
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.
Want to see more full solutions like this?
Chapter 25 Solutions
Organic Chemistry-Package(Custom)
- Using the conditions of spontaneity to deduce the signs of AH and AS Use the observations about each chemical reaction in the table below to decide the sign (positive or negative) of the reaction enthalpy AH and reaction entropy AS. Note: if you have not been given enough information to decide a sign, select the "unknown" option. reaction observations conclusions A The reverse of this reaction is always spontaneous but proceeds faster at temperatures above -48. °C. ΔΗ is (pick one) ✓ AS is (pick one) B This reaction is spontaneous except below 114. °C but proceeds at a slower rate below 135. °C. ΔΗ is (pick one) AS is (pick one) ΔΗ is C This reaction is exothermic and proceeds faster at temperatures above -43. °C. (pick one) AS is (pick one) v Х 5 ? 18 Ararrow_forwardion. A student proposes the following Lewis structure for the perchlorate (CIO) io : :0: : Cl : - - : :0: ك Assign a formal charge to each atom in the student's Lewis structure. atom central O formal charge ☐ top O ☐ right O ☐ bottom O ☐ Cl ☐arrow_forwardDecide whether these proposed Lewis structures are reasonable. proposed Lewis structure Yes. Is the proposed Lewis structure reasonable? Cl- : 2: :Z: :Z: N—N : 0: C C1: O CO No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* ☐ Yes. No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* | Yes. No, it has the wrong number of valence electrons. The correct number is: No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* | If two or more atoms of the same element don't satisfy the octet rule, just enter the chemical symbol as many times as necessary. For example, if two oxygen atoms don't satisfy the octet rule, enter "0,0". ☑arrow_forward
- Use the observations about each chemical reaction in the table below to decide the sign (positive or negative) of the reaction enthalpy AH and reaction entropy AS. Note: if you have not been given enough information to decide a sign, select the "unknown" option. reaction observations conclusions ΔΗ is (pick one) A This reaction is faster above 103. °C than below. AS is (pick one) ΔΗ is (pick one) B This reaction is spontaneous only above -9. °C. AS is (pick one) ΔΗ is (pick one) C The reverse of this reaction is always spontaneous. AS is (pick one) 18 Ararrow_forwardUse the observations about each chemical reaction in the table below to decide the sign (positive or negative) of the reaction enthalpy AH and reaction entropy AS. Note: if you have not been given enough information to decide a sign, select the "unknown" option. reaction observations conclusions A The reverse of this reaction is always spontaneous but proceeds slower at temperatures below 41. °C. ΔΗ is (pick one) AS is (pick one) ΔΗ is (pick one) B This reaction is spontaneous except above 94. °C. AS is (pick one) This reaction is always spontaneous, but ΔΗ is (pick one) C proceeds slower at temperatures below −14. °C. AS is (pick one) Х 00. 18 Ar 무ㅎ B 1 1arrow_forwardDraw the product of the reaction shown below. Ignore inorganic byproducts. + H CH3CH2OH HCI Drawingarrow_forward
- please explain this in simple termsarrow_forwardK Most Reactive Na (3 pts) Can the metal activity series (shown on the right) or a standard reduction potential table explain why potassium metal can be prepared from the reaction of molten KCI and Na metal but sodium metal is not prepared from the reaction of molten NaCl and K metal? Show how (not). Ca Mg Al с Zn Fe Sn Pb H Cu Ag Au Least Reactivearrow_forward(2 pts) Why is O2 more stable as a diatomic molecule than S2?arrow_forward
- Draw the Lewis structure for the polyatomic phosphite (PO¾³¯) a anion. Be sure to include all resonance structures that satisfy the octet rule. C I A [ ]¯arrow_forwardDecide whether these proposed Lewis structures are reasonable. proposed Lewis structure Is the proposed Lewis structure reasonable? Yes. :0: Cl C C1: 0=0: : 0 : : 0 : H C N No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* ☐ Yes. No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* Yes. ☐ No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* | * If two or more atoms of the same element don't satisfy the octet rule, just enter the chemical symbol as many times as necessary. For example, if two oxygen atoms don't satisfy the octet rule, enter "0,0".arrow_forwardDraw the Lewis structure for the polyatomic trisulfide anion. Be sure to include all resonance structures that satisfy the octet rule. с [ ] - Garrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning

