UNIVERSITY OF VICTORIA
FINAL EXAMINATION, DECEMBER 2007
CHEMISTRY 213 - F01
PRACTICAL SPECTROSCOPY
TIME: 3 HOURS
INSTRUCTOR: Dr Reg Mitchell
IN THIS EXAM THERE SHOULD BE 28 WHITE PAGES (check this)
(which includes THIS COVER SHEET) [NOTE: PAGES ARE PRINTED BOTH SIDES]
+ A BLUE SIGNATURE SHEET
YOU ALSO SHOULD HAVE
A GREEN COMPUTER SHEET
A YELLOW ANSWER SHEET PACK (2 sheets, 4 sides)
A PINK DATA SHEET PACK (3 sheets, 6 sides)
Report to the invigilator if any of these are missing now
ANSWER QUESTIONS 1-60 [1.2 marks each] ON THE GREEN COMPUTER SHEET
WITH A PENCIL = 78 marks;
ANSWERS THAT REQUIRE YOU TO DRAW A STRUCTURE, GIVE A FORMULA,
ETC, HAVE LETTERS AS QUESTION #’S. ANSWER THESE ON THE YELLOW
SHEETS PROVIDED. USE A PEN OR PENCIL, BUT MAKE SURE YOUR ANSWER IS
READABLE = 82 marks. Total Marks = 160; Total minutes = 180!
MAKE SURE YOUR NAME (LAST(FAMILY) NAME FIRST) AND REGISTRATION
NUMBER ARE ON BOTH THE GREEN COMPUTER SHEET AND THE YELLOW
ANSWER SHEETS - DO THIS NOW, AND ALSO SIGN THE BLUE SHEET
PLACE YOUR STUDENT ID ON THE TOP RIGHT CORNER OF THE TABLE
ELECTRONIC CALCULATORS ARE PERMITTED, BUT MUST NOT CONTAIN
STORED PROGRAMS OR FORMULAE
CHEM 213 2007 Final Exam Page 2
NUMBERED QUESTIONS: ANSWER ON THE GREEN COMPUTER SHEETPROVIDED USING A PENCIL; CHOICES MAY BE USED MORE THAN ONCE.SOME QUESTIONS MAY REQUIRE DATA SUPPLIED ON THE PINK SHEETS!
Four IR spectra (Q1-4) and ten compounds (a - j) are shown below. Assign each spectrumto a compound. | | | | | | | | | | 34 30 26 22 18 17 16 9 8 7 00's cm-1
Q1
Q2
Q3
Q4
| | | | | | | | | | 34 30 26 22 18 17 16 9 8 7 00's cm-1
CHEM 213 2007 Final Exam Page 3
Compounds a - j for Q 1-4
CH2COCH3 CHOCH2CH3 O
O
O
OO O COCH2CH3
O
NH2 H2N
O
CN CH2OH CC CH2ClH
COCH3
CH2CH3
(a) (b)(c)
(d) (e)
(f) (g) (h) (i) (j)
Compound A is aromatic and contains normal functional groups, and shows the followingir spectrum
Scale | | | | |3400 1600 1180 1050 750 cm-1
In its mass spectrum, A showed an M+ at 185 and an M+2 peak at 187 in a 1:1 ratio. Aswell an 8% (M+1) peak at 186 was seen. High resolution MS indicated only one nitrogenatom to be present in a molecule of A. Fragment peaks were seen at m/z 15, 30 and 106.
5 How many carbon atoms are present in a molecule of A(a) 3 (b) 4 (c) 5 (d) 6 (e) 7 (f) 8 (g) 9 (h) 10 (i) 11 (j) 12
Determine the molecular formula for A and write it on the yellow answer sheet [2 marks]
Determine the structure of A and draw it on the yellow answer sheet -show all H’s [6
CHEM 213 2007 Final Exam Page 4
marks]
Me2NOH
O RU-486
The structure of the abortion pill, mifeprex, known as RU-486 is shown above. Themolecule contains three non-interacting chromophores.Using the wavelength choices (nm) (a) 340-360 (b) 270-280 (c) 250-260 (d) 210-215 (e) 200-205 (f) 180-190and ε choices (a) 15,000 (b) 1,000 (c) 200 (d) 40 (e) 1
6 Where would you expect to find π3 6 π3* for the diene-one chromophore7 What ε value would this (Q#6) absorption have8 Where would you expect to find n 6 π3* for diene-one chromophore9 What ε value would this (Q#8) absorption have10 Where would you expect to find the longest wavelength absorption for the amino-
benzene chromophore11 Where would you expect to find π1 6 π1* for the benzene chromophore
Using the choices(a) hypsochromic shift (b) hyperchromic shift (c) bathochromic shift (d) hypochromic shift (e) no shift
12 How would you expect the wavelength of the absorption for the amino-benzenechromophore of RU-486 to change on addition of HCl
CHEM 213 2007 Final Exam Page 5
Lead paint on children’s toys has been in the news recently: Lead chromate PbCrO4 is verybright yellow13 At what wavelength (nm) is this compound absorbing light:(a) 670 (b) 600 (c) 550 (d) 500 (e) 450 (f) 400(g) 350 (h) 300 (i) 250 (j) 300-800
then using the transition choices:(a) π9 6 π9* (b) π1 6 π9* (c) π9 6 n* (d) n 6 π9* (e) L 6 M CT(f) M 6 L CT (g) d 6 d (h) π9 6d (i) d 6 π9* (j) π1 6 d*and ε choices: (a) 3000 (b) 300 (c) 30
14 What transition produces this absorption15 What would its ε value be
When soluble, chromates are carcinogenic, when reduced to pale green Cr (III)compounds, they are not 16 What transition would CrCl3 show (choices above)17 and what would its ε value be (choices above)18 and at what wavelength would its absorption be (choices below)(a) 670 (b) 600 (c) 550 (d) 500 (e) 450 (f) 400(g) 350 (h) 300 (i) 250 (j) 300-800
19 Men’s grey hair when treated with “Grecian Formula” forms some black leadsulfide - what wavelength of light does lead sulfide absorb
(a) 670 (b) 600 (c) 550 (d) 500 (e) 450 (f) 400(g) 350 (h) 300 (i) 250 (j) 300-800
CHEM 213 2007 Final Exam Page 6
As a defense mechanism, skunks emit a smelly compound B, which shows an M+ at m/z 90and also peaks at 91 and 92 in a 100:4.4:4.4 ratio. Fragment peaks were seen at m/z 29, 43and 57.[Isotopic data is available on the pink sheets]The 1H NMR spectrum (low temperature) of compound B is shown below:
Integration ratios 2 : 2 :2:1: 3Multiplicities q 5 6 t tThe peak (triplet) at δ 1.3 exchanges with D2O on warming or in the presence of NaOD(base), and becomes a singlet, and then the peak at δ 2.5 becomes a triplet.Determine the structure of compound B and write in the space provided on the yellowanswer sheet. [5 marks]
CHEM 213 2007 Final Exam Page 7
A product C was obtained from a reaction.The COSY and NOESY spectra of the product, compound C, are shown on the next page.Chemical shifts are approximate. Start by assigning the obvious chemical shifts, and then consider which hydrogens are coupled to these, and then which interact through space.Then choose one of the following 12 isomers of C as its structure and enter its number onthe yellow answer sheet [8 marks]Answer choices:
H
OMe
OMe
H
H
MeMe
Cl
H
H
H
OMe
OMe
H
Me
HMe
Cl
H
H
H
OMe
OMe
H
H
MeCl
Me
H
H
MeO
H
OMe
H
H
MeMe
Cl
H
H
MeO
H
H
MeO
H
MeMe
Cl
H
H
MeO
H
OMe
H
Me
HMe
Cl
H
H
MeO
H
H
MeO
Me
HMe
Cl
H
H
MeO
H
OMe
H
H
MeCl
Me
H
H
MeO
H
H
MeO
H
MeCl
Me
H
H
1 2 3
4 5 6
10 11 12
H
OMe
H
MeO
H
MeMe
Cl
H
H
H
OMe
H
MeO
Me
HMe
Cl
H
H
H
OMe
H
MeO
H
MeCl
Me
H
H
7 8 9
CHEM 213 2007 Final Exam Page 8
NOESY SPECTRUM OF C (approx chem shifts given)(note COSY correlations have been removed, and each peak is shown as a line)
1.0 d (3H)
1.6 s (3H)
2.2 ddd (1H)
2.6 dd (1H)2.8 qd (1H)
3.3 s (3H)
3.7 s (3H)
4.3 t (1H)
4.9 t (1H)
1.0
d (3
H)
1.6
s (3H
)
2.2
ddd
(1H
)
2.6
dd (1
H)
2.8
qd (1
H)
3.3
s (3H
)
3.7
s (3H
)
4.3
t (1H
)
4.9
t (1H
)NOESY
CHEM 213 2007 Final Exam Page 9
COSY SPECTRUM OF C
1.0 d (3H)
1.6 s (3H)
2.2 ddd (1H)
2.6 dd (1H)2.8 qd (1H)
3.3 s (3H)
3.7 s (3H)
4.3 t (1H)
4.9 t (1H)1.
0 d
(3H
)
1.6
s (3H
)
2.2
ddd
(1H
)
2.6
dd (1
H)
2.8
qd (1
H)
3.3
s (3H
)
3.7
s (3H
)
4.3
t (1H
)
4.9
t (1H
)COSY
Do not forget to put your answer on the yellow sheet!
CHEM 213 2007 Final Exam Page 10
For the compound CN
Hc
Hb
OCH3Ha
CH3O
Use the choices of chemical shift(a) 7.81 (b) 7.57 (c) 7.35 (d) 7.27 (e) 7.17(f) 7.01 (g) 6.97 (h) 6.89 (i) 6.38 (j) 6.33
20 Calculate the chemical shift for Ha
21 Calculate the chemical shift for Hb
Using the choices:(a) AB (b) AX (c) A2 (d) AA’22 What will be the spin system for the protons Ha and Hb at 360 MHz23 If Ha were replaced by a -CN, what spin system would describe Hb and Hc
Using the choices (ppm):(a) 1 (b) 8 (c) 16 (d) 22 (e) 28 (f) 32 (g) 37 (h) 40 (i) 48 (j) 56
24 What will be the difference in carbon chemical shift between the two adjacent ringcarbons bearing the methoxyl and nitrile groups for the molecule at the top of page.
25 What colored Christmas lights would emit photons of energy 216 kJ/mole
(a) red (b) blue (c) green (d) yellow(e) orange (f) violet (g) white
CHEM 213 2007 Final Exam Page 11
For the molecule H2S, the S–H stretch appears at 2615 cm-1
26 At what frequency (Hz) would you expect to find the S–D stretch(a) 1.1 x 108 (b) 5.6 x 108 (c) 7.8 x 108 (d) 5.6 x 109 (e) 7.8 x 1011
(f) 5.6 x 1013 (g) 7.8 x 1013 (h) 1.1 x 1014 (i) 7.8 x 1015 (j) 1.1 x 1018
Using:(a) 0 (b) 1 (c) 2 (d) 3 (e) 4 (f) 7 (g) 17 (h) 18 (i) 21 (j) 24
27 How many ir active S–H stretches would you expect to see in H2S28 How many fundamental vibrations are possible
and using (cm-1) :(a) 2600 (b) 2200 (c) 1700 (d) 1300 (e) 800 (f) 200
29 When H2S is oxidized, SO2 is formed; where would you expect to find the S=Ostretch
We studied CO2 in class; azide ion, [N3]– (as its potassium salt) also shows 3 fundamentalfrequencies (bands), which are at 2041, 1344 and 645 cm-1
Using (a) none (b) 1 (c) 2 (d) 3 (e) 4 (f) 5 (g) 6 (h) linear (i) bent
30 Based on electron count, is azide linear or bent?31 Then, how many fundamental bands would you expect32 How many active ir bands would you expect
Using (a) P (b) Q (c) R (d) P, Q (e) P, R (f) Q, R (g) P, Q, R
33 Which branches should the 2041 cm-1 band show34 Which branches should the 645 cm-1 band show
CHEM 213 2007 Final Exam Page 12
The 2041 cm-1 fundamental frequency for azide shows a band in which the rotationalspacing constant, B, is 3 cm-1.
35 At what frequency would you find the transition from v=0;J=2 to v=1;J=3(a) 2062 (b) 2059 (c) 2056 (d) 2053 (e) 2050(f) 2047 (g) 2035 (h) 2032 (i) 2029 (j) 2026
36 Would this line appear in the (a) P branch (b) Q branch (c) R branch (d) P and R branches (e) all branches (f) none of the branches
and using the choices(a) 2050 (b) 2032 (c) 4082 (d) 4070 (e) 1020 (f) 1001(g) 6123 (h) 6080 (i) 8164 (j) 808837 Where would the first hotline be found (cm-1)38 Where would the second overtone be (cm-1)
39 If the spin quantum number for D is 1, how will the 31P NMR spectrum ofPD(OCH3)2 appear
(a) 1:2:1 triplet of septets (b) 1:1:1 triplet of septets(c) 1:3:1 triplet of septets (d) 1:1 doublet of septets(e) 3:1 doublet of septets (f) 1:2:1 triplet of quartets(g) 1:1:1 triplet of quartets (h) 1:3:1 triplet of quartets(i) 1:1 doublet of quartets (j) 3:1 doublet of quartets
40 At UVIC, we use the 360MHz proton magnet to observe 31P spectra. Whatfrequency (MHz) will the probe operate at to observe 31P (pink data sheet)
(a) 884 (b) 110 (c) 100 (d) 278 (e) 9(f) 1080 (g) 11 (h) 338 (i) 53 (j) 147
CHEM 213 2007 Final Exam Page 13
For the molecule D:
PtCl Cl
Cl
H
FFCl
H
Assume 2JPt,F = 100 Hz, 3JPt,H = 60 Hz, 4JF,F = 5 Hz and all 5JX,Z are zero. Assume normalother couplings.
using:(a) s (b) d (c) t (d) q (e) dd (f) dt (g) tt (h) ddd (i)ddt (j) dddd
41 How will the 195Pt spectrum appear42 How will the 1H spectrum appear for a molecule that does not contain 195Pt43 How will the 1H spectrum appear for a molecule that only contains 195Pt44 How will the 19F spectrum appear for a molecule that does not contain 195Pt45 How will the 19F spectrum appear for a molecule that only contains 195Pt
46 What will be the width (Hz) of the 195Pt spectrum (i.e. distance in Hz between far lefthand and far right hand lines)
(a) 320 (b) 240 (c) 180 (d) 120 (e) 60(f) 480 (g) 380 (h) 280 (i) 200 (j) 100
47 In the natural abundance 19F spectrum, what is the separation in Hz of the tallestpeaks
(a) 200 (b)120 (c) 100 (d) 60 (e) 20 (f) 5 (g) 1
48 What is the spin system for this compound with a spin active Pt (a) ABC (b) A2B2C (c) AA’BB’C (d) AA’B2C (e) AA’BB’X (f) ABX (g) AMX (h) A2M2X (i) AA’M2X (j) AA’MM’X
CHEM 213 2007 Final Exam Page 14
49 For the compound F2CH-PtCl3, if 2JPt,H = 100 Hz, 2JPt,F =150Hz and 2JH,F = 50 Hz,and if the proton spectrum shows the most shielded line is 2400 Hz downfield fromTMS, what is the chemical shift of this H. The spectrum was run at 400 MHz
(a) -6.50 (b) +6.50 (c) +6.25 (d) -6.25 (e) -6.00(f) +6.00 (g) -5.75 (h) +5.75 (i) -5.50 (j) +5.50
For the hydrogen of the compound referred to in Q49, what would be the intensities of thelines in the real hydrogen spectrum of a sample that only contains spin active platinum-write your answer using the format 1:1:2:1 etc on the yellow answer sheet [3 marks]Hint: you might want first to draw to scale the positions of the lines of the spectrum, spacebelow
CHEM 213 2007 Final Exam Page 15
THE OBJECTIVE IN THE FOLLOWING QUESTIONS IS TO SOLVE THESTRUCTURES. THERE ARE SOME QUESTIONS TO ANSWER ON THE GREENCOMPUTER SHEETS; YOU WILL DRAW YOUR SOLUTION TO EACHSTRUCTURE ON THE YELLOW SHEETS. WORK SPACE IS PROVIDED AFTER EACHQUESTION, THIS WILL NOT BE MARKED; ONLY GIVE YOUR FINAL ANSWER ONTHE YELLOW SHEETS, giving more than one answer leads to penalties.
ALL Proton spectra are 300 MHz
COMPOUND E, C5H8O2
50 How many DBE has compound E(a) 0 (b) 0.5 (c) 1 (d) 1.5 (e) 2 (f) 2.5 (g) 3 (h) 3.5 (i) 4 (j) 4.5
The IR spectrum:
| 1760 cm-1
51 What functional group is present in compound E(a) alcohol (b) aldehyde (c) acid (d) alcohol-ketone (e) ether(f) ester (g) alcohol-aldehyde (h) ketone (i) ether-aldehyde (j) anhydride
13C NMR:169s 153s 102t 21q 20q
CHEM 213 2007 Final Exam Page 16
1H NMR Spectrum
52 Consider the proton spectrum above carefully, then how many chemically differenthydrogens are there
(a) 1 (b) 2 (c) 3 (d) 4 (e) 5 (f) 6 (g) 7 (h) 8
Write your proton integration values on the yellow answer sheet in the place providedin the form a:b:c:etc [2 marks]
Draw your structure for compound E on the yellow answer sheet in the place provided [7 marks]
CHEM 213 2007 Final Exam Page 17
Compound F gave the mass spectrum shown below:
208,210 287,289,291The portion on the right is an expansion of the 285-295 regionA high resolution mass spectrum on the CHON containing fragment of the moleculegave m/z = 129.057 (±0.004)Formula m/zC H N O C H N O m/z10 9 - - 129.070 9 7 1 - 129.0589 5 - 1 129.034 8 19 1 - 129.1518 17 - 1 129.128 8 5 2 - 129.0458 3 1 1 129.021 7 17 2 - 129.1397 15 1 1 129.115 7 13 - 2 129.0927 3 3 - 129.033 7 1 2 1 129.0086 15 3 - 129.127 6 13 2 1 129.1036 11 1 2 129.079 6 9 - 3 129.0556 1 4 - 129.020 5 13 4 - 129.1145 11 3 - 129.090 5 9 2 2 129.0665 7 1 3 129.043 5 5 - 4 129.0194 11 5 - 129.101 4 9 4 1 129.0784 7 3 2 129.054 2 5 6 1 129.053
Determine the molecular formula for compound F and enter it on the yellow answer sheetin the space provided. [4 marks]
CHEM 213 2007 Final Exam Page 18
53 How many DBE are in compound F(a) 0 (b) 1 (c) 2 (d) 3 (e) 4 (f) 5 (g) 5.5 (h) 6 (i) 6.5 (j) 7
IR: an intense peak at 2221 cm-1
54 Which functional group is present in F(a) alcohol (b) aldehyde (c) ketone (d) acid (e) ester (f) acetylene(g) amine (h) amide (i) nitrile (j) acid bromide
The 13C NMR spectrum and the DEPT135 are shown below:
solvent
CHEM 213 2007 Final Exam Page 19
DEPT 135
Using (a) 0 (b) 1 (c) 2 (d) 3 (e) 4 (f) 5 (g) 6 (h) 7
55 How many protons are on the carbon at δ 133.556 How many protons are on the carbon at δ 29.5
CHEM 213 2007 Final Exam Page 20
1H NMR Spectrum [500MHz]
Integrations 1 : 2 solvent : 4
Draw your structure for compound F on the yellow answer sheet in the place provided[8 marks]
CHEM 213 2007 Final Exam Page 21
Compound G, C11H19NSi [note: Si is more electropositive than carbon, but is in the same group]
57 How many DBE in G(a) 0 (b) 1 (c) 2 (d) 3 (e) 4 (f) 5 (g) 6 (h) 7
IR Spectrum:
| | | | 3300 (single peak) ~1100 735 698 cm-1
1H NMR Spectrum [300MHz]:
Integrations: 5 : 2 : 2 : 1 : 9The peak at δ 1.2 exchanges with D2O
13C NMR 141(s) 129(d)128(d)127(d) 58(t) 40(t) -3(q)
CHEM 213 2007 Final Exam Page 22
Draw your structure for compound G on the yellow answer sheet in the place provided[10 marks]
CHEM 213 2007 Final Exam Page 23
COMPOUND H, C12H16O3
58 How many DBE are present in compound H(a) 0 (b) 1 (c) 2 (d) 3 (e) 4 (f) 5 (g) 6 (h) 7 (i) 8 (j) 9
The IR spectrum :
| 1699 cm-1
The 1H NMR spectrum [300MHz]:
Integrations: 1 : 1 3:3 :2 : 3 : 3
The 13C NMR spectrum: 202s 162s 159s 128d 126s 120s 106d 62q 56q 35t 21q 12q
CHEM 213 2007 Final Exam Page 24
From the above data, you should be able to get four or more isomers as possible structures.
The protons at δ 1.2 show a strong correlation to the carbon at δ 202 in the HMQC (J=10)which is also correlated to an aromatic proton in the long range Hetcor spectrum.
This will reduce the possible number of isomers to TWO - draw your structures for thesetwo isomers of compound G on the yellow answer sheet in the place provided[10 marks]Then use the following data to decide which is isomer G and circle this isomer on the yellowanswer sheet [ 5 marks]
An HMQC (J=135 Hz) [Short range Hetcor] spectrum of compound HHMQC (J=135 Hz)Short range Hetcor
1.2
t
2.1
s
3.0
q3.7
s3.
9 s
6.7
d
7.5
d
12 q
21 q
35 t
56 q
62 q
106 d
120 s
126 s128 d
159 s162 s
202 s
CHEM 213 2007 Final Exam Page 25
An HMQC (J=10 Hz) long range Hetcor spectrum of compound HHMQC (J=10 Hz)Long range Hetcor
1.2
t
2.1
s
3.0
q3.7
s3.
9 s
6.7
d
7.5
d
12 q
21 q
35 t
56 q
62 q
106 d
120 s
126 s128 d
159 s162 s
202 s
Reminder: circle the correct isomer for compound H on the yellow answer sheet in thespace provided. [ 5 marks]
CHEM 213 2007 Final Exam Page 26
COMPOUND I, C9H8O4
59 How many DBE are in compound I(a) 0 (b) 1 (c) 2 (d) 3 (e) 4 (f) 5 (g) 6 (h) 7 (i) 8 (j)9
The IR spectrum of compound I:
| | |3400 2400 1706 cm-1
60 What is the main functional group present in compound I(a) alcohol (b) ether (c) aldehyde (d) ketone (e) ester(f) acid (g) anhydride (h) amide
The 13C NMR spectrum of I:177s 148s 147s 126s 122d 110d 109d 99t 41t
The proton spectrum of I is on the next page:
CHEM 213 2007 Final Exam Page 27
The proton spectrum of I:
One of the hydrogens (not shown above) appears as a broad peak at δ 13 which exchangeswith D2O; the small peak at δ 7.24 is CHCl3
Remaining integrations 3 : 2 : 2
Note the peak at δ 7 is complex, but if it were 1st order would have been two doublets and asingletThe hydrogens at δ 3.5 show an HMQC (J=10) long range hetcorr to TWO carbons at δ110 and 122.Now solve the general structure for compound I - hint: have you used all your DBE.The hetcor above also allows you to specify which isomer you have.
Check your result with the data shown below, and then
draw the structure of compound I on the yellow answer sheet [12 marks]
CHEM 213 2007 Final Exam Page 28
3.5
s
5.9
s
6.7
d, d
, s
41 t
99 t
109 d
122 d
126 s
147 s148 s
177 s
110 d
HMQC (J=10 Hz)Long range Hetcor
HMQC (J=135) Short range hetcor
3.5
s
5.9
s
6.7
d, d
, s41 t
99 t
109 d
122 d
126 s
147 s148 s
177 s
110 d
HMQC (J=135 Hz)Short range Hetcor
HMQC (J=10) [Long range Hetcor]
CHEM 213 2007 Final Exam Page 29
-END-
FINAL EXAMINATION, DECEMBER 2007 YELLOW ANSWER SHEETS
CHEMISTRY 213 - F01 PRACTICAL SPECTROSCOPY
LAST NAME:
FIRST NAME AND INITIAL:
REGISTRATION NUMBER:
ALSO PUT YOUR NAME ON SHEET TWO (Side 3).
GIVE ONLY YOUR FINAL STRUCTURES ON THIS SHEET, SPACE FOR ROUGH
WORK IS PROVIDED ON THE QUESTION SHEET. Part marks will be given for partial
structures or partly correct structures; do NOT give ANY of the detail as to how you
derived the structure. THESE PAGES ARE PRINTED BOTH SIDES!
MAKE SURE YOU SHOW ALL ATOMS INCLUDING HYDROGENS
IN YOUR FINAL STRUCTURES
MARKS FROM THIS SHEET [/82] =
{Page 3} FORMULA FOR COMPOUND A [2 MARKS] =
{Page 3} STRUCTURE FOR COMPOUND A [ 6 MARKS]
Yellow Answer Sheet 1, page 2 213 Final 2007
{Page 6} STRUCTURE FOR COMPOUND B [5 marks] =
{Page 7} STRUCTURE FOR COMPOUND C [8 marks] =
[a number from 1-12 is required]
{Page 14} Relative intensities of the hydrogen lines for compound of question 49 [3 marks]
[format required = 1:b:c: etc] =
{Page 16} COMPOUND E: Proton Integration values [a:b:c: etc][2 marks]=
{Page 16} STRUCTURE FOR COMPOUND E (show all H’s) [7 marks]
Yellow Answer Sheet 2, page 3 213 Final 2007
LAST NAME FIRST NAME
{Page 18} MOLECULAR FORMULA FOR COMPOUND F [4 marks]
{Page 20} STRUCTURE FOR COMPOUND F (show all H’s) [8 marks]
{Page 22} STRUCTURE FOR COMPOUND G (show all H’s) [10 marks]
Yellow Answer Sheet 2, page 4 213 Final 2007
{Page 24} TWO ISOMERS FOR COMPOUND H (show all H’s) [10 marks]
{Page 25} CIRCLE correct isomer [5 marks]
{Page 27} STRUCTURE FOR COMPOUND I (show all H’s) [12 marks]