A retrosynthetic analysis of 1 was undertaken suggesting a forward synthesis starting from compounds 2, 5 and 6. F3C. OH F3C. OH H2N. Br (b) NH2 1 2 но
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Suggest and explain two synthetic methods for the conversion of compound 6 to compound 4. Include side reactions
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- Complete the following reactions by giving appropriate reagents: Zn(Hg) (1)? AICI HCI HNO₂ CI H₂SO4 (3)? (4)? NO₂ (2)?Show how the synthetic scheme developed in Problem 23.67 can be modified to synthesize this triiodobenzoic acid X-ray contrast agent.(c) Treating lactone B with two equivalents of phenylmagnesium bromide, followed by hydrolysis in aqueous acid, gives a compound with the molecular formula C18H22O2, as shown below. Propose a structural formula for this compound. 1. PhMgBr (2 eq.) 2. H'/H>O C18H2202 bj 1o 14 10I f6 40 & 3 4 00 (8)
- Q1/ Do as required: 1- The role of HSO, in Preparation of Nitrobenzene. Explain 2- The using of NaOH with 2-naphthol in preparation of azo dye? 3- Preparation of Nitrobenzene in cool phase. 4- Adding HCI in the preparation of aniline from nitrobenzene. 5- When acetanilide reacts with bromine (x), acetanilide gives p-bromo acetanilide only, why? 6- In an experiment Hydrolysis of Acetanilide What color does the litmus naner4. Using arrows to show electron movements, write the stepwise mechanism for the formation of the main reaction product in the following reactions: (a) 1) CH₂MgBr, Et₂0 2) H3O+ HCI ? ? (b) O Br (Ph)3PCH₂CH₂Ph Li THF, -70 deg C to r.t. ? (c) O 1) LiAlH4, Et₂0 2) H3O+ 3) NaOH 4) CH₂ Br ?2. Provide the structure of E-2,5-dimethyloct-5-enoic acid. 3. a. Name the structure with the following 'H NMR spectrum. 8 (ppm) = 12.71 (1H, s), 8.04 (2H, d), 7.30 (2H, d), 2.41 (3H, s)
- 8. Answer both parts A and B. A: Give mechanisms for all three reactions (a-c). H,1BO/HO- (a) HO, 18ö (b) H;C H3C OH + H®OCPH; (c) Ph Ph MEOH/MeO- -Ph -Ph + Me,0 Me-O Ph Ph When MeCO2Et is heated with acid in H2180 and the reaction is quenched before it is complete, both starting material and the ethanoic acid produced are labelled with 180. Explain. B:Propose the structures of the intermediate compounds and the reagents needed to complete the following sequence of reactions. CI H₂SO4 (1)? (2)? HNO3 H₂SO4 AICI3 (3)? (4)? NO₂ KMnO4 (5)?Provide the reagents necessary to carry out the following conversion using a Stork enamine synthesis. O LO -O; H3O+ CH3NH/H₂SO4; NaOCH 3; (CH3)2NH/H2SO4; (CH3)2NH/H2SO4; CH3NH/H₂SO4; =O; H3O+ =O; H3O+ -O; H3O+ FO; H3O+
- Several 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.Reaction of p-cresol with two equivalents of 2-methylprop-1-ene affords BHT, a preservative with molecular formula C15H24O. BHT gives the following 1H NMR spectral data: 1.4 (singlet, 18 H), 2.27 (singlet, 3 H), 5.0 (singlet, 1 H), and 7.0 (singlet, 2 H) ppm. What is the structure of BHT? Draw a stepwise mechanism illustrating how it is formed.(R)-Pulegone is converted to (R)-citronellic acid by addition of HCI followed by treatment with NaOH. CI 1. NAOH 2. HCI HCI HO (R)-Pulegone (R)-Citronellic acid Propose a mechanism for each step in this transformation and account for the regiose- lectivity of HCI addition.