_TIME
OF CADET_~
SECTION!HR~_ DEPARTURE
_
DEPARTMENT OF CHEMISTRY & LIFE SCIENCE
CH383,2007-2008 WPR II, AlC Hour 26 October 2007 120 minutes McMurry, Organic Chemistry, 7th ed. Chapters: 5-6, 13 Experiment: 2-4
INSTRUCTIONS 1. Do not mark on this exam or open it until "begin work" is given. 2. Solve problems in the space provided. SHOW ALL WORK. ANSWER ALL QUESTIONS. 3. Molecular model kits are permitted; however, models may only be assembled after "begin work" is given. The molecular model instruction booklet is not permitted. General and Organic Chemistry RDCs are authorized. Calculators are NOT authorized. 4. There are 11 pages in this exam. Report any illegible or missing pages to the OIC in the hallway. Write your name in the spaces provided.
(TOTAL WEIGHT: 200 POINTS)
DO NOT WRITE IN THIS SPACE
PROBLEM
MAX SCORE
CUT
YOUR SCORE
I
80
II
SO
40 30 200 20
III IV
TOTAL GRADE
EXTRA CREDIT
Name: Problem I, Fundamentals, 80 points
---------
(12) 1. What is the IUPAC name for the following compounds?
a.
b.
/
; -' r1 , I'
L._Ci\\
I
I,
,~
I,
I
1.-
c.~
d.
(I
(
\
)
I
(12) 2. Draw the following structures: a. 3-ethyl-2-methyl-2-hexene
//
b. (E)-3-bromo-l-fluoro-2-methylpropene
/"
\
/
/r-----J )-:::::;:':--1"
... ........
c. 3-bromo-2-methylcyc1ohexene
d. 5-isopropyl-l-methy1cyc1opentene
/~/
i
.-:
\--1
(
(/
(3) 3. ~ch of the following statement(s) about ethene is(are) incorrect? (a.; The H-C-H bond angles are approximately 109.5. \'-\:): All of the hydrogen atoms are in the same plane. c. There are a total of five sigma bonds. d. The carbon atoms are Sp2 hybridized. CH383, AY07-08 WPRII, AlC Hour 1
Name: Problem I, Fundamentals, 80 points (continued)
---------
(3) 4. Which species below is the intermediate in the free radical addition of HBr to 1 butene?
A)
B)
..--~':.~-.....
H 3C-CH2 -CH2-CH2
.
-',-/,
C) H3C-CH2-CH-CH2Br
(12) 5. Consider the following reaction energy diagram:
D
B
E
A
G
Progress of rxn
a. Write the letter(s) that identify any intermediate(s).
-"("=-':_ '-'.'_ _
b. Write the letter(s) that identify any transition state(s). - -
c. Is this reaction exergonic or endergonic?
_
CH383, AY07-08 WPRII, AlC Hour
2
Name:- - - - - - - - Problem I, Fundamentals, 80 points (continued)
(4) 6. Circle the point on the potential energy diagram that corresponds to the species below for the reaction of 2-methylpropene with hydrogen chloride.
energy
reaction coordinate
(3) 7. Which of the following correctly depicts the mechanistic first step in the addition of HBr to 2-methylpropene?
L)CH n
3
0
H
lJr
(3) 8. Which of the following is the key intermediate in the Markovnikov addition of HBr to I-butene?
CH383, AY07-08 WPRlI, AlC Hour
3
Name: Problem I, Fundamentals, 80 points (continued)
---------
(3) 9. Which of the following is the most stable carbocation?
CH3
/"
....--
-,
~-
I.
II.
III.
oe
0 Oe (5
e
v.
6
i
\.
IV.
CH3
(3) 10. According to the Hammond Postulate, which of the following is correct?
\ a. 1 The transition state of an exergonic reaction step will be more reactant-like '--./ that product-like. b. All transition states are more product-like that reactant-like. c. All transition states are more reactant-like that product-like. d. The transition state of an endergonic reaction step will be more reactant-like that product-like. e. The intermediate of an endergonic reaction step will be more reactant-like than product-like.
CH383, AY07-08 WPRII, Ale Hour
4
Name:- - - - - - - - Problem I, Fundamentals, 80 points (continued)
(8) 11. For the following reactions draw the more stable organic product: a.
a
CH3
Hel
/ 'r ... (\_c.
L/~
b.~
Rei
~
/~.'I I
BC
(8) 12. For the following compounds write the number of IH NMR and signals you would expect: a.
0
NMR
b.
~
~
lH NMR signals:
BC NMR signals:
Lf \
I
1H
NMR signals:
1
'7 (,
)
BC NMR signals:
(6) 13. What would the splitting pattern in lH NMR be of the proton marked by the arrow (---.)?
(
Splitting pattern:
_...:...T~...:...r-'-i,(_.::...:5__ ._ _ I
..)
;
Splitting pattern:
_
CH383, AY07-08 WPRlI, AlC Hour
5
Name: - - - - - - - - - Problem II, Mechanisms, 50 points
(30) 1. Draw the mechanism for each reaction shown below. Show all lone pair electrons, any formal charges, the movement of electrons with electron-pushing arrows, and the structure of all reactants, intermediates and products as you complete the transformation. D:n._~_~~,Rthe~~::~~:~tates for your mechanism.
a.
--.-.-/
'
P :ci:
--',
/~ 1 ."
H-Cl:
t
'.
+
~-
\
\
'-
/,,1'
- ~ _ . __
._----_
/
..
,,//
/,/
/"
/
//
r.'
1'
i
,
.'-_.
b.
,r:.,..
I ..
H-Cl:
.,
+
."
---~---
----"
CH383, AY07-08 WPRlI, AlC Hour
6
Name: - - - - - - - - - Problem II, Mechanisms, 50 points (continued)
(20) 2. Draw and completely label an energy diagram corresponding to the mechanism you have drawn in part 1a. Assume the reaction is exergonic.
\\
\ (L
'I
II
I
I
~, '~\\-~i
//'
" ..
I
(
;
I I I
f
t\
\
I
i
" c/(,
~
i~)
CH383, AY07-08 WPRII, AlC Hour
7
Name:- - - - - - - - - Problem III, Spectroscopy, 40 points Based on the spectroscopic information below, propose a structure for the compound with molecular formula CSHIOO. You must show all work and justify your proposal.
100
t1S-1'lI.I-169~
oIJ ;;: (
80
20
-I.
10 20 30
o
L
40
1111
50 60
,II
70 80
I,II
90 100
Iii
110 120
m/z
/
l./
eooo
~:.j
I,
0
( 1 ___
E,l
m
7
~
III
I
., ,
,
f
i
I
L
I
I
I
I
I
9
HSP-.o:10-293
7
6
5
4
3
Z
1
0
ppm
NMR Spectral Data: ppm splitting ppm 153.4 singlet 126.0 138.4 singlet 122.8
13 C
splitting doublet singlet
---
ppm 122.5 112.9
splitting doublet doublet
I
~
./
ppm 20.0 11.4
splitting quartet quartet
CH383, AY07-08 WPRII, AlC Hour
8
Name:- - - - - - - - Problem IV, Laboratory, 30 points
In Experiment 3 you conducted a solid-liquid extraction oftrimyristin from nutmeg. Trimyristin is made from the condensation of glycerol and myristic acid. The structures of the three molecules are shown below.
o
OH OH glycerol
)--(CH2 ) 12 CH 3
o
myristic acid
o-{
o
(CH 2) 12 CH 3
trimyristin
(4) 1. Circle and name each functional group found in glycerol and myristic acid.
(6) 2. Overall, is the trimyristin molecule polar or nonpolar? Explain.
.- I .
J
0'
:(
. i
[
(6) 3. Briefly explain how the extraction oftrimyristin from nutmeg is aided by refluxing the reaction mixture.
-[
/
.
.
-i--"
.'
.
)i "
, "
r-'
CH383, AY07-08 WPRlI, AlC Hour
9
Name:- - - - - - - - - Problem IV, Laboratory, 30 points (continued)
(6) 4. Why was diethyl ether used in this experiment as the extraction solvent as opposed to a more polar solvent.
7ft"
(8) 5. Explain how one might use infrared spectroscopy to distinguish myristic acid from glycerol.
/
---r-;
f
,,
CH383, AY07-08 WPRII, AlC Hour
10
~
.. -'
Name:
----------
Extra Credit, 20 points Draw the structure of the molecule with molecular formula C4HsCl2 that best fits both the lH NMR and l3C NMR. Support your answer by labeling the spectra and your molecule. , !
G/---
-L
-
'1.:'--
<1'
L
1---
7
6
5
4
3
2
o
ppm
)
I
I
I
I
I
I
I
I
I
I
I
200
180
160
140
120
100
80
60
40
20
o
COS-03-793
CH383, AY07-08 WPRII, AlC Hour
11
APPROVED SOLUTION
CADET
SECTIONIHR~
TIME OF DEPARTURE
_
DEPARTMENT OF CHEMISTRY & LIFE SCIENCE
CH383,2007-2008 WPR II, G Hour 26 October 2007 120 minutes McMurry, Organic Chemistry, 7th. ed. Chapters: 5-6, 13 Experiment: 2-4
INSTRUCTIONS 1. Do not mark on this exam or open it until "begin work" is given. 2. Solve problems in the space provided. SHOW ALL WORK. ANSWER ALL QUESTIONS. 3. Molecular model kits are permitted; however, models may only be assembled after "begin work" is given. The molecular model instruction booklet is not pennitted. General and Organic Chemistry RDCs are authorized. Calculators are NOT authorized. 4. There are 11 pages in this exam. Report any illegible or missing pages to the OIC in the hallway. Write your name in the spaces provided.
(TOTAL WEIGHT: 200 POINTS)
DO NOT WRITE IN THIS SPACE
PROBLEM
MAX SCORE
CUT
YOUR SCORE
I II
80 50
40
III
IV
30
TOTAL GRADE
EXTRA CREDIT
200
20
APPROVED SOLUTION
Problem I, Fundamentals, 80 points
Name:- - - - - - - - -
(12) I. What is the IUPAC name for the following compounds?
a.
b.
cl
(c.')
c.
d.
(J -l{ S -d; (J.i Dr 0 -- ~--l.e.~I\e...
Br
(12) 2. Draw the following structures: a. 3-ethyl-2-methyl-l-pentene b. (Z)-3-bromo-I-fluoro-2-methyl-2-hexene
F
c. 2-chloro-3-ethylcycloheptene
d. 5-t-butyl-3-ethylcyclohexene
(3) 3. Which of the following statement(s) about ethene is(are) incorrect? a. The H-C-H bond angles are approximately 120. b. All of the hydrogen atoms are in the same plane. c. There are a total of five sigma bonds.
@ The carbon atoms are Sp3 hybridized.
CH383, AY07-08 WPRlI, G Hour
1
APPROVED SOLUTION
Problem I, Fundamentals, 80 points (continued)
Name:
---------
(12) 4. Consider the following reaction energy diagram:
D
B
A
Progress of rxn
a. Write the letter(s) that identify any intennediate(s). b. Write the letter(s) that identify any transition state(s). c. Is this reaction exergonic or endergonic?
J
C.
8, ()
j
f\d(JfC[D('.!~L
(3) 5. Which species below is the intennediate in the free radical addition ofHBr to 1 butene?
A)
B)
D)
H 3C-CHz-CH-CHz I Br
.
CH383, AY07-08 WPRII, G Hour
2
APPROVED SOLUTION
Problem I, Fundamentals, 80 points (continued)
Name:- - - - , . - - - -
(4) 6. Circle the point on the potential energy diagram that corresponds to the species
below for the reaction of 2-methylpropene with hydrogen chloride.
energy
reaction coordina.te
(3) 7. Which of the following correctly depicts the mechanistic first step in the addition
ofHBr to 2-methylpropene?
@(CH3
nC=CH2
"---/ lJ
H-Br
(3) 8. Which of the following is the key intermediate in the Markovnikov addition of
HBr to I-butene?
CH383, AY07-08 WPRII, G Hour
3
Name:- - - - - - - - Problem I, Fundamentals, 80 points (continued)
(3) 9. Which of the following is the most stable carbocation?
ll.
v.
ill.
(3) 10. According to the Hammond Postulate, which of the following is correct?
a. The transition state of an endergonic reaction step will be more reactant-like that product-like. b. The intermediate of an endergonic reaction step will be more reactant-like ~ ~~han product-like. Ls/fhe transition state of an exergonic reaction step will be more reactant-like that product-like. d. All transition states are more product-like that reactant-like. e. All transition states are more reactant-like that product-like.
CH383, AY07-08 WPRII, G Hour
4
APPROVED SOLUTION
Problem I, Fundamentals, 80 points (continued)
Name:- - - - - - - - -
(8) 11. For the following reactions draw the more stable organic product:
g,-.
a.
HBr
~
b.
HBr
(8) For 12. the following compounds write the number of IH NMR and DC NMR signals you would expect:
a.
b.
IH NMR signals: DC NMR signals:
'J.
IH NMR signals: DC NMR signals:
!i
b
_3 __
(6) 13. What would the splitting pattern in IH NMR be of the proton marked by the arrow (---+)?
b.
HXO,~HH
H H
~
X
H
'"
Splitting pattern: CH383, AY07-08
L
H
fAC
,-k+
Splitting pattern:
[--- ,-p
i
b- t
5
WPRII, G Hour
Name: Problem II, Mechanisms, 50 points
---------
(30) 1. Draw the mechanism for each reaction shown below. Show all lone pair electrons, any formal charges, the movement of electrons with electron-pushing arrows, and the structure of all reactants, intermediates/and products as you complete the transformation. Do not draw the transition states for your mechanism.
a.
~
H-~;: +
L
~..
0
~
f
T
b.
,B .
..! '
CH383, AY07-08 WPRII, G Hour
6
Name:_ _ _ _ _ _ _--1
APPROVED SOLU"'fJGN
roblem II, Mechanisms, 50 points (continued)
(20) 2. Draw and completely label an energy diagram corresponding to the mechanism [you have drawn in part lao Assume the reaction is exergonic.
___r -I
1S:.1-~
b }
--
-
p
~.------
CH383, AY07-08
WPRII, G Hour
7
Name:' - - - - - - - - Problem III, Spectroscopy, 40 points Based on the spectroscopic information below, propose a structure for the compound with molecular formula CgHIOO. You must show all work and justify your proposal.
100
"5......... 0710
80
'0;
~
60
~
J;;
:;:;
> "
0>
~
40
20
30
40
50
60
70
80
90
100
110
120
m/z
l
.-------------------------~
o.
(Yb14
....
..DO
....
q
G
U .. 1f1If.... 61t .. 1
1...
'Ill
~ c.. of
)
~
11
10
9
8
7
6
5
4
3
o
ppm
)pectralD ata: ppm splitting ppm splitting ppm I 138.6 singlet 128.5 doublet lr' 63.5 1\ f; 39.2 129.0 doublet Itt 126.3 doublet CH383, AY07-08 WPRII, G Hour
8
splitting triplet triplet
Name:- - - - - - - - Problem N, Laboratory, 30 points
In Experiment 3 you conducted a solid-liquid extraction oftrimyristin from nutmeg.
Trimyristin is made from the condensation of glycerol and myristic acid. The structures ofthe three molecules are shown below.
OH OH OH
glycerol
trimyristin
(4) 1. Circle and name each functional group found in trimyristin and myristic acid.
(6) 2. Overall, is the trimyristin molecule polar or nonpolar? Explain.
(6) 3. Briefly explain how the extraction oftrimyristin from nutmeg is aided by refluxing the reaction mixture.
---r1 f /....~
"'<>-"
I"
J ""J.,
r<lcJ~ .+k,~ "t
r
f\ LA "'-'"!'
.j... .
I.
vv
,k-'"'
I'A
I"l
I
VI
~ '- Cl
J'
+.0'
'-4
(D
j
IDw(,
jb
It'
c t..+
Iv'<' j.
~4"IVrArlL ~ fr; ~T~f."'i j,l, d 1 1 ~ \ '" c, ,JJ ,~ ,11 f /0 etle" (/ ~ n,. '),.
{>(
I~,--f
0? (C' C\~-f' \
+1~ {r;'11'7 / j+, A
I
I
r"
CH383, AY07-08 WPRII, G Hour
9
Name:- - - - - - Problem N, Laboratory, 30 points (continued)
(6) 4. Why was diethyl ether used in this experiment as the extraction solvent as opposed to a more polar solvent.
(8) 5. Explain how one might use infrared spectroscopy to distinguish myristic acid from trimyristin.
CH383, AY07-08 WPRlI, G Hour
10
--...'
'.-/
-
-
,
Name:. _ - - - - - - -
Extra Credit, 20 points Draw the structure of the molecule with molecular formula C4H gClz that best fits both the
IH NMR and 13C NMR. Support your answer by labeling the spectra and your molecule.
lc
LJ 4 =- (J.x lj) i J.- /0 -I D:: 0
'V'
q
I
10
9
8
7
6
5
4
3
2
o
tFM-/Jo-04S
ppm
3
I
J-'
c/
C/
I 40
I
I
I
I
I
ZOO
180
160
140
120
T 100
l
r
60
I
80
20
o
(05-03-705
CH383, AY07-08 WPRII, G Hour
11
APPROVED SOLUTION
CADET SECTIONIHR TIME OF DEPARTURE _
DEPARTMENT OF CHEMISTRY & LIFE SCIENCE CH383, 2007-2008 WPR II, I Hour 26 October 2007 120 minutes McMurry, Organic Chemistry, 7th ed. Chapters: 5-6, 13 Experiment: 2-4
INSTRUCTIONS 1. Do not mark on this exam or open it until "begin work" is given. 2. Solve problems in the space provided. SHOW ALL WORK. ANSWER ALL QUESTIONS. 3. Molecular model kits are permitted; however, models may only be assembled after "begin work" is given. The molecular model instruction booklet is not permitted. General and Organic Chemistry RDCs are authorized. Calculators are NOT authorized. 4. There are 11 pages in this exam. Report any illegible or missing pages to the OIC in the hallway. Write your name in the spaces provided.
(TOTAL WEIGHT: 200 POINTS)
DO NOT WRITE IN THIS SPACE
PROBLEM
MAX SCORE
CUT
YOUR SCORE
I II
I
80 50 40 30 200 20
III
IV
TOTAL GRADE EXTRA CREDIT
APPHOVED SOLUTION
Problem I, Fundamentals, 80 points
Name:- - - - - - - -
(12) 1. What is the IUPAC name for the following compounds?
a.
b.
c.
d.
CI
(2:\ -q:"dJoro-'!Yf"-e:t~1-1~ep~f'e(12) 2. Draw the following structures: a. cis-5-ethyl-4-methyl-2-octene b. (E)-1-bromo-3-fluoro-2-methyl-2-hexene
CI
c. 3-bromo-2-ethylcyclopentene
(I
(3) 3. Which of the following statement(s) about ethene is(are) incorrect? a. The H-C-H bond angles are approximately 120. b. All of the hydrogen atoms are in the same plane.
k) There are a total of four sigma bonds.
'(( The carbon atoms are Sp2 hybridized.
CH383, AY07-08 WPRII, I Hour 1
Name:- - - - - - - - Problem I, Fundamentals, 80 points (continued)
(12) 4. Consider the following reaction energy diagram:
D
B
A
Progress of rxn
a. Write the letter(s) that identify any intennediate(s). b. Write the letter(s) that identify any transition state(s). c. Is this reaction exergonic or endergonic?
C
()! U
'" f'\
..erdQrc, of',) ~_
J
(3) 5. Which species below is the intennediate in the free radical addition ofHBr to 1 butene?
A) B)
H3C-CH2-CH-CH2Br
.
D)
H 3C-CHz-CH-CH2 I Br
.
CH383, AY07-08 WPRII, I Hour
2
P'.P?20VED SOLUTlOf\J
Problem I, Fundamentals, 80 points (continued)
Name:
_
(4) 6. Circle the point on the potential energy diagram that corresponds to the species
below for the reaction of 2-methylpropene with hydrogen chloride.
energy
reaction coordinate
(3) 7. Which of the following is the key intermediate in the Markovnikov addition of
HBr to I-butene?
G3
C) CH3CH29HCH2
Br
(3) 8. Which of the following correctly depicts the mechanistic first step in the addition
ofHBr to 2-methylpropene?
@(CH]nvH~I
..
. D). (CH3hc=cHi
\
~U
H - Br
CH383, AY07-08 WPRII, I Hour
3
Name:- - - - - - - - -
Problem I, Fundamentals, 80 points (continued)
(3) 9. According to the Hammond Postulate, which of the following is correct? a. The intermediate of an endergonic reaction step will be more reactant-like than product-like. The transition state of an exergonic reaction step will be more reactant-like that product-like. c. The transition state of an endergonic reaction step will be more reactant-like that product-like. d. All transition states are more product-like that reactant-like. e. All transition states are more reactant-like that product-like.
G)
(3) 10. Which of the following is the most stable carbocation? CH3
1.
6
e
ll.
ID.
00 (5 0 0
4
V.
CH383, AY07-08 WPRII, I Hour
J.:='??O\fED SOLUTION
Problem I, Fundamentals, 80 points (continued)
Name:- - - - - - - -
(8) 11. For the following reactions draw the more stable organic product:
a.
HBr
L
b.
HBr
(8) 12. For the following compounds write the number of IH NMR and B C NMR
signals you would expect:
b.
Cl
0
IH NMR signals:
?-
1H
NMR signals: NMR signals:
J
l3C NMR signals:
3
BC
~
(6) 13. What would the splitting pattern in 1H NMR be of the proton marked by the arrow (---.)?
H
HXO
H" H
n
)
H
H
H
H
Splitting pattern: CH383, AY07-08
_t-,-r--,-!IDi'"-~_-t _ _
i
Splitting pattern: 5
_(.e-"
'+ ~_f\-+'1_~_'_'_ _
WPRII, I Hour
j
_"i-" ,
.J
j
'cD SOL'U"r' ""I ! J:J,.J
L. '
Name:- - - - - - - - Problem II, Mechanisms, 50 points
(30) 1. Draw the mechanism for each reaction shown below. Show all lone pair electrons, any formal charges, the movement of electrons with electron-pushing arrows, and the structure of all reactants, intermediates and products as you complete the transformation. Do!!.Q! draw thrransition states for your mechanism.
f
a.
'Br:
...
/
b.
H-Br: ~.
~)---\ \~ II
+
~
CH383, AYO?-08 WPRII, I Hour
6
Name:- - - - - - - Problem II, Mechanisms, 50 points (continued)
(20) 2. Draw and completely label an energy diagram corresponding to the mechanism you have drawn in part 1a. Assume the reaction is exergonic.
f
)
b.,{~J (I rJ
,,0
CH383, AY07-08 WPRII, I Hour
7
Name:- - - - - - - - Problem III, Spectroscopy, 40 points Based on the spectroscopic information below, propose a structure for the compound with molecular formula CgHIOO. You must show all work and justify your proposal.
100
I1S-Pflj-DSSO
Q{J__ ~-<&')./.)--=/~-lo~~t :: If
...
/.
80
I"
I'I'qJ /} ~Il.
lS If). o~ fOX.140(]'l~ "
D' -;:. 9t-og
J b4 VI.)
(J)
...
.~
t
40 20
X
&
C>
I ~400'- ~ I:J-.)"U,
L-
0
10
IOD
I.
.1
40
,1"
50 60
.1.
J
70 80
L
90
.1.
100 110 120
20
30
m/z
IAYtJiIlI1U,U",1
~ -.
,
I
I'l
'-
!
f----
{:
1-1
;!
q!,
)Ie{
<:
--'~'J JJ
7 6
H J II
5
4
ppm
3
2
a
13C NMR Spectral Data: ppm splitting ppm splitting 153.2 singlet J 129.4 doublet 130.3 singlet '1 127.0 doublet CH383, AY07-08 WPRII, I Hour
r
ppm
121.1 115.3
b
splitting ppm splitting doublet 7 22.9 triplet y 14.0 quartet doublet
8
Name:- - - - - - - - Problem N, Laboratory, 30 points
In Experiment 3 you conducted a solid-liquid extraction oftrimyristin from nutmeg. Trimyristin is made from the condensation of glycerol and myristic acid. The structures of the three molecules are shown below.
o/~lo I
glycerol
myristic acid
trimyristin
(4) 1. Circle and name each functional group found in trimyristin and myristic acid.
(6) 2. Overall, is the trimyristin molecule polar or nonpolar? Explain.
Je
Me>.
1(; '~"1
!
I\(jr,
pal
0 I'
LC.I.~ v'"'
fL~ j1~r J{~'-'Ps.
(,;
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CH383, AY07-08 WPRII, I Hour
9
Name:- - - - - - - - Problem N, Laboratory, 30 points (continued)
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(8) 5. Explain how one might use infrared spectroscopy to distinguish myristic acid from trimyristin.
CH383, AY07-08 WPRII, I Hour
10
Name:- - - - - - - - Extra Credit, 20 points Draw the structure of the molecule with molecular formula C4H gCh that best fits both the lH NMR and B C NMR. Support your answer by labeling the spectra and your molecule. *Both signals are triplets
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CH383, AY07-08 WPRII, I Hour
11