1.Treatment of 3-methyl-2-butanol with hydrogen chloride yielded only a trace amount of 2-chloro-3-methylbutane. An isomeric chloride was isolated in 97% yield. Explain why an isomeric compound is formed instead, and suggest a reasonable structure for this product. 2) Acid-catalyzed hydration of 2-Methyl-1-butene yields two alcohols. The major product does not undergo oxidation, while the minor product will undergo oxidation. Explain why, by showing the structures of the products. 3) The Williamson ether synthesis cannot be used to prepare tert-butyl phenyl ether. Explain why this method cannot be used in this case. 4) Show the structure of the main product when 2,2-dimethyloxirane reacts in methanol. (a) in the presence of an acid, (b) with added sodium methoxide.
1.Treatment of 3-methyl-2-butanol with hydrogen chloride yielded only a trace amount of 2-chloro-3-methylbutane.
An isomeric chloride was isolated in 97% yield. Explain why an isomeric compound is formed instead, and
suggest a reasonable structure for this product.
2) Acid-catalyzed hydration of 2-Methyl-1-butene yields two alcohols. The major product does not undergo
oxidation, while the minor product will undergo oxidation. Explain why, by showing the structures of the
products.
3) The
be used in this case.
4) Show the structure of the main product when 2,2-dimethyloxirane reacts in methanol.
(a) in the presence of an acid,
(b) with added sodium methoxide.
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