1) HNO3, H₂SO4 2) EtCI, AICI3 NO₂ Et dentify the flaw(s) in the synthesis. Select all that apply. There is too much steric hindrance for the first reaction to take place at the desired position. ☐ The first reaction does not give the desired product because a carbocation rearrangement occurs. ✔ There is too much steric hindrance for the second reaction to take place at the desired position. The group added first is an ortho/para director, but a meta director is needed. The second reaction fails because the ring is too deactivated. The second reaction does not give the desired product because a carbocation rearrangement occurs. ✔ The group added first is a meta director, but an ortho/para director is needed.
1) HNO3, H₂SO4 2) EtCI, AICI3 NO₂ Et dentify the flaw(s) in the synthesis. Select all that apply. There is too much steric hindrance for the first reaction to take place at the desired position. ☐ The first reaction does not give the desired product because a carbocation rearrangement occurs. ✔ There is too much steric hindrance for the second reaction to take place at the desired position. The group added first is an ortho/para director, but a meta director is needed. The second reaction fails because the ring is too deactivated. The second reaction does not give the desired product because a carbocation rearrangement occurs. ✔ The group added first is a meta director, but an ortho/para director is needed.
Chapter4: On Solving Mechanism Problems
Section: Chapter Questions
Problem 3EQ
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Question
Identify the flaws in the given synthesis.
Transcribed Image Text:1) HNO3, H₂SO4.
2) EtCI, AICI3
NO₂
Et
Identify the flaw(s) in the synthesis. Select all that apply.
There is too much steric hindrance for the first reaction to take place at the desired position.
The first reaction does not give the desired product because a carbocation rearrangement occurs.
There is too much steric hindrance for the second reaction to take place at the desired position.
The group added first is an ortho/para director, but a meta director is needed.
The second reaction fails because the ring is too deactivated.
The second reaction does not give the desired product because a carbocation rearrangement occurs.
The group added first is a meta director, but an ortho/para director is needed.
Transcribed Image Text:1) Br₂, FeBr3
០០
2)
AICI
Br
Identify the flaw(s) in the synthesis. Select all that apply.
The second reaction fails because the ring is too deactivated.
The first reaction does not give the desired product because a carbocation rearrangement occurs.
The group added first is a meta director, but an ortho/para director is needed.
There is too much steric hindrance for the first reaction to take place at the desired position.
The second reaction does not give the desired product because a carbocation rearrangement occurs.
There is too much steric hindrance for the second reaction to take place at the desired position.
The group added first is an ortho/para director, but a meta director is needed.
Expert Solution
Step 1
The electron withdrawing groups at benzene ring deactivates the ring and are meta directing. But in case of nitrobenzene it is too much deactivated to give a further electrophilic reaction.
The electron donating groups at benzene activates the benzene ring and ortho and para directing.
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