Textbook Question
Propose a mechanism for both parts of the Wolff–Kishner reduction of cyclohexanone: the formation of the hydrazone, and then the base-catalyzed reduction with evolution of nitrogen gas.
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Ch. 18 - Ketones and Aldehydes
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 18, Problem 34c
Predict the major products of the following reactions.
(c) 
Verified step by step guidance1
Step 1: Identify the functional groups in the given molecule. The molecule contains an aldehyde group (-CHO) and a ketone group (C=O) attached to a cyclohexane ring.
Step 2: Recognize the reagent used in the reaction. The reagent is Tollens' reagent, which consists of [Ag(NH3)2]+ and OH-. Tollens' reagent selectively oxidizes aldehydes to carboxylic acids while leaving ketones unaffected.
Step 3: Predict the reaction mechanism. The aldehyde group (-CHO) will be oxidized by Tollens' reagent to form a carboxylic acid group (-COOH). The ketone group (C=O) will remain unchanged because Tollens' reagent does not react with ketones.
Step 4: Write the structure of the major product. Replace the aldehyde group (-CHO) with a carboxylic acid group (-COOH) while keeping the ketone group (C=O) intact.
Step 5: Verify the stereochemistry and connectivity of the product. Ensure that the cyclohexane ring remains unchanged and the functional groups are correctly positioned in the major product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Reaction Mechanisms
Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. Familiarity with mechanisms helps predict the outcome of reactions and the stability of products formed.
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Heck Reaction Mechanism
Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups allows chemists to predict reactivity patterns and the types of reactions that can occur, which is essential for determining the major products of a reaction.
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Regioselectivity and Stereoselectivity
Regioselectivity refers to the preference of a chemical reaction to occur at one location over another in a molecule, while stereoselectivity involves the preference for the formation of one stereoisomer over others. Understanding these concepts is vital for predicting the major products, especially in reactions involving multiple possible sites of reaction or stereochemical outcomes.
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Related Practice
Textbook Question
Predict the major products of the following reactions.
(a)
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Textbook Question
Predict the major products of the following reactions.
(d)
806
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Textbook Question
Propose a mechanism for both parts of the Wolff–Kishner reduction of cyclohexanone: the formation of the hydrazone, and then the base-catalyzed reduction with evolution of nitrogen gas.
808
views
Textbook Question
Predict the major products of the following reactions.
(b)
865
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Textbook Question
Show how Wittig reactions might be used to synthesize the following compounds. In each case, start with an alkyl halide and a ketone or an aldehyde.
(c) Ph–CH=CH–CH=CH–Ph
(d)
1879
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