2 steps BU4NF C9H1602 A + B ÓSIME,tBu (i) Enone C can be prepared from alkyne A and aldehyde B in two steps via a gold-catalysed reaction. Identify A and B and provide reagents/conditions for a synthesis of C. (ii) Give the structure of D and classify the ring-closing reaction for its formation from C according to Baldwin's rules
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- Devise efficient laboratory syntheses of ethers and epoxides, including the following:(a) The Williamson ether synthesis(b) Alkoxymercuration-demercuration(c) Peroxyacid epoxidation(d) Base-promoted cyclization of halohydrins(e) Formation of silyl ethersPredict the products of reactions of ethers and epoxides, including the following:(a) Cleavage and autoxidation of ethers(b) Acid- and base-promoted opening of epoxides(c) Reactions of epoxides with organometallic reagents(d) Cleavage of silyl ethers(v) Compound K can be synthesised in excellent yield via a Robinson annulation between a,ß- unsaturated ketone H and ketone J. Provide detailed reaction mechanisms to account for the formation of product K. H KOH EtOH K
- A key step in the synthesis of the narcotic analgesic meperidine (tradename Demerol) is the conversion of phenylacetonitrile to X. (a) What isthe structure of X? (b) What reactions convert X to meperidine ?(b) acid, HNO3 to produce compound L. The reaction of compound L with bromine, Br2 in the presence of iron tribromide, FeBr3 produced compound M. Benzene also undergoes Fridel-crafts alkylation reaction with chloroethane, CH;CH2CI using catalyst N to produce compound P. Benzene, CeHe undergoes substitution reaction with concentrated nitric Benzena, CsHe menjalani tindak balas penukargantian dengan asid nitrik, HNO, pekat untuk menghasilkan sebatian L. Tindak balas sebatian L dengan bromin, Brz dengan kehadiran ferum tribromida, FeBrs menghasilkan sebatian M. Benzena juga menjalani tindak balas alkilasi Fridel-crafts dengan kloroetana, CH3CH2CI dengan menggunakan pemangkin N untuk menghasilkan sebatian P. (i) Draw the structural formula of L, M and P. Lukiskan formula struktur bagi sebatian L, M dan P. (ii) State catalyst N. Nyatakan pemangkin N. (iii) Show the formation of electrophile that will be reacted with benzene for the formation of compound P.The endiandric acids comprise a group of unsaturated carboxylic acidsisolated from a tree that grows in the rainforests of eastern Australia.The methyl esters of endiandric acids D and E have been prepared frompolyene Y by a series of two successive electrocyclic reactions: thermalring closure of the conjugated tetraene followed by ring closure of theresulting conjugated triene. (a) Draw the structures (includingstereochemistry) of the methyl esters of endiandric acids D and E. (b)The methyl ester of endiandric acid E undergoes an intramolecular [4 +2] cycloaddition to form the methyl ester of endiandric acid A. Propose apossible structure for endiandric acid A.
- Ozonolysis of compound D will produce compound E and compound F as products. Hydrationof compound D will produce compound G as major product. Compound D is a major productobtained from dehydrohalogenation of 2-chloro-3-methylbutane. a) Identify the structural formula for compound D, E, F and G.b) Suggest suitable reagent(s) and condition(s) needed for dehydrohalogenation of 2-chloro-3-methylbutaneV) Outline a synthesis of the following compound from benzene and other appropriate organic or inorganic reagents. ? CH3 ? CO2H Excess ?D is an intermediate in the synthesis of rosiglitazone (trade name Avandia), a drug used to treat type 2 diabetes. Suggest two different methods to prepare the ether in D by substitution reactions.
- Rank the compounds in each group according to their reactivity towardelectrophilic substitution.(a) Chlorobenzene, o-dichlorobenzene, benzene(b) p-Bromonitrobenzene , nitrobenzene, phenol(c) Fluorobenzene, benzaldehyde, a-xylene(d) Benzonitrile, p-methylbenzonitr ile,p-methoxybenzonitrileb) Arrange the following compounds according to the reactivity towards nitration. Give reasons for your choice. CCH3 NHČCH, CH34. (a) Answer ALL parts. Suggest a synthesis of the following alkene (A) using a Wittig reaction strategy. Draw the starting material(s), key reagent and a full reaction mechanism including an explanation of the observed geometry. OMe A