Why Don't Carboxylic Acids Have Double Bonds in Their Parent Chains?

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Discussion Overview

The discussion revolves around the structural characteristics of carboxylic acids, specifically the absence of double bonds in their parent chains, and the relationship between carboxylic acids and amides. Participants explore examples and clarify misconceptions regarding these functional groups.

Discussion Character

  • Exploratory
  • Technical explanation
  • Conceptual clarification

Main Points Raised

  • One participant notes the absence of double bonds in carboxylic acids and questions whether this is coincidental or has a specific reason.
  • Another participant counters that double bonds can exist in the parent chain of carboxylic acids, citing 2-propenoic acid (acrylic acid) as an example.
  • A participant raises a question about the formation of amides from carboxylic acids and ammonia, expressing confusion over the naming of the resulting compounds as ammonium ethanoate and questioning why they are not considered amides.
  • The same participant also inquires about the reaction of carboxylic acids with amines and seeks clarification on the conditions required to form an amide.

Areas of Agreement / Disagreement

Participants exhibit some disagreement regarding the presence of double bonds in carboxylic acids, with one asserting their absence and another providing a counterexample. The discussion about the formation of amides from carboxylic acids remains unresolved, with confusion expressed over the naming conventions and reaction products.

Contextual Notes

The discussion includes references to specific chemical reactions and naming conventions, which may depend on varying interpretations and definitions within organic chemistry. The participants' understanding of the relationship between carboxylic acids, amides, and esters appears to be incomplete or misaligned.

Who May Find This Useful

This discussion may be useful for students and individuals studying organic chemistry, particularly those interested in functional groups and their reactions.

preet
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I haven't seen any carboxylic acids with double bonds in their parent chains... is this just coincidence or is there a reason that I am not seeing any? I know you can have benzanoic acid ... and even though that's not technically double bonds, its more then one (and its cylic, so its different)... so yeah... just wanted to know why I only saw parent alkane chains in carboxylic acids. Thanks.
 
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preet said:
I haven't seen any carboxylic acids with double bonds in their parent chains... is this just coincidence or is there a reason that I am not seeing any? I know you can have benzanoic acid ... and even though that's not technically double bonds, its more then one (and its cylic, so its different)... so yeah... just wanted to know why I only saw parent alkane chains in carboxylic acids. Thanks.

Of course, you can have double bonds in the parent chain. 2-Propenoic acid (ethylenecarboxylic acid or acrylic acid) is one of the simplest of these. http://www.chemicalland21.com/industrialchem/functional Monomer/ACRYLIC ACID.htm
 
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Thanks a lot =)
 
I have another question. My textbook says I can think of "amides" as the combination of a carboxylic acid and ammonia or an amine.

So letsay I react my carboxylic acid with ammonia...
CH3COOH + NH3 ---> CH3COONH4

Is this an amide? The name for this compound says it is ammonium ethanoate (http://www.chemguide.co.uk/organicprops/acids/acidity.html) so this means it is an ester right? Why?

another example is with an amine...
CH3COOH + CH3NH2 ---> CH3COOHCH3NH3

Again, this is an ester (according to the site)... so what am I missing here? What kind of reaction with ammonia or amines do I need to create an amide from a carboxylic acid? TiA

Preet
 

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