Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Question
Chapter 11, Problem 36P
Interpretation Introduction
Interpretation: The given experimental observation has to be explained.
Concept Introduction:
The reactions of acetyl chloride with
On reaction with amines, acetyl chloride forms amides.
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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
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inophen
Acetanilide
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Predict the NMR spectra of Acetanilide, p-acetamidobenzene sulphonamide and p-aminobenzene sulphonamide
What products are formed when all of the amide and ester bonds are hydrolyzed in each of the following compounds? Tamiflu [part (a)] is the trade name of the antiviral agent oseltamivir, thought to be the most effective agent in treating influenza. Aspartame [part (b)] is the artificial sweetener used in Equal and many diet beverages. One of the products of this hydrolysis reaction is the amino acid phenylalanine. Infants afflicted with phenylketonuria cannot metabolize this amino acid, so it accumulates, causing mental retardation. When the affliction is identified early, a diet limiting the consumption of phenylalanine (and compounds like aspartame that are converted to it) can make a normal life possible.
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
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- What products are formed when all of the amide and ester bonds arehydrolyzed in each of the following compounds? Tamiflu [part (a)] is the trade name of the antiviral agent oseltamivir, thought to be the most effective agent in treating influenza. Aspartame [part (b)] is the artificial sweetener used in Equal and many diet beverages. One of the products of this hydrolysis reaction is the amino acid phenylalanine. Infants afflicted with phenylketonuria cannot metabolize this amino acid, so it accumulates, causing mental retardation. When the affliction is identified early, a diet limiting the consumption of phenylalanine (and compounds like aspartame that are converted to it) can make a normal life possible.arrow_forwardWhat product is obtained when ethylamine reacts with excess methyl iodide in a basic solution of potassium carbonate?arrow_forwardIndicate whether the following statement is true or false. Aliphatic amines are more basic than ammonia, whereas aromatic amines are less basic than ammonia. When amines are reacted with bases, they form ammonium salts. Benzenesulfonyl chloride or p-toluenesulfonylchloride give N-substituted sulfonamides with primary and secondary amines. Derivative of primary amines is insoluble in dilute NaOHarrow_forward
- What products are formed when all of the amide and ester bonds are hydrolyzed in each of the following compounds? Tamiu [part (a)] is the trade name of the antiviral agent oseltamivir, thought to be the most effective agent in treating inuenza. Aspartame [part (b)] is the articial sweetener used in Equal and many diet beverages. One of the products ofthis hydrolysis reaction is the amino acid phenylalanine. Infants afflicted with phenylketonuria cannot metabolize this amino acid, so it accumulates, causing mental retardation. When the affliction is identied early, a diet limiting the consumption of phenylalanine (and compounds like aspartame that are converted to it) can make a normal life possible.arrow_forwardWhy is methyl salicylate so easily absorbed through the skin?arrow_forwardWhy do you wash the dichloromethane solution of your reductive amination product with sodium bicarbonate, rather than dilute aqueous HCl? a) Sodium bicarbonate is a good method of removing aldehydes from organic solvent.b) The amine product will be protonated by acid and remain in the aqueous layer as a salt.c) Sodium bicarbonate transfers the amine starting material into the aqueous layer.d) Sodium bicarbonate reacts with leftover NaBH(OAc)3 and removes it from the mixture.arrow_forward
- What aldehyde or ketone and nitrogen component are needed to synthesize N-ethylcyclohexanamine by a reductive amination reaction?arrow_forwardWhat is the relationship between benzophenone and benzhydrol. Looking at their NMR, what changes would happen to benzophenone to benzhydrol?arrow_forwardEarly organic chemists used the Hofmann elimination reaction as the last step of a process known as a Hofmann degradation—a method used to identify amines. In a Hofmann degradation, an amine is methylated with excess methyl iodide in a basic solution, treated with silver oxide to convert the quaternary ammonium iodide to a quaternary ammonium hydroxide, and then heated to allow it to undergo a Hofmann elimination. Once the alkene product is identified, working backward gives the structure of the amine. Identify the amine in each of the following cases: a. 4-Methyl-2-pentene is obtained from the Hofmann degradation of a primary amine. b. 3-Methyl-1-butene is obtained from the Hofmann degradation of a primary amine. c. 2-Methyl-1-3-butadiene is obtained from two successive Hofmann degradations of a secondary amine.arrow_forward
- What chemical test will you use to differentiate acetanilide from aniline?arrow_forwardDraw the structure of N-phenylacetamide and Diethylstilbesterol.arrow_forwardThe following compounds are named incorrectly. Draw the structure of each compound and give it a correct name (either IUPAC or common is acceptable.) a) N-phenyl-N-ethyl-2-propanamine b) N-sec-butyl-N-propylmethanamine c) N-methyl-N-ethyl-4-ethylpentanamide d) 2,5-diethylhexanoic acid f Googlo Chegg Course Hero orarrow_forward
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