Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
Question
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Chapter 23, Problem 23.54AP
Interpretation Introduction

(a)

Interpretation:

The synthesis of alizarin yellow R which is obtained by the reaction of aniline, salicyclic acid and other reagents is to be stated.

Concept introduction:

The chemical reaction in which an electrophile group is replaced by another functional group is called the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.

Friedal Craft acylation is an electrophilic aromatic substitution reaction. In this reaction, synthesis of monoacylated product takes place from the reaction between aromatic rings and acyl chlorides.

Interpretation Introduction

(b)

Interpretation:

The structure of alizarin yellow R which is in the yellow form at pH=9 is to be drawn.

Concept introduction:

An acid is a substance which has a tendency to lose a hydrogen ion, H+. Acidic solution turns blue litmus paper into red and is sour in taste. The pH value ranges from 0 to 7. A base is a substance which has a tendency to release a hydroxide ion, OH in water. Basic solutions turn red litmus paper into blue and are bitter in taste. The pH value ranges from 8 to 14. Bases are slippery when touched.

Interpretation Introduction

(c)

Interpretation:

The structure of alizarin yellow R at pH>12 is to be drawn.

Concept introduction:

An acid is a substance which has a tendency to lose a hydrogen ion, H+. Acidic solution turns blue litmus paper into red and is sour in taste. The pH value ranges from 0 to 7.

A base is a substance which has a tendency to release a hydroxide ion, OH in water. Basic solutions turn red litmus paper into blue and are bitter in taste. The pH value ranges from 8 to 14. Bases are slippery when touched.

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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

Chapter 23 Solutions

Organic Chemistry

Ch. 23 - Prob. 23.11PCh. 23 - Prob. 23.12PCh. 23 - Prob. 23.13PCh. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Prob. 23.18PCh. 23 - Prob. 23.19PCh. 23 - Prob. 23.20PCh. 23 - Prob. 23.21PCh. 23 - Prob. 23.22PCh. 23 - Prob. 23.23PCh. 23 - Prob. 23.24PCh. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - Prob. 23.29PCh. 23 - Prob. 23.30PCh. 23 - Prob. 23.31PCh. 23 - Prob. 23.32PCh. 23 - Prob. 23.33PCh. 23 - Prob. 23.34PCh. 23 - Prob. 23.35PCh. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - Prob. 23.38PCh. 23 - Prob. 23.39PCh. 23 - Prob. 23.40PCh. 23 - Prob. 23.41PCh. 23 - Prob. 23.42PCh. 23 - Prob. 23.43PCh. 23 - Prob. 23.44APCh. 23 - Prob. 23.45APCh. 23 - Prob. 23.46APCh. 23 - Prob. 23.47APCh. 23 - Prob. 23.48APCh. 23 - Prob. 23.49APCh. 23 - Prob. 23.50APCh. 23 - Prob. 23.51APCh. 23 - Prob. 23.52APCh. 23 - Prob. 23.53APCh. 23 - Prob. 23.54APCh. 23 - Prob. 23.55APCh. 23 - Prob. 23.56APCh. 23 - Prob. 23.57APCh. 23 - Prob. 23.58APCh. 23 - Prob. 23.59APCh. 23 - Prob. 23.60APCh. 23 - Prob. 23.61APCh. 23 - Prob. 23.62APCh. 23 - Prob. 23.63APCh. 23 - Prob. 23.64APCh. 23 - Prob. 23.65APCh. 23 - Prob. 23.66APCh. 23 - Prob. 23.67APCh. 23 - Prob. 23.68APCh. 23 - Prob. 23.69APCh. 23 - Prob. 23.70APCh. 23 - Prob. 23.71APCh. 23 - Prob. 23.72APCh. 23 - Prob. 23.73APCh. 23 - Prob. 23.74APCh. 23 - Prob. 23.75APCh. 23 - Prob. 23.76APCh. 23 - Prob. 23.77APCh. 23 - Prob. 23.78APCh. 23 - Prob. 23.79APCh. 23 - Prob. 23.80APCh. 23 - Prob. 23.81AP
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