Bond sizes in organic chemistry

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Discussion Overview

The discussion revolves around bond sizes in organic chemistry, specifically focusing on the lengths of various carbon and oxygen bonds. Participants are exploring the relationships between bond lengths and atomic sizes while considering the construction of molecular models for organic acids.

Discussion Character

  • Exploratory
  • Technical explanation
  • Homework-related

Main Points Raised

  • One participant inquires about the ratio of C-C bond lengths to C=C bond lengths, expressing a belief that the single bond is roughly twice as long as the double bond.
  • Another participant asserts that C-H bonds are not closer together than C-C bonds, emphasizing the nature of sigma bonds.
  • There is a claim that C=O bonds should not differ significantly in closeness compared to C=C bonds, as both involve one sigma and one pi bond.
  • One participant provides specific bond lengths in picometers for various combinations, suggesting that bond lengths depend on the sizes of the atoms involved.
  • Participants discuss the implications of atomic radii on model construction, noting that the sum of atomic radii affects how models should be built with styrofoam balls and sticks.
  • There is a mention of the empirical atomic radii for hydrogen, carbon, nitrogen, oxygen, chlorine, and bromine, indicating that O is smaller than C.
  • One participant suggests an alternative modeling approach that uses uniformly sized balls to represent atoms, focusing on bond lengths rather than atomic sizes.

Areas of Agreement / Disagreement

Participants express differing views on the significance of atomic size differences and the relationships between bond lengths. There is no consensus on the exact ratios or the implications for model building, indicating ongoing debate and exploration of the topic.

Contextual Notes

Participants note that bond lengths are defined as internuclear distances and depend on the sizes of the atoms involved. The discussion includes various assumptions about bond types and atomic radii, which may not be universally agreed upon.

decamij
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I know that a double bond has the two atoms closer to each other than a single bond. I have to build an organic acid model for chemistry and would like to know:
- Is there a ratio between the lengths of C-C bonds to C=C bonds?
- Are C-H bonds closer together than C-C bonds?
- Are C=O bonds closer together than C=C bonds?
- If I'm building a model out of styrofoam balls and sticks, would C and O atoms be essentially the same size (i know O has a smaller atomic radius than C, but is it significant) --> i intend on using a colour code (black - C, red - O)

The first question is my top priority. Any help would make a huge difference - thanx!
 
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decamij said:
I have to build an organic acid model for chemistry and would like to know:
- Is there a ratio between the lengths of C-C bonds to C=C bonds?

From what i know of,it's roughly 2.That is the simple bond is twice as "long" as the double one.

decamij said:
- Are C-H bonds closer together than C-C bonds?

No,it's the nature of the bond that is essential:in this simple sigma bonds for both situations...

decamij said:
- Are C=O bonds closer together than C=C bonds?

I see no reason why they should be different...One sigma,one pi,double bond...

decamij said:
If I'm building a model out of styrofoam balls and sticks, would C and O atoms be essentially the same size (i know O has a smaller atomic radius than C, but is it significant) --> i intend on using a colour code (black - C, red - O)

No,there is no significant radius difference.You can put the O atom a bit bigger,but not significantly...

Daniel.
 
Dexter, that's not right !
decamij said:
I know that a double bond has the two atoms closer to each other than a single bond. I have to build an organic acid model for chemistry and would like to know:
- Is there a ratio between the lengths of C-C bonds to C=C bonds?
- Are C-H bonds closer together than C-C bonds?
- Are C=O bonds closer together than C=C bonds?

These are roughly the bond lengths of the various combinations that you might need (in picometers) :

H--N 101
H--O 96
O--O 148

C--C 154
C=C 134
C[itex]\equiv[/itex]C 120

c--H 109
C--N 147
C--O 143
C--Cl 177
C--Br 194

Empirical atomic radii of various atoms (in pm) are roughly ("atomic radius" is as such, a very vague term as it can be defined and measured in different ways) :

H 25
C 70
N 65
O 60
Cl 100
Br 115

Since the bond length is defined as the internuclear distance (ie : the sum of the covalent radii, in the case of a single bond) it does depend on the size of the atoms involved.

If you are using styrofoam balls and sticks, remember that the length of stick exposed is given by :
[tex]length~exposed = bond~length - (radius1 + radius2)[/tex].
If the sum of the radii equals (or exceeds) the bond length, then no part of the stick will be exposed, and the balls will have to be touching each other. In fact, if the bond legth is greater than the sum of the radii (eg : C=C), you will have to flatten part of the C atoms (the balls) to make the distance correct.


If I'm building a model out of styrofoam balls and sticks, would C and O atoms be essentially the same size (i know O has a smaller atomic radius than C, but is it significant) --> i intend on using a colour code (black - C, red - O)

The first question is my top priority. Any help would make a huge difference - thanx!

Yes, O is smaller. See the numbers above, for the atomic radii.

Another way of making such models involves using small balls (all of the same size, but different colors) to represent the atoms, but leave out information about the atomic radii. By making the balls small compared to the length of the sticks, you only have to worry about bond lengths, which will now be equal to the lengths of the sticks.
 
Last edited:
I forgot to include

C=O 127 pm
 

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