Topic: Why does the methyl become a wedge? (Read 3155 times)

noor123 · « **on:** October 13, 2014, 11:20:33 AM »

I understand the mechanism of the antimarkovnikov addition due to the peroxide, but i dont understand why the methyl group is the wedge and not the Br?

zsinger · « **Reply #1 on:** October 13, 2014, 01:00:54 PM »

Does it matter?

noor123 · « **Reply #2 on:** October 13, 2014, 01:05:55 PM »

Im not sure...

kriggy · « **Reply #3 on:** October 13, 2014, 01:26:10 PM »

I think it could easily be dashed too (is dashed the proper term used in this case?

)

Irlanur · « **Reply #4 on:** October 13, 2014, 03:50:23 PM »

there's no chiral information at the carbon with the bromine. But without a chiral reagent, the product would be a racemat

C-hemCards · « **Reply #5 on:** October 13, 2014, 09:17:50 PM »

Yep, that should not be drawn like that. There should be no stereochemical information contained in that product structure.

Babcock_Hall · « **Reply #6 on:** October 15, 2014, 05:02:16 PM »

Quote from: noor123 on October 13, 2014, 11:20:33 AM

I understand the mechanism of the antimarkovnikov addition due to the peroxide, but i dont understand why the methyl group is the wedge and not the Br?

The Br atom is not on a stereogenic carbon atom. It would make no sense to put a wedge there. The carbon atom with the methyl group is a stereogenic center. I might be tempted to draw the product in such as way as to indicate that it is a racemic mixture.

Topic: Why does the methyl become a wedge? (Read 3155 times)

noor123

Why does the methyl become a wedge?

zsinger

Re: Why does the methyl become a wedge?

noor123

Re: Why does the methyl become a wedge?

kriggy

Re: Why does the methyl become a wedge?

Irlanur

Re: Why does the methyl become a wedge?

C-hemCards

Re: Why does the methyl become a wedge?

Babcock_Hall

Re: Why does the methyl become a wedge?

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