6th Edition
Reginald H. Garrett + 1 other
ISBN: 9781305577206




6th Edition
Reginald H. Garrett + 1 other
ISBN: 9781305577206
Textbook Problem

Answers to all problems are at the end of this book. Detailed solutions are available in the Student Solutions Manual, Study Guide, and Problems Book.

Understanding Stereochemical Transformations of Amino Acids

Absolute configurations of the amino acids are referenced to D- and L-glyceraldehyde on the basis of chemical transformations that can convert the molecule of interest to either of these reference isomeric structures. In such reactions, the stereochemical consequences for the asymmetric centers must be understood for each reaction step.

Propose a sequence of reactions that would demonstrate that L(-)-serine is stereochemically related to l(- )-glyceraldehyde.

Interpretation Introduction

To propose:

Propose a sequence of reactions which would establish that L (-) Serine is stereo chemically related to L (-) glyceraldehyde.


Amino acids are so named because they all are weak acids. All amino acids have at least two dissociable hydrogens, (diprotic), and some have three dissociable hydrogens and are triprotic.


The reactions which convert L(-) serine to L (-) glyceraldehyde must maintain the stereochemistry. If an inversion in stereochemistry happens, the stereochemistry should be inverted back before L(-) glyceraldehyde is formed.

The first reaction can be a conversion of one amino acid to another. The removal of the hydroxyl group of L(-) serine produces L(-) alanine.

A nucleophilic substitution can convert L(-)-alanine to 2-bromopropanoic acid with an inversion n stereochemistry.

The nucleophilic substitution of a hydroxyl for bromine will invert the stereochemistry back to the stereochemistry of L (-)-serine.

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