UNIVERSITY OF VICTORIA FINAL EXAMINATION, DECEMBER …

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


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


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


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


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]


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


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


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!


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


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


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


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


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


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


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]


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]


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


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


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]


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)


Draw your structure for compound G on the yellow answer sheet in the place provided[10 marks]


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


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


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]


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:


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]


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]


-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]


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]


{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]

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UNIVERSITY OF VICTORIA FINAL EXAMINATION, DECEMBER …