Domanda del libro di testo
Given the following Keq values, how much stronger of a base is acetate (CH3CO2-) than chloride (Cl⁻)?
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Ch. 4 - Acids and Bases/Electron Flow
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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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
Capitolo 3, Problema 26
Design an acid–base extraction scheme to separate a mixture of the basic amine N,N-dimethylaniline and naphthalene.
Guida verificata passo dopo passo1
Step 1: Recognize the chemical properties of the compounds. N,N-dimethylaniline is a basic amine due to the nitrogen atom with lone pairs, which can accept protons. Naphthalene is a neutral aromatic hydrocarbon and does not react with acids or bases under normal conditions.
Step 2: Add the mixture of N,N-dimethylaniline and naphthalene to an organic solvent, such as diethyl ether or dichloromethane, to dissolve both compounds.
Step 3: Perform an acid extraction by adding an aqueous solution of a strong acid, such as hydrochloric acid (HCl). The acid will protonate the basic amine (N,N-dimethylaniline), converting it into its water-soluble ionic form (N,N-dimethylaniline hydrochloride), while naphthalene remains in the organic layer.
Step 4: Separate the two layers using a separatory funnel. The aqueous layer will contain the protonated N,N-dimethylaniline, and the organic layer will contain naphthalene.
Step 5: Recover N,N-dimethylaniline by neutralizing the aqueous layer with a base, such as sodium hydroxide (NaOH). This will regenerate the free amine, which can then be extracted back into an organic solvent. Evaporate the solvent to isolate N,N-dimethylaniline, and evaporate the organic layer to isolate naphthalene.
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Concetti chiave
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Acid-Base Extraction
Acid-base extraction is a technique used to separate compounds based on their acid-base properties. In this process, a mixture is treated with an acid or base to convert one or more components into their ionic forms, which are more soluble in water. This allows for the selective removal of either acidic or basic compounds from the mixture, facilitating their separation.
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02:49
The Lewis definition of acids and bases.
N,N-Dimethylaniline
N,N-Dimethylaniline is a basic amine with the chemical formula C8H11N. It contains a nitrogen atom bonded to two methyl groups and an aniline group, making it a weak base. Its basicity allows it to react with acids to form water-soluble salts, which can be exploited in an acid-base extraction to separate it from non-polar compounds like naphthalene.
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Percorso guidato
3:06Synthesis of Amino Acids: N-Phthalimidomalonic Ester Synthesis Concept 1
Naphthalene
Naphthalene is a polycyclic aromatic hydrocarbon consisting of two fused benzene rings, with the formula C10H8. It is a non-polar compound that is insoluble in water but soluble in organic solvents. In an acid-base extraction, naphthalene remains in the organic layer while the basic amine can be converted to its salt form and extracted into the aqueous layer, allowing for effective separation.
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Given the following Keq values, how much stronger of an acid is methanol (CH3OH) than acetylene (HC≡CH)?
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Given the Keq values for the following acid–base reactions, identify the strongest acid and the strongest base.
(c)
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An unknown acid (HA) has been identified as very strong. What does this tell you about the stability of the conjugate base, A⁻? Is it strong or weak? Is it reactive or unreactive?
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Given that the indicated pKa values correspond to the acid dissociation reactions shown, calculate the ratio of acid to conjugate base for the reactions shown.
(a)
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An unknown base (B⁻) has been identified as very weak. What does this tell you about the strength of its conjugate acid, HB? Is it stable or unstable? Is it reactive or unreactive?
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