Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 11.8, Problem 14P
Using the mechanism for the acid—catalyzed hydrolysis of an ester as your guide, write the mechanism—showing all the curved arrow—for the acid—catalyzed reaction of acetic acid and methanol to form methyl acetate. Use HB+ and :B to represent the proton—donating and proton—removing species, respectively.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Using the mechanism for the acid-catalyzed hydrolysis of an ester as your guide, write the mechanism— showing all the curved arrows—for the acid-catalyzed reaction of acetic acid and methanol to form methyl acetate. Use HB+ and :B to represent the proton-donating and proton-removing species, respectively.
Draw the molecules involved in the synthesis of aspirin. Is the forward reaction hydrolysis or condensation? Is the reverse reaction hydrolysis or condensation? Describe what occurs un each type of reaction with respect to acetylsalicylic acid.
arrange the following compound types in order of decreasing ease of hydrolysis: acid halides, acid anhydrides, esters, and amides. Use > in your arrangement.
Chapter 11 Solutions
Essential Organic Chemistry, Global Edition
Ch. 11.1 - The aromas of many flowers and fruits are due to...Ch. 11.1 - Name the following compounds:Ch. 11.1 - Prob. 3PCh. 11.2 - Prob. 4PCh. 11.2 - Prob. 5PCh. 11.4 - a. What is the product of the reaction of acetyl...Ch. 11.4 - Prob. 7PCh. 11.5 - Using the pKa values listed in Table 11.1, predict...Ch. 11.6 - Starting with acetyl chloride, what neutral...Ch. 11.6 - Prob. 10P
Ch. 11.7 - Prob. 11PCh. 11.8 - Prob. 13PCh. 11.8 - Using the mechanism for the acidcatalyzed...Ch. 11.8 - Prob. 15PCh. 11.8 - Prob. 16PCh. 11.8 - Prob. 17PCh. 11.9 - Prob. 18PCh. 11.10 - Show how each of the following esters could be...Ch. 11.11 - Which of the following reactions would lead to the...Ch. 11.12 - Prob. 22PCh. 11.12 - Prob. 23PCh. 11.13 - Prob. 24PCh. 11.13 - Prob. 25PCh. 11.14 - Prob. 26PCh. 11.14 - Prob. 27PCh. 11.14 - Prob. 28PCh. 11.15 - Prob. 29PCh. 11.15 - How would you synthesize the following compounds...Ch. 11 - Write a structure for each of the following a. N,N...Ch. 11 - Prob. 32PCh. 11 - Which ester is more reactive, methyl acetate or...Ch. 11 - What products would be formed from the reaction of...Ch. 11 - What products would be obtained from the following...Ch. 11 - Prob. 36PCh. 11 - a. Which compound would you expect to have a...Ch. 11 - a. List the following esters in order of...Ch. 11 - D. N. Kursanov, a Russian chemist, proved that the...Ch. 11 - Prob. 40PCh. 11 - Using an alcohol for one method and an alkyl...Ch. 11 - Prob. 42PCh. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - Prob. 47PCh. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Show how the following compounds could be prepared...Ch. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Prob. 53P
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
- When the conjugate acid of aniline, C6H5NH3+, reacts with the acetate ion, the following reaction takes place: C6H5NH3+(aq)+CH3COO(aq)C6H5NH2(aq)+CH3COOH(aq) If Kafor C6H5NH3+ is 1.35105 and Kafor CH3COOH is 1.86105 , what is K for the reaction?arrow_forwardFor the hydrolysis reaction of an alkyl halide with NaCN, H30*, which of the following is produced intermediately. O Carboxylic acid O Nitrile O Amine O Amidearrow_forwardThe esterification reaction of 1 mL each of 1-propanol and propanoic acid is catalyzed with 2-3 drops of sulfuric acid, which is then placed in a test tube in a hot-water bath. After 15 or more minutes, ice water was added. Propyl propanoate is formed. Write the complete equation for the reaction and describe the odor or 1-propanol, propanoic acid, and propyl propanoate.arrow_forward
- b) Compounds in which the –OH of the carboxyl group is replaced by certain other groups are called carboxylic acid derivatives. The most important of which are acyl halides, acid anhydrides, esters and amides. Discuss the relationship between carboxylic acid, acid chloride and acid anhydridearrow_forwardPrepare CH3COOC2H5, ethyl acetate, using ethyl alcohol. Write the chemical reaction. The pain reliever acetaminophen is produced by reacting 4-aminophenol with acetic anhydride. Outline a synthesis of acetaminophen from 4-aminophenol including any needed inorganic reagents.arrow_forwardMany multi-step organic reaction mechanisms involve proton transfer steps. For example, the first step of Fischer esterification of carboxylic acids(as shown with acedic acid) is activation of the acid by protonation. Based on your understanding of which reaction pathway is more favorable, explain why using chemical structures.arrow_forward
- The oxidation of 3-methylbutanal with potassium permanganate in an acid medium produces compound A and the reduction of cyclohexanone with NaBH4 produces compound B. Indicate the CORRECT alternative: a) A reacts rapidly with water to produce a carboxylic acid. b) Reaction of B with methylamine produces an amide. c) Reaction of A with an acyl chloride produces an ester. d) B reacts with HCN to produce a cyanohydrin. e) The reaction of A and B in an acid medium produces cyclohexyl 3-methylbutanoate.arrow_forward1 Aromatic amines can be made from reacting benzene in the presence of concentrated nitric and sulfuric acid. a State the electrophile in the first stage of this reaction. b State the conditions required to reduce the nitro group to an amine group. c Draw the skeletal formula and state the name of the amine product of this two-stage reaction.arrow_forwardName: 2) When water is introduced into an ester under high temperature conditions, esters are hydrolyzed into their carboxylic acid and alcohol components. Draw the structure of the resulting carboxylic acid and alcohol when the ester shown below is hydrolyzed. + H20 3) Why is it important that the test tube be thoroughly dry before making esters? Use the principles of chemical equilibrium to explain your answer.arrow_forward
- Upon completion of a chemical reaction, you find you have a mixture of benzoic acid and ethyl benzoate. Propose a procedure to separate the ethyl benzoate from the mixture. You should look up the structures of benzoic acid and ethyl benzoate.arrow_forwardSelect the reagents which can be reacted together in the presence of an acid catalyst and heat to produce the following ester. 00 Propionic Acid Methanol Pentanoic Acid Butanoic acid Propanol Pentanol ((( ^arrow_forwardAldehydes and ketones undergo condensation reaction with 2, 4-dinitrophenylhydrazine. Write an equation for the reaction of 2, 4-dinitrophenylhydrazine with any one of the pheromones. What makes 2, 4-dinitrophenylhydrazine suitable for characterizing aldehydes and ketones?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Characteristic Reactions of Benzene and Phenols; Author: Linda Hanson;https://www.youtube.com/watch?v=tjEqEjDd87E;License: Standard YouTube License, CC-BY
An Overview of Aldehydes and Ketones: Crash Course Organic Chemistry #27; Author: Crash Course;https://www.youtube.com/watch?v=-fBPX-4kFlw;License: Standard Youtube License