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- Give the major product for the reaction. Pyrrolidine is a secondary amine. CH CH O CH CH! O OH CH2 O CH. I CH.CH Ї TCH CHE OH CH CH₂CH₂ CH.CH CH.OH2 0= RO pyrrolidine. 2 GH CH2 3 HCI H,0 TOH OH: CH₂CH₂ TCH CH: CH₂CH. CH₂CH₂Although codeine occurs in low concentration in the opium poppy, most of the codeine used in medicine is prepared from morphine (the principal component of opium) by the following reaction. Explain why selective methylation occurs at only one OH in morphine to give codeine. Codeine is a less potent and less addictive analgesic than morphine. но. CH,0. [1 кон H [2] CH3I H. CH3 H Ho morphine H. CH3 Ho codeineb) Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an explanation for the failure of the reaction to take place as indicated. OMe HO + OMe + OH HO + CH; OH
- Provide the mechanism for this reaction (include arrow pushing) ОН 2-lodobenzoic acid K2S2O8 H2SO4 ОН OSO3H ОН 양 diphenyliodonium-2-Carboxylate benzyne18) The following reaction undergoes three distinct steps: imine formation, electrophilic aromatic substitution, and decarboxylation. Draw each of the intermediates from each of these three steps as well as the final product. BS NH₂ OH heatArrange the following compounds in order of decreasing reactivity towards hydrolysis. H2N. H3CO NAI IYK КАН BCS
- 4) Rank the following compounds in order of increasing reactivity (least to most reactive) with respect to acyl substitution. I. methyl benzoate II. benzoylchloride III. benzamide III < | < ||What major organic product would you expect to obtain when acetic anhydride reacts with CH;CH;CH;OH? А. СH,COОН + CH,CH,OH В. СН:CH:COОН + СH:CH2OН С. СH:COOCН.CH-CH; + CH:СООН D. CH;COOCH2CH¿CH3 + CH3CH2OHWhich of the following compounds will form a yellow solid when dissolved in a basic, aqueous solution of I2?(a) butanoic acid; (b) pentan-2-one; (c) pentan-3-one; (d) cyclohexanone; (e) pentanal
- NOC XT Ph CH₂ Both primary and secondary amines add to a ß-unsaturated aldehydes and ketones to yield ß-amino aldehydes and ketones rather than the alternative imines. Under typical reaction conditions, both direct and conjugate modes of addition occur rapidly. But because the reactions are reversible, they generally proceed with thermodynamic control rather than kinetic control so the more stable conjugate addition product is often obtained to the complete exclusion of the less stable direct addition product. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H H CH3NH₂ CH3 H-A :A Ph NHCH3 вон CH3 :A H-A 8ba) Provide the complete mechanism for the following reaction. MeO CH;CH2NH2 CH;OH b) Design a synthesis for this primary amine starting from benzene. CH2CH2NH2 ноImine hydrolysis is rapid under strongly acidic conditions (H2O, 1 equivalent HCI), but imine formation is slow under the same conditions. Provide a reasonable explanation for the observed reactivity. NH +H2O, 1 eq. HCI NH3 FAST NH -H20, 1 eq. HCI NH3 SLOW