Aromaticity and orgoman ch12Q22

[babowc]

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Do I have the triple bond with 2 too many pi electrons?
I thought the triple bond had 2 sets of pi bonds? = 4 pi electrons?

 

[babowc]

For this Q, shouldn't the ch2ch2ch3 attach onto the benzene and the Br attach on the benzylic position? I thought the answer would be B, but the solutions says C.
I went back to my ochem2 notes, and sure enough... I have what would agree with B.



Nevermind, found my own answer... the Friedel craft alkylation makes the major product through hydride shift...

 

[KyoPhan]

Do I have the triple bond with 2 too many pi electrons?
I thought the triple bond had 2 sets of pi bonds? = 4 pi electrons?

There are 2 pi bonds in that triple bond; however, you only count one of them because only 1 of them is in the same plane as the others.

 

[cmF]

For this Q, shouldn't the ch2ch2ch3 attach onto the benzene and the Br attach on the benzylic position? I thought the answer would be B, but the solutions says C.
I went back to my ochem2 notes, and sure enough... I have what would agree with B.

View attachment 23591

Nevermind, found my own answer... the Friedel craft alkylation makes the major product through hydride shift...

yikes, that's a tricky one! Another example of where orgoman could be a little bit more in depth in his solutions 😡

 

[babowc]

yikes, that's a tricky one! Another example of where orgoman could be a little bit more in depth in his solutions 😡

I believe hydride shift was covered in previous chapters. It starts to lack explanation toward the end of the book.. I'm on ch13 now, and there are hardly any explanations, haha