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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Part C The perspective formula of isoleucine, an amino acid, is provided below. HOOC H₂NIC H 川 CH3 CH,CH3 Draw the Newman projection in staggered conformation for isoleucine by viewing the molecule along the C-2-C-3 bond. 1. Edit the Newman projection on the canvas. 2. Replace the appropriate hydrogens with the appropriate -CH3 or other groups. 3. If you need to start over, Undo or choose a Newman projection from the Templates toolbar (bottom). Important: Never delete the hydrogen atoms or bonds directly attached to the template, and do not move them by dragging or dropping them. That will break the projections structures. Only replace them! ▸ View Available Hint(s) 0 2 H± 3D EXP. L ד י CONT. 2 H 0 N о
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