Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 22, Problem 41P
Interpretation Introduction

Interpretation:

The number of acetonide groups present in the given compound based on the 13C NMR spectrum is to be determined.

Concept introduction:

The acetonides are a group of cyclic acetals that act as a protective group for vicinal-cis -OH groups of carbohydrates. It can be removed by the hydrolysis of ketal.

The 13C NMR or the carbon-13 nuclear magnetic resonance is an analytical technique in chemistry to know the carbon atoms in the structure of a compound. It is an important tool in structure elucidation of organic compounds. It can detect the only C13 isotopes and not C12 as the latter has zero net spins.

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Compare the 13C NMR spectra of isoborneol and camphor. Explain which peaks can be used to determine whether the oxidation was successful. Propose a mechanism for this oxidation. To simplify the structures, use benzyl alcohol to draw the mechanism instead of isoborneol. Include the formation of any byproduct(s) in the mechanism.
Attached is the H NMR for an unknown aldehyde reacted with acetophenone (in an aldol reaction) The aldehyde is either p-anisaldehyde or p-tolualdehye   Using the 1H NMR spectrum, draw the structure of the compound and assign the various resonances to the hydrogen nuclei responsible for them.  Which peak(s) were most significant in helping you identify your compound? Give a brief explanation for how you identified your compound. Briefly explain why signal c gives complex splitting.
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