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What is the criteria in selecting which of the available groups adjacent to a carbocation is the most favourable to be shifted?

I have two compounds: (I'm unable to post the structures, so I have to write it here)

1) A methyl and an ethyl available for shift to a carbocation

2) A nitrobenzyl and anisole as the substituents for aryl shift.

Our teacher said that in 1)Ethyl shifts on the grounds of stability of the resultant carbocation and

In 2) anisole shifts because it has "more electron donating tendency than nitrobenzene"

The two answers seem contradictory to me. Is it correct?

user92523
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  • Carbocations are stabilised by electron donation. I fail to see any contradiction in the two statements – Waylander Apr 21 '20 at 09:32
  • The first reason was stability of the resulting carbocation and the second, the stability of the carbocation before the shift – user92523 Apr 21 '20 at 09:34
  • https://chemistry.stackexchange.com/questions/31599/migratory-preference-in-a-rearrangement-involving-carbocations – Mithoron Apr 21 '20 at 15:05

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