Doubt from Alcohols and Ethers

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Q.67 - I am getting (C), but answer is (B). I thought like as the electron donating power of the lower oxygen is more than the upper one (the upper one has resonance so charge will be delocalized) the lower oxygen will attack the alkyl halide.

Q.68 - I am getting (C), but answer is given as (D).

See in question one Na2CO3 will take acidic Hydrogen that is from benzene hydroxyl. Then it will attack on R-X.

Thanks, I understood.
Can you help me with the second question ?

Yeah off course I am doing.

See it will attack on one degree carbon atom because dil KOH will undergo SN2 mechanisms.

I didn't understand, can you please write the mechanism ?

See br2/ccl4 will undergo anti addition reaction after that oh(-) will attack one degrees bromine.
I will upload mechanism within a minute.

image

But shouldn't intra-molecular cyclisation occur before the attack of KOH?

Then it will come to original compound.

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I meant like this, we wouldn't get the original compound.

I think Then it will not undergo next reaction.

Yeah even I think that. So is the answer (D)?

If it were multi correct then would we have (C) as also the answer ?

No it can’t be the answer for in multiple choice B if it is asked A and B both then I can be the answer.

I didn't get you.

It cannot be the answer in multiple choice questions because reaction is going further. But if it is asked both products A and B. Then it can be the answer (that is your product).

Oho, thanks !

But bhaiya can you tell me what type of reaction is the displacement of the -OH group from KOH by the -OH already present ?

I haven't seen any reaction as such till now and if I am not wrong -OH is a poor leaving group so that's why I am asking.

There is no reaction in OH group is being displaced by OH group.

But -OH is a poor leaving group right ? Then how can it be removed ?

From where it has removed.i think in the question we are not removing OH from KOH.
It can remove with the help of NGP REACTION.