EBK GET READY FOR ORGANIC CHEMISTRY
EBK GET READY FOR ORGANIC CHEMISTRY
2nd Edition
ISBN: 9780321830555
Author: KARTY
Publisher: VST
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Chapter 11, Problem 11.60P
Interpretation Introduction

Interpretation:

The structures of compounds E through I in the given reaction scheme are to be determined.

Concept introduction:

The triple bond in alkynes is sufficiently electron rich. The pi electrons in alkynes are easily accessible, and hence they readily show electrophilic addition reactions. Alkynes undergo acid catalyzed hydration reactions to yield a ketone. Step 1 is the electrophilic addition of proton, which produces a resonance-stabilized vinylic carbocation intermediate. In Step 2, water behaves as a nucleophile, attacking the positively charged carbon atom of that intermediate. Deprotonation in Step 3 produces the uncharged OH group, which is attached to an alkene carbon. The product of Step 3 is an enol. Under these conditions, the enol tautomerizes to the more stable keto form. Tetrafluoromethanesulfuric acid, also known as triflic acid, and 2, 2, 2-trifluoroethanol make it a strong acid that can be used as a catalyst in the acid-catalyzed hydration reactions of alkynes.

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Chapter 11 Solutions

EBK GET READY FOR ORGANIC CHEMISTRY

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