EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 3, Problem 3.52AP
Interpretation Introduction

(a)

Interpretation:

The structure of ascorbic acid as it exists at the physiological pH (pH =7.4) is to be stated.

Concept introduction:

The pKa of the acid describes the pH at which the acid will be found in the protonated form or dissociated form. The acid is found in dissociated form in the pH range equal to pKa1 to pKa+1.

Interpretation Introduction

(b)

Interpretation:

The resonance structures of the structure of ascorbic acid as it exists at the physiological pH (pH =7.4) using curved-arrow notation are to be stated.

Concept introduction:

Resonance is the phenomena of the delocalization of pi electrons to give extra stability to the molecule. This extra stability comes from the distribution of the energy of the molecule in the resonance structures formed.

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Identify the missing starting materials/ reagents/ products in the following reactions. Show the stereochemistry clearly in the structures, if any. If there is a major product, draw the structures of the major product with stereochemistry clearly indicated where applicable. Show only the diastereomers (you do not have to draw the pairs of enantiomers). If you believe that multiple products are formed in approximately equal amounts (hence neither is the major product), draw the structures of the products, and show the detailed mechanism of these reactions to justify the formation of the multiple products. If you believe no product is formed, explain why briefly. (6 mark for each, except f and g, which are 10 mark each)
3. What starting material would you use to synthesize 3-hydroxypentanoic acid using a NaBH4 reduction?
1. Give stereochemical (Fischer projection) formulas for all (but no extras) the stereoisomers that could theoretically form during the reduction of a. the carbonyl group of 2-methyl-3--pentanone b. both carbonyl groups of 2,4-pentanedione (careful!) 2. Predict the products of the reduction of O=CCH2CH2CH2C=O with a. LiAlH4 b. NaBH4 CH3 OH
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