Dirk Emde
Mark Rosen
November 12, 2010
CHM 2210
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Molecular Weight: 138.12 g/mol
Chemical Formula: (HO)C6H4(COOH)
Appearance: Fine, white crystals.
Odor: Odorless or slight phenolic odor.
Density: 1.44 g/mL @ 20°C (68°F)
pH: 2.4
Boiling Point: 211°C (412°F)
Melting Point:
157 - 159°C (315 - 318°F) Sublimes @ 76°C
(169°F)
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Warning! Harmful if swallowed, inhaled or
absorbed through skin.
Affects central nervous system, kidneys, and
pancreas.
Causes irritation to skin, eyes and respiratory
tract.
Oral rat LD50: 891 mg/kg
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IUPAC name: 2hydroxybenzoic
acid
Arene Ring
Carboxylic Acid
group off carbon 1
Alcohol group off
carbon 2
0 stereocenters
Prochiral
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3500–3200 O–H
stretch
3300–2500 O–H
stretch carboxylic
acids
3100–3000 C–H
stretch aromatics
1760–1690 C=O
stretch carboxylic
acids
1600–1400 C–C
stretch (in–ring)
aromatics
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Acetylsalicylic acid is marketed
as aspirin.
Best known for its use in antiacne treatments.
Written about by Hippocrates in
the 5th century BC.
First isolated and named by the
German chemist Johann Andreas
Buchner in 1826.
1.
2.
3.
Nucleophilic addition of OH- to ester carbonyl
group forms alkoxide intermediate.
Water receives H from OH and forms hydronium
Elimination of alkoxide ion forms carboxylic acid
4. Alkoxide ion is protonated via hydrogen
from carboxylic acid and forms
carboxylate ion.
5. 
Electronegative
oxygen
protonated via
Description
of isMech
prior created hydronium, forming
carboxylic acid and reforming alcohol.
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We’d like to give special thanks to Professor
Becker for assistance with mechanism.
Thanks to Simon Tang from the tutoring
center for help with layout of presentation
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Dirk Emde
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Mark Rosen
1.
2.
3.
4.
Baker, J.T., Material Safety Data Sheets.
www.jtbaker.com/europe/msds/ 1997-2000
Mallonckrodt
Baker inc.
Diarmuid, Jeffreys. (2005) Aspirin. The remarkable story
ofa
wonder drug. New York, Ny: Bloomsbury pp.
38-40
McMurry, John Organic Chemistry 7th Edition Cengage
Learning Inc. Belmont, Ca. 2008
Spectral Database for Organic Compounds.
http://riod01.ibase.aist.gojp/sdbs/cgibin/cre_index.c
gi?lan g=eng. Last updated March 2010 AIST.
Japan