General, Organic, and Biological Chemistry - 4th edition
4th Edition
ISBN: 9781259883989
Author: by Janice Smith
Publisher: McGraw-Hill Education
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Question
Chapter 17.8, Problem 17.19P
Interpretation Introduction
Interpretation:
The carboxylic acid and amine that are needed to synthesis pain reliever phenacetin should be determined.
Concept Introduction:
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What 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.
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.
Rank the labeled N atoms in the anticancer drug imatinib (trade nameGleevec) in order of increasing basicity. Imatinib, sold as a salt withmethanesulfonic acid (CH3SO3H), is used for the treatment of chronicmyeloid leukemia as well as certain gastrointestinal tumors.
Chapter 17 Solutions
General, Organic, and Biological Chemistry - 4th edition
Ch. 17.1 - Draw out each compound to clearly show what groups...Ch. 17.1 - Prob. 17.2PCh. 17.1 - (a) Label each functional group in lisinopril, a...Ch. 17.2 - Give the IUPAC name for each compound. a. b. c.Ch. 17.2 - Give the structure corresponding to each IUPAC...Ch. 17.2 - Prob. 17.5PCh. 17.2 - Give an acceptable name for each ester. a. CH3(...Ch. 17.2 - Prob. 17.6PCh. 17.2 - Prob. 17.7PCh. 17.2 - Prob. 17.8P
Ch. 17.2 - Prob. 17.9PCh. 17.3 - Which compound in each pair has the higher boiling...Ch. 17.4 - Prob. 17.11PCh. 17.5 - In addition to ethyl butanoate (Section 17.5),...Ch. 17.6 - Prob. 17.3PPCh. 17.6 - Prob. 17.13PCh. 17.6 - Which compound ¡n each pair ¡s more water soluble?...Ch. 17.6 - Prob. 17.5PPCh. 17.6 - Prob. 17.14PCh. 17.6 - Prob. 17.15PCh. 17.7 - Ibuprofen is another pain reliever that is a...Ch. 17.8 - Prob. 17.6PPCh. 17.8 - Prob. 17.17PCh. 17.8 - Prob. 17.18PCh. 17.8 - Prob. 17.7PPCh. 17.8 - Prob. 17.19PCh. 17.9 - Prob. 17.8PPCh. 17.9 - Prob. 17.20PCh. 17.9 - Prob. 17.21PCh. 17.9 - Prob. 17.22PCh. 17.9 - Prob. 17.9PPCh. 17.9 - Prob. 17.23PCh. 17.9 - Prob. 17.24PCh. 17.10 - Prob. 17.10PPCh. 17.10 - Prob. 17.25PCh. 17.11 - Prob. 17.26PCh. 17 - Prob. 27PCh. 17 - Prob. 28PCh. 17 - Prob. 29PCh. 17 - Prob. 30PCh. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - Prob. 33PCh. 17 - Prob. 34PCh. 17 - Prob. 35PCh. 17 - Give an acceptable name for each ester. a. CH3CO2(...Ch. 17 - Prob. 37PCh. 17 - Prob. 38PCh. 17 - Prob. 39PCh. 17 - Prob. 40PCh. 17 - Prob. 41PCh. 17 - Prob. 42PCh. 17 - Prob. 43PCh. 17 - Draw the structure corresponding to each name. a....Ch. 17 - Draw the structure corresponding to each name. a....Ch. 17 - Draw the structure corresponding to each name. a....Ch. 17 - Prob. 47PCh. 17 - Prob. 48PCh. 17 - Prob. 49PCh. 17 - Prob. 50PCh. 17 - Prob. 51PCh. 17 - Prob. 52PCh. 17 - Prob. 53PCh. 17 - Prob. 54PCh. 17 - What ester is formed when butanoic acid...Ch. 17 - Prob. 56PCh. 17 - Prob. 57PCh. 17 - Prob. 58PCh. 17 - Prob. 59PCh. 17 - Prob. 60PCh. 17 - Prob. 61PCh. 17 - Prob. 62PCh. 17 - Prob. 63PCh. 17 - Prob. 64PCh. 17 - Prob. 65PCh. 17 - Prob. 66PCh. 17 - What products are formed when each ester is...Ch. 17 - Prob. 68PCh. 17 - Prob. 69PCh. 17 - Prob. 70PCh. 17 - Prob. 71PCh. 17 - Prob. 72PCh. 17 - Prob. 73PCh. 17 - Prob. 74PCh. 17 - Draw the products formed in each reaction. a. b....Ch. 17 - Draw the products formed in each reaction. a. b....Ch. 17 - Answer the following questions about A, depicted...Ch. 17 - Answer the following questions about B, depicted...Ch. 17 - Prob. 79PCh. 17 - Prob. 80PCh. 17 - Prob. 81PCh. 17 - Prob. 82PCh. 17 - Prob. 83PCh. 17 - Prob. 84PCh. 17 - Prob. 85PCh. 17 - Prob. 86PCh. 17 - Prob. 87PCh. 17 - Prob. 88PCh. 17 - Prob. 89CPCh. 17 - Lactams can be hydrolyzed with base, just like...
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Similar questions
- Show how to convert amines to other functional groups, and devise multistepsyntheses using amines as starting materials and intermediatesarrow_forwardRank the labeled N atoms in the anticancer drug imatinib (trade name Gleevec) in order of increasing basicity. Imatinib, sold as a salt with methanesulfonic acid (CH3SO3H), is used for the treatment of chronic myeloid leukemia as well as certain gastrointestinal tumors.arrow_forwardSafrole, which is isolated from sassafras, 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
- Although 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_forwardSynthadotin is a promising anticancer drug in clinical trials. a.Identify the functional groups. b.Classify any amine or amide as 1°, 2°, or 3°. c.At which sites can synthadotin hydrogen bond to another molecule like itself? d. Label two nucleophilic sites. e. Label two electrophilic sites. f. What product is formed when synthadotin is treated with HCl?arrow_forwardMaraviroc, a drug used to treat HIV, is prepared by reductive amination of aldehyde A with amine B. What is the structure of maraviroc, if the most basic N atom of amine B is used in reductive amination?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 starting materials are needed to prepare each drug using reductive amination? Give all possible pairs of compounds when more than one route is possible.arrow_forwardRank the labeled nitrogen atoms in each compound in order of increasing basicity. Histamine causes the runny nose and watery eyes associated with allergies, and trazodone is a drug used as a sedative and antidepressant.arrow_forward
- Devise a synthesis of benzocaine, ethyl p-aminobenzoate (H2NC6H4CO2CH2CH3), from benzene, organic alcohols, and any needed organic or inorganic reagents. Benzocaine is the active ingredient in the topical anesthetic Orajel (Section 18.15C).arrow_forwardEnalapril, a drug used to treat hypertension, is prepared from compounds D and E by reductive amination. What is the structure of enalapril?arrow_forwardStanozolol is an anabolic steroid that promotes muscle growth. Althoughstanozolol has been used by athletes and body builders, many physicaland psychological problems result from prolonged use and it is bannedin competitive sports. Explain why the pKa of the N—H bond in the pyrazole ring iscomparable to the pKa of the O—H bond, making it considerably moreacidic than amines such as CH3NH2 (pKa = 40).arrow_forward
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