Domanda del libro di testo
Predict which member of each pair will be more acidic. Explain your answers.
d. 2,2-dichloropropan-1-ol or 2,2-difluoropropan-1-ol
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Ch.10 - Structure and Synthesis of Alcohols
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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TOC.tableOfContents
- 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
Capitolo 10, Problema 9
A nitro group (–NO2) effectively stabilizes a negative charge on an adjacent carbon atom through resonance:
Two of the following nitrophenols are much more acidic than phenol itself. The third compound is only slightly more acidic than phenol. Use resonance structures of the appropriate phenoxide ions to show why two of these anions should be unusually stable.
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Guida verificata passo dopo passo1
Identify the nitrophenols: 2-nitrophenol, 3-nitrophenol, and 4-nitrophenol. These compounds have a nitro group (¬NO2) attached to the benzene ring at different positions relative to the hydroxyl group (¬OH).
Understand the effect of the nitro group on acidity: The nitro group is an electron-withdrawing group that can stabilize a negative charge through resonance. This stabilization increases the acidity of the phenol by making the phenoxide ion more stable.
Analyze the resonance structures: For 2-nitrophenol and 4-nitrophenol, the nitro group is positioned such that it can participate in resonance with the phenoxide ion, effectively stabilizing the negative charge. Draw resonance structures showing the delocalization of electrons from the phenoxide ion to the nitro group.
Compare the stability of the phenoxide ions: The resonance structures for 2-nitrophenol and 4-nitrophenol show significant stabilization of the negative charge due to the nitro group. In contrast, 3-nitrophenol does not have the nitro group in a position that allows effective resonance stabilization, making it only slightly more acidic than phenol.
Conclude which nitrophenols are more acidic: Based on the resonance stabilization, 2-nitrophenol and 4-nitrophenol are much more acidic than phenol itself, while 3-nitrophenol is only slightly more acidic due to less effective resonance stabilization.
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Resonance
Resonance is a concept in organic chemistry that describes the delocalization of electrons in molecules where the bonding cannot be expressed by a single Lewis structure. Instead, multiple structures, known as resonance structures, are used to represent the molecule's electron distribution. This delocalization stabilizes the molecule, as seen in nitrophenols, where the negative charge can be spread over multiple atoms.
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03:04
Drawing Resonance Structures
Acidity and Conjugate Bases
Acidity in organic compounds is often determined by the stability of their conjugate bases. A more stable conjugate base corresponds to a stronger acid. In the case of nitrophenols, the presence of the nitro group enhances the stability of the phenoxide ion through resonance, making the compound more acidic compared to phenol, which lacks such stabilization.
Video consigliato:
02:11Equilibrium constant and conjugates.
Electronegative Substituents
Electronegative substituents, like nitro groups, can significantly influence the acidity of organic compounds. They stabilize negative charges through resonance or inductive effects, thereby increasing acidity. In nitrophenols, the nitro group withdraws electron density, facilitating the stabilization of the phenoxide ion and enhancing the overall acidity of the compound.
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1:47Electronegativity
Pratica correlata
Domanda del libro di testo
Without looking them up, rank the following compounds in decreasing order of acidity. These examples represent large classes of compounds that differ widely in acidity.
water, ethanol, 2-chloroethanol, tert-butyl alcohol, ammonia, sulfuric acid, hexane, hex-1-yne, acetic acid
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Domanda del libro di testo
For each molecular formula, draw all the possible constitutional isomers of alcohols with that formula. Give the IUPAC name for each alcohol.
(a) C3H8O
(b) C4H10O
(c) C3H6O
(d) C3H4O
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Domanda del libro di testo
The following compounds are only slightly soluble in water, but one of them is very soluble in a dilute aqueous solution of sodium hydroxide. The other is still only slightly soluble.
(a) Explain the difference in solubility of these compounds in dilute sodium hydroxide.
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1
rank
Domanda del libro di testo
Predict which member of each pair will be more acidic. Explain your answers.
c. 2-chloroethanol or 2,2-dichloroethanol
1159
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Domanda del libro di testo
The following compounds are only slightly soluble in water, but one of them is very soluble in a dilute aqueous solution of sodium hydroxide. The other is still only slightly soluble.
(b) Show how this difference might be exploited to separate a mixture of these two compounds using a separatory funnel.
1555
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