Concept explainers
Show by a series of equations how could synthesize each of the following compounds from the indicated starting material and any necessary organic or inorganic reagents:
(a)
(b)
(c)
(d)
(e)
(f) from
(g)
(h)
(i)
Interpretation:
The way in which each of the given compounds can be synthesized from the indicated starting material and any necessary organic or inorganic reagents is to be shown by using a series of equations.
Concept Introduction:
Hydroboration reaction is a two-step reaction that involves conversion of an alkene into alcohol. This type of reaction follows anti-Markovnikov's rule.In acid-catalyzed dehydration, a saturated compound is converted to an unsaturated compound with the removal of a water molecule in the presence of an acid catalyst.
Grignard reagent is prepared by the reaction of alkyl or aryl bromide with magnesium metal in the presence of ether.
Thionyl chloride
Lithium aluminium hydride is a strong reducing agent. The reduction of carboxylic acid by
Oxidation reaction involves increase in the
Answer to Problem 18P
Solution:
a)The reaction that shows the preparation of
b)The reaction that shows the preparation of
c)The reaction that shows the preparation of
d)The reaction that shows the preparation of
e) The reaction that shows the preparation of
f) The reaction that shows the preparation of
g) The reaction that shows the preparation of
h) The reaction that shows the preparation of
i) The reaction that shows the preparation of
Explanation of Solution
a)
In the synthesis of
Thus, the reaction that shows the preparation of
b)
The reaction that shows the preparation of
The first step of the required synthesis is the reaction of acid with the given alcohol. This step is the dehydration of alcohol. In the next step, hydroboration of alkene is done, which is then followed by hydrolysis. This results in the formation of
Thus, the required acid is synthesized.
c)
In the required synthesis, the first step is the reaction of the given alcohol with
d)
In this synthesis, the first step is the reaction of the given carboxylic acid with thionyl chloride to form acyl chloride. In the next step, acyl chloride reacts with diazomethane to form diazoketones. In the last step of the synthesis reaction, the diazoketones give the final product in the presence of metal catalyst and water. The given reaction is an example of Arndt-Eistert synthesis.
Therefore, the required product is synthesized.
e)
In the required synthesis, the first step is the hydrolysis of
Therefore, the required product is synthesized.
f)
The reaction of
Therefore, the required product is synthesized.
g)
In the required synthesis, the first step is the nitration of
Thus, the required product was synthesized.
h)
In the synthesis of
Therefore, the given compound was synthesized.
i)
Sodium amide is a strong base and acts as s strong nucleophile.The reaction that shows the preparation of
In the above synthesis, the first step is the reaction of
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Chapter 19 Solutions
Organic Chemistry - Standalone book
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning