(a) Interpretation: A stepwise mechanism for the given reaction is to be drawn. Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.
(a) Interpretation: A stepwise mechanism for the given reaction is to be drawn. Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.
Solution Summary: The author describes Pinacol rearrangement as an acid catalyzed conversion of 1, 2-diols into carbonyl compounds.
Definition Definition Chemical compound containing two hydroxyl ( - OH ) groups. When naming such compounds, the suffix -diol is added to the name of parent chain alkane.
Chapter 9, Problem 9.81P
Interpretation Introduction
(a)
Interpretation: A stepwise mechanism for the given reaction is to be drawn.
Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.
Interpretation Introduction
(b)
Interpretation: The rearrangement product formed from diol D is to be drawn.
Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of 1, 2-diols into carbonyl compounds. The reactant of the reaction is named as pinacol and the product of the reaction is named as pinacolone.
a) Draw two different enol tautomers of 2-methylcyclohexanone. (b) Draw two constitutional isomers that are not tautomers, but contain a C = C and an OH group.
(a) What is the major alkene formed when A is dehydrated with H2SO4? (b) What is the major alkene formed when A is treated with POCl3 and pyridine? Explain why the major product is different in these reactions.
1,2-Diols are converted to carbonyl compounds when treated with strongacids, in a reaction called the pinacol rearrangement. (a) Draw a stepwisemechanism for this reaction. (Hint: The reaction proceeds by way ofcarbocation intermediates.) (b) Assuming that the pinacol rearrangementoccurs via the more stable carbocation, draw the rearrangement productformed from diol D.
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