Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 22 - Condensations and Alpha Substitutions of Carbonyl Compounds - Problems - Page 1048: Problem 22-1 b

Answer

(Z)-1-phenylprop-1-en-2-ol (enol 1) will predominate at equilibrium as its double bond is conjugated with the benzene ring which makes it more stable than 3-phenylprop-1-en-2-ol (enol 2).

Work Step by Step

Conjugated systems are more stable than non-conjugated due to factors such as delocalization of charge through resonance and hybridization energy, in other words, delocalization lowers the overall energy of the molecule and increases stability.
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