[maltasian]

I can't seem to get these questions.  Any help would be great!

1. thionyl chloride is the double acid chloride of which acid? What are the products of its reaction with water?

2. Account for the acidity of the benzenesulfonamides derived from primary amines.

3. Why is NaOH necessary in the reactions with amines with acetic anhydride or benzenesulfonyl chloride? What would be the result is it were omitted?

[maltasian]

For the first one I would think that sulfur dioxide and HCl would be formed...I don't know what the double acid chloride is though.

For the second question, does it have anything to do with in order to crystallize, HCl must be added.

For the third question, does it help to distinguish between primary, secondary and tertiary amines.  I don't know what would happen if it were omitted.

[movies]

1) Draw the structure of a generic carboxylic acid, and then the corresponding acid chloride.  How could you apply the same relationship to thionyl chloride?

The products from the reaction with water look right.  It's a very vigorous reaction too, I might add!

2) Crystallization doesn't factor into the acidity.  Lots of sulfonamides are crystalline without a molecule of HCl.  What features make something a stronger acid?  How are the electronics of nitrogen changed when the benzene sulfonyl group is added?

3) Draw out the complete, balanced equation for the reaction of an amine (for simplicity, use a primary amine).  Suppose that half of your starting materials reacted.  Would you expect any interactions between the products you produced and the remaining starting materials?  What interactions would you expect with additional NaOH in the reaction pot?

The interaction you are looking for with only affect primary and secondary amines.  Tertiary amines generally don't undergo reactions with acetic anhydride of sulfonyl chlorides.