third practice exam chem 256 - organic chemistry ii prof
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Third Practice ExamCHEM 256 - Organic Chemistry II
Prof. BastinSpring 2015
Name
Pnovide clear, congise-answers using unambiquous, carefully drawn sFuctures (whereappropriate) for all of the questions. Good luck and enjoy!-
l) 112 pts
. 2) ll2pts
3) , 18 pts
a) /6 pts
5) t10 pts
6) tl2 pts
7) t12 pts
8) /8 pts
9) /6 pts
l0) 114 pts
Bastin - Third Practice Exam
l) (12 pts) Provide structures for the following compounds.
a) sec-butyl alcoholot\I
,N
b) cis-2-ethylcyclobutanol
c) (D-hex-3-en-2-one
c\;c\ 3
Chem 256 - Spring 2015
q.''\Aw
Ct
f) 3 4-dichlorohexandial
c\or \u
uAo
d) m-chl oroacetophenone
c-\e) dichloroacetaldehyde
O c\
Bastin - Third Practice Exam Chem 256 - Spring 2015
2) (12 pts) hovide either common or IUPAC names for the following compounds.
a)
b)
, \,5 -\.s"d\,."f -3-\re-Yc{c\>c\e
o
A qqdT\\Xr5. .sc t\*oqo\
(Z)-q-\oy.^.^\oc
tl) -\eFr\-o\A
d' ) -.v \obrcxrnr c"-\.\\\ \e
H
(q)- t - t"+c"c\o\
OH
b- l*ocu -5; -s -\l - ) \,e\""n=\
Bastin - Third Practice Exam Chem 256 - Spring 2015
3) (8 pts) Identify the symmetrical relationship (homotopic, enantiotopic, diastereotopic) of theunderlined atoms in the following molecules.
a)Hec
,, cHs
lzHH
\"o .i\t$ .-
\,"..s\c.(eo\$(-
b)
c)H
Hsc /t\cH3H3c$y'sH.
H
\o sns\r$ .
4
\oonr\u g.- L
Bastin - Third Practice Exam Chem 256 - Spring 2015
4) (6 pts) Indicate the number of peaks that a 1a; r3C-NMR spectrum and (b) 'H-NMR spectrum
of each of the following molecules would contain?,\ Nl f\Ru) .'t
\
b)
ao
H.C\
I\S
'N3
qt.}
3
3Ll
Cto
t\
..St') -AI
\tt
c)
Bastin - Third Practice Exarn
A"'^-.
Chem 256 - Spring 2015
5) (l-0-qts) Following -are thrye compounds with the molecular formula CnHrO, and three tH-NMR spec!.m. Assign each compound its corect spectmm and assign all signals to theircorresponding hydrogens.
"\ro-"n-tlo
(2)
-")- o
(3)
"\5t
b
A a oo
6
Bastin - Third Practice Exam Chem 256 - Spring 2015
a
I. . :
': -:
nt t
,:..
c\, *$
\) c\!
2
2H 3H
I
3H
D
bq
( L) q\\3 nevt rc tt
\q\ . r no*\ \ r
e>o + C\\ s
6) ( l2 pts) hovide the structure of a compound with the molecular formula C.HO using the IRand 'H-NMR provided below. Justify your structure by assigning ALL the appropriate peaksin the IR and NMR spectra and with a short narrative describing what structural informationeach piece of data provided.
Du= q *- \r1,
A\s r\:Cz(* o S
e.$6rs^-\it
l0
Integration
\o* rps{t r^) s\c- c\ Qc^Ot*) re \
c)
;,1i
V.>41
f.
ril \k/Ft : tripbl
qv|ltgl-
t . ,-
7) ( l2 pts) Provide the structure of a compound with the molecular formula C3H6O2 using theIR, [H-NMR, and ''C-NMR provided below. Justify your structure by assigning ALL theappropriate peaks in the IR and NMR spectra and with a short narrative describing whatstructural information each piece of data provided.
Bastin - Third Practice Exam Chem 256 - Spring 2015
cu. o\\.^dJ1> r\:
bt'13'n
3 C.- lbD n5 - o: 'tY *o'^"\
. l
c.^l\o:r.-r\ r c^fo>n
= 3-9'1t \
S\nte_ c\
c.^-,\'y[ \ r
Qt'€>{ri\ / N
e=a or d str.
lr\:, , ft \
L2- ,st C^tr\r\.\i(
to
Integration rH\--c$le
' 'C-NMR spectrum shows peaks at 14,60, and\)
ano
b
A.'
2H
'r'tl-
H@
r6s rtoo 12@
l*'-*+Ft
YD*, | \ - - tu.j)-\k" v.\ t\.( c\ f\uf lc^\i-r t
Bastin - Third Practice Exam Chem 256 - Spring 2015
8) (8 pts) Draw the product(s), if any, of the following reactions. Indicate stereochemistrywhere relevant.
a)
1) 2Li. ether -2) CH3CH2CHO
3) H2O
,^-/\8,
te) or \A
b)
c)
d)
9o,)-
oF
t\, 0. $arz
NaOH.
3) CH3CH2COCH2CH2CH3
Bastin - Third Practice Exam Chem 256 - Spring 2015
9) (6 pts) hovide the reagents needed to bring about the following transformations.
a)
i l B.\\-
-\-.
)) Eo
"5 D N,util..b.ul
\ ) b. \ , :
)) pe
b)
"o,. '/\,/
-\
ff
3)
c)oil
I
l0
Bastin - Third Practice Exam
l0) (14 pts) Provide a mechanism for the following reaction.
l) Ph3P2)nBuli
-3)O
il,t\-/
rv,/\.>1( \
Jf u'e';f=q
Chem 256 - Spring 2015
@
rafretxa( \P \r*
\ )
\ n6*?/t9J,
2D
,J*r\^sZI.-...-'V-
A,-aQha| -re"\ \
1La
,'-4-:( -Lij'.'\ \
l t
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