In the previous post, we talked about the nucleophilic aromatic substitution, looking at the specifics of the mechanism, regiochemistry, and the limitations.
Below are some additional examples to practice these concepts.
Nucleophilic Aromatic Substitution Practice Problems
Practice
1.
a)
Determine the product in each nucleophilic aromatic substitution reaction.
Answer
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Answer
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Answer
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Answer
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Answer
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Answer
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Answer
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Answer
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Answer
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2.
Suggest a synthesis of acetaminophen, also known as Tylenol, from benzene:
Answer
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3.
a)
Draw a possible mechanism for each synthetic transformation:
Answer
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Answer
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Answer
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4.
Identify the missing products and reagents in the following synthetic scheme which includes electrophilic aromatic substitution, nucleophilic aromatic substitution, epoxides, and Diels-Alder reaction:
Answer
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5.
a)
When the following phenoxide is reacted with 4-Nitrochlorobenzene, the expected product A of nucleophilic aromatic substitution is not formed. Instead, an isomer of compound A is formed. Identify the structures of both A and B and explain why only B is formed:
Answer
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Answer
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Solution
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6.
Draw the mechanism and identify the missing compounds in the following synthetic scheme:
Answer
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7.
Explain the formation of two isomers in the following SNAr by drawing the corresponding mechanisms:
Answer
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8.
Draw a plausible mechanism for the following 3 + 2 (3 atoms + 2 atoms) cycloaddition (recall the Diels-Alder reaction) reaction that goes via in situ benzyne formation.
Hint: recall that fluoride has a high affinity for silicon
Answer
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9.
Check Also
- Electrophilic Aromatic Substitution – The Mechanism
- The Halogenation of Benzene
- The Nitration of Benzene
- The Sulfonation of Benzene
- Activating and Deactivating Groups
- Friedel-Crafts Alkylation with Practice Problems
- Friedel-Crafts Acylation with Practice Problems
- Vilsmeier-Haack Reaction
- The Alkylation of Benzene by Acylation-Reduction
- Ortho, Para, Meta in EAS with Practice Problems
- Ortho, Para, and Meta in Disubstituted Benzenes
- Why Are Halogens Ortho-, Para- Directors yet Deactivators?
- Is Phenyl an Ortho/Para or Meta Director?
- Limitations of Electrophilic Aromatic Substitution Reactions
- Orientation in Benzene Rings With More Than One Substituent
- Synthesis of Aromatic Compounds From Benzene
- Arenediazonium Salts in Electrophilic Aromatic Substitution
- Reactions at the Benzylic Position
- Benzylic Bromination
- Nucleophilic Aromatic Substitution
- Reactions of Phenols
- Reactions of Aniline
- Meta Substitution on Activated Aromatic Ring
- Electrophilic Aromatic Substitution Practice Problems
- Aromatic Compounds Quiz
- Reactions Map of Aromatic Compounds
It’s really nice. Very helpful
Thanks a lot
For number 1e, how do we get an ethoxide and not an alcohol?
A typo – thanks for pointing that out.
Comparing benzyne formation in Q3b and Q4. The substrate is same but the benzyne and the final products are very different. Please explain. Thanks
That is a good question. The key here is the regiochemistry of the benzyne (aryne, more generally) formation. When the EWG and the halogen are meta-oriented, there are two possibilities for where the triple bond can form. And it turns out that the hydrogen ortho to the EWG is more acidic and is removed by the base. This is due to the stabilizing effect of the EWG:
You can also read about this in March’s Advanced Organic Chemistry, 7th ed., p. 778.
With that said, the major regioisomer in 3B should be like it is in 4.