Textbook Question
Use bond-dissociation enthalpies (Table 4-2, p. 167) to calculate values of ΔH° for the following reactions.
a. CH3—CH3 + I2 → CH3CH2I + HI
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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 40a,b
Label each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).
(a) CH3CH2CH(CH3)2
(b) (CH3)3CCH2CH3
Verified step by step guidance1
Step 1: Understand the concept of primary, secondary, and tertiary hydrogen atoms. Primary hydrogens are attached to a carbon that is bonded to only one other carbon. Secondary hydrogens are attached to a carbon bonded to two other carbons. Tertiary hydrogens are attached to a carbon bonded to three other carbons.
Step 2: Analyze compound a, CH3CH2CH(CH3)2. Start by identifying the types of carbon atoms present. The first carbon (CH3-) is bonded to one other carbon, making it a primary carbon. The second carbon (CH2-) is bonded to two other carbons, making it a secondary carbon. The third carbon (CH-) is bonded to three other carbons, making it a tertiary carbon.
Step 3: Label the hydrogen atoms in compound a. The hydrogens on the CH3 group are primary hydrogens. The hydrogens on the CH2 group are secondary hydrogens. The hydrogen on the CH group is a tertiary hydrogen.
Step 4: Analyze compound b, (CH3)3CCH2CH3. Identify the types of carbon atoms. The first carbon (C-) is bonded to three other carbons, making it a tertiary carbon. The second carbon (CH2-) is bonded to two other carbons, making it a secondary carbon. The third carbon (CH3-) is bonded to one other carbon, making it a primary carbon.
Step 5: Label the hydrogen atoms in compound b. The hydrogens on the CH3 groups attached to the tertiary carbon are primary hydrogens. The hydrogens on the CH2 group are secondary hydrogens. The hydrogens on the CH3 group at the end are primary 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 (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.
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Carbon Atom Classification
Carbon atoms are classified as primary, secondary, or tertiary based on the number of other carbon atoms they are directly bonded to. A primary carbon is bonded to one other carbon, a secondary carbon to two, and a tertiary carbon to three. This classification helps in determining the type of hydrogen atoms attached to them.
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Structural Formula Analysis
Analyzing the structural formula of a compound involves identifying the connectivity of atoms within the molecule. This includes determining which carbon atoms are primary, secondary, or tertiary, and subsequently classifying the hydrogen atoms attached to them. Understanding the structure is crucial for accurate classification and understanding of molecular properties.
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Related Practice
Textbook Question
a. Draw an approximate reaction-energy diagram for the acid–base reaction of phenol (see below) with 1-molar aqueous sodium hydroxide solution.
b. On the same diagram, draw an approximate reaction-energy diagram for the acid–base reaction of tert-butyl alcohol (see below) with 1-molar aqueous sodium hydroxide solution.
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Textbook Question
Label each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).
(e)
(f)
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Textbook Question
Draw a reaction-energy diagram for a two-step endothermic reaction with a rate-limiting second step.
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Textbook Question
Treatment of tert-butyl alcohol with concentrated HCl gives tert-butyl chloride.
When the concentration of H+ is doubled, the reaction rate doubles. When the concentration of tert-butyl alcohol is tripled, the reaction rate triples. When the chloride ion concentration is quadrupled, however, the reaction rate is unchanged. Write the rate equation for this reaction.
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Textbook Question
Label each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).
(c) (CH3)2CHCH(CH3)CH2CH3
(d)
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