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- Although 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 codeineTreatment of acetylene with a suitable base affords lithium acetylide, which was used as a reagent in a partial synthesis of the antitumor natural product (+)-acutiphycin. (Org. Lett. 2014, 16, 1168-1171) Possible bases to consider H-C=C-H Acetylene Step 1 Li :Base T H-O: Li Lithium hydroxide (LiOH) three steps Lithium acetylide Draw the structure of lithium acetylide. Draw Your Solution di. Η Η Η Η | | | | H-C-C-C-C: II HH HH Butyllithium (BuLi) OR CEC- Li OH CH3 -H CH3 Lithium diisopropyl amide (LDA) OMe H3C H H₂C many steps Li HO OH I (+)-Acutiphycin CH3 CH₂ "OH1. Show the products of the reductive amination reactions below; a) Acetone + NH3, followed by H2/Ni2 b) Acetone + CH3NH2, followed by LIBH3CN c) Acetone + (CH3)2NH, followed by LIBH3CN 2. Write the reaction and the names of the products formed in the reaction of aniline and N-methylaniline with: a) NaNO3+HCI followed by CuClI b) NaNO3+HCI followed by Cu20, Cu2*, H20
- 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 8bO NaBH4 Synthesis #2: Select a different set of two substrates and one reagent that could be combined to prepare benzphetamine. tymen Ph Ph Ph Ph NH Ph H O NaBH3CN, H+ 20= ano [H*], NaBH-CN NucleophileNicotinic acid, more commonly named niacin, is one of the B vitamins. Show how nico- tinic acid can be converted to (a) ethyl nicotinate and then to (b) nicotinamide. COH COET CNH, Nicotinic acid Ethyl nicotinate Nicotinamide (Niacin)
- Following is an outline of a synthesis of the bronchodilator carbuterol, a beta-2 adrenergic blocker with high selectivity for airway smooth muscle receptors. Q.Why is it necessary to add the benzyl group, PhCH2—, as a blocking group in Step 1?1. Draw the major product of the reaction of 1-butanol and the following reagents. (a) PBr3 (b) SOCI2, py (c) HCI, ZNCI2 (d) Conc. H2SO4, heat (e) PCC, CH2CI2 (f) NażCr,O7, H2SO4, H2O (g) Li (h) NaH (i) TMSCI, Et3N (1) TSCI, pyridine (k) Na (1) Potassium tert-butoxideThe widely used anticoagulant warfarin (see "Chemical Connections: From Moldy Clover to a Blood Thinner" in Chapter 18) is synthesized from 4-hydroxycoumarin, benzaldehyde, and acetone as shown in this retrosynthesis. Show how warfarin is synthesized from these reagents. OH OH Acetone + Warfarin 4Нydroxy- (a synthetic anticoagulant; racemic) coumarin Benzaldehyde
- Following are two possible retrosynthetic analyses for the anticholinergic drug cycri- mine. Fill in the details of each potential synthesis. O: OH + H. Cycrimine (гасemic)3 Treatment of 1-aminoadamantane, C„H„N, with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R,N, involves two successive S,2 reactions and gives compound A. Propose a structural formula for compound A. R&N NH, + Br. C15H93NO, + 2 R,NH Br OCH Br 1-Aminoadamantane Methyl 2,4-dibromobutanoate Aهاچ دے لاداع 8. Provide a mechanistic and resonance explanation as to why bromination (Br₂/FeBr3) of acetophenone occurs meta compared to bromination of anisole, which occurs para. For simplicity, go ahead and use "Br+" as the electrophile. Draw the mechanism for the reaction and resonance structures of the Substrate before the reaction occurs. دے 8 A ۲ دے CHEM 242 Act 2.2 Aromatics Compounds and EAS Reactions ام ole cu 1 سی are m-cs کے are ) معمار د لا تحت 6 ماك less ructeep lilic