The P and log P values for aspirin may not be accurate. Aspirin decomposes slowly in aqueous solutions. One product is acetic acid which is completely miscible in water. The titration of the aqueous layer (now containing acetic acid) will require more NaOH than anticipated and the resulting value will o too. cmall (In other orde conticic acid may ho oor coluble in water

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Chapter1: Chemical Foundations
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Class Average 2022
Aspirin*
Gentisic Acid
log P = 0.96
P = 4.6
log P = 0.65
P = 10.0
The P and log P values for aspirin may not be accurate. Aspirin decomposes slowly in aqueous
solutions. One product is acetic acid which is completely miscible in water. The titration of the
aqueous layer (now containing acetic acid) will require more NaOH than anticipated and the
resulting P value will be too small. (In other words, gentisic acid may be more soluble in water
than aspirin.)
Benzoic Acid
P = 17.4
P = 1.8
log P = 1.2
Propionic Acid
Salicylic Acid
P= 18.5| log P = 1.2
log P = 0.24
Hippuric Acid
P = 2.2
log P = 0.32
Butyric Acid
P = 4.9
log P = 0.67
Valeric Acid
P = 11.7
log P = 1.0
Transcribed Image Text:Class Average 2022 Aspirin* Gentisic Acid log P = 0.96 P = 4.6 log P = 0.65 P = 10.0 The P and log P values for aspirin may not be accurate. Aspirin decomposes slowly in aqueous solutions. One product is acetic acid which is completely miscible in water. The titration of the aqueous layer (now containing acetic acid) will require more NaOH than anticipated and the resulting P value will be too small. (In other words, gentisic acid may be more soluble in water than aspirin.) Benzoic Acid P = 17.4 P = 1.8 log P = 1.2 Propionic Acid Salicylic Acid P= 18.5| log P = 1.2 log P = 0.24 Hippuric Acid P = 2.2 log P = 0.32 Butyric Acid P = 4.9 log P = 0.67 Valeric Acid P = 11.7 log P = 1.0
+Table 4: Carboxylic Acids (Part C)
Mol. Wt.
(g/mol)
Propionic acid
Butyric acid
Valeric acid
# of H-bond
donor sites²
# of H-bond Part. Coeff.
acceptor sites³
1.8
4.9
11.7
Log P
0.24
0.67
1.0
2A H-bond donor site is any H in the molecule that is bonded to a nitrogen or oxygen.
3A
³A H-bond acceptor site is any atom that has one or more lone pair of electrons.
I
Transcribed Image Text:+Table 4: Carboxylic Acids (Part C) Mol. Wt. (g/mol) Propionic acid Butyric acid Valeric acid # of H-bond donor sites² # of H-bond Part. Coeff. acceptor sites³ 1.8 4.9 11.7 Log P 0.24 0.67 1.0 2A H-bond donor site is any H in the molecule that is bonded to a nitrogen or oxygen. 3A ³A H-bond acceptor site is any atom that has one or more lone pair of electrons. I
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