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Topic: Help anyone? -->ISOMERS of CH3COOH (ACETIC ACID)  (Read 28765 times)

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Offline jogger4life

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Help anyone? -->ISOMERS of CH3COOH (ACETIC ACID)
« on: November 27, 2007, 05:48:53 PM »
Okay..so I'm working on this problem and it's not too difficult. I'm just not sure how many isomers there are for acetic acid. So far I have three. Does anyone know how many there are total?

The orders I have so far are: HHCCHOOH, OCHCHHOH, CH3COOH..

Thanks in advance for any help...

Offline ARGOS++

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Re: Help anyone? -->ISOMERS of CH3COOH (ACETIC ACID)
« Reply #1 on: November 27, 2007, 06:14:44 PM »
Dear Jogger4life;

Probably not all (I did no proof!), but a few as a Hint on:
(Use the search option: Formula.)

Good Luck!
                   ARGOS++

P.S.:    There are other links you may search on the left, top boarder of this page. 


Offline Borek

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Re: Help anyone? -->ISOMERS of CH3COOH (ACETIC ACID)
« Reply #2 on: November 27, 2007, 06:49:58 PM »
To be honest with you I have no idea how to read your formulas. Use SMILES or something :(
ChemBuddy chemical calculators - stoichiometry, pH, concentration, buffer preparation, titrations.info

Offline jogger4life

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Re: Help anyone? -->ISOMERS of CH3COOH (ACETIC ACID)
« Reply #3 on: November 27, 2007, 07:04:01 PM »
Thanks for the site ARGOS++. okay so far I have..the following below..if there is a H above or below a C/O (etc) assume there is a bond there. I didn't show single/dbl bonds..I'm really just interested in the order.

       H
H-O-C-C-O
       H H
________________

          H
H-C-O-C-H
   O     H
______________
   H
H-C-C-O-H
   H O
______________
H
O-C-C-O
    H H H

_____________

can anyone else think of an isomer for Acetic acid besides these ones?
I'm not interested in any rings..we haven't covered that much yet in class. I'm just looking for the maximum amount of lewis dot structures. I'm still working though..determined to find all of them!! ;D
Thank you for any help :)

Offline AWK

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Re: Help anyone? -->ISOMERS of CH3COOH (ACETIC ACID)
« Reply #4 on: November 28, 2007, 01:25:35 AM »
Formula 4 is an unstable (tautomeric) form of 1 and usually is not treated as  the isomer

One double bond is an equivalent of one ring, In your case only one oxirane (cyclic C2O skeleton) is theoretically possible
AWK

Offline sjb

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Re: Help anyone? -->ISOMERS of CH3COOH (ACETIC ACID)
« Reply #5 on: November 28, 2007, 04:24:31 AM »
Do you mean stable isomers, or just isomers you can draw on paper?

1) Acetic Acid
2) Methyl formate
3) 2-oxoethanol (or is it 2-hydroxyacetaldeyde?)
4) 1,1-dihydroxyethylene
5) E-1,2-dihydroxyethylene
6) Z-1,2-dihydroxyethylene
7) ethylene peroxide? H2C=CHOOH

And with rings

7+1) (2R)-2-hydroxyoxirane (silly code converts the correct number into a smiley)
9) (2S)-2-hydroxyoxirane
10) 1,2-dioxetane
11) 1,3-dioxetane

Of course some of these are more stable than others...

Offline AWK

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Re: Help anyone? -->ISOMERS of CH3COOH (ACETIC ACID)
« Reply #6 on: November 28, 2007, 04:56:34 AM »
3) 2-oxoethanal
Quote
5) E-1,2-dihydroxyethylene
6) Z-1,2-dihydroxyethylene
tautomers of 3 (unstable - an equilibrium greatly prefers 3)
Quote
4) 1,1-dihydroxyethylene
tautomer of 1 - equilibrium prefers 1
7 and 10 extremely chemically unstable
but from formal point ovf view OK
AWK

Offline sjb

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Re: Help anyone? -->ISOMERS of CH3COOH (ACETIC ACID)
« Reply #7 on: November 28, 2007, 05:19:42 AM »
3) 2-oxoethanal
Quote
5) E-1,2-dihydroxyethylene
6) Z-1,2-dihydroxyethylene
tautomers of 3 (unstable - an equilibrium greatly prefers 3)
Quote
4) 1,1-dihydroxyethylene
tautomer of 1 - equilibrium prefers 1
7 and 10 extremely chemically unstable
but from formal point ovf view OK

OK, no problem, I did stress paper isomers, and I'm reasonably sure derivatives of these do exist, if not the free species.

Are you sure about 3 being 2-oxoethanal? I thought oxo in effect meant the C=O group, so to me this name is an alternative for glyoxal (I see I've missed an 'haitch' in aldehyde though :) ).

S

Offline AWK

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Re: Help anyone? -->ISOMERS of CH3COOH (ACETIC ACID)
« Reply #8 on: November 28, 2007, 05:23:08 AM »
2-hydroxyetanal
AWK

Offline jogger4life

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Re: Help anyone? -->ISOMERS of CH3COOH (ACETIC ACID)
« Reply #9 on: November 28, 2007, 09:27:01 PM »
wow thanks for all the help everyone..I'm turning in the paper tomorrow so I'm not in need of any more help. :)

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