Interpretation:
A retrosynthesis of diphenadione has to be given.
Concept introduction:
Retro synthesis: It is a technique of planning an
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Chapter 19 Solutions
OWL V2 with MindTap Reader and Student Solutions Manual eBook for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- Show how to synthesize the following amines from the indicated starting materials below. Each of the final products may require several sequential steps. Draw the structure for each of the steps and show the reagents required. Starting material Final product b) Benzene m-bromoaniline c) ethylbenzene p-ethylaniline + o-ethylaniline d) benzene p-bromoaniline + o-bromoanilinearrow_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_forward8 (Chemical Connections 19C) Once it has been opened, and particularly if it has been left open to the air, a bottle of aspirin may develop a vinegar-like odor. Explain how this might happen.arrow_forward
- 17-35 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_forward6. The reaction between aniline and nitrous acid at low temperature yields A) an N-nitroso amine B) a diazonium salt C) a nitrile D) an amine nitrite salt 7. An organic nitrogen compound, X, gives ammonia on warming with dilute aqueous sodium hydroxide, X could be A) ethanamide B) ethylamine C) phenylamine D) amino ethanoic acidarrow_forwardEistrogens are female sex hormones, the most potent of which is B-estradiol. OH H,C но B-Estradiol In recent years, chemists have focused on designing and synthesizing molecules that bind to estrogen receptors. One target of this research has been nonsteroidal estrogen antagonists, compounds that interact with estrogen receptors and block the effects of both endogenous and exogenous estrogens. A feature common to one type of nonste- roidal estrogen antagonist is the presence of a 1,2-diphenylethylene with one of the benzene rings bearing a dialkylaminoethoxyl substituent. The first nonsteroidal estrogen antagonist of this type to achieve clinical importance was tamoxifen, now an important drug in the treatment of breast cancer. Tamoxifen has the Z configuration shown here. но NMe, NMeg ? B NMeg ? "NMe, ОН Tamoxifen Propose reagents for the conversion of A to tamoxifen. Note: The final step in this synthesis gives a mixture of E and Z isomers.arrow_forward
- In the mid-1930s a substance was isolated from a fungus that is a parasite of ryes and other grasses. This alkaloid, lysergic acid, has been of great interest to chemists because of its strange, dramatic action on the human mind. Many derivatives of lysergic acid are known, some with medicinal applications. Perhaps the best known derivative of lysergic acid is the potent hallucinogen lysergic acid diethylamide (LSD): మగవా జి N-H LSD (CH25N;O) Like other alkaloids, LSD is a weak base, with Kp = 7.6 × 107. What is the pH of a 0.94 M solution of LSD? pH =arrow_forwardIf you attempted to make soap from butanoic acid by forming sodium butanoate, would your preparation have the properties to act as an emulsifying agent (soap)?arrow_forwardShow how to synthesize the following amines from the indicated starting materials below. Each of the final products may require several sequential steps. Draw the structure for each of the steps and show the reagents required. Starting material Final product h) 4-ethyl-3-methylhexan-1-ol 4-ethyl-3-methylhexan-1-amine i) 2-phenylacetyl chloride N-N-dimethyl-2-phenylethan-1-amine j) ethyl acetate N-ethylpropan-2-aminearrow_forward
- A mixture of the compounds shown below is dissolved in cyclohexane. An aqueous solution of NaOH is added to the solution, and two layers are formed. Which compound(s) is(are) found in the aqueous layer? он HO Benzoic acid Beta-naphthol Naphthalene O Benzoic acid only O Beta-naphthol only O Naphthalene O Both Benzoic acid and beta-naphthol O Both beta-naphthol and naphthalenearrow_forwardnoradrenaline and serotonin in the spinal cord. Deduce the structure of this new compound, given its molecular neuron to another. Noradrenaline (also called norepinephrine) and serotonin are neurotransmitters that act in its) Neurotransmitters are small molecules that are produced by the body to send messages from one the central nervous system. A recently report synthetic compound has effects that are similar to baul formula (CəH13NO) and the following 'H NMR spectral data. Show your work by labeling your proposed structure with the corresponding letters for the signals listed below. a) 1.1 6 (2H, broad singlet) b) 2.7 6 (2H, triplet) c) 2.9 6 (2H, triplet) d) 3.8 6 (3H, singlet) e) 6.8 6 (2H, doublet) f) 7.1 6 (2H, doublet)arrow_forwardIn 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_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
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