Domanda del libro di testo
Thiols are prone to dimerize through the formation of a disulfide bond in a reaction that stylists use to induce permanent curls in hair. What type of reagent would you use to effect this transformation?
1035
views
Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
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. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblema 115a
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblema 115aCapitolo 12, Problema 115a
Benzyl ethers make excellent protecting groups according to the general scheme shown here.
(a) How would you protect the 1° alcohol as a benzyl ether in the first step?
Guida verificata passo dopo passo1
Identify the primary alcohol in the given structure. The primary alcohol is the hydroxyl group (OH) attached to the terminal carbon atom.
To protect the primary alcohol as a benzyl ether, you need to perform a reaction with benzyl chloride (C6H5CH2Cl) in the presence of a base. The base is typically a strong base like sodium hydride (NaH) or potassium carbonate (K2CO3).
The base deprotonates the alcohol, forming an alkoxide ion. This alkoxide ion is a good nucleophile and will attack the benzyl chloride, resulting in the formation of a benzyl ether.
The reaction can be represented as: \( \text{ROH} + \text{C}_6\text{H}_5\text{CH}_2\text{Cl} \xrightarrow{\text{Base}} \text{ROCH}_2\text{C}_6\text{H}_5} \), where ROH is the primary alcohol and ROCH2C6H5 is the benzyl ether.
Ensure that the reaction conditions are anhydrous to prevent any side reactions with water, which could interfere with the formation of the benzyl ether.
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.
Protecting Groups
Protecting groups are chemical groups used to temporarily mask a functional group to prevent it from reacting under certain conditions. In organic synthesis, they are crucial for selective reactions, allowing chemists to modify specific parts of a molecule without affecting others. Benzyl ethers are commonly used as protecting groups for alcohols due to their stability and ease of removal under reductive conditions.
Video consigliato:
02:44
Protecting Groups
Formation of Benzyl Ethers
The formation of benzyl ethers typically involves the reaction of an alcohol with benzyl chloride in the presence of a base, such as sodium or potassium carbonate. This reaction proceeds via an SN2 mechanism, where the alcohol acts as a nucleophile, displacing the chloride ion from benzyl chloride. This process effectively protects the alcohol group by converting it into a benzyl ether.
Video consigliato:
Percorso guidato
1:01Reactions at Benzylic Positions Concept 1
Deprotection of Benzyl Ethers
Deprotection of benzyl ethers is commonly achieved through hydrogenolysis, which involves the use of hydrogen gas and a palladium catalyst. This reaction cleaves the ether bond, regenerating the original alcohol and releasing toluene as a byproduct. The mild conditions of hydrogenolysis make it a preferred method for deprotecting benzyl ethers without affecting other sensitive functional groups in the molecule.
Video consigliato:
Percorso guidato
0:58Reactions at Benzylic Positions Concept 4
Pratica correlata
Domanda del libro di testo
Suggest a mechanism for the following substitution reaction.
1067
views
Domanda del libro di testo
The acid-catalyzed dehydration we learned in this chapter is reversible, as shown below.
(b) Without looking back, how do you know this mechanism is correct?
858
views
Domanda del libro di testo
The acid-catalyzed dehydration we learned in this chapter is reversible, as shown below.
(a) Propose a mechanism for the formation of an alcohol from an alkene.
1538
views
Domanda del libro di testo
A chemist attempted the reaction below, one we introduce in Chapter 17, expecting the reaction between a strong nucleophile and a ketone in water to give an alkoxide product.
(a) Why did the reaction fail?
(b) How could the reaction conditions be changed to give a successful reaction?
980
views
Domanda del libro di testo
In Chapter 12, we learned that crown ethers were used to increase the rate of SN2 reactions (Assessment 12.80). Suggest a synthesis of 15-crown-5 using the reactions learned here in Chapter 13.
888
views