Textbook Question
Predict the products formed when cyclohexanone reacts with the following reagents.
(i) hydrazine, then hot, fused KOH
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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 53k
Predict the products formed when cyclohexanone reacts with the following reagents.
(k) sodium cyanide
Verified step by step guidance1
Step 1: Recognize the functional group in cyclohexanone. Cyclohexanone is a ketone, which contains a carbonyl group (C=O). This group is highly reactive and can undergo nucleophilic addition reactions.
Step 2: Understand the role of sodium cyanide (NaCN). Sodium cyanide provides the cyanide ion (CN⁻), which is a strong nucleophile capable of attacking the electrophilic carbon atom in the carbonyl group.
Step 3: Analyze the mechanism of the reaction. The cyanide ion (CN⁻) attacks the carbonyl carbon, breaking the π bond of the C=O group. This results in the formation of a tetrahedral intermediate.
Step 4: Consider the protonation step. After the nucleophilic attack, the negatively charged oxygen atom in the intermediate is typically protonated by a proton source (e.g., water or an acid), leading to the formation of a stable product.
Step 5: Predict the product. The reaction between cyclohexanone and sodium cyanide forms a cyanohydrin, which is characterized by the addition of a hydroxyl group (-OH) and a cyano group (-CN) to the original carbonyl carbon.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Addition
Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically in a carbonyl group. In the case of cyclohexanone, the carbonyl carbon is susceptible to attack by nucleophiles like cyanide ions. This reaction leads to the formation of a new carbon-carbon bond, resulting in an alcohol or a cyanohydrin depending on the conditions.
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Nucleophilic Addition
Cyanohydrin Formation
Cyanohydrin formation occurs when a carbonyl compound, such as cyclohexanone, reacts with a cyanide ion. The nucleophilic cyanide attacks the electrophilic carbon of the carbonyl, leading to the addition of the cyanide group and the conversion of the carbonyl into a hydroxyl group. This reaction is significant in organic synthesis as cyanohydrins can serve as intermediates for further transformations.
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Reactivity of Carbonyl Compounds
Carbonyl compounds, including ketones like cyclohexanone, exhibit distinct reactivity due to the polarized carbon-oxygen double bond. The carbon atom is electrophilic, making it a target for nucleophiles. Understanding the reactivity patterns of carbonyl compounds is crucial for predicting the outcomes of reactions, such as the formation of products when they interact with nucleophiles like sodium cyanide.
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Related Practice
Textbook Question
Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.
(a) PhMgBr, then H3O+
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Textbook Question
Predict the products formed when cyclohexanone reacts with the following reagents.
(l) acidic hydrolysis of the product from (k)
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Textbook Question
Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.
b. Tollens reagent
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Textbook Question
Predict the products formed when cyclohexanone reacts with the following reagents.
(h) sodium acetylide, then mild H3O+
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Textbook Question
Predict the products formed when cyclohexanone reacts with the following reagents.
g. Tollens reagent
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