JEE Chemistry Club

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satan 29

05:51

@Safdar @YusufHasan can you explain this?

Jayadithya

06:07

Safdar

06:31

@satan29 position given has least steric hinderance. most -ve carbon is either side of cyclopentane ring more steric hinderance on other side,

satan 29

@Safdar why not ortho to c(me)3?

Safdar

@satan29 Steric Hindrance is super high..

it is a t-butyl group after all..

satan 29

oh haan t-butyl hai

the bracket fooled me

by the way

c(me)3 will not show HC

and what about Inductive effect?

Safdar

@satan29 also true.. so that is why ortho would be on either cyclo ring..

@satan29 Steric is more big of an issue that the tiny -I it gives

satan 29

yes, gotcha

thanks!

8 hours later…

satan 29

14:31

hi all

kya haal

1 hour later…

Guru Vishnu

15:51

Hi everyone!

Here, why did the author refuse to do a carbocation rearrangement for the intermediate shown separately in the bottom?

For me, it seems the tertiary carbocation must be more stable than the vinylic carbocation due to electronegativity and resonance reasons.

It would be helpful if someone can confirm the book is wrong. Thanks!

user434058

16:16

@GuruVishnu Such rearrangements do happen (it has been experimentally verified), however, in all the questions that I have encountered in practice books for JEE, this rearrangement has always been ignored. So, there's a general consensus among JEE aspirants to not do such a rearrangement.

Guru Vishnu

@FakeMod Ok. Thank you for the clarification :-)

I think, as you said, this might be JEE specific as I was unable to find this example in the international version of Solomons.