[insertwittyname]

Is this an acceptable way to step down a carboxylic acid?

[OrgXemProf]

OK. However, I can name that tune in three notes (four if you count preparation of the silver carboxylate salt):

1. Convert the acid to its silver salt (CH3CH2CO2- Ag+) and react with Br2 (i. e., Hunsdiecker reaction; proceeds via an intermediate hypohalite, which undergoes decarboxylation followed by subsequent radical combination to afford the corresponding alkyl bromide (CH3CH2Br). Reference: http://en.wikipedia.org/wiki/Hunsdiecker_reaction

2. SN2 reaction of ethyl bromide with NaOH affords ethanol

3. Oxidation of ethanol to acetic acid can be performed by using any of several reagents/conditions, e. g., KMnO4, Jones osidation, pyridinium dichromate in DMF, Heyns oxidation, ruthenium tetroxide, etc. Reference: http://en.wikipedia.org/wiki/Oxidation_of_primary_alcohols_to_carboxylic_acids

[orgopete]

OK. However, I can name that tune in three notes (four if you count preparation of the silver carboxylate salt):

1. Convert the acid to its silver salt (CH3CH2CO2- Ag+) and react with Br2 (i. e., Hunsdiecker reaction; proceeds via an intermediate hypohalite, which undergoes decarboxylation followed by subsequent radical combination to afford the corresponding alkyl bromide (CH3CH2Br). Reference: http://en.wikipedia.org/wiki/Hunsdiecker_reaction

2. SN2 reaction of ethyl bromide with NaOH affords ethanol

3. Oxidation of ethanol to acetic acid can be performed by using any of several reagents/conditions, e. g., KMnO4, Jones osidation, pyridinium dichromate in DMF, Heyns oxidation, ruthenium tetroxide, etc. Reference: http://en.wikipedia.org/wiki/Oxidation_of_primary_alcohols_to_carboxylic_acids

This always a problem if a poster asks someone to suggest a route that was discussed in a class we did not attend.

I can describe another route the poster may not know also. The poster's route is reasonable. It may use chemistry just discussed. I wasn't in the class, so I don't know which reactions were mentioned. The Hunsdieker is a little unusual. It may have been the preferred route, but ...?

[OrgXemProf]

Well, orgo, you have scored a valid point.

After having read your latest post I consulted the most current edition of a widely used undergraduate organic chemistry textbook (L. G. Wade. Jr., "Organic Chemistry", 8th Edition) wherein I find no mention of Hunsdiecker or his reaction. Ah, how soon they forget!

In the future I plan to check an undergraduate textbook before I post a potential solution to a synthetic problem just to make certain that it's fair game for students currently enrolled in an undergraduate organic chemistry course.

(Parenthetically, and in my own defense, I might mention that a description of the Hunsdiecker reaction appears in an old edition of J. E. McMurry, Organic Chemistry that's been sitting on my bookshelf for many years.)

Nevertheless... point well taken.

[insertwittyname]

Thanks for the alternative, OrgXemProf. I've read the Hunsdiecker reaction (I.L Finar, Vol1, 6th Ed), but couldn't really apply it.
And thanks also Orgopete for the point raised! have a mole point each