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- Propose a pericyclic mechanism to account for the following transformation:Friedel-Crafts alkylations usually invariably result in a mixture of products, but Friedel acylations never do. Why? a) none of these b) alkylations require catalyst c) benzene with alkyl groups are more reactive than acylbenzenes d) the reagents used in alkylations are strongerA. Provide the necessary reagents. B. Provide the necessary eragnets and the step by step mechanism.
- Muscone synthesis is possible via an intramolecular Prins reaction. The starting point is cyclododecatriene, which his subjected topartial ozonolysis.With one aldehyde group protected,the other is reacted with isobutenyl magnesium chloride, and the protecting group is hydrolysed off. Then follows what is formally a Prins reaction,and etherification results in cyclisation to the bicyclic dihydropyran. Hydrogenation (at high T) finally gives racemic muscone. a. How to remove the protective group? b. What happens if you don't use a protective group?Muscone synthesis is possible via an intramolecular Prins reaction. The starting point is cyclododecatriene, which his subjected topartial ozonolysis.With one aldehyde group protected,the other is reacted with isobutenyl magnesium chloride, and the protecting group is hydrolysed off. Then follows what is formally a Prins reaction,and etherification results in cyclisation to the bicyclic dihydropyran. Hydrogenation (at high T) finally gives racemic muscone. a. What is the protective group used in the muscone synthesis above? b. What is the name of the reagent used as the protecting group? c. What groups are protected in the above muscone synthesis ?Explain how and why rearrangements occurduring Friedel-Crafts alkylation reactions formingmore than 1 product. Also illustrate therearrangement reaction from the aboveexample.
- Provide the neccessary reagents next to the arrowsDevise 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 ethersA. For each reaction1) Provide the missing reagents/conditions or major organic products as appropriate2) Assign each reaction as Oxidation or Reduction unless otherwise directed3) Pay attention to stereochemistry including racemic mixtures unless specified
- Acetoxybenzene (PhOC(=O)OCH3) is much less reactive than ethoxybenzene (PhOCH2CH3) in electrophilic aromatic substitution reactions. Suggest an explanation for this result, based on an analysis of the inductive and resonance electronic effects of the two substituents on the stability of theWheland intermediate for para substitution by an electrophile E+Drawing Hydrohalogenation with a Carbocation RearrangementDraw a stepwise mechanism for the following reaction.Synthesize each compound from benzene. Use a diazonium salt as one of the synthetic intermediates.
