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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: cheshplja on January 08, 2023, 06:13:17 AM

Title: Chirality of a molecule
Post by: cheshplja on January 08, 2023, 06:13:17 AM

Hi. I have a problem and I need help solving it.

I have this molecule, which is a male produced sex pheromone (component) of a beetle. I know that it (3,5-dimethyl-6-(1-methylbutyl)-pyran-2-one) is chiral and I've identified the chiral center. But I'm an ecologist, not a chemist and it's been a few years since I've attended organic chemistry classes. Can you guys help me determine which of the bottom two in the image is the S and R enantiomer and an explanation would be welcome as well. Did I even draw these correctly?

Thank you in advance.

Title: Re: Chirality of a molecule
Post by: Hunter2 on January 08, 2023, 08:26:37 AM

The left molecule is S and the right one R configurated. Exchange the substituents that hydrogen is on bottom. H with Methyl and Ethyl with the pyranering. Order is pyrane, Ethyl, Methyl.

Title: Re: Chirality of a molecule
Post by: cheshplja on January 08, 2023, 04:47:46 PM

Thanks for your help. Much appreciated :)

Title: Re: Chirality of a molecule
Post by: clarkstill on January 09, 2023, 08:24:36 AM

Quote from: Hunter2 on January 08, 2023, 08:26:37 AM

The left molecule is S and the right one R configurated. Exchange the substituents that hydrogen is on bottom. H with Methyl and Ethyl with the pyranering. Order is pyrane, Ethyl, Methyl.

Don't you mean left is (R)?

Title: Re: Chirality of a molecule
Post by: Vidya on January 20, 2023, 07:11:34 AM

Yes - left is R and right is S