Methoxy benzene (anisole) reacts with a mixture of FeBr3 and Br2 and the major products obtained...
Methoxy benzene (anisole) reacts with a mixture of FeBr3 and Br2 and the major products obtained are ortho- and para-substituted. Draw the 3 major and minor products of the reaction and use resonance structures of the carbocation intermediate to explain why ortho and para substitution occur in preference to the meta-substitution.
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Methoxy benzene (anisole) reacts with a mixture of FeBr3 and Br2
and the major products obtained...
We saw in this experiment that an ester group with the carbonyl carbon attached to the...
We saw in this experiment that an ester group with the carbonyl carbon attached to the benzene ring serves as a meta-director, resulting in methyl Meta-nitrobenzoate as the major product of the reaction. Given that a methoxy (-OCH_3) group attached to the benzene ring serves as an orthopara director, draw the major products of the reaction shown below. Use your pre-lab lecture notes to answer this question. Explain using the resonance structures (referred to as the "sigma complex") why the...
When there is an electron-withdrawing group on a benzene ring (eg. compounds such as nitrobenzenebenzoic acid,...
When there is an electron-withdrawing group on a benzene ring (eg. compounds such as nitrobenzenebenzoic acid, acetophenone, etc, resonance structures can be drawn that indicate the positions on the benzene ring that are least nucleophilic (because they have a positive charge on the carbon at that position). Because these positions are much less nucleophilic, the substitution reaction will not occur here; instead, substitution will occur at the other position(s) on the ring. As a result, which position(s) are most nucleophilic...
(V) 10pts. When aniline (C6H3-NH2) reacts with bromonium ion (NO2. the nitro group can become bonded...
(V) 10pts. When aniline (C6H3-NH2) reacts with bromonium ion (NO2. the nitro group can become bonded to a carbon at one of the three possible positions: ortho, meta, and para to the -NH2 group in the benzene ring. Consider meta and ortho attack and draw RESONANCE STRUCTURES for the carbocations that result when NO2 undergoes electrophilic aromatic substitution to aniline. Then, on the basis of these resonance structures, explain whether the --NH2, group.is meta director, or ortho/para director. Show which...
#1. Using curved arrows to symbolize electrons, write a complete reaction mechanism for the bromination of...
#1. Using curved arrows to symbolize electrons, write a complete reaction mechanism for the bromination of acetanilide to create the product. Include the resonance structures for any charged, delocalized intermediates that are involved. #2. Why does performing the experiment at 0 degrees Celsius help you identify some of the relative rates of reactivity? #3. Explain why a methyl group is a mildly activating group while a methoxy group is strong activating. #4. Explain why-- NH2 act as an activator and--...
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...
Question 3 1s 3 ORTHO Today we learned about adding a second group to a mono-substituted...
Question 3
1s 3 ORTHO Today we learned about adding a second group to a mono-substituted benzene ring. Any group on a benzene will affect the rate of the reaction (activated or deactivated relative to benzene) and the regioselectivity Where does the electrophile add? Ortho? Meta? Para? Some combination thereof? We found that EDGs (electron-donating groups) direct the electrophile to the ortho and para positions while EWGs (electron-withdrawing groups) direct the electrophile to the meta position. Now, it is time...
Please answer questions completely and clearly. Will leave a LIKE when done so. Thank you. 2....
Please answer questions completely and clearly. Will leave a
LIKE when done so. Thank you.
2. Compound A undergoes electrophilic aromatic substitution. a. A reacts with E' at the ortho and meta positions. Draw the other resonance structures of the ortho and meta intermediates Et+ b. Is Compound A an ortho, para director or meta director? Give reasons c. You used salicylic acid in a nitration reaction in Lab 4c. Describe a synthesis of salicylic acid from phenol. State the...
5. When benzamide (the reactant shown) is treated with the acylium cation electrophile shown (generated by...
5. When benzamide (the reactant shown) is treated with the acylium cation electrophile shown (generated by combining concentrated acetyl chloride and aluminum trichloride), the first step of the reaction involves the benzene ring attacking the carbocation to form a sigma complex intermediate. (This curved arrows have been included in the reaction below.) Draw the sigma complex intermediate (including all resonance structures) resulting from meta attack (acyl group adds to meta carbon) and para attack (acyl group adds to para carbon)...
Draw the major 1.2- and 1,4-addition products obtained in the reaction shown. Assume that both are...
Draw the major 1.2- and 1,4-addition products obtained in the reaction shown. Assume that both are derived from the most stable carbocation intermediate + HBr • You do not have to consider stereochemistry • You do not have to explicitly draw Hatoms • If the 1,2- and 1,4- addition products are the same due to symmetry, only draw one structure. • Draw one structure per sketcher. Add additional sketchers using the drop down menu in the bottom right corner •...
2. Examine the following Electrophilic Aromatic Substitution reaction. 1) Provide the number of 13C NMR signals...
2. Examine the following Electrophilic Aromatic Substitution reaction. 1) Provide the number of 13C NMR signals expected in both the reactant and the product. 2) Provide the carbocation intermediate that allowed the transformation to happen at that position. 3) This molecule is (ortho, meta, para) substituted (circle one). 4) Using resonance arrows show how that carbocation can be distributed (delocalized) to multiple locations on the arene ring system. 5) Predict a different structure that can form from this delocalization. FeBrg,...
We saw in this experiment that an ester group with the carbonyl carbon attached to the benzene ring serves as a meta-director, resulting in methyl Meta-nitrobenzoate as the major product of the reaction. Given that a methoxy (-OCH_3) group attached to the benzene ring serves as an orthopara director, draw the major products of the reaction shown below. Use your pre-lab lecture notes to answer this question. Explain using the resonance structures (referred to as the "sigma complex") why the...
When there is an electron-withdrawing group on a benzene ring (eg. compounds such as nitrobenzenebenzoic acid, acetophenone, etc, resonance structures can be drawn that indicate the positions on the benzene ring that are least nucleophilic (because they have a positive charge on the carbon at that position). Because these positions are much less nucleophilic, the substitution reaction will not occur here; instead, substitution will occur at the other position(s) on the ring. As a result, which position(s) are most nucleophilic...
(V) 10pts. When aniline (C6H3-NH2) reacts with bromonium ion (NO2. the nitro group can become bonded to a carbon at one of the three possible positions: ortho, meta, and para to the -NH2 group in the benzene ring. Consider meta and ortho attack and draw RESONANCE STRUCTURES for the carbocations that result when NO2 undergoes electrophilic aromatic substitution to aniline. Then, on the basis of these resonance structures, explain whether the --NH2, group.is meta director, or ortho/para director. Show which...
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...
Question 3
1s 3 ORTHO Today we learned about adding a second group to a mono-substituted benzene ring. Any group on a benzene will affect the rate of the reaction (activated or deactivated relative to benzene) and the regioselectivity Where does the electrophile add? Ortho? Meta? Para? Some combination thereof? We found that EDGs (electron-donating groups) direct the electrophile to the ortho and para positions while EWGs (electron-withdrawing groups) direct the electrophile to the meta position. Now, it is time...
Please answer questions completely and clearly. Will leave a
LIKE when done so. Thank you.
2. Compound A undergoes electrophilic aromatic substitution. a. A reacts with E' at the ortho and meta positions. Draw the other resonance structures of the ortho and meta intermediates Et+ b. Is Compound A an ortho, para director or meta director? Give reasons c. You used salicylic acid in a nitration reaction in Lab 4c. Describe a synthesis of salicylic acid from phenol. State the...
5. When benzamide (the reactant shown) is treated with the acylium cation electrophile shown (generated by combining concentrated acetyl chloride and aluminum trichloride), the first step of the reaction involves the benzene ring attacking the carbocation to form a sigma complex intermediate. (This curved arrows have been included in the reaction below.) Draw the sigma complex intermediate (including all resonance structures) resulting from meta attack (acyl group adds to meta carbon) and para attack (acyl group adds to para carbon)...
Draw the major 1.2- and 1,4-addition products obtained in the reaction shown. Assume that both are derived from the most stable carbocation intermediate + HBr • You do not have to consider stereochemistry • You do not have to explicitly draw Hatoms • If the 1,2- and 1,4- addition products are the same due to symmetry, only draw one structure. • Draw one structure per sketcher. Add additional sketchers using the drop down menu in the bottom right corner •...
2. Examine the following Electrophilic Aromatic Substitution reaction. 1) Provide the number of 13C NMR signals expected in both the reactant and the product. 2) Provide the carbocation intermediate that allowed the transformation to happen at that position. 3) This molecule is (ortho, meta, para) substituted (circle one). 4) Using resonance arrows show how that carbocation can be distributed (delocalized) to multiple locations on the arene ring system. 5) Predict a different structure that can form from this delocalization. FeBrg,...
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