Free Version
Difficult

Acid-Catalyzed Alkene Hydration Product Analysis 2

ORGO1-YBFHEA

Acid-catalyzed hydration of alkenes can sometimes be impractical because they do not always go to completion and the product can react further to produce other minor products. The alkene hydration below, for instance, produced three products and also left starting material in the reaction mixture.

Each compound in the reaction mixture was separated by chromatography and characterized by IR and NMR spectroscopy.

Which of the 4 compounds best matches the spectra shown below?

Prominent IR features (sample was analyzed as thin film): strong peak at 2950 cm$^{–1}$

$^1$H NMR (in CDCl$_3$)

A
B
C
D