Electrophilic/Nucleophilic aromatic substitutions

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The discussion centers on the challenges faced in understanding electrophilic and nucleophilic aromatic substitution reactions. The user initially believed their reasoning for selecting substituents was sound, identifying -OH and NH2 as favorable for electrophilic substitution, but struggled with a specific problem involving an alkyl group. They questioned why their choice of the third option in that problem was incorrect, indicating a misunderstanding of the principles at play. Additionally, they expressed difficulty with a second question related to nucleophilic substitution. Clarification on these concepts is sought to improve their understanding and performance.
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Hello,

I thought I understood how to answer the questions (posted below, please follow the links) but apparently my reasoning is flawed.
Any help is appreciated!

http://www.darkpoetry.com/dp/19/102049
Here is how I answered this question: I looked at all the substituents, and decided whether they were conducive to an electrophilic aromatic subst. reaction. For example, NO2 is really not appropriate, while NH2 is etc. Following this, I found that -OH was a very good choice, and MeO was not bad either and so I picked this molecule. It turned out to be correct.
I did the same for the 2nd question, but inverting the principles since it is a nucleophilic substitution. I correctly chose the last choice.

However, this reasoning did not work for this problem:
http://www.darkpoetry.com/dp/19/102050
I thought in the 1st question, the 3rd choice would be more appropriate because of the alkyl group. Why isn't this correct?
I didn't get the 2nd question right either.

Thanks for your help!
 
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