Textbook Question
Calculate the pH of the following solutions.
a. 5.00 g of HBr in 100 mL of aqueous solution
b. 1.50 g of NaOH in 50 mL of aqueous solution
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Ch. 2 - Acids and Bases; Functional Groups
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 2, Problem 7a
Circle the member of each pair that is more soluble in water.
a. CH3CH2OCH2CH3 or CH3CH2CH2CH2CH3
b. CH3CH2OCH2CH3 or CH3CH2CH2OH
c. CH3CH2NHCH3 or CH3CH2CH2CH3
d. CH3CH2OH or CH3CH2CH2CH2OH
e. 
Verified step by step guidance1
Identify the functional groups in each compound. For example, ethers (R-O-R') and alcohols (R-OH) are more polar than alkanes (R-R') and can form hydrogen bonds with water, increasing solubility.
For part (a), compare CH3CH2OCH2CH3 (an ether) with CH3CH2CH2CH2CH3 (an alkane). Ethers are generally more soluble in water than alkanes due to their ability to form hydrogen bonds.
For part (b), compare CH3CH2OCH2CH3 (an ether) with CH3CH2CH2OH (an alcohol). Alcohols can form more hydrogen bonds with water than ethers, making them more soluble.
For part (c), compare CH3CH2NHCH3 (an amine) with CH3CH2CH2CH3 (an alkane). Amines can form hydrogen bonds with water, increasing their solubility compared to alkanes.
For part (d), compare CH3CH2OH (a primary alcohol) with CH3CH2CH2CH2OH (a primary alcohol with a longer carbon chain). Shorter chain alcohols are generally more soluble in water than longer chain alcohols due to less hydrophobic character.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Polarity and Solubility
Polarity refers to the distribution of electrical charge over the atoms in a molecule. Polar molecules, which have a significant difference in electronegativity between atoms, tend to dissolve well in polar solvents like water. Understanding the polarity of the compounds in the question is crucial for predicting their solubility in water.
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07:13
Functional Classification
Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the context of solubility, groups such as hydroxyl (-OH) and amino (-NH2) are polar and can form hydrogen bonds with water, enhancing solubility. Identifying these groups in the given compounds is essential for determining which is more soluble.
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02:36Identifying Functional Groups
Hydrogen Bonding
Hydrogen bonding is a type of attractive interaction between a hydrogen atom bonded to a highly electronegative atom and another electronegative atom. This interaction significantly influences the solubility of compounds in water. Molecules capable of forming hydrogen bonds with water will generally be more soluble, making it important to assess the ability of the compounds in the question to engage in such interactions.
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00:48The definition of hydrogenation.
Related Practice
Textbook Question
Ammonia appears in [TABLE 2-2 ] as both an acid and a conjugate base. a. Explain how ammonia can act as both an acid and a base. Which of these roles does it commonly fill in aqueous solutions?
b. Show how water can serve as both an acid and a base.
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Textbook Question
Ammonia appears in [TABLE 2-2] as both an acid and a conjugate base.
d. Show how methanol (CH3OH) can serve as both an acid and a base. Write an equation for the reaction of methanol with sulfuric acid.
Textbook Question
For each pair of compounds, circle the compound you expect to have the higher boiling point. Explain your reasoning.
(d) HOCH2—(CH2)4—CH2OH or (CH3)3CCH(OH)CH3
(e) (CH3CH2CH2)2NH or (CH3CH2)3N
(f)
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Textbook Question
Draw the hydrogen bonding that takes place between
c. a molecule of dimethyl ether and two molecules of water.
d. two molecules of trimethylamine and a molecule of water.
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Textbook Question
For each pair of compounds, circle the compound you expect to have the higher boiling point. Explain your reasoning.
a. (CH3)3C—C(CH3)3 or (CH3)2CH—CH2CH2—CH(CH3)2
b. CH3(CH2)6CH3 or CH3(CH2)5CH2OH
c. CH3CH2OCH2CH3 or CH3CH2CH2CH2OH
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