Domanda del libro di testo
A student, when solving the following 'predict-the-product' question, made a common mistake by writing the answer shown here. Explain why this reaction would not work as written.
958
views
Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
Non è quello che usi tu?Cambia libro di testoScegli un libro di testo diverso
TOC.tableOfContents
- 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 1: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes 2: 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 1: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification 2: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution 1: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution 2: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems 1: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems 2: Pericyclic Reactions54
- Ch. 23 - Benzene 1: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene 2: 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: 9780137566471Non è quello che usi tu?Cambia libro di testo
Tutti i libri di testo
Mullins 1st EditionCh. 17 - Carbonyl Addition Reactions: Aldehydes and KetonesProblema 20c
Mullins 1st EditionCh. 17 - Carbonyl Addition Reactions: Aldehydes and KetonesProblema 20cCapitolo 16, Problema 20c
Suggest an acetylide ion and a carbonyl that might be used to make the following products.
(c) 5-phenylhex-2-yn-1-ol
Guida verificata passo dopo passo1
Step 1: Recognize that the product, 5-phenylhex-2-yn-1-ol, contains a terminal alcohol (-OH group) and a triple bond (-C≡C-) in the structure. This suggests that the reaction involves the addition of an acetylide ion to a carbonyl compound.
Step 2: Identify the acetylide ion needed. The acetylide ion must contribute the triple bond and part of the carbon chain. In this case, the acetylide ion should be phenylethynide (C₆H₅-C≡C⁻), as it provides the phenyl group and the triple bond.
Step 3: Determine the carbonyl compound. The carbonyl compound must provide the remaining carbon chain and the terminal alcohol group after the reaction. For this product, the carbonyl compound should be propanal (CH₃-CH₂-CHO), as it contributes the three-carbon chain ending in an aldehyde group.
Step 4: Understand the reaction mechanism. The acetylide ion (C₆H₅-C≡C⁻) acts as a nucleophile and attacks the electrophilic carbon of the aldehyde group in propanal (CH₃-CH₂-CHO). This forms a new carbon-carbon bond.
Step 5: After the nucleophilic addition, the intermediate is protonated to yield the final product, 5-phenylhex-2-yn-1-ol. This protonation step typically occurs in the presence of water or a mild acid.
Risposta video verificata per un problema simile:
Questa soluzione video è stata consigliata dai nostri tutor come utile per risolvere questo problema.
Durata del video:
5mConcetti chiave
Ecco i concetti essenziali che devi comprendere per rispondere correttamente alla domanda.
Acetylide Ion
An acetylide ion is a negatively charged species formed by deprotonating a terminal alkyne. It is a strong nucleophile, capable of attacking electrophilic carbon centers, such as those found in carbonyl compounds. In organic synthesis, acetylide ions are often used to form carbon-carbon bonds, making them essential for constructing complex molecules.
Video consigliato:
Percorso guidato
3:39
Metal Ion Catalysis Concept 1
Carbonyl Compounds
Carbonyl compounds contain a carbon atom double-bonded to an oxygen atom (C=O). They include aldehydes and ketones, which are key intermediates in organic synthesis. The electrophilic nature of the carbonyl carbon allows it to react with nucleophiles, such as acetylide ions, facilitating the formation of alcohols and other functional groups in multi-step synthesis.
Video consigliato:
01:40Defining meso compounds.
Alkyne to Alcohol Conversion
The conversion of alkynes to alcohols typically involves nucleophilic addition reactions. In this context, an acetylide ion can react with a carbonyl compound to form an intermediate, which can then be protonated to yield an alcohol. This transformation is crucial for synthesizing alcohols with specific structures, such as the target product 5-phenylhex-2-yn-1-ol.
Video consigliato:
04:30Comparing and contrasting the Alcohol Conversions.
Pratica correlata
Domanda del libro di testo
Suggest a carbonyl to react with NaCN/HCN to produce the following cyanohydrins.
(a)
984
views
Domanda del libro di testo
Suggest an acetylide ion and a carbonyl that might be used to make the following products.
(a) oct-4-yn-3-ol
996
views
Domanda del libro di testo
Suggest the appropriate carbonyl and Wittig reagent to make the following alkenes.
a. (E)-7-methylnon-4-en-3-one
760
views
Domanda del libro di testo
Suggest an acetylide ion and a carbonyl that might be used to make the following products.
(b) 2,6-dimethylhept-3-yn-2-ol
833
views
Domanda del libro di testo
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)
857
views