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Aromatic heterocycles also undergo electrophilic aromatic
substitution reactions. When furan is treated with an electrophile,
the...
Furan undergoes electrophilic substitution with bromine, to yield 2-bromofuran
Furan undergoes electrophilic substitution with bromine, to yield 2-bromofuran, under milder conditions that benzene (no FeBrs catalyst required). a) Is furan aromatic? Give a justification that considers its reactivity and whether it meets all criteria for aromaticity. b) Propose electrophilic aromatic substitution mechanisms for the bromination of furan at the 2-position and at the 3-position. Include sufficient electron-pushing arrows to account for all electrons involved. Include any important resonance structures. c) Draw schematic reaction coordinate diagrams (energy on the y-axis and reaction coordinate...
a) Complete the generic mechanism for an electrophilic aromatic substitution (EAS) reaction using El as the...
a) Complete the generic mechanism for an electrophilic aromatic
substitution (EAS) reaction using El as the electrophile and show
how the sigma complex is resonance stabilized. Use curved arrows to
show the mechanism and the conversion between resonance structures.
Make sure to add any missing charges. Note the use of a generic
base in the last step. b) Label the reaction coordinate diagram for
a typical EAS reaction shown below by correctly placing the letter
for each structure on the...
Predict whether toluene or chlorobenzene would undergo electrophilic aromatic substitution more quickly when treated with Cl2/AlCl3....
Predict whether toluene or chlorobenzene would undergo electrophilic aromatic substitution more quickly when treated with Cl2/AlCl3. Explain your prediction. Draw the major product for each of the two reactions.
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:...
Benzene will engage in electrophile aromatic substitution reactions. Which of the following statemtns is NOT TRUE...
Benzene will engage in electrophile aromatic substitution
reactions. Which of the following statemtns is NOT TRUE about the
mechanism for this reaction? please help I dont know what to
put!
3. Benzene will engage in electrophilic aromatic substitution reactions. Which of the following statements is not true about the mechanism for this reaction? A. Formation of a carbocation intermediate is the rate-determining step. B. The carbocation intermediate has an sp3-hybridized carbon in the ring. C. Benzene is an electrophile. D....
where would the electrophile end up if the following molecule underwent an electrophilic aromatic substitution reaction....
where would the electrophile end up if the following molecule
underwent an electrophilic aromatic substitution reaction.
QUESTION 9a: Where would the electrophile end up if the following molecule underwent an electrophilic aromatic substitution reaction? Briefly explain your reasoning
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.
4. An energy diagram for electrophilic aromatic substitution of benzene with Br2 with FeBr3 as catalyst...
4. An energy diagram for electrophilic aromatic substitution of benzene with Br2 with FeBr3 as catalyst below. The rate-limiting step is formation of the sigma complex (Step 1). Generally, any factor that stabilizes the sigma complex also stabilizes the transition-state leading to that complex. This effect leads to a lower transition-state energy and a faster reaction. rate-limiting transition state reactants + Br + FeBrz Η Br FeBr + O energy intermediate products Br + HBr + FeBr 3 -45 kJ/mol...
+ H+ Electrophilic aromatic substitution is a two-step process. In the first step an electrophile, here...
+ H+ Electrophilic aromatic substitution is a two-step process. In the first step an electrophile, here generically shown as Y , reacts with the aromatic ring to form a resonance-stabilized carbocation intermediate. In the second step, loss of a proton from the site of attack restores aromaticity to the ring and completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions no XT + H H- A
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)
a) Complete the generic mechanism for an electrophilic aromatic
substitution (EAS) reaction using El as the electrophile and show
how the sigma complex is resonance stabilized. Use curved arrows to
show the mechanism and the conversion between resonance structures.
Make sure to add any missing charges. Note the use of a generic
base in the last step. b) Label the reaction coordinate diagram for
a typical EAS reaction shown below by correctly placing the letter
for each structure on the...
Predict whether toluene or chlorobenzene would undergo electrophilic aromatic substitution more quickly when treated with Cl2/AlCl3. Explain your prediction. Draw the major product for each of the two reactions.
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:...
Benzene will engage in electrophile aromatic substitution
reactions. Which of the following statemtns is NOT TRUE about the
mechanism for this reaction? please help I dont know what to
put!
3. Benzene will engage in electrophilic aromatic substitution reactions. Which of the following statements is not true about the mechanism for this reaction? A. Formation of a carbocation intermediate is the rate-determining step. B. The carbocation intermediate has an sp3-hybridized carbon in the ring. C. Benzene is an electrophile. D....
where would the electrophile end up if the following molecule
underwent an electrophilic aromatic substitution reaction.
QUESTION 9a: Where would the electrophile end up if the following molecule underwent an electrophilic aromatic substitution reaction? Briefly explain your reasoning
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.
4. An energy diagram for electrophilic aromatic substitution of benzene with Br2 with FeBr3 as catalyst below. The rate-limiting step is formation of the sigma complex (Step 1). Generally, any factor that stabilizes the sigma complex also stabilizes the transition-state leading to that complex. This effect leads to a lower transition-state energy and a faster reaction. rate-limiting transition state reactants + Br + FeBrz Η Br FeBr + O energy intermediate products Br + HBr + FeBr 3 -45 kJ/mol...
+ H+ Electrophilic aromatic substitution is a two-step process. In the first step an electrophile, here generically shown as Y , reacts with the aromatic ring to form a resonance-stabilized carbocation intermediate. In the second step, loss of a proton from the site of attack restores aromaticity to the ring and completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions no XT + H H- A
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)
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