Organic Chemistry - Standalone book
Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 26.4, Problem 7P
Interpretation Introduction

Interpretation:

A retrosynthetic analysis to plan a synthesis of isoleucine from 2-methyl-1-butanol is to be used and equations for the synthesis are to be written.

Concept Introduction:

Amino acids can be synthesized by the reaction of an aldehyde with NH4Cl and NaCN. It is known as the Strecker synthesis.

This is a double nucleophilic addition reaction that converts the aldehyde to an amino acid having one more carbon atom.

Hydrolysis of the nitrile group converts the nitrile to the carboxylic acid group.

Aldehydes can be obtained by the oxidation of primary alcohols with pyridinium chlorochromate. This reagent stops the oxidation at the aldehyde stage.

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Transmitance 3. Which one of the following compounds corresponds to this IR spectrum? Point out the absorption band(s) that helped you decide. OH H3C OH H₂C CH3 H3C CH3 H3C INFRARED SPECTRUM 0.8- 0.6 0.4- 0.2 3000 2000 1000 Wavenumber (cm-1) 4. Consider this compound: H3C On the structure above, label the different types of H's as A, B, C, etc. In table form, list the labeled signals, and for each one state the number of hydrogens, their shifts, and the splitting you would observe for these hydrogens in the ¹H NMR spectrum. Label # of hydrogens splitting Shift (2)
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