Google Answers Logo
View Question
 
Q: Organic Chemistry Mechanism Question. ( Answered 4 out of 5 stars,   0 Comments )
Question  
Subject: Organic Chemistry Mechanism Question.
Category: Science > Chemistry
Asked by: suziescrew-ga
List Price: $12.00
Posted: 01 May 2004 10:45 PDT
Expires: 31 May 2004 10:45 PDT
Question ID: 339429
What is the reaction mechanisim for converting benzoin to benzil using
HNO3 and EtOH?
Answer  
Subject: Re: Organic Chemistry Mechanism Question.
Answered By: brotine-ga on 01 May 2004 11:59 PDT
Rated:4 out of 5 stars
 
Hello, suziescrew.

Searching for this answer seems to require just the right combination
of chemical terms and plain English. Specifically, it means knowing
that HNO3 is nitric acid and EtOH is ethanol.

The clearest procedure is this experiment posting from the Department
of Chemistry at Pennsylvania State University, available at:
http://courses.chem.psu.edu/chem36/Experiments/Exp121.pdf

The textbook source is Macroscale and Microscale Organic Experiments,
2nd. Edition, by K. L. Williamson. Houghton Mifflin, Boston, 1994,
page 494.

"Procedure: Nitric Acid Oxidation of Benzoin
?
"Heat a mixture of 100 mg of benzoin and 0.35 mL of concentrated
nitric acid in a small beaker placed in boiling water for about 11
min. Carry out the reaction in the hood to avoid breathing evolved
nitrogen oxides. Be sure all the benzoin gets washed down inside the
tube and is oxidized. When reaction is complete, add 2 mL of water to
the reaction mixture, cool
to room temperature, and stir the mixture for a minute or two to
coagulate the precipitated product.

"Remove the solvent with a Pasteur pipette, and wash the solid with 2
mL more water. Dissolve the solid in 0.5 mL of hot ethanol, and add
water dropwise to the hot solution until the solution appears to be
cloudy, indicating it is saturated. Heat to bring the product
completely into solution, and allow it to cool slowly to room
temperature. Cool the tube in
ice, and isolate the product using the Hirsch funnel. Scrape the
benzil onto a piece of filter paper, squeeze out excess solvent, and
allow the solid to dry."

If you're interested, the Home Page for Penn State's "Introductory
Organic Laboratory" course is available at:
http://courses.chem.psu.edu/chem36/
linking to this and other experiments.


Search Strategy:
benzoin benzil HNO3

Good luck!
brotine-ga
suziescrew-ga rated this answer:4 out of 5 stars and gave an additional tip of: $1.00
thanks, got mostly what i needed

Comments  
There are no comments at this time.

Important Disclaimer: Answers and comments provided on Google Answers are general information, and are not intended to substitute for informed professional medical, psychiatric, psychological, tax, legal, investment, accounting, or other professional advice. Google does not endorse, and expressly disclaims liability for any product, manufacturer, distributor, service or service provider mentioned or any opinion expressed in answers or comments. Please read carefully the Google Answers Terms of Service.

If you feel that you have found inappropriate content, please let us know by emailing us at answers-support@google.com with the question ID listed above. Thank you.
Search Google Answers for
Google Answers  


Google Home - Answers FAQ - Terms of Service - Privacy Policy