(a)
Interpretation:
The product of reaction of m−cresol with concentrated H2SO4 is to be stated.
Concept introduction:
The
Answer to Problem 18.47AP
The products formed on reaction of m−cresol with concentrated H2SO4 are shown below.
Explanation of Solution
The reaction of m−cresol with concentrated H2SO4 is shown below.
Figure 1
This reaction is known as electrophilic substitution reaction. The ortho, para directing power of hydroxyl group is greater than the methyl group, therefore, the sulfonic group is directed according to the position of hydroxyl group. Due to the presence of H2SO4, SO3H is added as an electrophile and two products are formed. Therefore, the products are shown below.
Figure 2
The products formed on reaction of m−cresol with concentrated H2SO4 are shown in Figure 2.
(b)
Interpretation:
The product on reaction of m−cresol with Br2 in CCl4 (dark) is to be stated.
Concept introduction:
The chemical reaction in which an electrophile group is replaced by another functional group is known as electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.
Answer to Problem 18.47AP
The products formed on reaction of m−cresol with Br2 in CCl4 (dark) are shown below.
Explanation of Solution
The reaction of m−cresol with Br2 in CCl4 (dark) is shown below.
Figure 3
Under dark conditions, there is electrophilic substitution reaction. In this reaction, bromine will get substituted at the benzene ring. The position of the bromine depends on the hydroxyl group as it has more ortho, para directing power than methyl group. Therefore, the products formed on reaction of m−cresol with Br2 in CCl4 (dark) are shown below.
Figure 4
The products formed on reaction of m−cresol with Br2 in CCl4 (dark) are shown in Figure 4.
(c)
Interpretation:
The product on reaction of m−cresol with Br2 (excess) in CCl4, light is to be stated.
Concept introduction:
The chemical reaction in which an electrophile group is replaced by another functional group is known as electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.
Answer to Problem 18.47AP
The product on reaction of m−cresol with Br2 (excess) in CCl4, light is shown below.
Explanation of Solution
The reaction of m−cresol with Br2 (excess) in CCl4, is shown below.
Figure 5
Under light conditions, there will be bromine radical formed and benzylic substitution will take place. Further, due to excess of bromine, bromine will get substituted at the benzene ring. The position of the bromine depends on the hydroxyl group as it has more ortho, para directing power than methyl group. Therefore, the products formed on reaction of m−cresol with Br2 (excess) in CCl4 (light) are shown below.
Figure 6
The product on reaction of m−cresol with Br2 (excess) in CCl4, light is shown in Figure 6.
(d)
Interpretation:
The product on reaction of m−cresol with dilute HCl is to be stated.
Concept introduction:
The chemical reaction in which an electrophile group is replaced by another functional group is known as electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.
Answer to Problem 18.47AP
No product is formed on reaction of m−cresol with dilute HCl.
Explanation of Solution
The electron pair of oxygen of hydroxyl group is in conjugation with the phenyl ring. Due to this conjugation, it does not get protonated. Therefore, no reaction is taking place on adding dilute HCl to m−cresol.
There is no product formed on reaction of m−cresol with dilute HCl.
(e)
Interpretation:
The product on reaction of m−cresol with 0.1 M NaOH solution is to be stated.
Concept introduction:
The chemical reaction in which an electrophile group is replaced by another functional group is known as electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.
Answer to Problem 18.47AP
The product on reaction of m−cresol with 0.1 M NaOH solution is shown below.
Explanation of Solution
The reaction of m−cresol with 0.1 M NaOH solution is shown below.
Figure 7
On adding sodium hydroxide, the hydroxyl group gets deprotonated to form a phenolate ion. Therefore, the product formed on reaction of m−cresol with 0.1 M NaOH is shown below.
Figure 8
The product on reaction of m−cresol with 0.1 M NaOH is shown in Figure 8.
(f)
Interpretation:
The product on reaction of m−cresol with HNO3 is to be stated.
Concept introduction:
The chemical reaction in which an electrophile group is replaced by another functional group is known as electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.
Answer to Problem 18.47AP
The product on reaction of m−cresol with HNO3 is shown below.
Explanation of Solution
The reaction of m−cresol with HNO3 is shown below.
Figure 9
In this reaction, electrophilic substitution reaction occurs. Nitro will get substituted at the benzene ring. The position of the nitro group depends on the hydroxyl group as it has more ortho, para directing power than methyl group. Therefore, the products formed on reaction of m−cresol with HNO3 are shown below.
Figure 10
The product on reaction of m−cresol with HNO3 is shown in Figure 10.
(g)
Interpretation:
The product on reaction of m−cresol with given acyl chloride in presence of AlCl3 is to be stated.
Concept introduction:
The Friedel-Craft acylation is a type of electrophilic substitution reaction. AlCl3 is used as Lewis acid which ionizes the carbon-halogen bond of the acid chloride and forms a positively charged carbon electrophile which is resonance stabilized. Then the electrophile reacts with benzene
Answer to Problem 18.47AP
The products on reaction of m−cresol with given acyl chloride in presence of AlCl3 are shown below.
Explanation of Solution
The reaction of m−cresol with given acyl chloride in presence of AlCl3 is shown below.
Figure 11
The above reaction is an example of Friedel Crafts Acylation reaction. In the above reaction, C2H5COCl is an electrophile that gets substituted on the benzene ring. The position of the acyl group depends on the hydroxyl group as it has more ortho, directing power than the methyl group.
Figure 12
The products on reaction of m−cresol with given acyl chloride in presence of AlCl3 are shown in Figure 12.
(h)
Interpretation:
The product formed on reaction of m−cresol with Na2Cr2O7 in H2SO4 is to be stated.
Concept introduction:
Loss of electrons is classified as an oxidation reaction. Na2Cr2O7 is an oxidising agent. Benzoquinone is formed on oxidation of phenols. It is also known as para-quinone and has the molecular formula C6H4O2.
Answer to Problem 18.47AP
The product formed on reaction of m−cresol with Na2Cr2O7 in H2SO4 is shown below.
Explanation of Solution
The reaction of m−cresol with Na2Cr2O7 in H2SO4 is shown below.
Figure 13
The above reaction is an oxidation reaction. The phenol group that has no substitution at para group gets oxidized to p−quinone. In this reaction, Na2Cr2O7 is the oxidizing agent that oxidizes m−cresol. Therefore, the product formed on reaction of m−cresol with Na2Cr2O7 in H2SO4 is shown below.
Figure 14
The product formed on reaction of m−cresol with Na2Cr2O7 in H2SO4 is shown in Figure 14.
(i)
Interpretation:
The product on reaction of m−cresol with triflic anhydride in pyridine at 0°C is to be stated.
Concept introduction:
Stille reaction is an example of coupling reaction. In Stille reaction, the triflate reacts with trimethylstannane in presence of Pd catalyst and LiCl to give a coupled product of hydrocarbon part of trimethylstannane and triflate.
Answer to Problem 18.47AP
The product formed on reaction of m−cresol with triflic anhydride in pyridine at 0 °C is shown below.
Explanation of Solution
The reaction of m−cresol with triflic anhydride in pyridine at 0 °C is shown below.
Figure 15
In the above reaction, the triflic anhydride combines with the hydroxyl group of cresol to form m−tolyltrifluoromethanesulfonate. The product formed is a useful reactant in Stille coupling reaction. Therefore, the product formed on reaction of m−cresol with triflic anhydride in pyridine at 0°C is shown below.
Figure 16
The product on reaction of m−cresol with triflic anhydride in pyridine at 0°C is in Figure 16.
(j)
Interpretation:
The product on reaction of product of part (i) with (CH3)4Sn, excess LiCl, and Pd(PPh3)4 catalyst in dioxane is to be stated.
Concept introduction:
Stille reaction is an example of coupling reaction. In Stille reaction, the triflate reacts with trimethylstannane in presence of Pd catalyst and LiCl to give a coupled product of hydrocarbon part of trimethylstannane and triflate.
Answer to Problem 18.47AP
The product on reaction of product of part (i) with (CH3)4Sn, excess LiCl, and Pd(PPh3)4 catalyst in dioxane is shown below.
Explanation of Solution
The product of part (i) is shown below.
Figure 16
The reaction of product of part (i) with (CH3)4Sn, excess LiCl, and Pd(PPh3)4 catalyst in dioxane is shown below.
Figure 17
In the above reaction, m−tolyl trifluoromethanesulfonate reacts with (CH3)4Sn to form a stannane. The stannane then further couples with tetramethyl stannane to form m−xylene. Therefore, the product on reaction of product of part (i) with (CH3)4Sn, excess LiCl, and Pd(PPh3)4 catalyst in dioxane is shown below.
Figure 18
The product on reaction of product of part (i) with (CH3)4Sn, excess LiCl, and Pd(PPh3)4 catalyst in dioxane is shown in Figure 18.
(k)
Interpretation:
The product on reaction of product of part (i) with (E)−CH3CH=CH−B(OH)2, aqueous NaOH, and Pd(PPh3)4 catalyst is to be stated.
Concept introduction:
The Suzuki coupling reaction is a reaction in which an aryl or vinylic boronic acid is coupled to an aryl or vinylic iodide or bromide. It is a Pd(0) catalysed reaction. This reaction can be used to prepare biaryls, aryl-substituted
Answer to Problem 18.47AP
The product on reaction of product of part (i) with (E)−CH3CH=CH−B(OH)2, aqueous NaOH, and Pd(PPh3)4 catalyst is shown below.
Explanation of Solution
The product of part (i) is shown below.
Figure 16
The reaction of product of part (i) with (E)−CH3CH=CH−B(OH)2, aqueous NaOH, and Pd(PPh3)4 catalyst is shown below.
Figure 19
The above reaction is Suzuki coupling reaction. In this reaction, m−tolyl trifluoromethanesulfonate reacts with the boronic acid in presence of sodium hydroxide and Pd(PPh3)4 catalyst to give a coupled product. Therefore, the product on reaction of product of part (i) with (E)−CH3CH=CH−B(OH)2, aqueous NaOH, and Pd(PPh3)4 catalyst is
Figure 20
The product on reaction of product of part (i) with (E)−CH3CH=CH−B(OH)2, aqueous NaOH, and Pd(PPh3)4 catalyst is shown in Figure 20.
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