ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260826791
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 22, Problem 55P
Interpretation Introduction
Interpretation: The structure of Y is to be identified and the stepwise mechanism for the conversion of Y to rofecoxib is to be drawn.
Concept introduction: Claisen condensation takes place between two esters or between an ester and a
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Reaction of X and phenylacetic acid forms an intermediate Y, which undergoes an intramolecular reaction to yield rofecoxib. Rofecoxib is a nonsteroidal anti-inammatory agent once marketed under the trade name Vioxx, now withdrawn from the market because of increased risk of heart attacks from long-term use in some patients. Identify Y and draw a stepwise mechanism for its conversion to rofecoxib.
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 Collection
Etoposide, sold as a phosphate derivative with the trade name of Etopophos, is used for the treatment of lung cancer, testicular cancer, and lymphomas. (a) Locate the acetals in etoposide. (b) What products are formed when all of the acetals are hydrolyzed with aqueous acid?
Chapter 22 Solutions
ORGANIC CHEMISTRY
Ch. 22.1 - Prob. 1PCh. 22.1 - Prob. 2PCh. 22.1 - Problem 24.3
What unsaturated carbonyl compound is...Ch. 22.1 - Prob. 4PCh. 22.1 - Prob. 5PCh. 22.2 - Prob. 6PCh. 22.2 - Problem 24.7
Draw the products formed in each...Ch. 22.4 - Prob. 15PCh. 22.4 - Prob. 16PCh. 22.5 - Problem 24.16
What ester is formed when each...
Ch. 22.6 - Prob. 18PCh. 22.6 - Prob. 19PCh. 22.6 -
Draw the products of each reaction.
a. b.
Ch. 22.6 - Problem 24.20
Two steps in a synthesis of the...Ch. 22.7 - Prob. 22PCh. 22.8 - Problem 24.22
Which of the following compounds can...Ch. 22.8 - Prob. 24PCh. 22.8 - Problem 24.24
What starting materials are needed...Ch. 22 - Prob. 29PCh. 22 - 24.29 What steps are needed to convert A to B?
Ch. 22 - Prob. 31PCh. 22 - 24.31 Draw the product formed in each directed...Ch. 22 - Prob. 33PCh. 22 - 24.33 What starting materials are needed to...Ch. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - 24.36 Identify the structures of C and D in the...Ch. 22 - Prob. 38PCh. 22 - Prob. 39PCh. 22 - 24.39 Draw the product formed from a Claisen...Ch. 22 - Prob. 41PCh. 22 - 24.41 Even though B contains three ester groups, a...Ch. 22 - Prob. 43PCh. 22 - Prob. 44PCh. 22 - 24.44 Vetivone is isolated from vetiver, a...Ch. 22 - Draw the product of each Robinson annulation from...Ch. 22 - Prob. 50PCh. 22 - Prob. 51PCh. 22 - 24.52 Draw a stepwise mechanism for the following...Ch. 22 - Prob. 53PCh. 22 - Prob. 54PCh. 22 - Prob. 55PCh. 22 - Prob. 56PCh. 22 - Prob. 57PCh. 22 - Prob. 58PCh. 22 - Prob. 59PCh. 22 - 24.62 Devise a synthesis of each compound from ,...Ch. 22 - Prob. 63P
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
- Etoposide, sold as a phosphate derivative with the trade name ofEtopophos, is used for the treatment of lung cancer, testicular cancer,and lymphomas. What products are formed when all of the acetals are hydrolyzed with aqueous acid?arrow_forwardWhat products are formed by hydrolysis of each imine or enamine?arrow_forwardWhat carboxylic acid and amine are needed to synthesize the pain reliever phenacetin? Phenacetin was once a component of the over-the-counter pain reliever APC (aspirin, phenacetin, caffeine), but it is no longer used because of its kidney toxicity.arrow_forward
- Etoposide, sold as a phosphate derivative with the trade name ofEtopophos, is used for the treatment of lung cancer, testicular cancer,and lymphomas. Locate the acetals in etoposide.arrow_forwardAlthough γ-butyrolactone is a biologically inactive compound, it isconverted in the body to 4-hydroxybutanoic acid (GHB), an addictive andintoxicating recreational drug. Draw a stepwise mechanism for thisconversion in the presence of acid.arrow_forwardWhat carbonyl compound and amine or alcohol are needed to prepare each product?arrow_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_forwardWhat 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 Grignard reagent and carbonyl compound can be used to prepare theantidepressant venlafaxine (trade name Effexor)?arrow_forward
- Although γ-butyrolactone is a biologically inactive compound, it is converted in the body to 4-hydroxybutanoic acid (GHB), an addictive and intoxicating recreational drug. Draw a stepwise mechanism for this conversion in the presence of acid.arrow_forwardDraw the structure (including stereochemistry) of the cyclic hemiacetal(s) formed when each hydroxy carbonyl compound is treated with aqueous acid.arrow_forwardAlthough γ-butyrolactone (Problem 19.62) is a biologically inactive compound, it is converted in the body to 4-hydroxybutanoic acid (GHB), an addictive and intoxicating recreational drug (Section 19.5). Draw a stepwise mechanism for this conversion in the presence of acid.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning