Textbook Question
Suggest a series of steps involving a cuprate reagent that would convert the reactant on the left to the product on the right. The ideal number of steps is shown.
(a)
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Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
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Mullins 1st EditionCh. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid DerivativesProblem 50
Mullins 1st EditionCh. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid DerivativesProblem 50Chapter 18, Problem 50
How would you synthesize the cyanohydrin shown?
Verified step by step guidance1
Step 1: Identify the functional groups in the target molecule. The cyanohydrin contains a hydroxyl group (-OH) and a nitrile group (-CN) attached to the same carbon atom.
Step 2: Recognize the precursor for cyanohydrin synthesis. Cyanohydrins are typically synthesized from aldehydes or ketones via nucleophilic addition of hydrogen cyanide (HCN). In this case, the precursor would be cyclohexanone, a ketone.
Step 3: Prepare the reaction conditions. Cyanohydrin synthesis requires the presence of HCN, which can be generated in situ using a combination of sodium cyanide (NaCN) and a weak acid like HCl. This provides the nucleophile (CN⁻) and the proton source (H⁺) for the reaction.
Step 4: Perform the nucleophilic addition reaction. The CN⁻ ion attacks the carbonyl carbon of cyclohexanone, forming a tetrahedral intermediate. Protonation of the oxygen atom in the intermediate leads to the formation of the hydroxyl group (-OH).
Step 5: Isolate and purify the cyanohydrin product. After the reaction is complete, the cyanohydrin can be separated and purified using standard techniques such as extraction and recrystallization.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Cyanohydrin Formation
Cyanohydrins are formed through the nucleophilic addition of hydrogen cyanide (HCN) to carbonyl compounds, such as aldehydes or ketones. The nucleophile, cyanide ion (CN-), attacks the electrophilic carbon of the carbonyl group, leading to the formation of a hydroxyl group and a cyano group on the same carbon atom.
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02:36
Nitrile Reduction
Nucleophilic Addition Reactions
Nucleophilic addition is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, resulting in the formation of a new bond. In the case of cyanohydrin synthesis, the nucleophile (CN-) adds to the carbonyl carbon, which is electron-deficient, facilitating the reaction and leading to the product formation.
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08:27Nucleophilic Addition
Mechanism of Reaction
Understanding the mechanism of the cyanohydrin formation involves recognizing the steps of nucleophilic attack, protonation, and stabilization of the intermediate. The reaction typically proceeds through the formation of a tetrahedral intermediate, which then collapses to yield the final cyanohydrin product, illustrating the importance of reaction mechanisms in predicting product formation.
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Related Practice
Textbook Question
Beginning with an amide, two different pathways produce the same compound. Predict the product of these two pathways.
1121
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Textbook Question
Suggest a series of steps involving a cuprate reagent that would convert the reactant on the left to the product on the right. The ideal number of steps is shown.
(b)
862
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Textbook Question
Give the nitrile and organometallic reagent you would use to make the following ketones. There are two possible answers for both.
(a)
981
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Textbook Question
Suggest a series of steps involving a cuprate reagent that would convert the reactant on the left to the product on the right. The ideal number of steps is shown.
(c)
782
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Textbook Question
Predict the product of the following reaction sequences.
(b)
1023
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