Textbook Question
The following names are all incorrect. Draw the structure represented by the incorrect name (or a consistent structure if the name is ambiguous), and give your drawing the correct name.
e. 2,5-dimethylcyclohexene
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Ch. 7 - Structure and Synthesis of Alkenes; Elimination
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 7, Problem 7a,b
The following names are all incorrect. Draw the structure represented by the incorrect name (or a consistent structure if the name is ambiguous), and give your drawing the correct name.
a. cis-dimethylpent-2-ene
b. 3-vinylhex-4-ene
Verified step by step guidance1
Step 1: Analyze the name 'cis-dimethylpent-2-ene'. The prefix 'cis' indicates that the two methyl groups should be on the same side of the double bond. The root 'pent' suggests a five-carbon chain, and '2-ene' indicates a double bond between the second and third carbon atoms.
Step 2: Draw the structure for 'cis-dimethylpent-2-ene'. Start with a five-carbon chain. Place a double bond between the second and third carbons. Add methyl groups to the second and third carbons on the same side of the double bond to satisfy the 'cis' configuration.
Step 3: Identify the correct IUPAC name for the structure drawn in Step 2. Ensure that the longest carbon chain containing the double bond is identified, and number the chain to give the double bond the lowest possible number. Check the position of substituents and their configuration.
Step 4: Analyze the name '3-vinylhex-4-ene'. The root 'hex' suggests a six-carbon chain, and '4-ene' indicates a double bond between the fourth and fifth carbon atoms. The prefix '3-vinyl' suggests a vinyl group (CH2=CH-) attached to the third carbon.
Step 5: Draw the structure for '3-vinylhex-4-ene'. Start with a six-carbon chain. Place a double bond between the fourth and fifth carbons. Attach a vinyl group to the third carbon. Identify the correct IUPAC name by ensuring the longest carbon chain containing the double bond is numbered correctly, and check the position of substituents.
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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 ensures that each compound has a unique and universally accepted name. Understanding the rules of IUPAC naming, such as identifying the longest carbon chain, numbering the chain to give substituents the lowest possible numbers, and correctly identifying functional groups, is crucial for naming and interpreting organic compounds.
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The different parts of an IUPAC name
Cis-Trans Isomerism
Cis-trans isomerism, also known as geometric isomerism, occurs in alkenes due to restricted rotation around the double bond. In 'cis' isomers, similar groups are on the same side of the double bond, while in 'trans' isomers, they are on opposite sides. Recognizing and correctly naming these isomers is essential for understanding their distinct physical and chemical properties.
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Alkene Structure and Substitution
Alkenes are hydrocarbons with at least one carbon-carbon double bond, which affects their reactivity and structure. The position of the double bond and the nature of substituents attached to the carbon chain influence the compound's name and properties. Identifying the correct position of the double bond and any substituents is key to drawing and naming alkenes accurately.
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Related Practice
Textbook Question
1. Determine which of the following compounds show cis-trans isomerism.
2. Draw and name the cis and trans (or Z and E) isomers of those that do.
c. hexa-2,4-diene
d. 3-methylpent-2-ene
Textbook Question
For each reaction, decide whether substitution or elimination (or both) is possible, and predict the products you expect. Label the major products.
b. 1-bromo-1-methylcyclohexane + triethylamine(Et3N:)
Textbook Question
1. Determine which of the following compounds show cis-trans isomerism.
2. Draw and name the cis and trans (or Z and E) isomers of those that do.
e. 2,3-dimethylpent-2-ene
f. 3,4-dibromocyclopentene
Textbook Question
1. Determine which of the following compounds show cis-trans isomerism.
2. Draw and name the cis and trans (or Z and E) isomers of those that do.
a. hex-3-ene
b.buta-1,3-diene
Textbook Question
The following names are all incorrect. Draw the structure represented by the incorrect name (or a consistent structure if the name is ambiguous), and give your drawing the correct name.
c. 2-methylcyclopentene
d. 6-chlorocyclohexadiene
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