What's with deuterium? an organic problem

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    Deuterium Organic
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Discussion Overview

The discussion revolves around the properties and behavior of deuterium in organic chemistry, particularly in relation to its stability and interactions compared to hydrogen. Participants explore concepts such as steric hindrance and hyperconjugation, as well as the implications of deuterium's nuclear composition.

Discussion Character

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

Main Points Raised

  • One participant notes that a positive charge is unstable near a ##-CD_3## group but stable near a ##CH_3## group, questioning the reasons behind this behavior.
  • Another participant asks about the number of neutrons or protons in deuterium.
  • Some participants suggest that steric hindrance may be the reason for the observed instability, attributing it to deuterium being heavier and thus larger than hydrogen.
  • One participant challenges the assumption that deuterium's additional neutron makes it larger, arguing that the size of the nucleus is negligible and that deuterium's greater mass leads to slower reactions.
  • There is a clarification of the acronym "IMHO," with participants expressing confusion about its meaning.

Areas of Agreement / Disagreement

Participants express differing views on the reasons for the instability associated with deuterium, with some attributing it to steric hindrance and others questioning this reasoning. The discussion remains unresolved regarding the exact factors influencing the behavior of deuterium.

Contextual Notes

Participants have not fully explored the implications of hyperconjugation in relation to deuterium, and there are unresolved assumptions about the effects of nuclear size on chemical behavior.

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Homework Statement


I did a question in which positive charge was unstable near to ##-CD_3## group but was stable near to ##CH_3## group.

Homework Equations

The Attempt at a Solution


Why is it like that? Is deuterium less active for hyperconjugation or it causes more steric hindrance? What's wrong with deuterium?
 
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How many neutrons or protons Deuterium has?
 
It has a proton and a neutron. So steric hindrance?
 
mooncrater said:
It has a proton and a neutron. So steric hindrance?
I am not sure but it looks that it is the only reason. What do you think?
 
Yup.. it seems to me it's steric hindrance only, as it's heavier(thus bigger) than hydrogen. And it can't be hyperconjugation as it has the same configuration. That's what I think.
 
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Do I understand correctly that you assume deuterium is larger than protium, because it has an additional neutron in nucleus? That must be off. The size of nucleus is negligible.

The only (in such cases) important difference is that D is twice heavier, so its reactions (broadly understood, not only in terms of pure chemistry, but also shape shifts) are much slower. I don't know what is the correct answer here, but that's the only valid approach IMHO.
 
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Borek said:
IMHO
What is IMHO? Something molecular hybrid orbital?
 
mooncrater said:
What is IMHO? Something molecular hybrid orbital?
In my humble opinion.
 
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Raghav Gupta said:
In my humble opinion.
Really? Okay...!
 

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