Domanda del libro di testo
Show how the following compounds can be prepared from benzene:
c.
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Ch. 18 - Reactions of Benzene and Substituted Benzenes
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 18 - Reactions of Benzene and Substituted BenzenesProblema 90
Bruice 8th EditionCh. 18 - Reactions of Benzene and Substituted BenzenesProblema 90Capitolo 18, Problema 90
When heated with chromic acid, compound A forms benzoic acid. Identify compound A from its 1H NMR spectrum.
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Step 1: Analyze the 1H NMR spectrum provided. The spectrum shows two distinct signals: one at approximately 7 ppm and another at approximately 2 ppm. The integration values indicate a ratio of 2:3 for these signals.
Step 2: The signal at 7 ppm corresponds to aromatic protons, which are characteristic of a benzene ring. This suggests that compound A contains an aromatic ring.
Step 3: The signal at 2 ppm corresponds to protons in a methyl group (-CH3) attached to the aromatic ring. This indicates that compound A likely has a methyl group directly bonded to the benzene ring.
Step 4: When heated with chromic acid, compound A forms benzoic acid. Chromic acid is a strong oxidizing agent that oxidizes methyl groups attached to aromatic rings into carboxylic acids (-COOH). This confirms that compound A is toluene (methylbenzene).
Step 5: To summarize, the 1H NMR spectrum and the reaction with chromic acid indicate that compound A is toluene, which upon oxidation forms benzoic acid.
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NMR Spectroscopy
Nuclear Magnetic Resonance (NMR) spectroscopy is a powerful analytical technique used to determine the structure of organic compounds. It provides information about the number of hydrogen atoms in different environments within a molecule, indicated by peaks in the spectrum. The chemical shift, measured in parts per million (PPM), reveals the electronic environment of the hydrogen atoms, helping to identify functional groups and molecular structure.
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General NMR Features
Chromic Acid Oxidation
Chromic acid is a strong oxidizing agent commonly used in organic chemistry to oxidize alcohols to carbonyl compounds and further to carboxylic acids. In this context, the oxidation of compound A to benzoic acid suggests that compound A is likely a primary or secondary alcohol or an aldehyde. Understanding this reaction is crucial for deducing the structure of compound A based on its transformation.
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Chemical Shifts in Aromatic Compounds
In NMR spectroscopy, aromatic protons typically resonate in the range of 6.5 to 8.5 PPM due to the deshielding effect of the aromatic ring. The presence of peaks at specific PPM values can indicate the number of hydrogen atoms on the aromatic ring and their relative positions. Analyzing these shifts helps in identifying the substitution pattern on the aromatic compound, which is essential for determining the structure of compound A.
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Propose a mechanism for the following reaction that explains why the configuration of the asymmetric center in the reactant is retained in the product:
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The pKa values of a few ortho-, meta-, and para-substituted benzoic acids are shown below:
The relative pKa values depend on the substituent. For chloro-substituted benzoic acids, the ortho isomer is the most acidic and the para isomer is the least acidic; for nitro-substituted benzoic acids, the ortho isomer is the most acidic and the meta isomer is the least acidic; and for amino-substituted benzoic acids, the meta isomer is the most acidic and the ortho isomer is the least acidic. Explain these relative acidities.
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