KProblem 21 of 24SubmitDraw the missing organic structuresin the following multistep synthesis.Show the final product atphysiological pH (pH = 7.4). Ignoreany inorganic byproducts formed.H0NH3Select toDrawHCNH+, H2OSelect toDrawSelect toDrawΔ

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Answered: K Problem 21 of 24 Submit Draw the…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter24: Amines And Heterocycles

Section24.SE: Something Extra

Problem 75AP

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Nitration of methyl benzoate: Weight of filler paper: 0.682g Mp product: 76-77 C Nitration of Acetanilide: Weight of filler paper: 0.691g Weight of filler paper product: 1.232g Mp product: 212-214 C Compound MM (g/mol) ortho mp (oC) meta mp (oC) para mp (oC) Nitroacetanilide 180.16 94 155 214-217 Methyl nitrobenzoate 181.15 -13 78-80 94-96 Theoretical yield of acetanilde: 0.6664g Theoretical yield of methyl benzoate: 0.7317g find theoretical yield of methyl nitrobenzoate percent yield of your methyl nitrobenzoate and melting point of your methyl nitrobenzoate
Which of the following bases are strong enough to deprotonate C6H5OH (pKa = 10) so that equilibrium favors the products: (a) H2O; (b) NaOH; (c) NaNH2; (d) CH3NH2; (e) NaHCO3; (f) NaSH; (g) NaH?
Which of the following bases are strong enough to deprotonate C6H5OH(pKa = 10) so that equilibrium favors the products:(a) H2O; (b) NaOH; (c) NaNH2; (d) CH3NH2; (e) NaHCO3; (f) NaSH; (g)NaH?
Isoleucine, another of the twenty amino acids found in proteins, is metabolized by a pathway that includes the following step. Propose a mechanism.
As far back as the 16th century, South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue. Chemical studies of Erythroxylon coca by Friedrich WĂ¶hler in 1862 resulted in the discovery of cocaine, C17H21NO4, as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, C9H15NO3. Oxidation of ecgonine with CrO3 yields a keto acid that readily loses CO2 on heating, giving tropinone. (a) What is a likely structure for the keto acid? (b) What is a likely structure for ecgonine, neglecting stereochemistry? (c) What is a likely structure for cocaine, neglecting stereochemistry?
Acid-catalyzed hydrolysis of a nitrile to give a carboxylic acid occurs by initial protonation of the nitrogen atom, followed by nucleophilic addition of water. Review the mechanism of base-catalyzed nitrile hydrolysis in Section 20-7 and then predict the products for each reaction below and write all of the steps involved in the acid-catalyzed reaction, using curved arrows to represent electron flow in each step.
1) CO2 (s) g) Ph(CH:)MgBr 2) 11 (aq) H'(aq)/A h) 6-Bromohexanoic Acid + NACN- 1) NaOEt/ELOH i) PhCOHC-CH2 + CH:(CO Et) 2) H (aq), A,-CO. Butanoic Acid 1 equivalent Bry/P H.NEt k) Methyl Benzoate NaOMe/MEOHI I) 2 (Ph) CHCOOME -
a) LDA b) CN Br DIBAL -OTHP THP MCPBA Hydrazine H₂N-NH2 KOH heat dil. HCIO4 -OH OH CN -OTHP
Heating compound X with aqueous formaldehyde forms Y (C17H23NO), which has been converted to a mixture of lupinine and epilupinine, alkaloids isolated from lupin, a perennial ornamental plant commonly seen on the roadside in parts of Alaska. Identify Y and explain how it is formed. HO но CH=0 one step NH2 C,,H23NO lupinine epilupinine Ph
12.Each of the following gives methylammonium chloride, CH3NH3+ CI, when hydrolyzed in aqueous acid solution except one. Which one? 0 A) NCH; ANCH₂ dal OBCHalstiuen bns noilspitinoqs8 8 priw ot ont to doirlw ablaiy woled nwore as eisteos Salubong beledal vilsoigolosi NHCH; NCH; O D))
Specialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic acid, NaOAc = Sodium Acetate; PhD phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N- bromosuccinimide, PBR3, SOCI2, AICI3, FeBr3, H2SO4, Li, Na, Mg, Brz2, CrO3, LDA = lithium diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH = disecondary isobutyl borane, KMNO4, HIO4 = periodic acid %3D %3D %3D %3D write the missing reagents and solvents over the arrows. Some transformation require multiple steps. In some cases there will be multiple arrows. -- -Li OH H- H.
Give the structure of possible product(s) during this reaction.More than one options may be correct.

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K Problem 21 of 24 Submit Draw the missing organic structures in the following multistep synthesis. Show the final product at physiological pH (pH = 7.4). Ignore any inorganic byproducts formed. H 0 NH3 Select to Draw HCN H+, H2O Select to Draw Select to Draw Δ