four bonds, so adjust the number of hydrogen atoms accordingly to complete the structure.
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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 standardized system for naming chemical compounds. It involves identifying the longest carbon chain, numbering the chain to give substituents the lowest possible numbers, and naming substituents as prefixes. Understanding this system is crucial for interpreting and drawing structures from chemical names.
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The different parts of an IUPAC name
Cycloalkanes
Cycloalkanes are saturated hydrocarbons with carbon atoms arranged in a ring structure. The prefix 'cyclo-' indicates the presence of a ring, and the suffix denotes the number of carbon atoms in the ring. Recognizing cycloalkane structures is essential for drawing compounds like sec-butylcycloheptane, which includes a cycloheptane ring.
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Substituents and Branching
Substituents are groups attached to the main carbon chain or ring, affecting the compound's name and structure. Terms like 'sec-butyl' and 'dimethyl' indicate specific branching patterns and positions. Understanding how to identify and position these substituents is key to accurately drawing complex structures like 2,3-dimethyl-4-propylnonane.
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Related Practice
Textbook Question
Each of the following descriptions applies to more than one alkane. In each case, draw and name two structures that match the description.
a. an isopropylheptane
b. a diethyldecane
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Textbook Question
Draw the structure that corresponds with each name.
e. 2,2,4,4-tetramethylhexane
f. trans-1,3-diethylcyclopentane
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Textbook Question
Draw the structure that corresponds with each name.
a. 3-ethyloctane
b. 4-isopropyldecane
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Textbook Question
Draw and name the five cycloalkane structures of formula C5H10. Can any of these structures give rise to geometric (cis-trans) isomerism? If so, show the cis and trans stereoisomers.
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Textbook Question
Which of the following structures represent the same compound? Which ones represent different compounds?
(f)
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