ORGANIC CHEMISTRY-OWL V2 ACCESS
8th Edition
ISBN: 9781305582422
Author: Brown
Publisher: CENGAGE L
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 18, Problem 18.42P
Interpretation Introduction
Interpretation:
The reagents and experimental conditions to carry out the synthesis of procaine from the given three compoubds has to be shown.
Concept introduction:
Acid-catalyzed ring-opening of
Base catalyzed ring opening of epoxide:
The nucleophile will attack at the less substituted position under basic conditions and then the alkoxide ion gets proton from alcohol which form the product.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
write the mechanism for a decarboxylation and state the structural features necessary for a decarboxylation.
The analgesic acetaminophen is synthesized by treating 4-aminophenol with one equivalent of acetic anhydride. Draw a structural formula for acetaminophen.
Propose a method to separate a mixture containing phenol, benzoic acid, naphthalene, and p-nitroaniline. Phenol is soluble in sodium hydroxide solution but insoluble in neutral water or sodium bicarbonate solution. Benzoic acid is soluble in either sodium hydroxide or sodium bicarbonate solutions. Write out the structures of the molecules in your scheme.
Chapter 18 Solutions
ORGANIC CHEMISTRY-OWL V2 ACCESS
Ch. 18.1 - Prob. 18.1PCh. 18.2 - Prob. 18.2PCh. 18.4 - Prob. 18.3PCh. 18.4 - Prob. 18.4PCh. 18.4 - Synthesis of nitriles by nucleophilic displacement...Ch. 18.5 - Complete the following transesterification...Ch. 18.6 - Complete and balance equations for the following...Ch. 18.8 - Prob. AQCh. 18.8 - Several compounds have been found to inhibit...Ch. 18.8 - Prob. CQ
Ch. 18.8 - The following sequence of steps is used to create...Ch. 18.9 - Prob. 18.8PCh. 18.9 - Prob. 18.9PCh. 18.10 - Prob. 18.10PCh. 18.10 - Show how to convert (R)-2-phenylpropanoic acid to...Ch. 18 - Prob. 18.12PCh. 18 - Write the IUPAC name for each compound. (a)...Ch. 18 - Prob. 18.14PCh. 18 - Prob. 18.15PCh. 18 - Propose a structural formula for compound A,...Ch. 18 - Propose a structural formula for compound B,...Ch. 18 - Propose a structural formula for each compound...Ch. 18 - Draw a structural formula for the principal...Ch. 18 - Prob. 18.20PCh. 18 - Prob. 18.21PCh. 18 - Prob. 18.22PCh. 18 - Prob. 18.23PCh. 18 - Prob. 18.24PCh. 18 - Show the product expected when the following...Ch. 18 - The reagent diisobutylaluminum hydride (DIBALH)...Ch. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Prob. 18.29PCh. 18 - Nicotinic acid, more commonly named niacin, is one...Ch. 18 - Prob. 18.31PCh. 18 - Prob. 18.32PCh. 18 - Prob. 18.33PCh. 18 - Prob. 18.34PCh. 18 - Prob. 18.35PCh. 18 - Isoniazid, a drug used to treat tuberculosis, is...Ch. 18 - Prob. 18.37PCh. 18 - A step in a synthesis of PGE1 (prostaglandin E1,...Ch. 18 - Prob. 18.39PCh. 18 - Prob. 18.40PCh. 18 - Show how to synthesize 5-nonanone from...Ch. 18 - Prob. 18.42PCh. 18 - The following sequence of steps converts...Ch. 18 - Prob. 18.44PCh. 18 - Prob. 18.45PCh. 18 - Prob. 18.46PCh. 18 - Prob. 18.47PCh. 18 - Following is a retrosynthetic analysis for the...Ch. 18 - Prob. 18.50PCh. 18 - Given this retrosynthetic analysis, propose a...Ch. 18 - Prob. 18.52PCh. 18 - Prob. 18.53PCh. 18 - Prob. 18.54PCh. 18 - In Problem 7.28, we saw this step in Johnsons...Ch. 18 - Prob. 18.56PCh. 18 - Prob. 18.57PCh. 18 - Prob. 18.58PCh. 18 - Prob. 18.59PCh. 18 - Prob. 18.60PCh. 18 - Prob. 18.61PCh. 18 - Prob. 18.62PCh. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Minoxidil is a molecule that causes hair growth in...Ch. 18 - Prob. 18.69PCh. 18 - Prob. 18.70PCh. 18 - Prob. 18.71P
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
- 7 What type of structural feature do the anhydrides of phosphoric acid have in common with carboxylic acids?arrow_forward17-35 Suppose that you take a bottle of benzaldehyde (a liquid, bp 179°C) from a shelf and find a white solid in the bottom of the bottle. The solid turns litmus red; that is, it is acidic. Yet aldehydes are neutral compounds. How can you explain these observations?arrow_forwardPropose you are given a mixture of naphthalene, propanoic acid, and diethyl amine. Explain, using a flow chart similar to that in #1, how you would separate these three compounds. Include all solvents and reagents, show the exact compound that is present at each juncture, and be clear about the experimental technique employed in each step.arrow_forward
- In the 1880's, Acetanilide, sold under the name Antifebrin, was widely used as a pain reliever and fever reducer. However, it had many adverse side effects, including cyanosis as a result of methemoglobinemia. The toxic side effects were the result of a small portion of acetanilide being hydrolyzed to aniline. Acetanilide was discontinued and replaced with phenacetin. Later studies show that both acetanilide and phenacetin are metabolized to acetaminophen. This metabolite, which we know as Tylenol, is responsible for the analgesic and antipyretic properties. Part 1: Show a detailed arrow pushing mechanism of the acid catalyzed hydrolysis of acetanilide to aniline Part 2: Propose a synthesis of Acetaminophen from phenol NH NH NH Phenacetin inophen Acetanilide Attach File Browse Local Files Browse Content Collectionarrow_forwardDimethyl disulfide, CH,S–SCH3, found in the vaginal secretions of female hamsters, acts as a sexual attractant for the male hamster. Write an equation for its synthesis from methanethiol.arrow_forwardPredict the products and proposemechanisms for the reactions ofcarboxylic acids with reducingagents, alcohols, amines, andorganometallic reagentsarrow_forward
- Ethyl butyrate, CH3CH2CH2CO2CH2CH3CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring. It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) Part A Given 7.30 gg of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100%% yield? Express your answer in grams to three significant figures. Part B A chemist ran the reaction and obtained 5.95 gg of ethyl butyrate. What was the percent yield? Express your answer as a percent to three significant figures. Part C The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0%% yield. How many grams would be produced from 7.30 gg of…arrow_forwardEthyl butyrate, CH3CH2CH2CO2CH2CH3CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring. It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) Given 8.45 gg of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100%% yield? Express your answer in grams to three significant figures. A chemist ran the reaction and obtained 5.50 gg of ethyl butyrate. What was the percent yield? Express your answer as a percent to three significant figures. The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0%% yield. How many grams would be produced from 8.45 gg of butanoic acid and excess…arrow_forwardUpon 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_forward
- Why is methyl salicylate so easily absorbed through the skin?arrow_forwardAspirin is the common name for the compound acetylsalicylic acid, widely used as a fever reducer and as a pain killer. Salicylic acid, whose name comes from Salix, the willow family of plants, was derived from willow bark extracts. In folk medicine, willow bark teas were used as headache remedies and other tonics. Nowadays, salicylic acid is administered in the form of aspirin which is less irritating to the stomach than salicylic acid. To prepare aspirin, salicylic acid is reacted with an excess of acetic anhydride. A small amount of a strong acid is used as a catalyst which speeds up the reaction. In this experiment, phosphoric acid will be used as the catalyst. The excess acetic acid will be quenched with the addition of water. The aspirin product is not very soluble in water so the aspirin product will precipitate when water is added. The synthesis reaction of aspirin is shown below: Actic anhydride 5 ml. Acetic acid Salicylic acid 28 Acetylsalicylie acid Procedure 1) Mix salicylic…arrow_forwardWhat are the safety hazards of these chemicals Acetic anhydride (108-24-7) Formic acid (64-18-60) Benzotriazole (95-14-7) N-Formylbenzotriazole (72773-04-7)arrow_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 Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT