Textbook Question
Using the BDEs in Table 4-2 (page 167),
(c) Suggest two reasons why iodine does not react well with methane.
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Ch.4 - The Study of Chemical Reactions
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 4, Problem 19c,d
Classify each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).
c. 2-methylbutane
d. cyclohexane
Verified step by step guidance1
Step 1: Understand the classification of hydrogen atoms. In organic chemistry, hydrogen atoms are classified based on the type of carbon atom they are attached to. A primary (1°) hydrogen is attached to a primary carbon, which is bonded to only one other carbon. A secondary (2°) hydrogen is attached to a secondary carbon, bonded to two other carbons. A tertiary (3°) hydrogen is attached to a tertiary carbon, bonded to three other carbons.
Step 2: Analyze the structure of 2-methylbutane. Draw the structure of 2-methylbutane, which is an alkane with a branched chain. The main chain is butane (four carbons), and there is a methyl group (CH₃) attached to the second carbon.
Step 3: Classify the hydrogen atoms in 2-methylbutane. Identify the types of carbon atoms in the structure. The first and last carbons in the chain are primary carbons, the second carbon is a tertiary carbon due to the methyl group, and the third carbon is a secondary carbon. Classify the hydrogen atoms based on these carbon types.
Step 4: Analyze the structure of cyclohexane. Cyclohexane is a cyclic alkane with six carbon atoms forming a ring. Each carbon in cyclohexane is bonded to two other carbons, making them secondary carbons.
Step 5: Classify the hydrogen atoms in cyclohexane. Since all the carbon atoms in cyclohexane are secondary, all the hydrogen atoms attached to these carbons are secondary (2°) hydrogens.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Hydrogen Atom Classification
In organic chemistry, hydrogen atoms are classified based on the carbon atom they are attached to. A primary hydrogen is attached to a primary carbon, which is bonded to only one other carbon. A secondary hydrogen is attached to a secondary carbon, bonded to two other carbons, and a tertiary hydrogen is attached to a tertiary carbon, bonded to three other carbons.
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Understanding the hydrogen isotopes.
Structure of 2-Methylbutane
2-Methylbutane is a branched alkane with the molecular formula C5H12. It consists of a butane backbone with a methyl group attached to the second carbon. Understanding its structure is crucial for identifying the types of hydrogen atoms present, as the branching affects the classification of the hydrogen atoms.
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Structure of Cyclohexane
Cyclohexane is a cyclic alkane with the molecular formula C6H12, forming a six-membered ring. All carbon atoms in cyclohexane are equivalent, each bonded to two other carbons, making all hydrogen atoms secondary. Recognizing the ring structure helps in determining the uniform classification of hydrogen atoms in cyclohexane.
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Related Practice
Textbook Question
Classify each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).
a. butane
b. isobutane
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Textbook Question
Alkoxy radicals (R—O•) are generally more stable than alkyl (R•) radicals. Write an equation showing an alkyl free radical (from burning gasoline) abstracting a hydrogen atom from tert-butyl alcohol, (CH3)3COH. Explain why tert-butyl alcohol works as an antiknock additive for gasoline
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Textbook Question
Use the information in Table 4-2 to explain why toluene (PhCH3) has a very high octane rating of 111. Write an equation to show how toluene reacts with an alkyl free radical to give a relatively stable radical.
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Textbook Question
Classify each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).
e. norbornane (bicyclo[2.2.1]heptane)
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Textbook Question
What would be the product ratio in the chlorination of propane if all the hydrogens were abstracted at equal rates?
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