[neobenzene]

Hi...I'm stumped at how to convert propene to 2,3-dimethyl butane. Any help would be gladly appreciated!

[discodermolide]

Hi...I'm stumped at how to convert propene to 2,3-dimethyl butane. Any help would be gladly appreciated!

Why don't you tell us what ideas you have. Then we may be able to put you on track.

[neobenzene]

Why don't you tell us what ideas you have. Then we may be able to put you on track.

I'm guessing we need to convert propene to an alkane first. So, I guessing we need to do hydrogenation in the presence of nickel or palladium. That will give us propane. After that, I'm not sure.

[discodermolide]

Why don't you tell us what ideas you have. Then we may be able to put you on track.

I'm guessing we need to convert propene to an alkane first. So, I guessing we need to do hydrogenation in the presence of nickel or palladium. That will give us propane. After that, I'm not sure.

Here are your two molecules, are you sure you are starting with propene?

[neobenzene]

Yes...I'm sure I'm starting with propene.

[discodermolide]

Yes...I'm sure I'm starting with propene.

OK, so you need to add 3 methyl groups, any ideas how this may be accomplished?

[neobenzene]

Absolutely no idea. Is there anything wrong with the method that I suggested earlier?

[discodermolide]

Absolutely no idea. Is there anything wrong with the method that I suggested earlier?

If you hydrogenate the double bond you will get a relatively (chemically) inert compound, propane. Better to keep the C=C and use it to elaborate the system toward your target.

[neobenzene]

If you hydrogenate the double bond you will get a relatively (chemically) inert compound, propane. Better to keep the C=C and use it to elaborate the system toward your target.

Ok...if I choose not to hydrogenate it...how should I proceed? How should I add three methyl groups?

[discodermolide]

If you hydrogenate the double bond you will get a relatively (chemically) inert compound, propane. Better to keep the C=C and use it to elaborate the system toward your target.

Ok...if I choose not to hydrogenate it...how should I proceed? How should I add three methyl groups?

Do you know any of the typical reactions of a C=C?

[neobenzene]

Do you know any of the typical reactions of a C=C?

Alkenes undergo hydrohalogenation. So, for example, if we treat CH3-CH=CH2 with HCl, we will get
CH3-CHCl-CH3, (by Markovnikov's rule), which is 2-chloro propane.

[discodermolide]

Do you know any of the typical reactions of a C=C?

Alkenes undergo hydrohalogenation. So, for example, if we treat CH3-CH=CH2 with HCl, we will get
CH3-CHCl-CH3, (by Markvnikov's rule), which is 2-chloro propane.

Great answer, you are now half-way to your target, so how would you couple 2 "isopropyl groups"? Hint, it is a well known name reaction.

[neobenzene]

I forget...what is isopropyl again? And can you please show me its exact structure?

[discodermolide]

I forget...what is isopropyl again?

here is a drawing of isopropyl chloride

[neobenzene]

Ok...so now we do Wurtz' reaction? In the presence of sodium and dry ether?