Textbook Question
Suggest an acetylide ion and a carbonyl that might be used to make the following products.
(c) 5-phenylhex-2-yn-1-ol
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Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones
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. 17 - Carbonyl Addition Reactions: Aldehydes and KetonesProblem 22a
Mullins 1st EditionCh. 17 - Carbonyl Addition Reactions: Aldehydes and KetonesProblem 22aChapter 16, Problem 22a
Suggest a carbonyl to react with NaCN/HCN to produce the following cyanohydrins.
(a) 
Verified step by step guidance1
Step 1: Understand the reaction mechanism. The reaction between a carbonyl compound and NaCN/HCN involves the nucleophilic addition of the cyanide ion (CN⁻) to the carbonyl carbon, forming a cyanohydrin.
Step 2: Identify the structure of the cyanohydrin product. Analyze the given image to determine the structure of the cyanohydrin, focusing on the functional groups and the carbon skeleton.
Step 3: Determine the carbonyl precursor. Since cyanohydrins are formed by the addition of CN⁻ to the carbonyl carbon, the carbonyl compound should have the same carbon skeleton as the cyanohydrin minus the CN group.
Step 4: Consider the stereochemistry. If the cyanohydrin has chiral centers, consider the stereochemistry of the starting carbonyl compound, as it can influence the stereochemistry of the product.
Step 5: Suggest the carbonyl compound. Based on the analysis, suggest a carbonyl compound (either an aldehyde or ketone) that would react with NaCN/HCN to yield the cyanohydrin with the desired structure.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Carbonyl Compounds
Carbonyl compounds, characterized by the presence of a carbon-oxygen double bond (C=O), include aldehydes and ketones. They are highly reactive due to the electrophilic nature of the carbon atom, making them susceptible to nucleophilic attack. Understanding the structure and reactivity of carbonyls is essential for predicting their behavior in reactions, such as those with nucleophiles like cyanide.
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Nucleophilic Addition
Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, leading to the formation of a new bond. In the case of carbonyl compounds, nucleophiles such as NaCN or HCN can add to the carbonyl carbon, resulting in the formation of cyanohydrins. This mechanism is crucial for understanding how to synthesize various organic compounds from carbonyl precursors.
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Cyanohydrins
Cyanohydrins are organic compounds formed by the addition of hydrogen cyanide (HCN) to carbonyl compounds, resulting in a hydroxyl group (-OH) and a cyano group (-CN) attached to the same carbon atom. They are important intermediates in organic synthesis and can be further transformed into various functional groups. Recognizing the structure and properties of cyanohydrins is vital for predicting their reactivity and potential applications in organic chemistry.
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Related Practice
Textbook Question
Identify the hemiacetal functional group in each of the following molecules. These molecules may not be stable enough to be the favorable product in an equilibrium reaction.
(c)
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Textbook Question
Suggest an acetylide ion and a carbonyl that might be used to make the following products.
(a) oct-4-yn-3-ol
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Textbook Question
Suggest the appropriate carbonyl and Wittig reagent to make the following alkenes.
a. (E)-7-methylnon-4-en-3-one
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Textbook Question
Suggest an acetylide ion and a carbonyl that might be used to make the following products.
(b) 2,6-dimethylhept-3-yn-2-ol
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Textbook Question
For each of the following carbonyl addition reactions, would you expect a racemic mixture or a mixture enriched in one stereoisomer? In each case, draw both possible stereoisomeric products.
(a)
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