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We saw in this experiment that an ester group with the carbonyl carbon attached to the...
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.
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...
(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...
2. Not only does an aromatic ring itself affect the reactivity of an acid derivative (an ester, o...
2. Not only does an aromatic ring itself affect the reactivity of an acid derivative (an ester, on last year's quiz), substituents on the aromatic ring can further modify the reactivity. First, we will consider a phenyl amide with a para-acetyl substituent: CH, (a) What is the n-effect (resonance) of the para-acetyl substituent? How will that affect the reactivity of the other (amide) carbonyl in the molecule below (increase or decrease, compared to the same amide but with no p-...
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...
Objectives - Section 1 • Identify a substituent as an ortho para director or a meta director, Draw the resonance st...
Objectives - Section 1 • Identify a substituent as an ortho para director or a meta director, Draw the resonance structure that explains the relative directing ability of a specific substituent. Classify a substituent as an activating or a deactivating group. Explain why the halogens are ortho/para directors but are deactivators. • 1. Draw the mechanism of the reaction below and use resonance structures of the arenium ion intermediate to explain why the starting material is an ortho/para director
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)...
#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--...
Nitro group (-NO.) as a strong deactivator, is a me tivator is a meta-director in electrophilie...
Nitro group (-NO.) as a strong deactivator, is a me tivator is a meta-director in electrophilie substitution reactions. Why? A) Because it decreases electron density mostly on ortho and para positions, thus making meta positions better reactive sites, B) Because it deactivates ortho and para positions and activates the meta positions. c) Because all deactivators are meta-directors. D) Because its resonance effect competes against its inductive effect and the resonance effect increases the electron density on meta positions. E) All...
Add the following questions to the final report: a) Why does the carbomethoxy group directs the...
Add the following questions to the final report: a) Why does the carbomethoxy group directs the reaction to positions that are meta to it? b) Why the formation of dinitrobenzaote is substantially disfavored ? c) Would you expect small amounts of the ortho and para substituted product? How would you remove them if they are formed ? d) Why does water have a retarding effect on the nitration ? e) Explain why Benzene has lower reactivity in electrophilic addition reactions...
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...
(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...
2. Not only does an aromatic ring itself affect the reactivity of an acid derivative (an ester, on last year's quiz), substituents on the aromatic ring can further modify the reactivity. First, we will consider a phenyl amide with a para-acetyl substituent: CH, (a) What is the n-effect (resonance) of the para-acetyl substituent? How will that affect the reactivity of the other (amide) carbonyl in the molecule below (increase or decrease, compared to the same amide but with no p-...
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...
Objectives - Section 1 • Identify a substituent as an ortho para director or a meta director, Draw the resonance structure that explains the relative directing ability of a specific substituent. Classify a substituent as an activating or a deactivating group. Explain why the halogens are ortho/para directors but are deactivators. • 1. Draw the mechanism of the reaction below and use resonance structures of the arenium ion intermediate to explain why the starting material is an ortho/para director
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)...
Nitro group (-NO.) as a strong deactivator, is a me tivator is a meta-director in electrophilie substitution reactions. Why? A) Because it decreases electron density mostly on ortho and para positions, thus making meta positions better reactive sites, B) Because it deactivates ortho and para positions and activates the meta positions. c) Because all deactivators are meta-directors. D) Because its resonance effect competes against its inductive effect and the resonance effect increases the electron density on meta positions. E) All...
Add the following questions to the final report: a) Why does the carbomethoxy group directs the reaction to positions that are meta to it? b) Why the formation of dinitrobenzaote is substantially disfavored ? c) Would you expect small amounts of the ortho and para substituted product? How would you remove them if they are formed ? d) Why does water have a retarding effect on the nitration ? e) Explain why Benzene has lower reactivity in electrophilic addition reactions...
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