Textbook Question
Draw the structures of the following compounds. (Includes both new and old names.)
(k) 3-methylhex-4-yn-2-ol
1
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 34b
Predict which member of each pair is more acidic, and explain the reasons for your predictions.
b. cyclohexanol or cyclohexanethiol
Verified step by step guidance1
Step 1: Understand the concept of acidity. Acidity is determined by the ability of a compound to donate a proton (H⁺). The stability of the conjugate base formed after losing the proton plays a key role in determining acidity. A more stable conjugate base corresponds to a stronger acid.
Step 2: Compare the functional groups in cyclohexanol and cyclohexanethiol. Cyclohexanol contains an -OH group, while cyclohexanethiol contains an -SH group. Both groups can lose a proton to form their respective conjugate bases: cyclohexoxide (C₆H₁₁O⁻) and cyclohexanethiolate (C₆H₁₁S⁻).
Step 3: Analyze the electronegativity of oxygen and sulfur. Oxygen is more electronegative than sulfur, meaning it can better stabilize the negative charge on the conjugate base. This makes the conjugate base of cyclohexanol (C₆H₁₁O⁻) more stable than the conjugate base of cyclohexanethiol (C₆H₁₁S⁻).
Step 4: Consider the bond strength between the hydrogen atom and the heteroatom (O or S). The O-H bond in cyclohexanol is stronger than the S-H bond in cyclohexanethiol, making it easier for cyclohexanethiol to lose a proton compared to cyclohexanol.
Step 5: Conclude based on the above analysis. Cyclohexanethiol is more acidic than cyclohexanol because its conjugate base (C₆H₁₁S⁻) is less stable, and the S-H bond is weaker, allowing for easier proton donation.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
2mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acidity and pKa
Acidity in organic chemistry refers to the tendency of a compound to donate a proton (H+). The strength of an acid is often measured by its pKa value; lower pKa values indicate stronger acids. Understanding the pKa helps predict which compound in a pair is more acidic, as the one with the lower pKa will more readily donate a proton.
Recommended video:
Guided course
07:45
Identifying pKa values
Functional Groups and Their Effects
Different functional groups influence the acidity of a compound due to their electronic properties. For instance, alcohols (like cyclohexanol) have a hydroxyl (-OH) group, while thiols (like cyclohexanethiol) have a sulfhydryl (-SH) group. The electronegativity and size of the atoms involved can affect the stability of the conjugate base formed after deprotonation, impacting acidity.
Recommended video:
Guided course
02:36Identifying Functional Groups
Inductive Effect
The inductive effect refers to the electron-withdrawing or electron-donating influence of substituents on a molecule. In the case of cyclohexanol and cyclohexanethiol, the sulfur atom in thiols is larger and less electronegative than oxygen, which can lead to a weaker stabilization of the conjugate base. This difference in stabilization can help determine which compound is more acidic.
Recommended video:
Guided course
01:47Understanding the Inductive Effect.
Related Practice
Textbook Question
Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(a)
(b)
1
views
Textbook Question
Predict which member of each pair has the higher boiling point, and explain the reasons for your predictions.
a. hexan-1-ol or 3,3-dimethylbutan-1-ol
b. hexan-2-one or hexan-2-ol
1
views
Textbook Question
Predict which member of each group is most soluble in water, and explain the reasons for your predictions.
a. butan-1-ol, pentan-1-ol, or propan-2-ol
1
views
Textbook Question
Predict which member of each pair is more acidic, and explain the reasons for your predictions.
a. cyclopentanol or 3-chlorophenol
1
views
Textbook Question
Predict which member of each group is most soluble in water, and explain the reasons for your predictions.
b. chlorocyclohexane, cyclohexanol, or cyclohexane-1,2-diol
1
views