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Hot goIITian

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10 Jan 2007 19:22:29 IST

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Question on Nomenclature

None

Please name the compound---

HOOC--CH2-CH2--O--CH2--CH2--O--CH2--CH2--COOH ?

{ GIVE THE RULE BEHIND IT ALSO........ PLEASE}

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smriti.mathur

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12 Jan 2007 08:35:21 IST

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This is a symmetrical molecule, hence numbering can be done from any side. For convenience , it is done from the left side. The carbon atoms of -COOH groups are also numbered. There are two functional groups present, carboxylic acid group and ether group. Out of these two, the principal functional group will be carboxylic acid (from the preference table mentioned in all books having IUPAC nomenclature). So the name of this compound would be,

HOOC-CH₂ -CH₂-O-CH₂ -CH₂-O-CH₂-CH₂-COOH

1 2 3 4 5 6 7 8

3,5-diepoxy Octan-1,8 dioic acid

10904him

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12 Jan 2007 14:06:32 IST

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Actually the answer given for this question on the IUPAC site is

3,3' (oxy-bis-(ethylene oxy )) dipropanoic acid
[This is the example given in the IUPAC nomenclature document]

smriti.mathur

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13 Jan 2007 12:58:21 IST

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Dear 10904him,

How is it a propane derivative and which are the three Carbon atoms constituting the main chain? Further, the term 'bis' is used for two identical complex substituents. Here there are no substituents, there is just one single chain !!

10904him

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13 Jan 2007 15:12:42 IST

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How can the IUPAC be wrong .If you do not believe it then you can have a look at iupac.org didi.

Krishnan Ramachandran

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13 Jan 2007 16:32:32 IST

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Both the answers are correct as the complex substituents needed is ethylene oxy--group sandwiched between the two oxy-groups..this is again joined by 2 propanoic acids...the first name is based on simple chain rule name while the second is based on the isomeric form of the compound...so both r correct
The numbering in case of isomeric nomenclature will be as follows
HOOC-CH2 -CH2-O-CH2 -CH2-O-CH2-CH2-COOH
1 2 3 4 4' 3' 2' 1'
3,3' (oxy-bis-(ethylene oxy )) dipropanoic acid is the isomeric name of the compound

'',' Off to a nu start!!

Blazing goIITian

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14 Jan 2007 20:52:37 IST

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the ans. should be

4,7-dioxydec-1,10-dioic acid

Aditya Arora

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17 Jan 2007 00:50:39 IST

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i am sorry, Smriti mam, but as 8 carbons are not connected with each other { there are two oxygen atoms separating them } it annot be octane dioic acid.

'',' Off to a nu start!!

Blazing goIITian

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17 Jan 2007 15:20:26 IST

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in such type of compds. i think O atoms r also numbered

10904him

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19 Jan 2007 20:15:16 IST

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For this question two answers are given the first one I have already stated and the other answer is given such that the oxygen atoms have also been numbered

'',' Off to a nu start!!

Blazing goIITian

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20 Jan 2007 17:22:28 IST

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thats what i said

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