OCHEM: alpha and beta

[joonkimdds]

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Destroyer 15 says COOH from COOH-C-C=O is beta keto.

destroyer 42 says O=C-C-OH is alpha hydroxy ketone

I think we don't count the carbonyl carbon and the carbon attached to the carbonyl carbon is alpha and then beta.

Shouldn't the first one be called alpha keto since COOH is attached to the alpha carbon of carbonyl carbon?

 

[Shinpe]

Destroyer 15 says COOH from COOH-C-C=O is beta keto.

destroyer 42 says O=C-C-OH is alpha hydroxy ketone

I think we don't count the carbonyl carbon and the carbon attached to the carbonyl carbon is alpha and then beta.

Shouldn't the first one be called alpha keto since COOH is attached to the alpha carbon of carbonyl carbon?

I believe it should be beta keto carboxylic acid right?? the C in COOH doesn't count. The next one is alphan, and the one after (C=O) is beta. so beta-keto carboxylic

 

[joonkimdds]

I believe it should be beta keto carboxylic acid right?? the C in COOH doesn't count. The next one is alphan, and the one after (C=O) is beta. so beta-keto carboxylic

No, the first one is beta, 2nd one is alpha, that's what the book says.

 

[Shinpe]

No, the first one is beta, 2nd one is alpha, that's what the book says.

So I think it should be C(doesnt count)OOH-C(alpha)-C(beta)=O or C(beta)OOH-C(alpha)-C(doesnt count)=O depending on which group you wanna say what's beta to what. In the first, the carbonyl is beta to carboxylic acid. the second one the carboxylic acid is beta to the carbonyl. same thing

The 42 is o=C(doesnt count)-C(alpha)-OH

 

[joonkimdds]

Oh so I guess C of COOH also counts. I thought C in functional group doesn't count but I guess I was wrong.

 

[Pajamasam9090]

I'm glancing at it right now. You're talking about carbon "C" correct?

The C in the COOH indeed doesn't count. If you look, that makes the alpha carbon the carbon that the COOH is connected to the ring with. Next Carbon in the ring (going down) is the ketone group. Since it's the second carbon it is beta.

^_^ at least that's what I think.

and in 42...
you have the COOH group on the second Carbon so the next carbon to the right is just one over, which would make it alpha. There's an alcohol group so it's called alpha hydroxy.

 

[dentrilla]

http://en.wikipedia.org/wiki/Keto_acid