[theanonymous]

The structure (below) I drew at the bottom is wrong
Here's the SMILES string...
CC1=CCC=CC1

In the first electron transfer, the carbon to which the sodium electron adds creates a carbanion and the carbon "para" to the carbanion is a carbon radical which becomes a carbanion upon electron transfer from the second sodium atom. Since the carbanion is negatively charged, it would not be low in energy if it formed on a carbon bonded to an alkyl group (an electron pump). This results in the alkyl group being bonded to a double bond carbon (sp2 carbon) and not to an sp3 carbon.

But what's the answer?

[Calicum]

Birch Reduction

[theanonymous]

Birch Reduction

Can you show me using this link? http://cactus.nci.nih.gov/translate/

[discodermolide]

Look here: http://en.wikipedia.org/wiki/Birch_reduction

[theanonymous]

Look here: http://en.wikipedia.org/wiki/Birch_reduction

I looked at that like 4 min ago.
That's what I did and I still got it wrong...

[discodermolide]

How about this product?

[Dan]

That's what I did and I still got it wrong...

You replaced the isopropyl group with a methyl group.

[Borek]

Here's the SMILES string...
CC1=CCC=CC1

If you know SMILES, why don't you use [smiles]CC1=CCC=CC1[/smiles] tags?

[curiouscat]

Here's the SMILES string...
CC1=CCC=CC1

If you know SMILES, why don't you use [smiles]CC1=CCC=CC1[/smiles] tags?

Adding frills

[theanonymous]

How about this product?

Oh
wait...

[theanonymous]

That's what I did and I still got it wrong...

You replaced the isopropyl group with a methyl group.

Ohhhh... for some reason I thought the 2 extra lines on the isopropyl group were implied Hydrogens...
Thanks a bunch!!

[theanonymous]

How about this product?

That makes more sense!
Thanks!!

[theanonymous]

What about this one though?
Do I do the same thing with the Birch Reduction?



Like this?



Because this is what I had in my notes...

In the first electron transfer, the carbon to which the sodium electron adds creates a carbanion and the carbon "para" to the carbanion is a carbon radical which becomes a carbanion upon electron transfer from the second sodium atom. Since the carbanion is negatively charged, it would not be low in energy if it formed on a carbon bonded to an alkyl group (an electron pump). This results in the alkyl group being bonded to a double bond carbon (sp2 carbon) and not to an sp3 carbon.

[theanonymous]

Either that or it's this, no?

[theanonymous]

I think I got the one above right...

I'm not sure about this one though...



I got:


Does that look right?
Because if the alkyl group possesses a benzylic hydrogen then that carbon will be oxidized to a carboxylic acid.

So if THIS one is right, then what's the product for this one? o.O



I tried doing but Webassign said I was wrong...