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Organic Chemistry 1

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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.

Ross V. Weatherman. Created for Albert.io. Copyright 2016. All rights reserved.

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$_3$)

Ross V. Weatherman. Created for Albert.io. Copyright 2016. All rights reserved.

A

Ross V. Weatherman. Created for Albert.io. Copyright 2016. All rights reserved.

B

Ross V. Weatherman. Created for Albert.io. Copyright 2016. All rights reserved.

C

Ross V. Weatherman. Created for Albert.io. Copyright 2016. All rights reserved.

D

Ross V. Weatherman. Created for Albert.io. Copyright 2016. All rights reserved.