describe why phenols exhibit the unusual characteristic of reacting in electrophilic aromatic substitution without a Lewis...
describe why phenols exhibit the unusual characteristic of reacting in electrophilic aromatic substitution without a Lewis acid catalyst
Homework Answers
ANSWER:
Phenols exhibit the unusual characteristic of reacting in
electrophilic aromatic substitution without Lewis acid such as
AlCl3 or FeBr3 due to highly
activating effect of OH group attached to benzene ring towards
electrophilic substitution reaction. In electrophilic substitution
Lewis acids are basically required for polarization of electrophile
attacking, in case of phenols polarization takes place without
Lewis acids. Or reaction can proceed without need of Lewis acids.
OH group being electron donating group releases electrons to benzene ring by resonance. Thus making it more electron rich center. Or it highly activates ring to electrophilic substitution reactions. Polarization takes place without Lewis acid.
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describe why phenols exhibit the unusual characteristic of
reacting in electrophilic aromatic substitution without a Lewis...
Nitration of phenols is a classic example of an electrophilic aromatic substitution reaction. a) Why does...
Nitration of phenols is a classic example of an electrophilic aromatic substitution reaction. a) Why does the nitration of phenol (hydroxybenzene) proceed only in the ortho- and para-positions on the ring? b) Draw the resonance structures that highlight the ortho- and para-directing nature of hydroxy substituents. Make sure to include the structures that showcase the movement of the charges in the ring.
250 ChemActivity 29 Electrophilic Aromatic Substitution no ChemActivity 29 Part A: Electrophilic Aromatic Substitution (What products...
250 ChemActivity 29 Electrophilic Aromatic Substitution no ChemActivity 29 Part A: Electrophilic Aromatic Substitution (What products are formed when a strong electrophile is added to benzene?) Model 1: (review) Electrophilic Addition of HCI Rani o g cyclohexene carbocation intermediate Run 2 U X benzene This product carbocation intermediate DOES NOT Critical Thinking Questions 1 For Rxn I (above) draw curved arrows showing the mechanism of electrophilic addition of HCl. Include an appropriate carbocation intermediate in the box above. Figure 1:...
You’re developing a regiospecific electrophilic aromatic substitution catalyst. To determine the regioselectivity, you’ve performed a bromination...
You’re developing a regiospecific electrophilic aromatic
substitution catalyst. To determine the regioselectivity, you’ve
performed a bromination reaction on phenol. According to the
1H-NMR, what is the product?
1. You're developing a regiospecific electrophilic aromatic substitution catalyst. To determine the regioselectivity, you've performed a bromination reaction on phenol. According to the 1H-NMR, what is the product? (5 pts) OH Bro (1 eq) Electrophilic Catalyst 'H NMR Spectrum (200 MHZ, CDCI, solution) expansion exchanges with D20 10 9 8 7 6 5...
Why must the sodium hypochlorite in the electrophilic aromatic substitution reaction be added to the reaction...
Why must the sodium hypochlorite in the electrophilic aromatic substitution reaction be added to the reaction mixture in ice?
7. Explain with the use of appropriate resonance structures, the regioselectivity of the electrophilic aromatic substitution...
7. Explain with the use of appropriate resonance structures, the regioselectivity of the electrophilic aromatic substitution reaction - i.e. why is electrophilic aromatic substitution of acetanilide less favoured at the 3-position than at the 2- or the 4-positions.
Electrophiles for the electrophilic aromatic substitution reactions have to be very strong to react with the...
Electrophiles for the electrophilic aromatic substitution
reactions have to be very strong to react with the stable aromatic
rings. A nitronium ion is needed for nitration of aromatic rings.
Complete the mechanism of the formation of the nitronium ion from
concentrated nitric acid in concentrated sulfuric acid.
organic chemistry 353 2. (4 pts.) Arrange the following in order of increasing electrophilic aromatic substitution...
organic chemistry 353
2. (4 pts.) Arrange the following in order of increasing electrophilic aromatic substitution reactivity (4 = most reactive): SO3H OH e 3. (4 pts.) Briefly describe why alkenes undergo addition and aromatic compounds undergo substitution. n Briefly describe w 4. (5 pts. Provide an example of an EAS reaction creates an arene that is less reactive than benzene (be specific, include reagents, you do not need to show the mechanism)
N(CH3)3 OH 1. heat 95% 5% (E & Z) он 2. H2N a - Proton transfer dSN2 Nucleophilic substitution b- Lewis acid/base e-Electrophilic aromatic substitution c=E2 elimination f= g Nucleophilic subs at...
N(CH3)3 OH 1. heat 95% 5% (E & Z) он 2. H2N a - Proton transfer dSN2 Nucleophilic substitution b- Lewis acid/base e-Electrophilic aromatic substitution c=E2 elimination f= g Nucleophilic subs at carbonyl(acyl Xfer) h-Conjugate (nucleophilic) addn r-carbonyl nucleophilic addn Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a i for your answers. 1. 2.
N(CH3)3 OH 1. heat 95% 5% (E & Z) он 2. H2N a -...
Consider the -N=O group and describe its directing properties in electrophilic aromatic substitution. The -N=O is...
Consider the -N=O group and describe its directing properties in electrophilic aromatic substitution. The -N=O is a ortho,para/meta director because of: -induction away from the ring -resonance into the ring -induction towards the ring -resonance away from the ring
1. You're developing a regiospecific electrophilic aromatic substitution catalyst. To determine the regioselectivity, you've performed a...
1. You're developing a regiospecific electrophilic aromatic substitution catalyst. To determine the regioselectivity, you've performed a bromination reaction on phenol. According to the 1H-NMR, what is the product? (5 pts) -OH Br2 (1 eq) ? Electrophilic Catalyst "H NMR Spectrum 200 MHz, CDCI, solution) expansion exchanges with D20 10 9 8 7 6 5 4 3 2 1 0 8 (ppm) 2. What is the final product for the following reactions? (5 pts) 1)Br2, FeBrz, 2HSUNO
250 ChemActivity 29 Electrophilic Aromatic Substitution no ChemActivity 29 Part A: Electrophilic Aromatic Substitution (What products are formed when a strong electrophile is added to benzene?) Model 1: (review) Electrophilic Addition of HCI Rani o g cyclohexene carbocation intermediate Run 2 U X benzene This product carbocation intermediate DOES NOT Critical Thinking Questions 1 For Rxn I (above) draw curved arrows showing the mechanism of electrophilic addition of HCl. Include an appropriate carbocation intermediate in the box above. Figure 1:...
You’re developing a regiospecific electrophilic aromatic
substitution catalyst. To determine the regioselectivity, you’ve
performed a bromination reaction on phenol. According to the
1H-NMR, what is the product?
1. You're developing a regiospecific electrophilic aromatic substitution catalyst. To determine the regioselectivity, you've performed a bromination reaction on phenol. According to the 1H-NMR, what is the product? (5 pts) OH Bro (1 eq) Electrophilic Catalyst 'H NMR Spectrum (200 MHZ, CDCI, solution) expansion exchanges with D20 10 9 8 7 6 5...
7. Explain with the use of appropriate resonance structures, the regioselectivity of the electrophilic aromatic substitution reaction - i.e. why is electrophilic aromatic substitution of acetanilide less favoured at the 3-position than at the 2- or the 4-positions.
Electrophiles for the electrophilic aromatic substitution
reactions have to be very strong to react with the stable aromatic
rings. A nitronium ion is needed for nitration of aromatic rings.
Complete the mechanism of the formation of the nitronium ion from
concentrated nitric acid in concentrated sulfuric acid.
organic chemistry 353
2. (4 pts.) Arrange the following in order of increasing electrophilic aromatic substitution reactivity (4 = most reactive): SO3H OH e 3. (4 pts.) Briefly describe why alkenes undergo addition and aromatic compounds undergo substitution. n Briefly describe w 4. (5 pts. Provide an example of an EAS reaction creates an arene that is less reactive than benzene (be specific, include reagents, you do not need to show the mechanism)
N(CH3)3 OH 1. heat 95% 5% (E & Z) он 2. H2N a - Proton transfer dSN2 Nucleophilic substitution b- Lewis acid/base e-Electrophilic aromatic substitution c=E2 elimination f= g Nucleophilic subs at carbonyl(acyl Xfer) h-Conjugate (nucleophilic) addn r-carbonyl nucleophilic addn Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a i for your answers. 1. 2.
N(CH3)3 OH 1. heat 95% 5% (E & Z) он 2. H2N a -...
1. You're developing a regiospecific electrophilic aromatic substitution catalyst. To determine the regioselectivity, you've performed a bromination reaction on phenol. According to the 1H-NMR, what is the product? (5 pts) -OH Br2 (1 eq) ? Electrophilic Catalyst "H NMR Spectrum 200 MHz, CDCI, solution) expansion exchanges with D20 10 9 8 7 6 5 4 3 2 1 0 8 (ppm) 2. What is the final product for the following reactions? (5 pts) 1)Br2, FeBrz, 2HSUNO
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