Textbook Question
Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.
(a) PhMgBr, then H3O+
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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 54b
Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.
b. Tollens reagent
Verified step by step guidance1
Step 1: Recognize the functional group in cyclohexanecarbaldehyde. Cyclohexanecarbaldehyde contains an aldehyde functional group (-CHO) attached to a cyclohexane ring.
Step 2: Understand the nature of Tollens reagent. Tollens reagent is a mild oxidizing agent, typically consisting of ammoniacal silver nitrate ([Ag(NH3)2]+). It selectively oxidizes aldehydes to carboxylic acids while leaving other functional groups unaffected.
Step 3: Predict the reaction mechanism. The aldehyde group in cyclohexanecarbaldehyde will be oxidized by Tollens reagent. The silver ion in Tollens reagent is reduced to metallic silver (Ag), which often forms a shiny silver mirror on the reaction vessel.
Step 4: Write the chemical transformation. The aldehyde group (-CHO) is converted into a carboxylic acid group (-COOH). The product formed will be cyclohexanecarboxylic acid.
Step 5: Summarize the reaction. The reaction involves the oxidation of cyclohexanecarbaldehyde to cyclohexanecarboxylic acid, with the reduction of silver ions to metallic silver as a side product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Tollens' Reagent
Tollens' reagent is a solution of silver nitrate in ammonia, commonly used to test for aldehydes. It contains the complex ion [Ag(NH3)2]+, which oxidizes aldehydes to carboxylic acids while reducing silver ions to metallic silver. This reaction is characterized by the formation of a silver mirror on the reaction vessel, indicating the presence of an aldehyde.
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Reagents
Aldehyde Reactivity
Aldehydes are highly reactive compounds due to the presence of a carbonyl group (C=O) at the end of their carbon chain. This reactivity allows them to undergo various chemical reactions, including oxidation and nucleophilic addition. In the case of Tollens' reagent, the aldehyde is oxidized to a carboxylic acid, demonstrating its susceptibility to oxidation.
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Cyclohexanecarbaldehyde Structure
Cyclohexanecarbaldehyde is a cyclic aldehyde with a six-membered carbon ring and an aldehyde functional group attached to one of the carbons. Its structure influences its reactivity, as the steric and electronic environment around the carbonyl group can affect how it interacts with reagents like Tollens' reagent. Understanding its structure is crucial for predicting the products of its reactions.
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Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.
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