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- Identify A, B, and C, intermediates in the synthesis of the five-membered ring called an α- methylene-γ-butyrolactone. This heterocyclic ring system is present in some antitumor agents.Identify A, B, and C, intermediates in the synthesis of the five-membered ring called an α-methylene-γ-butyrolactone. This heterocyclic ring system is present in some antitumor agents.The widely used anticoagulant warfarin (see Chemical Connections: From Moldy Clover to a Blood Thinner in Chapter 18) is synthesized from 4-hydroxycoumarin, benzaldehyde, and acetone as shown in this retrosynthesis. Show how warfarin is synthesized from these reagents.
- Following is the structure of miconazole, the active antifungal agent in a number of over-the-counter preparations, including Monistat, that are used to treat vaginal yeast infections. One of the compounds needed for the synthesis of miconazole is the trichloro derivative of toluene shown on its right. (a) Show how this derivative can be synthesized from toluene. (b) How many stereoisomers are possible for miconazole?The compound eutypine is an antibacterial agent isolated from the fungus Eutypa lata. This fungus results in a disease common to vineyards called eutyposis. Give a sequence of reactions that will take the following reactant and give eutypine when the other reactants used in the sequence are acetylene and acetone.Taxol is a powerful anticancer agent that was first isolated from the bark of the Pacific yew tree (Taxus brevifolia) in 1967 The structure of Taxol, shown below wasn't elucidated until 1971. Taxol prevents tumor growth by inhibiting the division C cells, or mitosis, in some types of cancer cells; and in other types of cancer cells, it induces cell death. or apoptosis. Taxol is now commonly prescribed as a treatment for breast and ovarian cancers. What functional groups are NOT present in taxol? NH OH .0.... Taxol (paclitaxel) HO Select one: O a. Aldehyde and Alcohol O b. Amide and Aldehyde Oc. Ester and Alcohol O d. Ketone and Ether O e. Carboxylic Acid and Amine OH
- When acetonitrile is treated with concentrated sulfuric acid and tert-butanol, followed by water, a product is formed whose 'H NMR spectrum exhibits the following three signals: singlet, 1.3 ppm, 9 H; singlet, 2.0 ppm, 3 H; and broad singlet, 8.2 ppm, 1 H. Its IR spectrum exhibits one broad absorption of medium intensity between 3300 and 3500 cm-1, and a narrow, intense absorption near 1650 cm¯1. A key intermediate is shown. Draw the structure of the product, and draw the complete, detailed mechanism for the reaction. CH3 CH3 H2SO4 (conc) H2O ? + H3C H3C H3C-C=Ñ-c `CH3 CH3 HOSeveral sulfonylureas, a class of compounds containing RSO2NHCONHR, are useful drugs as orally active replacements for injected insulin in patients with adult-onset diabetes. These drugs decrease blood glucose concentrations by stimulating b cells of the pancreas to release insulin and by increasing the sensitivity of insulin receptors in peripheral tissues to insulin stimulation. Tolbutamide is synthesized by the reaction of the sodium salt of p-toluenesulfonamide and ethyl N-butylcarbamate . Propose a mechanism for this step.A compound has a 'H NMR signal around & 2.2 ppm. What structural feature is likely to be present in the compound? OA hydroxyl group O A carbonyl group O An aromatic ring OA carbon-carbon triple bond OA cyclohexyl ring O An aldehyde
- Acetylenic fatty acids are found in many tropical plants. Compound H, C18H2502, is one such compound; it absorbs 5 equivalents of H2 when treated with H2 over a Pd/C catalyst. Ozonolysis of compound H produces the following products: pentanal (CH3(CH2)3CHO) 2-охоасetic acid (HOOCCHO) oxalic acid (HooccOOH) nonanedioic acid (HOOC(CH2)7COOH) Draw the structure of compound H. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. ..Williamson Ether Synthesis of Phenacetin Background: Synthesize phenacetin from acetaminophen (Tylenol) via a Williamson ether synthesis.The Williamson ether synthesis is one of the simplest methods used to make ethers. The reaction is named after Alexander Williamson, who discovered the reaction in 1850. In this reaction, an alkoxide anion reacts with an alkyl halide via a substitution reaction. RO-Na+ + R` – X → R-O-R` + NaX Alkoxides are strong nucleophiles that tend to react via an SN2 mechanism. As a result, the reaction works best with primary alkyl halides. In a traditional Williamson ether synthesis, the alkoxide is generated by reacting sodium hydride (NaH) with an alcohol. ROH + NaH → RO-Na+ + H2 While this reaction is very efficient, it does pose a fire hazard, as it is possible for hydrogen gas to ignite. In this lab, the alkoxide will be created using sodium hydroxide (NaOH). This is a much safer option, eliminating a…Complete the statements by providing the reagents necessary to complete each step of the synthesis. Ketone reacted with CO₂H and then yielded a derivative, which was treated with 1) (i) C6H5MgBr (ii) H3O+ 2) (i) DIBAL-H (ii). H3O+ 3) Sia2BH,H202, NaOH 4) CH2N2 (diazamethane) CO₂C2H5 5) PCC (an oxidant) 6) H2SO4, H2O, heat 7) HgSO4/ H2SO4 8) C₂H5OH, H3O*, heat TABLE OF REAGENTS to form an unsaturated carboxylic acid, treatment with to yield unsaturated aldehyde as the final product. CHO MacBook Air 9) C6H5 CH2 P(C6H5)3; NaOH 10) PCC (an oxidant) 11) NaCN, H₂SO4 12) PhCH2CHO, H3O*