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Draw the mechanism of mclafferty rearrangement for cyclopentanone
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- Bromoetherification, the addition of the elements of Br and OR to a double bond, is a common method for constructing rings containing oxygen atoms. This reaction has been used in the synthesis of the polyether antibiotic monensin (Problem 21.36). Draw a stepwise mechanism for the following intramolecular bromoetherification reaction. Br Br2 + HBrFriedel crafts Acylation of P-cresol?Explain why benzaldehyde is less reactive than cyclohexanecarbaldehyde toward nucleophilic attack.
- Does the compound below undergo saponification reaction? Why?Wittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and ketones. (a) Draw the structure of the triphenylphosphonium salt and Wittig reagent formed from each chloroether. (b) Draw the structural formula of the product formed by treating each Wittig reagent with cyclopentanone. Note that the functional group is an enol ether or, alternatively, a vinyl ether. (c) Draw the structural formula of the product formed on acid-catalyzed hydrolysis of each enol ether from part (b).58) Draw the product resulting from the following reaction. Indicate any relevant stereo chemistry. Eto EtOH
- a) 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;ÓHDraw the principal organic product for the reaction of 1-bromopentane with lithium in diethyl ether, followed by formaldehyde in diethyl ether, and then followed by dilute acid.Draw the product formed when the following compound undergoes an intramolecular Heck reaction. Indicate the stereochemistry at all double bonds and tetrahedral stereogenic centers.
