Textbook Question
Using the BDEs in Table 4-2 (page 167),
(c) Suggest two reasons why iodine does not react well with methane.
1
views
Ch.4 - The Study of Chemical Reactions
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Not the one you use?Change textbookSelect a different textbook
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 19a,b
Classify each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).
a. butane
b. isobutane
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 butane. Butane is a straight-chain alkane with the molecular formula C₄H₁₀. Draw the structure of butane: CH₃-CH₂-CH₂-CH₃. Identify the types of carbon atoms present in butane.
Step 3: Classify the hydrogen atoms in butane. In butane, the terminal CH₃ groups are primary carbons, each bonded to one other carbon. Therefore, the hydrogens attached to these CH₃ groups are primary hydrogens. The CH₂ groups are secondary carbons, each bonded to two other carbons, so the hydrogens attached to these CH₂ groups are secondary hydrogens.
Step 4: Analyze the structure of isobutane. Isobutane is a branched alkane with the molecular formula C₄H₁₀. Draw the structure of isobutane: (CH₃)₂CH-CH₃. Identify the types of carbon atoms present in isobutane.
Step 5: Classify the hydrogen atoms in isobutane. In isobutane, the central carbon is a tertiary carbon, bonded to three other carbons, so the hydrogens attached to this carbon are tertiary hydrogens. The terminal CH₃ groups are primary carbons, each bonded to one other carbon, so the hydrogens attached to these CH₃ groups are primary hydrogens.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
4mWas this helpful?
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 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, and a tertiary (3°) hydrogen is attached to a tertiary carbon, bonded to three other carbons.
Recommended video:
Guided course
03:06
Understanding the hydrogen isotopes.
Structure of Butane
Butane is a straight-chain alkane with the molecular formula C4H10. It consists of four carbon atoms connected in a linear sequence. In butane, the terminal carbon atoms are primary, each bonded to three hydrogens, while the two central carbon atoms are secondary, each bonded to two hydrogens.
Recommended video:
Guided course
03:04Drawing Resonance Structures
Structure of Isobutane
Isobutane, also known as methylpropane, is a branched-chain alkane with the molecular formula C4H10. It has a central carbon atom bonded to three other carbon atoms, making it tertiary, and this carbon is bonded to one hydrogen. The remaining carbon atoms are primary, each bonded to three hydrogens.
Recommended video:
Guided course
03:04Drawing Resonance Structures
Related Practice
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
7
views
Textbook Question
a. Using the BDEs in Table 4-2 (page 167), compute the value of ΔH° for each step in the iodination of methane.
b. Compute the overall value of ΔH° for iodination.
1
views
Textbook Question
Classify each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).
c. 2-methylbutane
d. cyclohexane
2
views
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)
1
views
Textbook Question
What would be the product ratio in the chlorination of propane if all the hydrogens were abstracted at equal rates?
5
views