Multiple Choice
In nucleophilic acyl substitution, which of the following best describes the key mechanistic step that distinguishes it from nucleophilic substitution at alkyl halides?
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- 1. A Review of General Chemistry5h 5m
- Summary23m
- Intro to Organic Chemistry5m
- Atomic Structure16m
- Wave Function9m
- Molecular Orbitals17m
- Sigma and Pi Bonds10m
- Octet Rule12m
- Bonding Preferences12m
- Formal Charges6m
- Skeletal Structure14m
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- Constitutional Isomers14m
- Resonance Structures46m
- Hybridization23m
- Molecular Geometry16m
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- 2. Molecular Representations1h 14m
- 3. Acids and Bases2h 46m
- 4. Alkanes and Cycloalkanes4h 17m
- IUPAC Naming29m
- Alkyl Groups13m
- Naming Cycloalkanes10m
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- Naming Alkyl Halides7m
- Naming Alkenes3m
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- 5. Chirality3h 39m
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- R and S Configuration43m
- Enantiomers vs. Diastereomers13m
- Atropisomers9m
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- Test 3:Disubstituted Cycloalkanes13m
- What is the Relationship Between Isomers?16m
- Fischer Projection10m
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- Optical Activity5m
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- Non-Carbon Chiral Centers8m
- 6. Thermodynamics and Kinetics1h 22m
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- Addition Reaction6m
- Markovnikov5m
- Hydrohalogenation6m
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- Williamson Ether Synthesis3m
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- 16. Conjugated Systems6h 13m
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- Orbital Diagram:3-atoms- Allylic Ions13m
- Orbital Diagram:4-atoms- 1,3-butadiene11m
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- 20. Phenols55m
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- Acid Chloride to Ketone7m
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- 22. Carboxylic Acid Derivatives: NAS2h 51m
- Carboxylic Acid Derivatives7m
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- Diacid Nomenclature6m
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- Naming Nitriles3m
- Acid Chloride Nomenclature5m
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- Nucleophilic Acyl Substitution18m
- Carboxylic Acid to Acid Chloride6m
- Fischer Esterification5m
- Acid-Catalyzed Ester Hydrolysis4m
- Saponification3m
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- Lactones, Lactams and Cyclization Reactions10m
- Carboxylation5m
- Decarboxylation Mechanism14m
- Review of Nitriles46m
- 23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
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- Tautomerization9m
- Tautomers of Dicarbonyl Compounds6m
- Enolate4m
- Acid-Catalyzed Alpha-Halogentation4m
- Base-Catalyzed Alpha-Halogentation3m
- Haloform Reaction8m
- Hell-Volhard-Zelinski Reaction3m
- Overview of Alpha-Alkylations and Acylations5m
- Enolate Alkylation and Acylation12m
- Enamine Alkylation and Acylation16m
- Beta-Dicarbonyl Synthesis Pathway7m
- Acetoacetic Ester Synthesis13m
- Malonic Ester Synthesis15m
- 25. Condensation Chemistry2h 9m
- 26. Amines1h 43m
- 27. Heterocycles2h 0m
- Nomenclature of Heterocycles15m
- Acid-Base Properties of Nitrogen Heterocycles10m
- Reactions of Pyrrole, Furan, and Thiophene13m
- Directing Effects in Substituted Pyrroles, Furans, and Thiophenes16m
- Addition Reactions of Furan8m
- EAS Reactions of Pyridine17m
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- Side-Chain Reactions of Substituted Pyridines20m
- 28. Carbohydrates5h 53m
- Monosaccharide20m
- Monosaccharides - D and L Isomerism9m
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- Reducing Sugars23m
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- Monosaccharides - Kiliani-Fischer23m
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- Disaccharide30m
- Polysaccharide11m
- 29. Amino Acids4h 20m
- Proteins and Amino Acids19m
- L and D Amino Acids14m
- Polar Amino Acids14m
- Amino Acid Chart1h 18m
- Acid-Base Properties of Amino Acids33m
- Isoelectric Point14m
- Amino Acid Synthesis: HVZ Method12m
- Synthesis of Amino Acids: Acetamidomalonic Ester Synthesis16m
- Synthesis of Amino Acids: N-Phthalimidomalonic Ester Synthesis13m
- Synthesis of Amino Acids: Strecker Synthesis13m
- Reactions of Amino Acids: Esterification7m
- Reactions of Amino Acids: Acylation3m
- Reactions of Amino Acids: Hydrogenolysis6m
- Reactions of Amino Acids: Ninhydrin Test11m
- 30. Peptides and Proteins2h 42m
- Peptides12m
- Primary Protein Structure4m
- Secondary Protein Structure17m
- Tertiary Protein Structure11m
- Disulfide Bonds17m
- Quaternary Protein Structure10m
- Summary of Protein Structure7m
- Intro to Peptide Sequencing2m
- Peptide Sequencing: Partial Hydrolysis25m
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- Peptide Sequencing: Edman Degradation28m
- Merrifield Solid-Phase Peptide Synthesis18m
- 31. Catalysis in Organic Reactions1h 30m
- 32. Lipids 2h 50m
- 33. The Organic Chemistry of Metabolic Pathways2h 52m
- Intro to Metabolism6m
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- Intro to Coenzymes3m
- Coenzymes in Metabolism16m
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- Catabolism of Carbohydrates: Glycolysis27m
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- Pyruvate Oxidation (Simplified)4m
- Anaerobic Respiration11m
- Catabolism of Fats: Glycerol Metabolism11m
- Intro to Citric Acid Cycle7m
- Structures of the Citric Acid Cycle19m
- The Citric Acid Cycle35m
- 34. Nucleic Acids1h 32m
- 35. Transition Metals6h 14m
- Electron Configuration of Elements45m
- Coordination Complexes20m
- Ligands24m
- Electron Counting10m
- The 18 and 16 Electron Rule13m
- Cross-Coupling General Reactions40m
- Heck Reaction40m
- Stille Reaction13m
- Suzuki Reaction25m
- Sonogashira Coupling Reaction17m
- Fukuyama Coupling Reaction15m
- Kumada Coupling Reaction13m
- Negishi Coupling Reaction16m
- Buchwald-Hartwig Amination Reaction19m
- Eglinton Reaction17m
- Catalytic Allylic Alkylation18m
- Alkene Metathesis23m
- 36. Synthetic Polymers1h 49m
- Introduction to Polymers6m
- Chain-Growth Polymers10m
- Radical Polymerization15m
- Cationic Polymerization8m
- Anionic Polymerization8m
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- Step-Growth Polymers11m
- Step-Growth Polymers: Urethane6m
- Step-Growth Polymers: Polyurethane Mechanism10m
- Step-Growth Polymers: Epoxy Resin8m
- Polymers Structure and Properties8m
22. Carboxylic Acid Derivatives: NAS
Nucleophilic Acyl Substitution
Struggling with Organic Chemistry?
Join thousands of students who trust us to help them ace their exams!Watch the first videoMultiple Choice
Determine the major product for the following reaction.
A
B
C
D
Verified step by step guidance1
Identify the starting material as a carboxylic acid, specifically butanoic acid, which has the structure CH3CH2CH2COOH.
Recognize that the reaction involves two steps: first, treatment with NaOH, and second, reaction with CH3CH2Br.
In the first step, NaOH, a strong base, deprotonates the carboxylic acid to form the carboxylate anion, CH3CH2CH2COO⁻.
In the second step, the carboxylate anion acts as a nucleophile and attacks the electrophilic carbon in CH3CH2Br, resulting in a nucleophilic substitution reaction (SN2 mechanism).
The major product of this reaction is an ester, specifically ethyl butanoate, with the structure CH3CH2CH2COOCH2CH3.
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