Imine and Enamine Mechanisms Provide a complete mechanism to account for the formation of the following imine product. H2NCH, CH trace H3O* Provide a complete mechanism to account for the formation of the following enamine product. HN(CH,)2 trace H,O
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- : Treatment of (CHa)CHCH(OH)CH,CH3 with TSOH affords two products (M and N) with molecular formula CgH12. The 'H NMR spectra of M and N are given below. Propose structures for M and N and draw a mechanism to explain their formation. 1H NMR of M 3H 1H NMR of N 3H 3H 3 H 1H 3 H 2 H 2H 2H 8 7 6 4 1 0 9 8. 2 1 ppm ppm 4.III. Give a detailed mechanism for the following reaction: OH ОНRank the following carboxylic acid derivatives in decreasing order (most to least) of reactivity towards nucleophilic substitution CI NH2 OCH3 ONa II IV OI> IV> III > || O > IV > || >I O I> II| > || > IV O II > IV > 1> I
- When a methyl ester is hydrolyzed under acidic conditions in H,180, the 180 isotope ends up in the carboxylic acid. When a tert-butyl ester is hydrolyzed under the same conditions, the labeled oxygen ends up in the alcohol product. (a) Propose mechanisms to account for these observations. (b) Explain why each ester undergoes the respective mechanism. CH3 + Но-СНЗ 18 + H180 H ОНc) Draw a mechanism for the formation of EtCH2COOH from the reaction of MeCOCH(Et)COOEt with ww w m NaOH in EtOH. d) Suggest a mechanism for the following reaction and explain the driving force for the reaction: Me i) NaOEVEIOH Me Co,Et CO,Et i) H*What would be a proposed mechanism to get from cyclohexanol to cis-2-methoxycyclohexanol? I know how to get from cyclohexanol to trans-2-methoxycyclohexanol would be to go through acid-catalyzed dehydration via H2SO4, then epoxide ring formation via mCPBA and then alcohol-catalyzed opening, but don't know how to do for the cis version, if possible.
- + hv H.2 + Propose a mechanism for the reaction that fully accounts for the formation of both products.X6-156. Arrange the following substituted anilines in increasing order of reactivity toward acetic anhydride: sllo NH2 ร้อเป็น NH2 NH2 edi NH2 O₂N. (a) (b) ---- (c) (d) bund NO2 CI H3C-N-CH3 Insmiy X 6-157. Suggest a mechanism for the preparation of acetic anhydride from acetic acid and acetyl chloride in the presence pyridine (an amine base).Reaction of phenol with acetone in the presence of an acid catalyst gives a compound known as bisphenol A, which is used in the production of epoxy and polycarbonate resins Propose a mechanism for the formation of bisphenol A. OH H;PO, + H,O НО HO Phenol Acetone Bisphenol A
- The reaction of methylpropene with HBr, under radical conditions, gives two intermediates. Propose a mechanism for the formation of the two products. Propose a mechanism for the following reaction and use electronic factors to account for the formation of a major product: CH2 CH2Br N-Bromosuccinimide (NBS) ho, CCI4 Draw the structure of an antioxidant, Vitamin E free radical and use resonance structures o account for its stability.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?A step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.