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Show the steps in the acid-catalyzed formation of a cyclic acetal from ethylene glycol.
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- Recalling the reactions of alcohols from Chapter 10, show how to synthesize each compound from an organohalogen compound and an oxirane, followed by a transformation of the resulting hydroxyl group to the desired oxygen-containing functional group.Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. We study this reaction in Chapter 16. Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of each reaction is given in the problem.A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:
- Hydration of aldehydes and ketones can be catalyzed by acid or base. Bases catalyze hydration by: protonating the carbonyl oxygen making the carbonyl group more electrophilic employing hydroxide ion, which is a better nucleophile than water making the carbonyl group less electrophilic shifting the equilibrium position of the reaction to favor productsGive the reagents and intermediate products for the following two-step reaction.Prepare the following compounds starting from benzaldehyde and the appropriate ketone. Provide reactions for preparing the ketones starting from aromatic hydrocarbon compounds.
- Draw the structure of the major organic product(s) for the following reaction between an acetylenic anion and an alkyl halide. (The reaction stoichiometry is 1:1.)Acid-catalyzed dehydration of secondary and tertiary alcohols proceeds through an E1 mechanism. The first step is the protonation of the alcohol oxygen to form an oxonium ion. Dehydration of 3-methyl-2-butanol forms one major and two minor organic products. Draw the structures, including hydrogen atoms, of the three organic products of this reaction. н н :бн н Нас. Нас. CHз CH3 ČH3 CH3 3-methyl-2-butanol an oxonium ion Major Product Minor Product Minor ProductIn snythesizing diethyl ether from ethanol using concentrated sulfuric acid, increasing the reaction temperature to 180 ºC will produce less of the desired ether.
- Desribe the reaction product.a)Step by step show the reaction of 1 mol of water from the 3,3-dimethyl-2-pentanol compound in acid-catalyzed medium.Name the main product formed. b)Indicate whether the resulting product shows the geometric isomer or not. c)Write the products formed when the product is ozonized and oxidized.complete the following syntheses