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What reagents are required to carry out the following synthesis?
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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 85a
Bruice 8th EditionCh. 18 - Reactions of Benzene and Substituted BenzenesProblema 85aCapitolo 18, Problema 85a
Identify A–J:
Guida verificata passo dopo passo1
Step 1: Analyze the first reaction. The starting material is benzene, and it reacts with CH3CH2CCl/AlCl3. This is a Friedel-Crafts acylation reaction, where the acyl group (CH3CH2CO-) is introduced onto the benzene ring. The product A will be an aromatic ketone.
Step 2: Examine the second reaction. Compound A reacts with hydrazine (H2NNH2) in the presence of a base (HO-) and heat (Δ). This is the Wolff-Kishner reduction, which converts the carbonyl group (C=O) in ketones to a methylene group (-CH2). The product B will be an alkylbenzene.
Step 3: Note the presence of ethylene glycol (HOCH2CH2OH) in the second step. Ethylene glycol is often used as a solvent or stabilizing agent in high-temperature reactions, but it does not directly participate in the Wolff-Kishner reduction.
Step 4: Summarize the transformations. Compound A is formed by the acylation of benzene, resulting in an aromatic ketone. Compound B is formed by the reduction of the ketone group in A to a methylene group, yielding an alkylbenzene.
Step 5: To identify A and B, consider the specific acyl group introduced in the first step (CH3CH2CO-) and the subsequent reduction of the ketone group. A is ethyl phenyl ketone (C6H5COCH2CH3), and B is ethylbenzene (C6H5CH2CH3).
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Friedel-Crafts Acylation
Friedel-Crafts acylation is a key reaction in organic chemistry that introduces an acyl group into an aromatic ring. This reaction typically involves the use of an acyl chloride and a Lewis acid catalyst, such as AlCl3, to form an acylaromatic compound. The product, compound A in the diagram, retains the aromaticity of the benzene ring while adding a carbonyl functional group.
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05:20
Friedel-Crafts Acylation
Wolff-Kishner Reduction
The Wolff-Kishner reduction is a method used to convert carbonyl compounds into alkanes by removing the oxygen functionality. This reaction employs hydrazine (H2NNH2) and a strong base, often under heat, to facilitate the reduction. In the provided diagram, the transformation from compound A to compound B illustrates this reduction process, resulting in the formation of an alkane.
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04:57Mechanism
Hydrazine and Base Reaction
Hydrazine (H2NNH2) acts as a reducing agent in organic reactions, particularly in the Wolff-Kishner reduction. When combined with a strong base, it promotes the conversion of carbonyl groups to hydrocarbons. The reaction typically requires heating to drive the elimination of nitrogen gas, leading to the formation of the final product, which is a diol in this case, as shown in the transformation from compound B.
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02:43Recognizing Acid-Base Reactions.
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Identify A–J:
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Identify A–J:
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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.
a. Cl: ortho > meta > para
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What reagents are required to carry out the following synthesis?
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