ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
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Chapter 22, Problem 55P
Interpretation Introduction

Interpretation:

It is to be determined if the shown 13C NMR spectrum matches 1-amino-2-methyl-2-propanol or 2-amino-2-methyl-1-propanol. It is to be determined if this compound can be prepared by the reaction of an epoxide with ammonia.

Concept introduction:

13C NMR spectrum provides information about the different types of carbons present in the compound.

The position of the carbon signal in 13C NMR spectrum depends on whether it is a primary, secondary, or tertiary carbon.

Presence of an electronegative (electron rich) atom or group on a carbon deshields it, moving its signal downfield.

Epoxides react with nucleophiles, with the addition of the nucleophile to one of the ring carbons. This leads to opening of the epoxide ring and conversion of the ether linkage to alcohol.

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