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Chemistry question help please

Hi, please could I have some help on this question?
Question: state the number of peaks on the carbon 13 nmr spectrum of methylpropanedioic acid?
I thought it would be 5 because there are 5 different carbon environments?
Thanks!

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Original post
by anonymous56754
Hi, please could I have some help on this question?
Question: state the number of peaks on the carbon 13 nmr spectrum of methylpropanedioic acid?
I thought it would be 5 because there are 5 different carbon environments?
Thanks!

Methylpropanedioic acid is HOOC-CH(CH3)-COOH

That is four carbon atoms in total. Because the -COOH groups are bonded to the same CH group, they are chemically equivalent (they are also magnetically equivalent, but this is an undergrad level detail) and so the -COOH groups correspond to the same carbon environment and thus you have one -COOH signal, one -CH- signal and one -CH3 signal. That makes a total of 3.

My suspicion is that you misinterpreted the name as dimethylpropanedioic acid (e.g (CH3)2C(COOH)2) and assumed that there is a signal for each carbon. Whilst there are five carbons in this structure, the two -CH3’s are equivalent to each other (since they are both bonded to a -C(CH3)(COOH)2) and the two -COOH’s are also equivalent to each other (as they are both bonded to a -C(CH3)2COOH).

Reply 2

Original post
by TypicalNerd
Methylpropanedioic acid is HOOC-CH(CH3)-COOH
That is four carbon atoms in total. Because the -COOH groups are bonded to the same CH group, they are chemically equivalent (they are also magnetically equivalent, but this is an undergrad level detail) and so the -COOH groups correspond to the same carbon environment and thus you have one -COOH signal, one -CH- signal and one -CH3 signal. That makes a total of 3.
My suspicion is that you misinterpreted the name as dimethylpropanedioic acid (e.g (CH3)2C(COOH)2) and assumed that there is a signal for each carbon. Whilst there are five carbons in this structure, the two -CH3’s are equivalent to each other (since they are both bonded to a -C(CH3)(COOH)2) and the two -COOH’s are also equivalent to each other (as they are both bonded to a -C(CH3)2COOH).

ohhh, i understand. I think i drew it out wrong, thanks!

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