Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 19, Problem 19.69AP
Interpretation Introduction

(a)

Interpretation:

The synthesis of isotopically labelled alcohol using H2O18 is to be stated.

Concept introduction:

Elements which have the same atomic number but different atomic mass are known as isotopes. Due to the difference in the mass numbers, their natural abundance also differs. The chemical properties of isotopes are similar.

Interpretation Introduction

(b)

Interpretation:

The synthesis of the isotopically labelled alcohol using LiAlD4 is to be stated.

Concept introduction:

Elements which have the same atomic number but different atomic mass are known as isotopes. Due to the difference in the mass numbers, their natural abundance also differs. The chemical properties of isotopes are similar.

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Propose a structural formula for compound A, C4H10O, consistent with the following 1H-NMR and IR spectra. Please assign all the appropriate peaks in the IR and NMR spectra and provide a short narrative describing what structural information each piece of data provided.
A compound A, C7H12, was found to be optically active. On catalytic reduction over platinum catalyst, 2 equivalents of hydrogen were absorbed, yielding compound B, C7H16. On ozonolysis of A, two fragments were obtained. One fragment was identified as acetic acid. The other fragment, compound C, was an optically active carboxylic acid, C5H10O2. Write the reactions and draw structures for A, B and C.
Please propose a structural formula for compound A, C4H10O, consistent with the following 1H-NMR and IR spectra. Assign all the appropriate peaks in the IR and NMR spectra and provide a short narrative describing what structural information each piece of data provided.

Chapter 19 Solutions

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