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Bastin -Exam #3
Chem255 - Fall 201I
1) (8 pts) ProvideIUPAC namesfor the following compounds.
(a)
tgl'{),),g
t.',11$l-I - 3 ^{\u*n^o
--------.:
5C
(u)
(b)
(b-6-crNr\.)-k+\gn*
oC
(+)
(c)
q -Secb.,\.,\ \-.-,.\.,rt
(d)
r -\\
1lf\
\ \
I
\r,
l-r
n\r
I
-
'6, q -c\'rsnb-\n..,\
-') ,
\
IU 17l20r1
us\eno
Bastin -Exam #3
Chem255 - Fall 201I
2) (10 pts) Providestructuresfor the following compounds.
t\-.
\ry
,^Al I
'..
@@r;@p@
47+'t'2."."\
\*-"k
(c)@sad 16 g1y_!
-2-op19
Ie
'
(Q!f gns-s
ds(gop_y
I-3i elg e
/- -
tUt7t20rl
t- t-
Bastin - Exam #3
Chem255 - Fall 201I
3) (8.pts)Providea structuralformula for the cycloalkenestartingmaterial
for eachof the
following reactions.
(a)
cHs
HCI >
r-A*I
v\
cr
C\\,.J
,)R
\1'oR
,
lt
(b)
q.'
cHs
l) HBR2
9 \\ i
4) (s^pF) Indicate(by circlingon thestructure)
thefour isopreneunitsin thestructural
formula
of VitaminA (shownbelow).If youdon'tiecall*hut;; iroptin.
t wiiifiy"" know
f o r a 2 p tp e n a l ty.
""iiis,
., ,| r
') *
r't--
,/\
./
"
tt'
J1*'
rutTt20tr
4
Bastin - Exam #3
Chem255 - Fall 2011
5) (15 pts) Providethe reagentsneededto bring aboutthe following transformations.
a)
qn\
5
oo' r) o"o*
cR[..\u:3 It
:
\.t-\J)N"rb\, Hao
K tnnt.)q, N..o\\
"rrttt\oH
\l
\-,/
b)
Br
b.,
QSaoH
I
O
...rrt\lOCHa
.:tt''
\ *-RR, ,\\rl
)xro),\\*o\
r)hr p
d)
A
t) r xlou\\.
(e)
H*
Hao
OR
t) qtou")a I NJD
J) l.\"bH*
rur7l20rr
+ enantlomer
ri,r
+ enantlomer
Bastin - Exam #3
Chem255 - Fall 2011
6) (15 pts) Draw the product(s),if any, of the following reactions.Indicatestereochemistry
whererelevant. Pleasedo NOT write the mechanismson this page(usethe back of the
pages).
a)
tr "N
|
'
A\J
\a'
-rdiHz
tt'c-
d "o
\_,t
\\l
c.\c\i\-,r'r
b1r
o \\l;'"'
tfs
( ''v.'$:.-r
' ,)
i-.
i ,.. $t
\: :' -.\ d't''' )
\o.$.
b)
2)H2O2,CH3COOH
b
i'v''''''' "
:'.
Y -s\ J: 1
a*..srry\l
it
t
. r- cl\
o
o\.\ ?
c)
1) NaNH2
2) CH3CH2BT
Rs, '''.\ '\' >r
c.r\'.
k
d)
*,c
Brr
Q n..t\
+
@
'
)'-' > l
Qqp.St.)fi'\rrpq-
e)
O \\
1) Hg(OAc)2,HzO
2) NaBHa
rU rT12011
\
\\
Frc_r(
-
I i.,
q
"..\lNt
j-K: u
o
-"1r\..^.rsY:e
f
Bastin- Exam#3
Chem255 - Fall 201I
fQq\e^\t
7) (12pts)Thesexattrac
of the codling moth hasthe molecularformula
is pheromoneabsorbstwo molar equivalentsof
(l-decanol refersto an OH being
hydrogenand is convertedto 3-ethyl-7-methyl-1-decanol
locate4glthel+Eiition of a decanechain). On treatmentwith ozonefollowed by treatment
pheromoneproduces
producesCH3CH2CHTCOCH3,
CH3CH2CH'COCH3,
CH3CH,COCH2CH2CHC
wate}he pheromone
w4l€inc and watelhe
CH3CH,COCH2CHTCHO,
,t \'-and w{@nc
'
Neglectingthe stereochemistryof the double bonds,write a general
OHtCffpII.
structurefor this pheromone.
Cr3H24O.On catalytic_ drogenatio
6h-.'r,
lcrtr) rs
\,?.
t9t
\,
;\
t,''on"t"rt.
r ,fr-
)A '
Qt
C r.HJ\c
\N i.Gt
1Til
r'+\
\ it*
bu= )
I
o.
')
r) (cu)
f
ln\
"
\'"1
K o lc \ , 1
rS
\
I
I
coc\\3
C \\s c\q*,
\
I
.|
\,\r
\
\\
,\
\
)u
I\
- ' \ ' il
o
o\\ca*'>or\
Tht .,
\uQS
\
u
tU rTl20ll
\Jr
\\ -0'+ l' \ f ou
I o
I
)l$s
+
\*
D
3tt
I
c\S\, y" c-*)c\\)c\o
@
l
** $
s.- \.
wrSe. *\,
h4
u-Q.
Bastin - Exam #3
Chem255 - Fall 201I
8) (12 fts). Providethe product(s)of the following reaction. Be sureto show all pertinent
stereochemistry.Also, draw a curved-arrowmechanismthat clearly explainshow each
productis formed and the stereochemistry
of eachproduct.
Bt,
-
\\-
)$'
) CD1!\
\vc)c'
c\r
\t\
V
Bc
crs .or$
:/
\
J"to't\
e*e
hc
/
);\
tu 17l20tl
I
Jo\'
Bastin - Exam #3
Chem255 - Fall 201I
9) (12 pts) Using a curved-arrowmechanism,structures,and words,explainwhy treating
propenoicacid with HCI givesonly 3-chloropropanoic
acid.
I\
oH
HCI
>
o
\t
A
rt\:c-\
at'-!
\ f\
i,\
}q\s
\r:
H
S-
o\\
OR
H
os-
,--iJ{ \\oocoes, 5t
\:
ns\
+ C
: q t.( \r$t1
vg\:\ue i
tr\\ \
Nrs\A.5\ir,,t
this
5:
\ rr\<\ r.^e\-\
S^u-=\
\s
1\-.*
\\-'*s
n
S\rr"\-p f
r
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rU t7 l20ll
9