Which of the following reaction sequences would convert 2- butanol into the deuterated compound below? CH;CH,CHCH3 он H;SO4 (1) BD3/THF A) heat (2) H202, NaOH Он H;SO4 D2/Pt B) heat он PBR3 (1) Mg, diethyl ether C) (2) D20 Он PBR3 N2OD, D20 D) A D B. C.
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- Prostaglandins (Section 26.7) are a group of structurally related compounds that function as biochemical regulators and exhibit a wide array of activity, including the regulation of blood pressure, blood clotting, gastric secretions, inflammation, kidney function, and reproductive systems. The following two-step transformation was employed by E. J. Corey during his classic prostaglandin synthesis. Identify the reagents that you would use to convert compound 1 to compound 3 and draw the structure of compound 2.Alcohols react with sulfonyl chlorides to form sulfonate esters. Only the O-H bond of the alcohol is broken in the reaction, and so no inversion of configuration occurs. The resulting sulfonate esters are reactive in SN1 and SN2 reactions since the sulfonate group is a very weak base and is therefore a good leaving group.Draw curved arrows to show the movement of electrons in this step of the mechanism.In the acid-catalyzed dehydration of 2-methyl-1-propanol, what carbocation would be formed if a hydride shift accompanied cleavage of the carbon–oxygen bond in the alkyloxonium ion? What ion would be formed as a result of a methyl shift? Which pathway do you think will predominate, a hydride shift or a methyl shift?
- Draw the organic products formed when cyclopentene is treated with each reagent. With some reagents, no reactionoccurs.a. H2 + Pd-Cb. H2 + Lindlar catalystc. Na, NH3d. CH3CO3He. [1] CH3CO3H; [2] H2O, HO–f. [1] OsO4 + NMO; [2] NaHSO3, H2Og. KMnO4, H2O, HO–h. [1] LiAlH4; [2] H2Oi. [1] O3; [2] CH3SCH3j. (CH3)3COOH, Ti[OCH(CH3)2]4, (–)-DETk. mCPBAl. Product in (k); then [1] LiAlH4; [2] H2OChemistry Please help explain this textbook question: Although N, N -dimethylaniline is extremely reactive toward electrophilic aromatic substitution and is readily substituted by weak electrophiles, such as diazonium and nitronium ions, this reactivity is greatly diminished by the introduction of an alkyl substituent in an ortho position.Why does naphthalene undergo electrophilic substitution at C1 instead of C2? Could you draw a structure for the intermediate that helps explain this?
- select the most appropriate reagent(s) to effect the change. K2Cr2O7, H+ H2, Pd 1. Disiamylborane, 2. HO–, H2O, H2O2 NaOCl H2SO4, HgSO4(a) Arrange the following compounds in an increasing order of their indicated property :(i) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid strength)(ii) CH3CH2CH (Br) COOH, CH3CH (Br) CH2COOH,(CH3)2CHCOOH, CH3CH2CH2COOH (acid strength)(b) How would you bring about the following conversions :(i) Propanone to Propene (ii) Benzoic acid to Benzaldehyde(iii) Bromobenzene to 1-phenylethanolThe following reactivity order has been found for the saponification of alkyl acetates by aqueous NaOH. Explain. CH3CO2CH3 > CH3CO2CH2CH3 > CH3CO2CH(CH3)2 > CH3CO2C(CH3)3
- 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?Why do you suppose only symmetrical ethers are prepared by the sulfuric-acid-catalyzed dehydration procedure? What product(s) would you expect if ethanol and 1-propanol were allowed to react together? In what ratio would the products be formed if the two alcohols were of equal reactivity?The following bicyclic ketone has two -carbons and three -hydrogens. When this molecule is treated with D2O in the presence of an acid catalyst, only two of the three -hydrogens exchange with deuterium. The -hydrogen at the bridgehead does not exchange. How do you account for the fact that two -hydrogens do exchange but the third does not? You will find it helpful to build models of the enols by which exchange of -hydrogens occurs.