Stereochemistry Question

[Meredith92]

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Please see attached picture

Can someone help explain why the CH2OH group is labeled as #2? Woudlnt the COHCH2CCH3CH3 group (currently labeled #3) have a higher priority since it also has an oxygen two carbons away AND it has the alkyl group attached?

Thanks!


(This is from TBR Organic Chemistry Chapter 3)

 

[Shjanzey]

Please see attached picture

Can someone help explain why the CH2OH group is labeled as #2? Woudlnt the COHCH2CCH3CH3 group (currently labeled #3) have a higher priority since it also has an oxygen two carbons away AND it has the alkyl group attached?

Thanks!

Good question. I would be inclined to agree with what you said, as opposed to how the picture is labelled. I would love to see an explanation for this.

 

[Postictal Raiden]

Please see attached picture

Can someone help explain why the CH2OH group is labeled as #2? Woudlnt the COHCH2CCH3CH3 group (currently labeled #3) have a higher priority since it also has an oxygen two carbons away AND it has the alkyl group attached?

Thanks!


(This is from TBR Organic Chemistry Chapter 3)

I agree with you. I think it's a typo in numbering the groups. Regardless, the configuration remains S.

 

[BerkReviewTeach]

Please see attached picture

Can someone help explain why the CH2OH group is labeled as #2? Woudlnt the COHCH2CCH3CH3 group (currently labeled #3) have a higher priority since it also has an oxygen two carbons away AND it has the alkyl group attached?

Thanks!


(This is from TBR Organic Chemistry Chapter 3)

You are right, that's a typo on the numbering. But the arrow is drawn correctly, so it is in fact S. Thanks for the catch. I'll forward it to the author.