Fill in the blanks: 12 0.x-xoge He Attempted Friedel-Crafts acylation of benzene with t- BUCOCI gives some of the expected ketone, as a minor product, and also some t-butyl benzene, but the major product is the disubstituted compound C. Explain how these compounds are formed and suggest the order in which the two substituents are added to form compound C. 1. ANSWER the following by filling the blanks.. Product A is formed by Product B is formed by In Product C the first reaction is
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- Butanone is formed when an alkyne is passed through a dil sol of H2SO4at 330K in presence of mercuric sulphate. Write the possible structure of the alkyne.A. In the synthesis of 1-bromobutane, what is the inorganic by-product left in the reaction flask following the distillation? Why was the bromoalkane the bottom layer in the separatory funnel? B. Predict the product when 1-methylcyclohexanol reacts with H2SO4 and KBr. Show the mechanism.Compelling evidence for the existence of a tetrahedral intermediate innucleophilic acyl substitution was obtained in a series of elegantexperiments carried out by Myron Bender in 1951. The key experimentwas the reaction of aqueous −OH with ethyl benzoate (C6H5COOCH2CH3)labeled at the carbonyl oxygen with 18O. Bender did not allow thehydrolysis to go to completion, and then examined the presence of alabel in the recovered starting material. He found that some of therecovered ethyl benzoate no longer contained a label at the carbonyloxygen. With reference to the accepted mechanism of nucleophilic acyl substitution, explain how this provides evidence for a tetrahedralintermediate.
- Aspirin, or 2-acetoxybenzoic acid, (C9H8O4) is often synthesised from salicylic acid.(i) Sketch and discuss any changes in the number of possible structural conformations ofaspirin relative to those of salicylic acid. (ii) Re-draw the structure predicted to be the lowest energy conformation of aspirin,indicating any expected stabilising and destabilising interactions. Justify your choice.tert-Butoxycarbonyl azide was developed as a reagent for peptide synthesis at OWL's home institution, the University of Massachusetts, by Prof. L.A. Carpino. It is prepared by treating tert-butoxycarbonyl chloride with sodium azide. Propose a structure for the initially-formed intermediate in this reaction.Cembrene, C20H32, is a diterpenoid hydrocarbon isolated from pine resin. Cembrene has a UV absorption at 245 nm, but dihydrocembrene (C20H34), the product of hydrogenation with 1 equivalent of H2, has no UV absorption. On exhaustive hydrogenation, 4 equivalents of H2 react, and octahydrocembrene, C20H40, is produced. On ozonolysis of cembrene, followed by treatment of the ozonide with zinc, four carbonylcontaining products are obtained: Propose a structure for cembrene that is consistent with its formation from geranylgeranyl diphosphate.
- Over the past several decades, chemists have developed a number of synthetic methodologies for the synthesis of steroid hormones. One of these, developed by Lutz Tietze at the Institut für Organische Chemie der Georg-August-Universität, Göttingen, Germany, used a double Heck reaction to create ring B of the steroid nucleus. As shown in the following retrosynthetic analysis, a key intermediate in his synthesis is compound (1). Two Heck reaction disconnects of this intermediate give compounds (2) and (3). Compound (2) contains the aromatic ring that becomes ring A of estrone. Compound (3) contains the fused five- and six-membered rings that become rings C and D of estrone. Q.Propose structural formulas for compounds (2) and (3).Over the past several decades, chemists have developed a number of synthetic methodologies for the synthesis of steroid hormones. One of these, developed by Lutz Tietze at the Institut für Organische Chemie der Georg-August-Universität, Göttingen, Germany, used a double Heck reaction to create ring B of the steroid nucleus. As shown in the following retrosynthetic analysis, a key intermediate in his synthesis is compound (1). Two Heck reaction disconnects of this intermediate give compounds (2) and (3). Compound (2) contains the aromatic ring that becomes ring A of estrone. Compound (3) contains the fused five- and six-membered rings that become rings C and D of estrone. Q.Name the types of functional groups in estroneOver the past several decades, chemists have developed a number of synthetic methodologies for the synthesis of steroid hormones. One of these, developed by Lutz Tietze at the Institut für Organische Chemie der Georg-August-Universität, Göttingen, Germany, used a double Heck reaction to create ring B of the steroid nucleus. As shown in the following retrosynthetic analysis, a key intermediate in his synthesis is compound (1). Two Heck reaction disconnects of this intermediate give compounds (2) and (3). Compound (2) contains the aromatic ring that becomes ring A of estrone. Compound (3) contains the fused five- and six-membered rings that become rings C and D of estrone. Q.How many chiral centers are present in estrone?
- Over the past several decades, chemists have developed a number of synthetic methodologies for the synthesis of steroid hormones. One of these, developed by Lutz Tietze at the Institut für Organische Chemie der Georg-August-Universität, Göttingen, Germany, used a double Heck reaction to create ring B of the steroid nucleus. As shown in the following retrosynthetic analysis, a key intermediate in his synthesis is compound (1). Two Heck reaction disconnects of this intermediate give compounds (2) and (3). Compound (2) contains the aromatic ring that becomes ring A of estrone. Compound (3) contains the fused five- and six-membered rings that become rings C and D of estrone. Q.Show how your proposals for compounds (2) and (3) can be converted to compound (1). (Note: In the course of developing this synthesis, Tietze discovered that vinylic bromides and iodides are more reactive in Heck reactions than are aryl bromides and iodides.)Over the past several decades, chemists have developed a number of synthetic methodologies for the synthesis of steroid hormones. One of these, developed by Lutz Tietze at the Institut für Organische Chemie der Georg-August-Universität, Göttingen, Germany, used a double Heck reaction to create ring B of the steroid nucleus. As shown in the following retrosynthetic analysis, a key intermediate in his synthesis is compound (1). Two Heck reaction disconnects of this intermediate give compounds (2) and (3). Compound (2) contains the aromatic ring that becomes ring A of estrone. Compound (3) contains the fused five- and six-membered rings that become rings C and D of estrone. Q. In the course of the double Heck reactions, two new chiral centers are created. Assume in compound (3), the precursor to rings C and D of estrone, that the fusion of rings C and D is trans and that the angular methyl group is above the plane of the ring. Given this stereochemistry, predict the stereochemistry of…Outline the synthesis of racemic 3-methyl-3-heptanol, Et(Me)C(*)OHn-Bu, starting from alcohols of four carbons or fewer and any inorganic reagents or solvent needed.