Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 20.8, Problem 7P
Interpretation Introduction
Interpretation:
The reaction mechanism for the hydrolysis of ethyl benzoate is to be proposed on the basis of the mentioned general mechanism for acid-catalyzed hydrolysis of ester.
Concept introduction:
The reaction in which the hydrolysis of an ester into alcohol and carboxylic acid takes place in the presence of an acid catalyst, such a reaction is commonly known as acid-catalyzed hydrolysis of an ester.
The hydrolysis of esters is catalyzed by either an acid or a base. Acidic hydrolysis is the reverse of esterification, and the ester is heated with a large excess of water containing a strong-acid catalyst.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Explain the reaction for the formation of acetal and hemiacetal.
Explain why N,N-disubstituted amide is less acidic than ester.
Why only methyl ketone do undergoes haloform reaction.
LDA is the base of choice for carbonyl compound to completely convert into enolate. Why?
HN
21.10 Suggest reagents.
HN
Ochem question:
Provide the stepwise mechanism for the synthesis of the following compound via an enamine
(see attached image)
Chapter 20 Solutions
Organic Chemistry - Standalone book
Ch. 20.1 - Prob. 1PCh. 20.2 - Prob. 2PCh. 20.3 - Prob. 3PCh. 20.4 - Prob. 4PCh. 20.5 - Prob. 5PCh. 20.8 - Prob. 6PCh. 20.8 - Prob. 7PCh. 20.8 - Prob. 8PCh. 20.9 - Prob. 9PCh. 20.9 - Prob. 10P
Ch. 20.9 - Prob. 11PCh. 20.9 - Prob. 12PCh. 20.10 - Prob. 13PCh. 20.10 - Prob. 14PCh. 20.11 - Prob. 15PCh. 20.11 - Prob. 16PCh. 20.11 - Prob. 17PCh. 20.12 - Prob. 18PCh. 20.12 - Prob. 19PCh. 20.12 - Prob. 20PCh. 20.12 - Prob. 21PCh. 20.13 - Prob. 22PCh. 20.13 - Prob. 23PCh. 20.14 - Prob. 24PCh. 20.15 - Prob. 25PCh. 20.16 - Prob. 26PCh. 20.17 - Prob. 27PCh. 20 - Prob. 28PCh. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - Write a structural formula for the principal...Ch. 20 - Prob. 32PCh. 20 - Prob. 33PCh. 20 - Prob. 34PCh. 20 - Prob. 35PCh. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - Prob. 40PCh. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - The preparation of the sex pheromone of the...Ch. 20 - Prob. 44PCh. 20 - Suggest a reasonable explanation for each of the...Ch. 20 - Prob. 46PCh. 20 - Prob. 47PCh. 20 - Prob. 48PCh. 20 - Prob. 49PCh. 20 - A compound has a molecular formula of C8H14O4, and...Ch. 20 - Prob. 51PCh. 20 - Prob. 52DSPCh. 20 - Prob. 53DSPCh. 20 - Prob. 54DSPCh. 20 - Prob. 55DSPCh. 20 - Prob. 56DSPCh. 20 - Thioesters Thioesters have the general formula ....Ch. 20 - Prob. 58DSP
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- F22 Provide the IUPAC name for each of the following esters. provide the IUPAC name for each of the following esters and acid anhydrides (22 & 24) (b) (c) CI KOxanoate; F.24 Provide the IUPAC name for each of the following acid anhydrides. (a) (b) (c)arrow_forwardBased on the following groups Acid chloride, Amide, Ester a) Select the most reactive group towards nucleophilic acyl substitution reaction. b) Describe the reasons in question (a). c) Identify the group(s) that can been synthesized from acid chloride.arrow_forwardProblem 25.14 What nitro compound, nitrile, and amide are reduced to each compound? a. CH,CHCH,NH, CH,NH, b. Problem 25.15 What amine is formed by reduction of each amide? CONH, b. "NHCH Problem 25.16 Explain why isopropylamine [(CH).CHNH] can be prepared by reduction of a nitro compound, but cannot be prepared by reduction of a nitrile, even though it is a 1* amine. Problem 25.17 Which amines cannot be prepared by reduction of an amide? NH O O Darrow_forward
- What product is formed when A is treated with Grubbs catalyst underhigh-dilution conditions? This reaction was a key step in the synthesis ofstemoamide, the naturally occurring amide described in the opening paragraph.arrow_forward22.65 When the following acid chloride is treated with AICI3, followed by HCl and Zn(Hg), a product is formed whose 'H NMR and IR spectra are shown here. Draw the product and propose a complete, detailed mechanism for the first of these two reactions. .CI 1. AICI3 2. HCI, Zn(Hg) 100 80- ? 60 40- * 20- 7 4 3 1 4500 4000 3500 3000 2500 2000 1500 1000 500 Chemical shift (ppm) Wavenumbers (cm-1)arrow_forwardShow how to synthesize the following compound using either the malonic ester synthesis or the acetoacetic ester synthesis. Q.) Cyclopropanecarboxylic acidarrow_forward
- Prob. 21.20 (p 845): Use retrosynthetic analysis to choose the appropriate B-dicarbonyl compound and alkyl halide to prepare the following: a) 3-Methylpentanoic acid c) 4-Methylpentanoic acidarrow_forwardDraw a detailed mechanism using curved arrow formalism of the synthesis of aspirin from salicylic acid and acetic anhydride.arrow_forwardSafrole, which is isolated from sassafras (Problem 21.33), can be converted to the illegal stimulant MDMA (3,4- methylenedioxymethamphetamine, “Ecstasy”) by a variety of methods. (a) Devise a synthesis that begins with safrole and uses a nucleophilic substitution reaction to introduce the amine. (b) Devise a synthesis that begins with safrole and uses reductive amination to introduce the amine.arrow_forward
- Safrole, which is isolated from sassafras (Problem 21.33), can be converted to the illegal stimulant MDMA (3,4-methylenedioxymethamphetamine, "Ecstasy") by a variety of methods. (a) Devise a synthesis that begins with safrole and uses a nucleophilic substitution reaction to introduce the amine. (b) Devise a synthesis that begins with safrole and uses reductive amination to introduce the amine. NHCH9 MDMA safrolearrow_forwardDevise a stepwise mechanism for the following reaction, a key step in the synthesis of the antibiotic abyssomicin C. Abyssomicin C was isolated from sediment collected from almost 1000 ft below the surface in the Sea of Japan.arrow_forwardShow how to synthesize the following compound using either the malonic ester synthesis or the acetoacetic ester synthesis. Q.) Cyclobutyl methyl ketonearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- 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
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning