Organic Chemistry: No. of chiral centres in Camphor

[DarkStalker]

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.

 

[danago]

How about the bottom-most carbon atom?

 

[DarkStalker]

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.

 

[danago]

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.

 

[DeeNos]

Hello, thank you for your question. Camphor is a compound that contains two chiral centers, as you correctly identified. The first chiral center is the carbon atom you mentioned, with four different groups attached to it. The second chiral center is located in the cyclohexane ring, where there are two different groups attached to each carbon atom. This results in a total of two chiral centers in camphor.

It is important to note that chiral centers are defined as carbon atoms with four different groups attached to them, and they are responsible for the optical activity of a compound. In camphor, these chiral centers give rise to different enantiomers, which have the same chemical formula but differ in their spatial arrangement.

I hope this helps clarify the number of chiral centers in camphor. If you have any further questions, please do not hesitate to ask. Thank you for your interest in organic chemistry.