Chapter 10: Problem 35
Show how you might bring about the following conversions. For any conversion involving more than one step, show each intermediate compound.
Chapter 10: Problem 35
Show how you might bring about the following conversions. For any conversion involving more than one step, show each intermediate compound.
All the tools & learning materials you need for study success - in one app.
Get started for free\(\alpha\)-Hydroxyketones and \(\alpha\)-hydroxyaldehydes are also oxidized by treatment with periodic acid. It is not the \(\alpha\)-hydroxyketone or aldehyde, however, that undergoes reaction with periodic acid, but the hydrate formed by addition of water to the carbonyl group of the \(\alpha\)-hydroxyketone or aldehyde. Write a mechanism for the oxidation of this \(\alpha\)-hydroxyaldehyde by \(\mathrm{HIO}_{4}\).
Complete the following acid-base reactions. Show all valence electrons on the interacting atoms and show by the use of curved arrows the flow of electrons in each reaction.
The tosylate of a primary alcohol normally undergoes an \(\mathrm{S}_{\mathrm{N}} 2\) reaction with hydroxide ion to give a primary alcohol. Reaction of this tosylate, however, gives a compound of molecular formula \(\mathrm{C}_{7} \mathrm{H}_{12} \mathrm{O}\). Propose a structural formula for this compound and a mechanism for its formation.
Select the stronger acid from each pair and explain your reasoning. For each stronger acid, write a structural formula for its conjugate base. (a) \(\mathrm{H}_{2} \mathrm{O}\) or \(\mathrm{H}_{2} \mathrm{CO}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{OH}\) or \(\mathrm{CH}_{3} \mathrm{COOH}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) or \(\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CH}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) or \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{SH}\)
Dihydropyran is synthesized by treating tetrahydrofurfuryl alcohol with an arenesulfonic acid, \(\mathrm{ArSO}_{3} \mathrm{H}\). Propose a mechanism for this conversion.
What do you think about this solution?
We value your feedback to improve our textbook solutions.