Organic Chemistry: No. of chiral centres in Camphor

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Discussion Overview

The discussion revolves around identifying the number of chiral centers in camphor, a topic within organic chemistry. Participants are analyzing a specific question related to the molecular structure and chirality of camphor, focusing on the characteristics of carbon atoms within its ring structure.

Discussion Character

  • Homework-related
  • Conceptual clarification
  • Debate/contested

Main Points Raised

  • One participant identifies the first carbon atom beneath the top-most CH3 group as a chiral center due to its four different substituents (C=O, CH2, CH3, C).
  • Another participant suggests that the bottom-most carbon atom could also be a chiral center, although they express uncertainty about their reasoning.
  • A later reply discusses the nature of chiral compounds, noting that typical examples often have terminal groups, which complicates the identification of chirality in a ring structure.
  • One participant argues that despite the ring structure, the bottom carbon can be considered chiral because it is bonded to different groups when analyzed closely.

Areas of Agreement / Disagreement

Participants do not reach a consensus on the identification of the second chiral center, with some suggesting it is the bottom-most carbon while others express uncertainty about the reasoning behind this identification.

Contextual Notes

Participants highlight the complexity of analyzing chirality in cyclic compounds, indicating that assumptions about symmetry may not apply as straightforwardly as in acyclic structures.

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Hello. I have a query regarding organic chemistry.

1. http://tinyurl.com/y9nvg2p
See question number 21.



2. Homework Equations : None



3. The first Carbon atom beneath the top-most CH3 group I can tell is a chiral centre, as it has 4 different groups attached to it (C=O, CH2, CH3, C). Apparently the answer is C, i.e 2 chiral centres. I can't locate the second one.

Thanks.
 
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How about the bottom-most carbon atom?
 
danago said:
How about the bottom-most carbon atom?

That's the answer, but I couldn't put together a solid reasoning. Normally chiral compounds that we're supposed to identify have, I don't know what to call it, terminal ends? E.g, like the chiral carbon would be bonded to H, OH, CH3, CO2H. That ring confused me. Taking the entire ring as a group, that Carbon is attached to the same group on both the ends.
 
You can do a similar kind of analysis even though it is a ring. If you look at the group directly either side of the bottom carbon, they are indeed the same (-CH2), however if you move along and look at the next group, it is a CH2 on the left side and a C=O on the right side i.e. The ring is not symmetrical, so you can kind of think of it as being bonded to 4 different groups.
 

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