Question

Hi, can anyone help me out with alcohol and acidity?

Answer 1

@Kainui

Answer 2

I know that the less alkyl groups you have, the more acidic the alcohol is

Answer 3

That's true, can you explain why more alkyl groups make it less acidic?

Answer 4

and if we add halogens it will be a better acid

Answer 5

I believe it connects with the inductive effect and electronegativity

Answer 6

it gets harder to deprotonate

Answer 7

so alcohol with halogen will become more acidic, the better EN of the halogen is

Answer 8

Yeah, exactly, so which ones are you sort of unsure about here, it sounds like you know how to do this haha

Answer 9

I'm so indecisive about it

Answer 10

tbh

Answer 11

I think no.5 is the most acidic compound here, and no.2 is the less

Answer 12

between those I'm quite confused

Answer 13

I mean, what's the difference between 3 and 2?

Answer 14

they both have cl

Answer 15

Well there's a difference in their connectivity right?

Answer 16

oh, then if it's further than it's a better acid

Answer 17

right?

Answer 18

Well if it's further away then its affect on the acidity of the alcohol will be less, right?

Answer 19

right, then it will be more acidic

Answer 20

Yeah sorry I read what you wrote as backwards haha

Answer 21

oh lol

Answer 22

so the more EN the halogen is, the more acidic it is

Answer 23

right?

Answer 24

5>4>1>3>2?

Answer 25

does it make any sense?

Answer 26

Wait, I think I might be in a state of confusion let me straighten this out haha

Answer 27

hahah ok

Answer 28

When you remove the hydrogen from the alcohol you will be leaving a negative charge behind, correct? So the closer and more electronegative group to that alcohol will be more acidic. So you said 5 is the most acidic molecule there, but it doesn't have any halogens on it!

Answer 29

oh right!

Answer 30

so I would go for 2>3>4>1>5?

Answer 31

now that you made this all clear

Answer 32

the closesr and more EN the halogen is the more acidic it is

Answer 33

closer

Answer 34

Yeah since it will better absorb that extra negative charge left behind when you remove a hydrogen, making it a more stable product by comparison to the others. The only thing I am sort of doubting about is that #2 hypochlorous acid. I think that might be right, I just feel like it's so small that it's sort of hard to say haha

Answer 35

I know right?!

Answer 36

wow you really made my day start on a high note!

Answer 37

Thanks allot!

Answer 38

Haha glad I could help =)

Answer 39

Is it possible to give you medals? you deserve them way than I am