Textbook Question
Draw a structure for each compound (includes old and new names).
g. vinylcyclopropane
h. (Z)-2-bromo-2-pentene
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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 40i
Draw a structure for each compound (includes old and new names).
i. (3Z,6E)-1,3,6-octatriene
Verified step by step guidance1
Start by understanding the nomenclature: (3Z,6E)-1,3,6-octatriene. This name indicates a compound with eight carbon atoms (octa-) and three double bonds (triene). The numbers 1, 3, and 6 indicate the positions of the double bonds in the carbon chain.
The stereochemistry is specified by (3Z,6E). 'Z' (from German 'zusammen') means the highest priority groups on the double bond are on the same side, while 'E' (from German 'entgegen') means they are on opposite sides. Apply this stereochemistry to the double bonds at positions 3 and 6.
Draw the carbon backbone: Start with a linear chain of eight carbon atoms. Number them from 1 to 8 to keep track of the positions for the double bonds.
Add the double bonds: Insert double bonds between carbons 1 and 2, 3 and 4, and 6 and 7. Ensure that the double bond between carbons 3 and 4 is 'Z' and the double bond between carbons 6 and 7 is 'E'.
Complete the structure by adding hydrogen atoms to satisfy the valency of carbon. Each carbon should have four bonds. Adjust the hydrogen atoms around the double bonds to reflect the stereochemistry ('Z' and 'E') as specified.
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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 systematic method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry. It provides a standard way to name compounds so that chemists can communicate unambiguously. Understanding the rules of IUPAC nomenclature is essential for interpreting and drawing the structure of a compound from its name.
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The different parts of an IUPAC name
Alkene Isomerism
Alkene isomerism refers to the existence of compounds with the same molecular formula but different structural arrangements due to the presence of double bonds. The terms 'E' and 'Z' denote the stereochemistry of alkenes, where 'E' (entgegen) indicates opposite sides and 'Z' (zusammen) indicates the same side of the double bond. Recognizing these isomers is crucial for accurately drawing the structure of alkenes.
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Conjugated Systems
A conjugated system in organic chemistry is a system of connected p-orbitals with delocalized electrons in a molecule, which in this case involves alternating single and double bonds. Conjugation can affect the stability and reactivity of a compound. Understanding conjugated systems is important for visualizing the structure and properties of compounds like 1,3,6-octatriene.
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Related Practice
Textbook Question
Draw a structure for each compound (includes old and new names).
a. 3-methylpent-1-ene
b. cis-3-methyl-3-hexene
c. 3,4-dibromobut-1-ene
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Textbook Question
Determine which compounds show cis-trans isomerism. Draw and label the isomers, using both the cis-trans and E-Z nomenclatures where applicable.
a. pent-1-ene
b. pent-2-ene
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Textbook Question
Label each structure as Z, E, or neither.
(a)
(b)
(c)
(d)
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Textbook Question
Draw a structure for each compound (includes old and new names).
d. 1,3-cyclohexadiene
e. cycloocta-1,4-diene
f. (Z)-3-methyl-2-octene
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Textbook Question
Determine which compounds show cis-trans isomerism. Draw and label the isomers, using both the cis-trans and E-Z nomenclatures where applicable.
c. hex-3-ene
d. 1,1-dibromopropene
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