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PIm. 342C/142P- Exam II - Fall2002 Nu,,,rNsmt

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Questionsmarkedwith an
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(points) I

(6) Iy The vinegarsoldin grocerystores(andsomeretailpharmacies)is usually3Vowlv acetic

J acid. Giventhatth" Ku andMW of aceticacidare 1.8x 10-5and60 g/mole,whatis the
pH of Vinegar?

-3-oso:* tT"Aq$"*
-
rL
}vs& -
= o,bl-i Pu::JsLoT L

FH=e,5Al,_z
roown$ (oS n l l
p
5l.\ c"

O $nilr CI*r"l
R*n
lcn"?o
lJ,;r 3c lHAc)''o'*m
Q)
r-\ r /1
(E ) tr-\Au + Ac-
-(r.5-i Fr rf x x
'
a21* x (( 0'b
'^ft C/n.tC.!{
\ t- / ) f
"2
,
V
- fif
l l H l-f
\ u r*Y,:
,rrll
(.%xrcl
-Ei Z- \
lO
l\4. - -- _\
\Hh*,\ a4L.ff
)(= nffi3 *f
= '0O31-t o^ 3 xtc n
f,tl
(4) ?a-.Ephedrineis a weaklybasiccornpoundwith pKu = 9.36. Whatis the K6 for ephedrine?'
X FK*:* Pk* + pk u
--l:l--=q.3b $ Tk u
'tu.rn
=ffi'1
\ \-/-r
(4) b. Write a chemical reaction with equilibrium constantequal to the yaiue calculatedin

'"
, it/t
! - l l L - _H
\t
f ' u = a " ? qx l b 5 + 2@sNc,L[nl
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B) df A pediatricianasksyou to preparea2Vo solutionof drugD in a flavoredsyrup. Drug D
is a weakacidwith pKn= 6.4, intrinsic solubilityof 0.006M, intrinsicpartition
coefficientof I0.2, andMW of I87.2 g/mole. You hayethreesyrupsavailable:orange,
grape,andcherrywhich arebufferedat pH2.8,6.0,and7.8,respectively.Which syrupor
syrupscouldyou use? Showwork andlogic whichjustifiesyour answer. _I
DIJnu=
J ^t, I
F,K*+ t"3 ' i;j- '
. i tq'-q,) >
PHp Sr:
W_ Pl(a
S'"r--*-L s . -* tCi,rgl** I
loo..'.s*-* tJ ffi- L D*on-r#
PH,j**b rr t r; 'g,*$nu.:
r*ri,*A
,oclbFl fr*rr"gs
\ )
T,\\ fi *^d
Y*'P =\,bt$ A 1,t03
Llt:"\
\'*p = lacc.use, Tp ^ pH o"bov€',1,(o?, bD
vnp
ffCg;.rt; -
Pr-.eCr"pulo*iOn[J-oril_ed

/ 4

\z/
v
a. ( TJor F Any compoundwhich producesOI{- when placed'inwatermust be a base.
\_/

€n '{D Any compftndwhosepIL i. lbsstlan 7 mustbe an acid.

vF r"$ A basiccompound
solutions
will bemoresolublein basic(ratherthanacidic)
"like
because dissolvefllike.'l
, / |{ + F{r,'""rf# l*1i-i-
V a. r odL) Theconjug#acid;if Y""i. uuiBi,l stbea strongacid.
/
A buffer must contain a conjugate-acid/conjugate'base
pair.
Q/e.(rdrF
HC! + l'/aAc d
You can make a buffer by mixing hydrochloric acid and sodium acetate.
j

Whentitratinga weakbasewith a strongacid,theequivaleffiint is

reachedwhenthepH = 7.
q t t, /)
y'-
,
v{: Q_},
/-\
IncreasingthepH will increasethe solubilityof a weaklyacidica;f=-€--
-
pl"l
A /fj
.q/L T o/'F ) The igtriasic partition coefficient of a basic drug increaseswhen the pH of
. ffi4
the aqueou-slhaseis increased.
/
\ . 'tr/z-
r / (r)orr
F r i . \-/ Adding acid to a bufferedsolution wili alwayscausethe pH to decreaseto
//
,o t b
:.
some extent.

7-
LY
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 .3

(3)-b. identifyiqlany conjugateacid(circle) and/orconjugatebase(box)in thereactionyou

,o\ w" wroteabove'
{3 )
\_.,o
(3) c. _The equilibrium constaatfor your reaction is:
/"\. \r/
"/;^
i . q 111. Y

ii. Kb iv' noneofthe above. )

/^
(5)'6a. Sketch a graph which best illustrates h re. Label
axes,provideunits,andall additional$ilaph-related
inf6frffifiJust is t aia in lecture.

)nk

@ry r"r'tss*t
(4) b. Write an equationwhich corresponds
to the graphabove.
\./ \^k = -Eo* L
+ rI n A -
e-'+

(3) c. Choosethe bestanswer:

The equation in part (b) applies to
*.,
i. 0-ordbr processes all of the above

i.r-- lY>- ii. 1"- orderprocesses none of the above

)^
- |
a4
{^J-
-:
>)-- 7>
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(.4)7: Atropine is a basewith pIQ = 9.65. Computethe Ku, write a balancedreaction

U correspondingto that K., idettify4conjugate

circle(s) and box(es)as done in ciass.
1o5lta-
I , Fkkg#^-
acid(s) and cor{ugate base(s)with

/..-
I
?k^ lo = t*

V^'
(5) 8, The iahinsic solubilityof Phenobarbikl(a weakacid) is 0.005M. Given that theI!
andmolecularweightof Phenobarbital are3.9 x 10-8and?32.?3g/mole,what is the
/nost concenffatedsolutionwhich couldbe formulatedat pH 8.3?

F,^' :e-
Sr
K * = 3 , qx # foearl _ I .
tw= t*,"e}t-fiko.
3o= O'0A51
S,: L= 1"1{Cg 0dJ
4*
l -

Ir 63-rT,*l
i+lo
0.Do5r1
Ird

Aspirin (ASA) undergoesl*-order degradationro salicyclicacid (Se).

\t'(nsn)

Extra credit
116) c. Write an equationand sketch a graph showing how (SA) dependson time.
r ) V
i '
l(>

|tts Fi)-
oD
[;r ffi\
 *rt&*pxi *Pk s *-*
10. Sulfisoxizoleis a weaklyaciddrug with Ku= 1.0x 10-5.Define(in termsof equiiibrium
concentrations)
thefollowing termsfor sulfisoxizole:

9
fracfion
(3)a. *nionized = {,li' = =Ls+
LI4SJSLS-J
*
a CIla.
apparenf
partition celt
coeffi --[utJ*
3$)"' intrinsicpartitioncoefficient=
Ko=
fU* o [-*,,,* iG-
fu* -
i1. Also'forsulfisoxizole,g(gfi thefollowing giaphsshowingasmuchdetail asI did in class
andindicatethepredominantchemicalspecie(s)presentat variouspoints.

'j (3)a. { vs.pH

i (3)b. K.* vs. pH

j (z),. 'I{ vs.pH

L " @ d . titrationof sulfisoxizolewith 0.1 M NaOH

a)

p odd
\,t o'5
H\ 3-

"pk"=
5 )F\ )H
l3

Dll $-+ rff rok*+ &

?F"P*n
g,t;vt,qldl4r Ft"

Pt{
lvv
llr
,
lv't
l F Yo i* no*
\ ' -
c{-fl*st{#b*f
as, w ?ll
-r
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te
(9 12'a, Followingthei.v. administration of a 100mgdoseof drug-Xto an adultmalepatient,
plasma samples arecollectedat 3 hours andThourspost-administration. Laboratorv
I
analy_sisof the samplesyieldsf concentrationsof 15.2 yg/ml anclI0.l pglml."Given
fl\-
that the eliminationof drug-Nis known to occurasa L$-orderprocess,write an
equationwith numericalcoefficients(andproperunits)which describesthe
concentration of drug-fi in plasmaasa functionof time.

At = A'eTi
i A.=fl*/'* lo?rr'-ilav,"\ 1 1rt{it l0,Ir4lu*
t-^
t+\" = eO .bL+\rn_
-u-
ih4

t (t^'f
\j

sl /, lo
1r t h{5

l l t\[ = \n tn i o *\<,t
-('(*''r
I f;l:l$:[\y''u#)
(3) d What is the
volumeof distributioa(pretend:"volumeof plasma,')fothis patient?

/tr
{A"X-X u*
/+: clc.o,+#s
3 t
tcro4''o Y3
ls= *lb]ot ffi;tt@"
It=
,l
lXlo vlwr*, F lcf,yffih i
;"E
iv^>
; 1
,i,
'
t a" M . f
\ '/ (
,. \
I "-,/ ,,,
I t
I h
@tr@ , b
nnMT \ x'P "U