Reaction between this aldehyde and ketone in base gives a compound A with the proton NMR spectrum: ô 1.10 (9H, s), 1.17 (9H, s), 6.4 (1H, d, J 15), and 7.0 (1H, d, J 15). What is its structure? (Don't forget stereochemistry!). When this compound reacts with HBr it gives compound B with this NMR spectrum: õu 1.08 (9H, s), 1.13 (9H, s), 2.71 (1H, dd, J1.9, 17.7), 3.25 (dd, J 10.0, 17.7), and 4.38 (1H, dd, J1.9, 10.0). Suggest a structure, assign the spectrum, and give a mechanism for the formation of B.

Reaction between this aldehyde and ketone in base gives a compound A with the proton NMR spectrum: ô 1.10 (9H, s), 1.17 (9H, s), 6.4 (1H, d, J 15), and 7.0 (1H, d, J 15). What is its structure? (Don't forget stereochemistry!). When this compound reacts with HBr it gives compound B with this NMR spectrum: õu 1.08 (9H, s), 1.13 (9H, s), 2.71 (1H, dd, J1.9, 17.7), 3.25 (dd, J 10.0, 17.7), and 4.38 (1H, dd, J1.9, 10.0). Suggest a structure, assign the spectrum, and give a mechanism for the formation of B.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.26P: Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily...

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