Concept explainers
(a)
Interpretation:
The reason for rate enhancement by considering the mechanism of saponification is to be explained.
Concept introduction:
Chemical species that has negative charge or lone pair of electrons on it are known as nucleophile. Nucleophiles attack on electron deficient atom and give addition or substitution products depending upon the bond strength of leaving group.
(b)
Interpretation:
If the saponification reaction of methyl
Concept introduction:
The
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Chapter 21 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
- Benzyl bromide (C6H5CH2Br) reacts rapidly with CH3OH to afford benzyl methyl ether (C6H5CH2OCH3). Draw a stepwise mechanism for the reaction, and explain why this 1° alkyl halide reacts rapidly with a weak nucleophile under conditions that favor an SN1 mechanism. Would you expect the para-substituted benzylic halides CH3OC6H4CH2Br and O2NC6H4CH2Br to each be more or less reactive than benzyl bromide in this reaction? Explain your reasoning.arrow_forwardPropylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glycol, another chiral molecule. A. Provide a mechanism for the acid-catalyzed hydrolysis of pure (R)-propylene oxide (treatment with H2SO4/H2O), showing the correct stereochemistry. B. Provide a mechanism for the treatment of pure (R)-propylene oxide with NaOH in water (base-catalyzed hydrolysis), showing the correct stereochemistry. C. Explain why acid-catalyzed hydrolysis of optically active propylene oxide gives a product with a rotation in the opposite direction from the product of the base catalyzed hydrolysis.arrow_forwardIdentify products A and B from the given 1H NMR data.a. Treatment of CH2 = CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A?b. Treatment of acetone [(CH3)2C = O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?arrow_forward
- Identify products A and B from the given 1H NMR data. a.Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A? b.Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?arrow_forwardFill in the missing reagents a-e in the following scheme:arrow_forwardIdentify the missing reagents a-f in the following scheme:arrow_forward
- Draw and Explain the reaction mechanism for the Williamson Ether reaction. Cresol is the nucleophilic component of the ether synthesis reaction and chloroacetic acid is the electrophilic component. Due to cresol being weak, a strong nucleophile has to be made before the reaction can begin. A base of KOH is added with cresol so that nucleophile can be strong before it is mixed with chloroacetic acid.arrow_forwardExplain why the treatment of anisole with HBr yields phenol and CH3Br, but not bromobenzene.arrow_forwardAnswer the following questions about 2-acetylcyclopentanone.a. What starting materials are needed to form 2-acetylcyclopentanone by a Claisen reaction that forms bond (a)?b. What starting materials are needed to form 2-acetylcyclopentanone by a Claisen reaction that forms bond (b)?c. What product is formed when 2-acetylcyclopentanone is treated with NaOCH2CH3, followed by CH3I?d. Draw the Robinson annulation product(s) formed by reaction of 2- acetylcyclopentanone with methyl vinyl ketone (CH2=CHCOCH3).e. Draw the structure of the most stable enol tautomer(s).arrow_forward
- The biosynthesis of lanosterol from squalene has intrigued chemists since its discovery. It is now possible, for example, to synthesize polycyclic compounds from acyclic or monocyclic precursors by reactions that form several C—C bonds in a single reaction mixture. a. Draw a stepwise mechanism for the following reaction.b. Show how X can be converted to 16,17-dehydroprogesterone.arrow_forwardp-Fluoronitrobenzene is more reactive toward hydroxide ion than is p-chloronitrobenzene. What does this tell you about the rate-determining step for nucleophilic aromatic substitution?arrow_forwardBrevicomin, the aggregation pheromone of the western pine bark beetle, contains a bicyclic bridged ring system and is prepared by the acid-catalyzed cyclization of 6,7-dihydroxynonan- 2-one. a. Suggest a structure for brevicomin. b. Devise a synthesis of 6,7-dihydroxynonan-2-one from 6-bromohexan-2-one. You may also use three-carbon alcohols and any required organic or inorganic reagents.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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