Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 21, Problem 52P
Interpretation Introduction

Interpretation:

A five-membered-ring lactone structure of aldonic acid is to be drawn.

Concept Introduction:

An aldonic acid is defined as an acid that belongs to the family of sugar acids and is formed when an aldehyde functional group of an aldose is oxidized to form a carboxylic acid functional group.  The general formula of aldonic acid is HOOC-(CHOH)n-CH2OH.  Here, n is the number of carbon units present in the chain other than terminal carbons.  It is generally found in its lactone form with the ring structure.  Lactones are cyclic compounds.  These are formed by intramolecular esterification of the corresponding Saccharide units.

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1 Please provide an efficient synthesis of the product below from the starting material. Use the starting material as the ONLY source of carbon atoms. Show the synthesis of each compound that would be used in the overall synthesis of the product. [This synthesis uses alkyne and alcohol chemistry.]
10- 4000 20 20 30- %Reflectance 60 50- 09 60- 40- Date: Thu Feb 06 17:30:02 2025 (GMT-05:0(UnknownP Scans: 8 Resolution: 2.000 70 70 88 80 3500 3000 2500 90 100 00 Wavenumbers (cm-1) 2000 1500 2983.10 2359.13 1602.52 1584.22 1451.19 1391.87 1367.07 1314.37 1174.34 1070.13 1027.33 1714.16 1269.47 1000 1106.08 1001.14 937.02 873.60 850.20 780.22 686.91 674.38 643.09 617.98 02/06/25 16:38:20
d. Draw arrow-pushing mechanism for an enzymatic retro-aldol reaction of the following hexose. Use B: and/or HA as needed. OH OH سية HO OH OH
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