Textbook Question
Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.
(e) (CH3)3C–O– + CH3CH2OH ⇌
2
views
Ch.10 - Structure and Synthesis of Alcohols
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 10, Problem 42d
Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.
(d) 
Verified step by step guidance1
Step 1: Identify the acid and base in the reaction. In this case, cyclopentanol (C5H9OH) acts as the acid because it can donate a proton (H+), and KOH acts as the base because it can accept a proton.
Step 2: Write the products of the acid-base reaction. Cyclopentanol will lose a proton to form cyclopentoxide (C5H9O−), and KOH will donate its hydroxide ion (OH−) to form water (H2O). The reaction can be represented as: C5H9OH + OH− ⇌ C5H9O− + H2O.
Step 3: Determine the direction of equilibrium. The equilibrium position depends on the relative acidity of cyclopentanol and water. Cyclopentanol has a pKa of approximately 16, while water has a pKa of 15.7. Since water is slightly more acidic than cyclopentanol, the equilibrium will favor the formation of cyclopentanol and hydroxide ions (reactants).
Step 4: Explain the reasoning. The equilibrium favors the side with the weaker acid and base. In this case, cyclopentanol (weaker acid) and hydroxide ion (weaker base) are favored over cyclopentoxide and water.
Step 5: Conclude the analysis. The equilibrium favors the reactants (cyclopentanol and KOH) because the acid (cyclopentanol) is weaker than water, and the base (OH−) is stronger than cyclopentoxide.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
5mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acid-Base Reactions
Acid-base reactions involve the transfer of protons (H+) between reactants. In this context, the hydroxyl group (OH-) acts as a weak acid, while KOH, a strong base, dissociates to provide hydroxide ions (OH-). Understanding the nature of the acids and bases involved is crucial for predicting the direction of the equilibrium.
Recommended video:
Guided course
02:49
The Lewis definition of acids and bases.
Equilibrium Position
The position of equilibrium in a chemical reaction indicates whether the reactants or products are favored. This can be influenced by factors such as the strength of the acids and bases involved, the stability of the resulting products, and the concentration of reactants and products. In this case, the equilibrium will favor the side with the weaker acid and base.
Recommended video:
2:49Reactions at the Allylic Position Concept 5
Strength of Acids and Bases
The strength of an acid or base is determined by its ability to donate or accept protons. Strong acids completely dissociate in solution, while weak acids do not. In this reaction, KOH is a strong base, which will drive the reaction towards the formation of water and the corresponding alkoxide, favoring the products over the reactants.
Recommended video:
2:50Acid-Base Catalysis Concept 3
Related Practice
Textbook Question
Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.
(g) KOH + CH3CH2OH ⇌
1
views
Textbook Question
Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.
(f) (CH3)3C–O– + H2O ⇌
1
views
Textbook Question
Show how you would synthesize the following:
c. cyclohexylmethanol from an alkyl halide using an SN2 reaction
Textbook Question
Show how you would synthesize the following:
f. 2,5-dimethylhexane from a four-carbon alkyl halide
1
views
Textbook Question
Show how you would synthesize the following:
e. cis-pent-2-en-1-thiol from a suitable alkenyl halide
2
views