Textbook Question
Many biological transformations can be simply classified as additions, eliminations, or substitutions. How would you classify the following reactions?
a. Fumaric acid to malic acid
Ch.13 Alkenes, Alkynes, and Aromatic Compounds
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187
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Table of contents
- Ch.1 Matter and Measurements27
- Ch.2 Atoms and the Periodic Table20
- Ch.3 Ionic Compounds8
- Ch.4 Molecular Compounds23
- Ch.5 Classification & Balancing of Chemical Reactions12
- Ch.6 Chemical Reactions: Mole and Mass Relationships28
- Ch.7 Chemical Reactions: Energy, Rate and Equilibrium64
- Ch.8 Gases, Liquids and Solids24
- Ch.9 Solutions52
- Ch.10 Acids and Bases25
- Ch.11 Nuclear Chemistry22
- Ch.12 Introduction to Organic Chemistry: Alkanes57
- Ch.13 Alkenes, Alkynes, and Aromatic Compounds47
- Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen50
- Ch.15 Aldehydes and Ketones45
- Ch.16 Amines42
- Ch.17 Carboxylic Acids and Their Derivatives57
- Ch.18 Amino Acids and Proteins82
- Ch.19 Enzymes and Vitamins63
- Ch.20 Carbohydrates44
- Ch.21 The Generation of Biochemical Energy65
- Ch.22 Carbohydrate Metabolism45
- Ch.23 Lipids42
- Ch.24 Lipid Metabolism33
- Ch.25 Protein and Amino Acid Metabolism24
- Ch.26 Nucleic Acids and Protein Synthesis45
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Not the one you use?Change textbook
Chapter 13, Problem 4
Which of the following substances exist as can cis–trans isomers? Draw both isomers for those that do.
a. 2,3-Dimethyl-2-pentene (condensed structures only)
b. 2-Methyl-2-hexene (both condensed and line structures)
c. 2-Hexene (line structures only)
Verified step by step guidance1
Step 1: Understand the concept of cis-trans isomerism. Cis-trans isomerism occurs in alkenes when there is restricted rotation around the double bond and two different groups are attached to each carbon of the double bond. For cis isomers, the similar groups are on the same side of the double bond, while for trans isomers, they are on opposite sides.
Step 2: Analyze the structure of 2,3-Dimethyl-2-pentene. The double bond is at the second carbon, and there are two methyl groups attached to the second and third carbons. Check if the carbons involved in the double bond have two different groups attached. If not, cis-trans isomerism is not possible.
Step 3: Analyze the structure of 2-Methyl-2-hexene. The double bond is at the second carbon, and there is a methyl group attached to the second carbon. Check if the carbons involved in the double bond have two different groups attached. If they do, draw both the cis and trans isomers in both condensed and line structures.
Step 4: Analyze the structure of 2-Hexene. The double bond is at the second carbon. Check if the carbons involved in the double bond have two different groups attached. If they do, draw both the cis and trans isomers in line structures.
Step 5: Summarize your findings. For each compound, determine whether cis-trans isomerism is possible based on the analysis. If it is, ensure you have drawn both the cis and trans isomers as specified in the problem (condensed or line structures).
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Cis-Trans Isomerism
Cis-trans isomerism, also known as geometric isomerism, occurs in compounds with restricted rotation around a double bond or a ring structure. In cis isomers, substituents are on the same side of the double bond, while in trans isomers, they are on opposite sides. This difference in spatial arrangement can significantly affect the physical and chemical properties of the compounds.
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2:47
Rules for Naming Alkenes Concept 1
Alkenes and Their Structure
Alkenes are hydrocarbons that contain at least one carbon-carbon double bond (C=C). The presence of this double bond allows for the possibility of cis-trans isomerism, as the double bond restricts rotation. The structure of alkenes can be represented using condensed formulas or line structures, which visually depict the arrangement of atoms and bonds.
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3:26Naming Alkenes Example 1
Drawing Isomers
Drawing isomers involves representing the different spatial arrangements of atoms in a molecule. For cis-trans isomers, it is essential to accurately depict the positions of substituents around the double bond. This can be done using condensed structures, which show the connectivity of atoms, or line structures, which provide a clearer view of the molecular geometry and bond angles.
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2:28Isomers Example 1
Related Practice
Textbook Question
Classify the following reactions as an addition, elimination, or substitution:
a. CH3Br + NaOH → CH3OH + NaBr
b. H2C═CH2 + HCl → CH3CH2Cl
c. CH3CH2Br → H2C═CH2 + HBr
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Textbook Question
Draw both condensed and line structures corresponding to the following IUPAC names:
a. 3-Methyl-1-heptene
b. 4,4-Dimethyl-2-pentyne
c. 2-Methyl-3-hexene
d. 1,3,3-Trimethylcyclohexene
Textbook Question
Many biological transformations can be simply classified as additions, eliminations, or substitutions. How would you classify the following reactions?
b. 2-Phosphoglyceric acid to phosphoenolpyruvic acid