[prncess23]

what are the major products of the reaction of acetic anhydride with:
a. diphenylamine
b. water 0with heat)
c. benzene in the presence of a Lewis acid
d. toluene in the presence of a Lewis acid
e. ethanol (with heat)

[sjb]

See, for instance, http://www.chemguide.co.uk/organicprops/anhydrides/oxygen.html or http://www.chemguide.co.uk/organicprops/anhydrides/nitrogen.html

[prncess23]

ok. cool so...ill do the easy one first...water...

b. (CH3CO)2O + H2O → 2 CH3CO2H

[StarvinMarvin]

to do the rest, (if you still have not figured out how to do it) try to look up reactions of alcohols and reactions of amines inany organic chemistry textbook. Or even on wikipedia.

[macman104]

These are all roughly the same, just different nucleophiles, no?

[StarvinMarvin]

basically, yes. With the small exception of c and d which have to be regarded rather separately.

[macman104]

Even then, your nucleophile can be regarded as the electron pair from the ring, attacking the electrophilic carbonyl (made more electrophilic by the complexation of the lewis acid).

It's not super relevant, but it helped tremendously for me when I recognized how common most organic reactions are, and I think it's well illustrated in this question.

[prncess23]

ok so i got all the answers except c.

a. acetic anhyride + diphenylamine= n.n-diphenylacetamide + acetic acid
b. acetic anhyride + water (with heat)= 2 acetic acid
c. acetic anhyride + benzene --->lewis acid--->acetophenone + acetic acid
d. toluene in the presence of a Lewis acid
e. acetic anhyride + ethanol (with heat)= ethyl acetate + acetic acid

how do i d?

[macman104]

Same way you did c.  Except the methyl group influences where the substitution is going to occur.  I assume you are familiar with friedel-crafts acylation?  Do you know about ortho/para directing groups?

[prncess23]

yes i am...but...is the product still going to be acetophenone???

[macman104]

Not quite, you aren't using benzene anymore, you're using toluene.

What carbons on the ring are favored by the methyl group for substitution (is it ortho/para directing or meta-directing)?  This will dictate which carbons the acetyl group will most likely attach to.