A few questions on esters

It reacts in the same way - it forms an ester, the difference is that a hydrogen is replaced by an alkyl group.

Here is the answer to the first one:

Have a go at the second one :smile:

Reply 2

AutVinceriAutMori

13

ukmd

Hi. I know that when CH3CH2OH + CH3COOH react , this produces (with a H+ catalyst) CH3COOCH2CH3 + H2O.

However, what happens when the hydroxy (OH) group is on the 2nd carbon, so, for example. Help me with these two (ie complete the equations and explain please!)

1) PROPAN-2-OL + ETHANOIC ACID
CH3CH(OH)CH3 + CH3COOH ->(this is supposed to be an equilibrium sign)

2) BUTAN-2-OL + ETHANOIC ACID
CH3CH2CH(OH)CH3 + CH3COOH ->(again, this is supposed to be an equilibrium sign)

Please complete the above 2 equations, and explain your answers, name the products as well if you have time (although I could do that easily, so maybe not)

Both would react to form esters, but at the different sites, obviously:
1) CH3CH(COOCCH3)CH3
and
2)CH3CH2CH(COOCCH3)CH3

Reply 3

OP

EierVonSatan

It reacts in the same way - it forms an ester, the difference is that a hydrogen is replaced by an alkyl group.

Here is the answer to the first one:

Have a go at the second one :smile:

And how do I name that lol? Thought it would be much simpler.... however, I cannot. How would I write that in "structural forumla" ?

Reply 4

ukmd

And how do I name that lol? Thought it would be much simpler.... however, I cannot.

Esters are named in the form 'alkyl carboxylate' so 2-propyl ethanoate for this one :smile:

How would I write that in "structural formula"?

(CH₃)₂CHOOCCH₃

Reply 5

OP

So the answers to my questions are :
1) PROPAN-2-OL + ETHANOIC ACID
CH3CH(OH)CH3 + CH3COOH ->(this is supposed to be an equilibrium sign) CH3CH(COOCCH3)CH3 + H2O ?

2) BUTAN-2-OL + ETHANOIC ACID
CH3CH2CH(OH)CH3 + CH3COOH ->(again, this is supposed to be an equilibrium sign) CH3CH2CH(COOCCH3)CH3 + H2O ?

That isn't the correct structural forumal for the products is it?

Reply 6

OP

EierVonSatan

Esters are named in the form 'alkyl carboxylate' so 2-propyl ethanoate for this one :smile:

(CH₃)₂CHOOCCH₃

That structural formula doers not match up with the name given does it??????????

Reply 7

AutVinceriAutMori

13

ukmd

So the answers to my questions are :
1) PROPAN-2-OL + ETHANOIC ACID
CH3CH(OH)CH3 + CH3COOH ->(this is supposed to be an equilibrium sign) CH3CH(COOCCH3)CH3 + H2O ?

2) BUTAN-2-OL + ETHANOIC ACID
CH3CH2CH(OH)CH3 + CH3COOH ->(again, this is supposed to be an equilibrium sign) CH3CH2CH(COOCCH3)CH3 + H2O ?

That isn't the correct structural forumal for the products is it?

Yes. All you is replacing hydroxy group with ester group

Reply 8

OP

AutVinceriAutMori

Yes. All you is replacing hydroxy group with ester group

Hi, you and the other helper are both giving me different answers, which is correct lol? :confused:

Reply 9

AutVinceriAutMori

13

ukmd

Hi, you and the other helper are both giving me different answers, which is correct lol? :confused:

Erm, ignore my orignal post on the name (I deleted it anyway), EvS knows better. Sorry for confusing

Reply 10

ukmd

That structural formula doers not match up with the name given does it??????????

It does

Would it be easier to see if I wrote it the 'other way round'?

CH₃COOCH(CH₃)₂

Reply 11

shengoc

12

ukmd

Hi, you and the other helper are both giving me different answers, which is correct lol? :confused:

can you not figure out? or have you not learnt anything from this learning process and are merely seeking for an answer?

Reply 12

OP

Does the other one (BUTAN-2-OL + ETHANOIC ACID) give the product CH3COOC(CH3)3 ? Or is that not correct?

Reply 13

OP

shengoc

can you not figure out? or have you not learnt anything from this learning process and are merely seeking for an answer?

That is why I came on here... 95% of the work I am fine with that I get given, any misconceptions I have or anything I am "struggling" with I come on TSR with. Sorry, but I don't go to Oxford.

Reply 14

shengoc

12

ukmd

That is why I came on here... 95% of the work I am fine with that I get given, any misconceptions I have or anything I am "struggling" with I come on TSR with. Sorry, but I don't go to Oxford.

chill, dude! my comment wasn't meant to offend, it was merely so that when pushed a little bit, you can figure out what you should do next with these hints; it should be the way of learning instead of being "spoon-fed" which very often happens in school.

ukmd

Does the other one (BUTAN-2-OL + ETHANOIC ACID) give the product CH3COOC(CH3)3 ? Or is that not correct?

Again you should draw out the structure, then it is the H from alcohol group that goes off and the OH from acid group that comes off, the remaining COO forms the ester bond.

Your structural formula gives the correct isomer, but doesn't really indicate the ester being formed at the 2 position of the original butan-2-ol.

Reply 15

ukmd

Does the other one (BUTAN-2-OL + ETHANOIC ACID) give the product CH3COOC(CH3)3 ? Or is that not correct?

Nope. Try drawing out the product you get from the reaction and then convert the drawing to the structural formula

That is the product between 2-methylpropan-2-ol and ethanoic acid.

Reply 16

OP

EierVonSatan

It does

Would it be easier to see if I wrote it the 'other way round'?

CH₃COOCH(CH₃)₂

I still don't know how you have named the above 2-propyl ethanoate ?

Reply 17

ukmd

I still don't know how you have named the above 2-propyl ethanoate ?

Right, can you name CH₃COOCH₂CH₃ ? :smile:

It's very similar to that :yep:

Reply 18

OP

EierVonSatan

Right, can you name CH₃COOCH₂CH₃ ? :smile:

It's very similar to that :yep:

ethyl ethanoate

Reply 19