[orgopete]

I'd like to see a reference for tis reaction. I don't think you can form his wih NaOH.

[curiouscat]

I'd like to see a reference for tis reaction. I don't think you can form his wih NaOH.

No clue at all. You might be right.

I was only typesetting his hard-to-read handwritten equations.

[souro10]

I'd like to see a reference for tis reaction. I don't think you can form his wih NaOH.

Why not? Which step? The aldol step or the condensation step?

I can't think of any objection one could have with the aldol step.
The condensation product is wrong though. The base will pull a proton from the most acidic (next to the carbonyl group, in this case there's only one such carbon ) source, leading to enolization, double bond migration, and loss of hydroxyl group to produce an alpha-beta unsaturated aldehyde.

[curiouscat]

I'd like to see a reference for tis reaction. I don't think you can form his wih NaOH.

The base will pull a proton from the most acidic (next to the carbonyl group, in this case there's only one such carbon ) source, leading to enolization, double bond migration, and loss of hydroxyl group to produce an alpha-beta unsaturated aldehyde.

This?

[souro10]

I'd like to see a reference for tis reaction. I don't think you can form his wih NaOH.

The base will pull a proton from the most acidic (next to the carbonyl group, in this case there's only one such carbon ) source, leading to enolization, double bond migration, and loss of hydroxyl group to produce an alpha-beta unsaturated aldehyde.

This?

Precisely! 

[sjb]

Texas carbon ahoy?

[souro10]

Sorry, I hadn't noticed the substituent!  Too much ignorance.

[neobenzene]

So, what is the final, correct answer??

[souro10]

The aldol product is the correct answer. It will not dehydrate in this case I think.

[neobenzene]

Why won't it dehydrate?

[orgopete]

Why won't it dehydrate?

The aldol addition product lacks an acidic proton, so elimination is similar to a dehydration of 2-butanol with base. the most acidic hydrogen would be the OH, further hampering elimination.

It would be difficult to predict exactly what will be the result. The aldol addition product could be the result, but other reactions might also occur with the aldehyde. 

[neobenzene]

The aldol addition product lacks an acidic proton, so elimination is similar to a dehydration of 2-butanol with base. the most acidic hydrogen would be the OH, further hampering elimination.

It would be difficult to predict exactly what will be the result. The aldol addition product could be the result, but other reactions might also occur with the aldehyde.

Thanks, orgopete!