Textbook Question
Propose mechanisms for the Birch reduction of anisole. Show why the observed orientation of reduction is favored in each case.
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Ch. 17 - Reactions of Aromatic Compounds
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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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 17, Problem 32c
Predict the major products of the following reactions.
(c) o-xylene + H2 (1000 psi, 100 °C, Rh catalyst)
Verified step by step guidance1
Step 1: Analyze the reaction conditions. The reaction involves hydrogen gas (H2) under high pressure (1000 psi) and moderate temperature (100 °C) with a rhodium (Rh) catalyst. These conditions are typical for catalytic hydrogenation reactions.
Step 2: Identify the functional group on the reactant. The reactant is a nitrobenzene derivative, with a nitro group (-NO2) attached to the benzene ring. Nitro groups are susceptible to reduction under hydrogenation conditions.
Step 3: Predict the transformation of the nitro group. Under catalytic hydrogenation, the nitro group (-NO2) is reduced to an amino group (-NH2). This is a common reaction pathway for nitro compounds in the presence of H2 and a metal catalyst.
Step 4: Consider the aromatic ring stability. The benzene ring itself is not hydrogenated under these conditions because aromatic rings are highly stable and require more extreme conditions for hydrogenation.
Step 5: Write the major product structure. The major product will be the benzene ring with the nitro group reduced to an amino group, resulting in aniline (C6H5NH2).
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Catalytic Hydrogenation
Catalytic hydrogenation is a chemical reaction that involves the addition of hydrogen (H2) to unsaturated organic compounds, typically in the presence of a catalyst. In this case, the Rhodium (Rh) catalyst facilitates the reaction, allowing for the conversion of double bonds in o-xylene to single bonds, resulting in the formation of saturated hydrocarbons.
Reaction Conditions
The reaction conditions, including pressure and temperature, significantly influence the outcome of catalytic reactions. Here, the high pressure (1000 psi) and elevated temperature (100 °C) promote the hydrogenation process, enhancing the reactivity of o-xylene and favoring the formation of saturated products over side reactions.
Product Prediction
Predicting the major products of a reaction involves understanding the structure of the starting material and the nature of the reaction conditions. In the case of o-xylene, the hydrogenation will likely lead to the formation of 1,2-dimethylcyclohexane, as the reaction saturates the aromatic ring, converting it into a cycloalkane structure.
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Predict the major products of the following reactions.
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