Difference between alpha-keto acid and keto acid

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Discussion Overview

The discussion centers on the differences between alpha-keto acids and keto acids, particularly focusing on the concept of the alpha carbon and its implications in chemical nomenclature. Participants explore the definitions and characteristics of these terms, as well as their applications in different contexts, including sugars.

Discussion Character

  • Homework-related
  • Conceptual clarification
  • Debate/contested
  • Technical explanation

Main Points Raised

  • One participant states that the difference between alpha-keto acids and keto acids is that alpha-keto acids contain an alpha carbon, but expresses uncertainty about the definition of the alpha carbon.
  • Another participant questions what an alpha carbon is in other contexts, suggesting examples from glucose and maltose.
  • One participant explains that an alpha-keto acid has a keto group next to the carboxylic acid (COOH), while a beta-keto acid has the keto group at the second carbon from COOH, referencing a visual aid.
  • Some participants note that the concepts of alpha, beta, and gamma carbons are widely used in chemistry, though not always formally defined.
  • There is a discussion about the naming conventions for alpha and beta carbons in cyclic sugars, indicating that these conventions differ from those used for keto acids.
  • One participant expresses uncertainty about the application of naming conventions in a specific image, suggesting that the position of the hydroxyl (OH) group may determine the naming rather than the carbon positions.

Areas of Agreement / Disagreement

Participants exhibit a mix of agreement and disagreement regarding the definitions and applications of alpha and beta nomenclature. While some points are clarified, there remains uncertainty and differing interpretations, particularly concerning cyclic sugars and the consistency of naming conventions.

Contextual Notes

Some participants highlight that the naming conventions for alpha and beta carbons can vary depending on the context, indicating a lack of formalization in some areas of chemistry.

soopo
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Homework Statement


What is the difference between alpha-keto acid and keto acid?

The Attempt at a Solution


I know that the difference is that alpha-keto acid contains an alpha carbon.
However, I do not know what the alpha carbon is in this case, and how I can show it.
 
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What is alpha carbon in other cases?
 
Borek said:
What is alpha carbon in other cases?

You can have alpha carbon, for example, in glucose and maltose.
 
What makes this carbon 'alpha'? Why is it called this way? How does it differ from 'beta'?
 
Borek said:
What makes this carbon 'alpha'? Why is it called this way? How does it differ from 'beta'?

I found the answer in Wikipedia.
Alpha keto-acid has keto group next to COOH, while beta keto-acid has keto group at the second Carbon from COOH.

The LHS molecule is alpha-keto acid, while RHS is beta-keto acid in the following picture.
http://dl.getdropbox.com/u/175564/alpha-beta-acids.png

Note that keto group in the RHS molecule is at the third carbon that is the second C from COOH.

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Is everything correct?
 
Last edited by a moderator:
If you were looking for the answer in wikipedia, it would be better to start at the very beginning:

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

soopo said:
The LHS molecule is alpha-keto acid, while RHS is beta-keto acid in the following picture.
http://dl.getdropbox.com/u/175564/alpha-beta-acids.png

Other left.
 
Last edited by a moderator:
Borek said:
If you were looking for the answer in wikipedia, it would be better to start at the very beginning:

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

Thank you!

So we have both alpha and beta carbons in both molecules
http://dl.getdropbox.com/u/175564/alpha-beta-carbons-updated.png

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Is the carbons now correctly labeled with alpha and beta carbons?
 
Last edited by a moderator:
OK now.

As you see concept of 'alpha'. 'beta' and 'gamma' carbons is widely used in chemistry. Not very formal, often very useful.
 
Borek said:
OK now.

As you see concept of 'alpha'. 'beta' and 'gamma' carbons is widely used in chemistry. Not very formal, often very useful.

I am unsure about alpha and beta carbons in http://www.laakis.com/wp-content/uploads/2008/12/picture-7.png" .

It seems that the same naming convention does not apply here.
Instead, the position of OH group seems to determine the name.
 
Last edited by a moderator:
  • #10
soopo said:
It seems that the same naming convention does not apply here.

Yes. As I told you - it is not formal. Still, widely used. See GHB for example.
 
  • #11
The alpha and beta conventions for sugars is completely different from the alpha, beta, gamma, etc. nomenclature that you were discussing previously.

For cyclic sugars, alpha refers to a cyclized sugar in which the OH group of the anomeric carbon (the carbon with two bonds to oxygen) is on the opposite side of the ring as the alkyl group on the ring.
 
  • #12
Ygggdrasil said:
The alpha and beta conventions for sugars is completely different from the alpha, beta, gamma, etc. nomenclature that you were discussing previously.

For cyclic sugars, alpha refers to a cyclized sugar in which the OH group of the anomeric carbon (the carbon with two bonds to oxygen) is on the opposite side of the ring as the alkyl group on the ring.

Thank you both!
 

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