Doubt from general organic chemistry


Why is a non planar ???
If it can rotate about single bond then why can't b rotate about single bond ??
@arush_kumar_singh
@Arush_Sharma
@Viraam_Rao

Because when B rotates about the single bond, that becomes the plane itself as the rest is linear

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in all possible conformations

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should I elaborate? @arush_kumar_singh
In B, All atoms of the rightmost C are in a single plane
And the rest is also in that plane as itvis linear and can only rotate

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But won't resonance restrict rotation in A ?

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Umm, I don't think so, to a very less extent maybe. If you're talking about this resonating structure,

we can see the second one is very unstable compared to first one, so its contribution to the hybrid will be negligible. That's what I think.

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Conformation means only rotation ..
Not resonsnce hybrids

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Yeah I agree that it is less stable than the first one but still it will contribute to the increased bond order right ?
So the bond order will increase to something less than 1.5 correct ?
@Shantanu_Thakur
Correct me if I am wrong

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Yes, that's what I think but I'm not very sure about that, moreover these kind of questions really don't want you to consider minor resonating structures. Just check the bond rotation in the structures they've given :slight_smile:

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Which of the following react with NaHCO_3
A- o-Nitrophenol
B- p-Nitrophenol
C- m-Nitrophenol
@Viraam_Rao

@arush_kumar_singh
B?

It is multiple ..
I just wanted to confirm as I cannot find any good source on net ..
Btw I know that o,p- dinitrophenol reacts but idk about mono substitute phenols

@arush_kumar_singh
Ohh I didnt know ortho reacts cuz theirs initially intra H bond.

Means
O and P reacts ??

@arush_kumar_singh
I thought only p reacts. Not sure about o.

@Supreeta_Sen
Plzz confirm #10

If you take only acidic character into account then it should be both o and p. But @Viraam_Rao is right about H bonding in ortho. Don’t know for sure. Will check.

@Supreeta_Sen

Please explain option B. Isnt it inductive ?

@arush_kumar_singh @Shantanu_Thakur @Chirag_Hegde

See 12 ncert part 2 page 390
@Viraam_Rao

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@arush_kumar_singh
Ohhh thanks.