Provide a plausible arrow pushing mechanism for the conversion of the furanose into the pyranose under acidic conditions. You do NOT have to show the mechanism for the reverse equilibrium reaction from the pyranose to the furanose. НО. cat. TSOH HO HO HO
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- Provide a plausible arrow pushing mechanism for the conversion of the furanose into the pyranose under acidic conditions. You do NOT have to show the mechanism for the reverse equilibrium reaction from the pyranose to the furanose. Но. cat. TSOH HO НО HOa) A specific example of the Curtius rearrangement of an acyl azide to an isocyanate. b) The anionic intermediate that undergoes rearrangement in the Hofmann rearrangement below. 2 equiv NaOH, „NH2 NH, Br, H20 CO2 c) The iminium ion that is reduced in the in the reductive amination below. d) The Michael addition adduct that is generated in the Robinson annulation below. catalytic NaOCH3, CH;OH H3C + H20 рH 45 A NABH;CN CH;ÓH1. Provide the mechanism of the reaction shown in the picture. 2. Explain why it cannot be done in basic conditions. 3. Why is the enol tautomer favored over the keto tautomer? Ph H3C OH H H3O+/H₂O HO H3C Ph
- This reaction shows that an aldol-type reaction can be performed with a deprotonated imine as the nucleophile. On hydrolysis, the product is the normal B-hydroxycarbonyl compound. Notice that LDA is used H3C N. 1. LDA Но ? as the base instead of HO¯. H3C H. H. (a) Explain why HO¯ cannot be used as a base for this 2. reaction. (b) Provide a detailed mechanism for this reaction, including the structure of the intermediate species not shown.Show how to synthesize the following compound using either the malonic ester synthesis or the acetoacetic ester synthesis. Q.) 4-Phenyl-2-butanonePerhydroazulene derivatives have shown usefulness in electronic display applications. (Beilstein J. Org. Chem. 2012, 8, 403-410) In a study to find an efficient route for the synthesis of the perhydroazulene skeleton, compound 1 was heated in an aqueous basic solution. (J. Org. Chem. 1983, 48, 5285-5288) The resulting intramolecular aldol condensation gave compound 2, a perhydroazulene derivative with the molecular formula C₁0H₁4O. Propose a structure for 2. Compound 1 Base C10H140 Compound 2
- Kindly draw the product that was fromed when phenylacetic acid was treated with the reagent, show the process and give some explanation. Thanks! a. [1] SOCI2; [2] CH3CH2CH2NH2 (excess) b. [1] SOCI2; [2] (CH3)2CHOH2. When the following pair of reactants are combined in the presence of a basic catalyst, a number of aldol addition products are possible (since both of the reactants possess an acidic alpha proton). a. b. C. CH3 + H₂C H NaOH/H₂O Draw the structures for the two possible enolate ions. Draw the structures for all possible aldol addition products (also show the enolate ion and electrophilic carbonyl compound responsible for each product). For each of the aldol addition products predicted in part b, draw the structures for all of the corresponding aldol condensation products after loss of water (if E/Z isomers are possible, show both isomers)Match the given product to its possible reaction. HO HO H₂N Choose... Choose... Aminolysis of benzoic acid Hydrolysis of benzoyl chloride Oxidation of benzoic acid Nucleophilic acyl substitution of benzoic acid with cyclopropane carboxylate Cleavage reaction using ozone in hydrogen peroxide Electrophilic addition of chlorine in ferric chloride Esterification of benzoic acid by addition of propanol Reduction of benzoic acid Choose... Choose... Choose... 45 « 47 «
- Given the information pictured, The final step of the reaction sequence uses PhLi. Provide a reason and possible mechanism by which this final elimination and hydrolysis reaction would occur.Show how to synthesize the following compound using either the malonic ester synthesis or the acetoacetic ester synthesis. Q.) Cyclobutyl methyl ketoneWhich of the following statements is FALSE? O A successful Claisen condensation requires an ester starting material with at least one alpha hydrogen. O The keto tautomer is usually more stable than the enol tautomer. O In a Claisen condensation, you want to match the alkoxide base with the -OR of the ester in order to avoid unwanted transesterification. O An alpha hydrogen on an ester is less acidic than an alpha hydrogen on an aldehyde. O The base-promoted halogenation of a ketone replaces all of the alpha-hydrogen atoms.