ORGANIC CHEMISTRY-WILEYPLUS ACCESS PKG.
ORGANIC CHEMISTRY-WILEYPLUS ACCESS PKG.
12th Edition
ISBN: 9781119766919
Author: Solomons
Publisher: WILEY
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Chapter 22, Problem 24P
Interpretation Introduction

Interpretation:

The understanding of the specificity of bacterial oxidation for commercial synthesis of the compound vitamin C is to be explained.

Concept Introduction:

▸ The chemical name for vitamin C is L-ascorbic acid. It is obtained commercially by converting the D-sorbitol into the L-ascorbic acid with the formation of an 2ketoLgluconic acid as its intermediate.

▸ The process involves two major steps which are the formation of Lsorbose form Dglucose and the second is the bacterial oxidation of D-Glucitol by the use of a microorganism, A. suboxydans.

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1. Answer the questions about the following reaction: (a) Draw in the arrows that can be used make this reaction occur and draw in the product of substitution in this reaction. Be sure to include any relevant stereochemistry in the product structure. + SK F Br + (b) In which solvent would this reaction proceed the fastest (Circle one) Methanol Acetone (c) Imagine that you are working for a chemical company and it was your job to perform a similar reaction to the one above, with the exception of the S atom in this reaction being replaced by an O atom. During the reaction, you observe the formation of three separate molecules instead of the single molecule obtained above. What is the likeliest other products that are formed? Draw them in the box provided.
3. For the reactions below, draw the arrows corresponding to the transformations and draw in the boxes the reactants or products as indicated. Note: Part A should have arrows drawn going from the reactants to the middle structure and the arrows on the middle structure that would yield the final structure. For part B, you will need to draw in the reactant before being able to draw the arrows corresponding to product formation. A. B. Rearrangement ΘΗ
2. Draw the arrows required to make the following reactions occur. Please ensure your arrows point from exactly where you want to exactly where you want. If it is unclear from where arrows start or where they end, only partial credit will be given. Note: You may need to draw in lone pairs before drawing the arrows. A. B. H-Br 人 C Θ CI H Cl Θ + Br O
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