Chapter 22, Problem 55P

Interpretation Introduction

Interpretation:

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

Concept introduction:

${}^{\text{13}}\text{C}$ NMR spectrum provides information about the different types of carbons present in the compound.

The position of the carbon signal in ${}^{\text{13}}\text{C}$ 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.