Propose a mechanism for formation of 2-carbethoxy-4-butanolactone and 4-butanolactone (y-butyrolactone) in the following sequence of reactions. COET 1. EtO-Na+ OEt 3. NaOH, H,O, heat EtO 4. HCI, heat 2-Carbethoxy- 4-Butanolactone 4-butanolactone (y-Butyrolactone)
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- 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 AFollowing is a retrosynthetic analysis for the synthesis of the herbicide (S)-Metolachlor from 2-ethyl-6-methylaniline, chloroacetic acid, acetone, and methanol. CI OMe OMe OMe 'N' HN N CI. + НО, Chloroacetic acid (S)-Metolachlor 3 NH2 CI + MEOH OMe Acetone Methanol 2-Ethyl-6-methylaniline Show reagents and experimental conditions for the synthesis of Metolachlor from these four organic starting materials. Your synthesis will most likely give a racemic mixture. The chiral catalyst used by Novartis for reduction in Step 2 gives 80% enantiomeric excess of the S enantiomer.A chemist wanted to synthesize the anesthetic 2-ethoxy-2-methylpropane. He used ethoxide ion and 2-chloro-2-methylpropane for his synthesis and ended up with no ether. What was the product of his synthesis? What reagents should he have used?
- H3C OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br₂ in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br Br зь P-Br Br H₂C H₂C SH Br BrFollowing 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?ANAL 728: Identifying an Unknown Aldehyde or Ketone 4. In the procedure for preparing semicarbazone derivatives, what is the pur- pose of adding sodium acetate to semicarbazide hydrochloride? TAE MOIT EMAN SHoS 10 shysshlA ruoolrU nn gniytiinshl18STJAMA InsmngizaA yiolsTodsl-911
- Identify each compound below as either a protic solvent or an aprotic solvent. H3C CH3 N N. H3C H,C CH3 `CH3 H3C-C=N N H3C-OH HO НО H Ethane-1,2-diol (Ethylene glycol) Methanamide Ethanenitrile Methanol Hexamethylphosphorotriamide (ΗMPA) (Formamide) (Acetonitrile) O=0The following scheme shows the retrosynthetic analysis of 1-isopentylaziridine to form series of intermediates via Functional Group Inversion (FGI). Choose the correct reagents of N-S for the respective conversion from the given list of reagents. N OH R. Br HO. List of reagents 1) ВН:/ТHF 2) Н:Ог, ОН HN. + CIHN. 1) Hg(OAАc)2, Н20 2) NaBH4 KOt-CH2CH2CH2CH3, SOC22 heat 1) NaBH, 2) Н:0 1) LIAIH4 2) Н.О NaOCH3, heat 1) PC14, CC14 H2CRO4, H2O PCC, CH2CI2Spasmolytol, as its name suggests, is an antispasmodic. Given this retrosynthetic analysis, propose a synthesis for spasmolytol from salicylic acid, ethylene oxide, and diethylamine. Br. NEto OH OCH3 ОН Br Spasmolytol Salicyclic acid
- CH, CH, O -COOH + CIH H,C- methacrylic acid 3-chloro-2-methylpropanoic acid CH, O CH, H,C- NH,"SH + H,C- SH H ammonium thiol n-Bu COOH Propose a reasonable mechanism for these 2 reactions.Propose a synthesis, showing reagents and conditions, to make 4-bromoaniline starting from benzene. Multiple reaction conditions may be required. A reaction mechnism is NOT needed. NH2 Brthis drug contains one or more building blocks derived from either ethylene oxide or epichlorohydrin.ldentify the part of each molecule that can be derived from one or the other of the building block and propose structural formulas for the nucleophile(s) that can be used along with either ethylene oxide or epichlorohydrin to synthesize each molecule. Me Me ono Diphenhydramine (Benadryl, an antihistamine)