Identify the functional groups and predict the solubility of Ciprofloxacin and amoxicillin. Provide drawing and explanation. Table on solubility is given and examples Thank you!

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter21: Lipids
Section: Chapter Questions
Problem 21.13P: 21-13 Rank the following in order of increasing solubility in water (assuming that all are made with...
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Identify the functional groups and predict the solubility of Ciprofloxacin and amoxicillin. Provide drawing and explanation. Table on solubility is given and examples Thank you!
Ciprofloxacin
F.
`OH
HN,
Amoxicillin
NH2 H
„CH3
CH3
НО
CO,H
Identify the functional groups present in each
drug and predict the drug solubility based on the
given table. (See attached examples)
Transcribed Image Text:Ciprofloxacin F. `OH HN, Amoxicillin NH2 H „CH3 CH3 НО CO,H Identify the functional groups present in each drug and predict the drug solubility based on the given table. (See attached examples)
pi Value
Fragment
C (aliphatic/cyclic)
+0.5
C (alkene-aliphatic/cyclic)
+0.33
(phenyl/benzene ring) C,H;-
+2.0
>/= to +0.5
Halogens (CI, F, Br)
+0.5
water insoluble
O,NO
+0.2
Intramolecular hydrogen bonding (IMHB)
+0.65
< +0.5
+0.5
water soluble
(carboxylic acid) O=C-O
-0.7
(amide) O=C-N
-0.7
O(hydroxyl, phenol, ether)
-1.0
N (amine-aliphatic/cyclic/aromatic)
-1.0
O,N (aliphatic)
-0.85
0,N (aromatic)
-0.28
Benzene 2
TOTAL: 3.95
WATER INSOLUBLE
C-aliphatic=0.5
N cyclic= -1
N
O=CN = -0.7
Benzene 2
HMHB= 0,65
C-aliphatic=0.5
Total: 5.28
Carbon
aliphatice
05
WATER INSOLUBLE
H,CO
Carbon
aliphatic=
0.5
Cyclic
alkene=0.33
H,CO
Carbon
alphatic=
OCH 05
OCN=-0.7
Carbon
OCH3 aliphatic=
6.5
Carbon
cyclic= 0.5
H.C
Benzene=2
Carbon
aliphatice
IMHB= 0.65
0.5
I ZI
Transcribed Image Text:pi Value Fragment C (aliphatic/cyclic) +0.5 C (alkene-aliphatic/cyclic) +0.33 (phenyl/benzene ring) C,H;- +2.0 >/= to +0.5 Halogens (CI, F, Br) +0.5 water insoluble O,NO +0.2 Intramolecular hydrogen bonding (IMHB) +0.65 < +0.5 +0.5 water soluble (carboxylic acid) O=C-O -0.7 (amide) O=C-N -0.7 O(hydroxyl, phenol, ether) -1.0 N (amine-aliphatic/cyclic/aromatic) -1.0 O,N (aliphatic) -0.85 0,N (aromatic) -0.28 Benzene 2 TOTAL: 3.95 WATER INSOLUBLE C-aliphatic=0.5 N cyclic= -1 N O=CN = -0.7 Benzene 2 HMHB= 0,65 C-aliphatic=0.5 Total: 5.28 Carbon aliphatice 05 WATER INSOLUBLE H,CO Carbon aliphatic= 0.5 Cyclic alkene=0.33 H,CO Carbon alphatic= OCH 05 OCN=-0.7 Carbon OCH3 aliphatic= 6.5 Carbon cyclic= 0.5 H.C Benzene=2 Carbon aliphatice IMHB= 0.65 0.5 I ZI
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