Nucleophile

Original post by otrivine

Which functioanl group in salicyclic acid can act as a nucleophile, give reasons?

I know its OH group and can donate 2 lone pair of electron but what othe reasons/

I would agree with you as if you remember that in Nucleophilic Substitution, OH- Is a Nucleophile which attacks haloalkanes.

Whereas the carbonyl group usually is attacked in Nucleophilic Addition.

Other than donating Lone pairs I would talk about Electronegativity difference being relatively high between Oxygen and Hydrogen which makes the Oxygen more negative and thereby it will be attracted towards a Positive area a lot more strongly.
I think, this is just me applying stuff with what I know, so I may be wrong.

Reply 2

Original post by propagation

I mean is it also correct to say that , the oxygen present makes the structure stable resulting in lower resonance energy?

Reply 3

Original post by otrivine

Which functioanl group in salicyclic acid can act as a nucleophile, give reasons?

I know its OH group and can donate 2 lone pair of electron but what othe reasons/

Oh and when the OH is detached from the Salicyclic acid it becomes OH- and so is eager to loose that extra electron.

Reply 4

Original post by propagation

Oh and when the OH is detached from the Salicyclic acid it becomes OH- and so is eager to loose that extra electron.

why?

Reply 5

Original post by otrivine

why?

Why?
Naturally the Hydroxyl group exists as OH-.
When attached it has lost that outer electron through bonding by donating one lone pair of electrons by co-ordinate bonding to get rid of that extra electron. When it is not bonded it has that extra electron and thereby 3 lone pairs. So to loose that extra electron it has to attack a positive region which is electron deficient to loose that extra electron to stabilise to it's neutral charge state.

That's what I believe.

Reply 6

Original post by otrivine

why?

Also unlike other nucleophiles the hydroxyl ion is negative not partially negative and so has a high electron density.
And so they are more likely to be more effective at donating a pair of electrons and as you will no an nucleophile is an electron pair donator.

Reply 7

Original post by propagation

is it cause the oxygen has a higher electron density which delcolised the ring and makes it more nucleophile?

Reply 8

Original post by otrivine

is it cause the oxygen has a higher electron density which delcolised the ring and makes it more nucleophile?

Now it's getting a bit more complex.

What level is this for uni or A-level?

Reply 9

Original post by propagation

Now it's getting a bit more complex.

What level is this for uni or A-level?

uni

Reply 10

Original post by propagation

Now it's getting a bit more complex.

What level is this for uni or A-level?

He's doing Pharmacy too!

Reply 11

Original post by otrivine

uni

Lol you probs don't want to listen to me I am A-level student. But if the stuff I am saying is sound I will analyse the structure and try and answer your last question for you.
Are you a chem student?

Reply 12

Original post by James A

He's doing Pharmacy too!

Ahh that is cool, you do this stuff in Pharmacy, wow that is cool ! :smile:

James what I have said, do you agree with me?

Reply 13

Original post by propagation

Ahh that is cool, you do this stuff in Pharmacy, wow that is cool ! :smile:

James what I have said, do you agree with me?

I would say so yeah, all the info you said seems right!

Reply 14

Original post by otrivine

is it cause the oxygen has a higher electron density which delcolised the ring and makes it more nucleophile?

I don't have a clue regarding that, but if I was to guess. I would say that the extra electron from the Oxygen has been played a part in the delocalised system which has made it more electron dense and thereby stabilised OH or the other way round the lone electron of Carbon has contributed to the delocalised system. Thereby when the OH leaves Benzene or Benzoic acid in this case the delocalised system is not changed, just the delocalised system becomes less electon dense but not enough to break the system.
So the Hydroxyl group is released as OH- .
The Hydroxyl group is the strongest Nucleophile as it is negativly charged overall. I don't what other things can distinguish why it's the best nucleophile.
hmmm, I am not sure??? I hope what I have said sort of makes sense or helps lead you to an answer. Also I have only learnt about arenes within the past week so I don't know if the stuff I talk about is detailed enough and most of what I have said is just me applying my basic chem knowledge.

Reply 15

Original post by James A

I would say so yeah, all the info you said seems right!

Ahh that is good :smile:

.

Do you have any idea regarding this?

Reply 16

Original post by propagation

Ahh that is good :smile:

.

Do you have any idea regarding this?

Well he said:

Which functioanl group in salicyclic acid can act as a nucleophile, give reasons?

I know its OH group and can donate 2 lone pair of electron but what othe reasons/

He answered the question himself I guess ---->..... the OH group has lone pairs on the oxygen.

There's nothing else to it, tbh.

Reply 17

Original post by James A

Well he said:

He answered the question himself I guess ---->..... the OH group has lone pairs on the oxygen.

There's nothing else to it, tbh.

I thought it has 3 lone pairs because of the negative charge??
You didn't say otherwise but he did, he said only 2.

Reply 18

Original post by propagation

I thought it has 3 lone pairs because of the negative charge??
You didn't say otherwise but he did, he said only 2.

Negative charge???????

The oxygen atom always has two lone pairs when bonded to two other atoms/groups.

By me saying lone pairs, I was referring to two lone pairs. It can't have three lone pairs.

Reply 19