Synthesize each compound from benzene. Use a diazonium salt as one of the synthetic intermediates.
a. c. e.
b. d. f.
(a)
Interpretation: The given compound is to be synthesized from benzene by the use of diazonium salt as one of the synthetic intermediates.
Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.
Answer to Problem 25.80P
The synthesis of a given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown below.
Explanation of Solution
In the first step of the synthesis, nitration of benzene ring takes place. The nitro group is meta directing, as a result the chlorination takes place at meta position in the second step. The nitro group converts to amine group on reaction with
Figure 1
The synthesis of a given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown in Figure 1.
(b)
Interpretation: The given compound is to be synthesized from benzene by the use of diazonium salt as one of the synthetic intermediates.
Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.
Answer to Problem 25.80P
The synthesis of a given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown below.
Explanation of Solution
In the first step of the synthesis, nitration of benzene ring takes place. The nitro group is meta directing, as a result the chlorination takes place at meta position in the next two steps. The nitro group converts to amine group on reaction with
Figure 2
The synthesis of a given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown in Figure 2.
(c)
Interpretation: The given compound is to be synthesized from benzene by the use of diazonium salt as one of the synthetic intermediates.
Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.
Answer to Problem 25.80P
The synthesis of a given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown below.
Explanation of Solution
The first step of synthesis of given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown below.
Figure 3
In the above step, benzene undergoes Friedel craft’s alkylation reaction to form toluene. It further reacts with
The second step of synthesis of given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown below.
Figure 4
The compound
The third step of synthesis of given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown below.
Figure 5
In the last step, the reduction of nitrile to amine takes place in the presence of
The synthesis of a given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown in Figure 3, Figure 4 and Figure 5.
(d)
Interpretation: The given compound is to be synthesized from benzene by the use of diazonium salt as one of the synthetic intermediates.
Concept introduction: Amines are the derivatives of ammonia consisting of a nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.
Answer to Problem 25.80P
The synthesis of a given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown below.
Explanation of Solution
The first step of synthesis of given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown below.
Figure 6
In the above step, benzene undergoes Friedel craft’s alkylation reaction to form ethylbenzene. It further reacts with
The second step of synthesis of given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown below.
Figure 7
The compound
The third step of synthesis of given compound from benzene, by the use of a diazonium salt as one of the synthetic intermediates, is shown below.
Figure 8
In the last step, the hydrolysis reaction takes place, which results in the formation of
The synthesis of a given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown in Figure 6, Figure 7 and Figure 8.
(e)
Interpretation: The given compound is to be synthesized from benzene by the use of diazonium salt as one of the synthetic intermediates.
Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.
Answer to Problem 25.80P
The synthesis of a given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown below.
Explanation of Solution
In the first step of the synthesis, nitration of benzene ring takes place. The nitro group is meta directing, as a result the bromination takes place at meta position in the second step. The nitro group converts to amine group on reaction with
Figure 9
The synthesis of a given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown in Figure 9.
(f)
Interpretation: The given compound is to be synthesized from benzene by the use of diazonium salt as one of the synthetic intermediates.
Concept introduction: Amines are the derivatives of ammonia consisting of a nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.
Answer to Problem 25.80P
The synthesis of given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates is shown below.
Explanation of Solution
The first step of synthesis of given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown below.
Figure 10
In the above step, benzene reacts with
The second step of synthesis of given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown below.
Figure 11
Nitrobenzene undergoes chlorination and reduction reaction to form
The third step of synthesis of given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown below.
Figure 12
In the last step,
The synthesis of a given compound from benzene, by the use of diazonium salt as one of the synthetic intermediates, is shown in Figure 10, Figure 11 and Figure 12.
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Chapter 25 Solutions
Organic Chemistry -Study Guide / Solution Manual (Custom)
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