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- (11) A OB C D A solution of which of the following alkyl halides in methanol will be optically active to begin but slowly lose most or all of its optical activity when heated? H H Br H3CBr Br (B) (A) T Br (C) (D)31. (8) Provide one reagent that will complete each transformation. (a) (b) (c) (d) OH & OH OH -CH₂OH CH₂OH ? HBr ? ? -CH₂CI OH (e) (f) ? (g) (h) -O+K H ? OH KMnO4 -OCH₂CH3 32. (12) Predict the 4 products resulting from reaction of the alkene with 1 equivalent of HBr (8 pts). (b) label the kinetic product (2 pts). (c) label the thermodynamic product (2 pts). OCH3 -OCH3 H OTS6B. Write a reaction scheme to selectively synthesize the following: OH OMe H3C OMe
- The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?1) Provide the reagent(s) and the reaction mechanism of the following reaction. H₂N
- OH - NH, Br2/KOH →product; 1. (a-hydroxy amide) Product of this Hoffmann bromamide reaction is : OH (a) Ph – Ĉ-CH3 (Ъ) Ph — CHO (c) Ph- CH3 (d) Ph – CH2 -NH2 NO2Provide the mechanism for the following reaction (1) PhMgBr (2 equiv) (2) H3O+ workup OHSeveral 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.
- Which of the following reactions will synthesize phenol from benzene? 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) warm H2SO4 and H2O 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) CuCN; 5) dilute acid and heat 1) Acetyl chloride & AlCl3; 2) bleach 1) Ph-N2+ + KI; 2) BrMgCH=CH2 in ether, followed by H3O+; 3) warm, conc'd KMnO4 1) Cl-CH(CH3)-CH2CH2CH3 + FeBr3; 2) hot, conc'd KMnO4Devise a synthesis of (E)-tetradec-11-enal, a sex pheromone of thespruce budworm, a pest that destroys fir and spruce forests, fromacetylene, Br(CH2)10OH, and any needed organic compounds orinorganic reagents.(a) 11. (b) What is the major product of the elimiation below? |||-- EtONa EtOH (C) (d)