Problem 1

IR Spectrum
(liquid film) 1718

4000 3000 2000 1600 1200 800 0.0

V (ern")

100 43
Mass Spectrum
0.5 CIl
o
80 .>t:. co
'"
CIl
0-
€'"
0
60 CIl
til
til
..c UV Spectrum
M+"
40 '5
'"
..c 29 72 1.0 '"
33.3 mg/10 ml
20 * 1.0 cm cell

Y C4H aO
1.5
solvent: ethanol

40 80 120 160 200 240 280 200 250 300 350

m/e A. (nm)
I I I I I I I I I I I

13C NMR Spectrum

(50.0 MHz, CDCI 3 solution)

II II
LlLillL
solvent I

--J -- --'~'__
proton coupled

proton decoupled

I III

I I I I I I I I I I I I

200 160 120 80 40 o 0 (ppm)

1H NMR Spectrum
(200 MHz, CDCI 3 solution)

TMS
1.

90
 Problem 2

IR Spectrum
(liquid film) 1715

4000 3000 2000 1600 1200 800

V (ern")

100 Mass Spectrum

80 -"
co
Q)
c.
60 Q) 45 No significant uv
Vl
co M+"
.0
74 absorption above 220 nm
40 '0
57
~
20
I, j C3 H 602
40 80 120 160 200 240 280
m/e

I I I I I I I I I I I I

13C NMR Spectrum

(50.0 MHz. COCI 3 solution)

I
DEPT CH2~ CH 3t CHt

proton decoupled

200
I I I

160
I I

120
I
solvent

80
I
•
I I

40
U I I

0 o(ppm)
1H NMR Spectrum
(200 MHz. COCI 3 solution)

exchanges
with 0 20
~

~
A
r---

12 11 ~
TMS
--1

I
I I I I I I I I I I I

10 9 8 7 6 5 4 3 2 1 0
o(ppm)

9
r Problem 3

IR Spectrum
(liquid film) 2984
1741 1243

4000 3000 2000 1600 1200 800 0.0

V (crn")

100 Mass Spectrum

43 0.5
80 "'"
'"0- Q)

60 Q)
(/) UV spectrum

40
'"
.a
'0 29 1.0 solvent: ethanol
Q'!. M+"= 88 15.4 mg /10 mls
20 path length: 1.00 cm

~ ,I I C4Ha02
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)

13C NMR Spectrum

(50.0 MHz, CDCI3 solution)

DEPT CH 2 t CH3~ CH~

Ll

proton decoupled solvent

III Il () (ppm)
200 160 120 80 40 0

1H NMR Spectrum
(200 MHz, CDCI3 solution)

TMS

10 9 8 7 6 5 4 3 2 1 o
s (ppm)

92
 Problem 4

,
c,
IR Spectrum 1744
(CCI4 solution)

4000 3000 2000 1600 1200 800

V (cm'")

100 57
Mass Spectrum
29
80 .><
Ctl
Q)
Co
60 Q)
en
No significant UV
Ctl
J::J
M+" = 88 absorption above 220 nm
40 '0
*'
20
I
40 80 120 160 200 240 280
m/e

I I I I I I I I I I I I
13C NMR Spectrum
(100,0 MHz, COCl a solution)

DEPT CH2 t CHat CHt

I I

proton decoupled solvent

I •
I I I I I I I I I I I I

200 160 120 80 40 o 0 (ppm)

1H NMR Spectrum
(200 MHz, COCl a solution)

expansion

2.0
,
10 ppm
I TMS

10 9 8 7 6 5 4 3 2 1 o
o(ppm)

93
 Problem 5

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800

V (ern")

100 Mass Spectrum

27
107/109
80 "''""
Q)
0-
60 Q)
en
No significant UV
'"
.c absorption above 220 nm
40 '0 M+"
~
20 186/188/190

~ .11 ,I, C2 H4 Br2

40 80 120 160 200 240 280

mle

13C NMR Spectrum

(50.0 MHz, CDCI 3 solution)

proton coupled
solvent

I ~
proton decoupled

• I o(ppm)
200 160 120 80 40 0

1H NMR Spectrum
(200 MHz, CDCI 3 solution)

TMS

l'
I I I I I I I I I I I

10 9 8 7 6 5 4 3 2 1 0
s (ppm)

94
 Problem 6

IR Spectrum
(liquid film)
1716

4000 3000 2000 1600 1200 800

V (ern")

100 Mass Spectrum UV Spectrum

43
80 ""
'"0.
Ql

60 CIlQl

40 '0
'"
.0 solvent: methanol

0~
M+' =86
20
I

40 80 120 160 200 240 280

m/e

I I I I I I I I I I I I

13C NMR Spectrum

(100 MHz, CDCI 3 solution)

proton decoupled
,
solvent

200 160 120 80 40 o s (ppm)

1H NMR Spectrum
(200 MHz, CDCI3 solution)

TMS
I

I I I I I I I I I I I

10 9 8 7 6 5 4 3 2 1 o
() (ppm)

95
 Problem 7

IR Spectrum 2249
(KBr disc)

4000 3000 2000 1600 1200 800

V (crn'")

100 Mass Spectrum

80 "'" 53
'"
Q)
o,
60 Q)
Ul
No significant UV
40
40 '0
'"
.I:l
M+" = 80 absorption above 220 nm
'#.
20
~ 1
40 80 120 160 200 240 280
m/e

13C NMR Spectrum

I
(100.0 MHz, CDCI 3 solution)

proton decoupled
- - - ' - - -
solvent L
200 160 120 80 40 o 0 (ppm)

1H NMR Spectrum
(400 MHz, CDCI3 solution)

TMS .

I I I I I I I I I 1

10 9 8 7 6 5 4 3 2 1 o
o(ppm)"

96
 Problem 8

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800

V (em")

100 Mass Spectrum

80 .,., 57
'"a.
<J)

60 <J)
Ul
No significant UV
'"
.."
absorption above 220 nm
40 '0 M+" =114 « 1%)
*-
20 99
II I

40 80 120 160 200 240 280

m/e

I I I I I I I I I I I I
13C NMR Spectrum
(50.0 MHz, CDC'3 solution)

proton decoupled solvent

I
I I I I

200 160 120 80 40 o 0 (ppm)

1H NMR Spectrum
(200 MHz, CDC'3 solution)

TMS

I
I I I I I , I I I I I

10 9 8 7 6 5 4 3 2 1 0
o (ppm)

97
 Problem 9

3458

IR Spectrum
(CCI4 solution)

4000 3000 2000 1600 1200 800

V (crn'")

100 Mass Spectrum

59
80 -'"
to
Q>
0-
60 Q> No significant UV
'"
to
.a
absorption above 220 nm
40 '0
M+' =118 « 1%)
20 *
,I J
40 80 120 160 200 240 280
m/e

I I I I I I I I I I I I

13C NMR Spectrum

(100.0 MHz, CDCI 3 solution)

proton decoupled
sOIV~.1
I I I I I I I I I I I I

200 160 120 80 40 0 S (ppm)

1H NMR Spectrum
(200 MHz, CDCI 3 solution) .. :
:<

~
,;,',
;:>
Exchanges with ..
s,"

°2° t~

"'
S- TMS

I 1
I I I I I I I I I -.1._

10 9 8 7 6 5 4 3 2 1 0
s (ppm)
;

98
 Problem 10

IR Spectrum
(KBrdisc) 1693

4000 3000 2000 1600 1200 800

V (cm'")

100 56 Mass Spectrum

M+' = 112
80 """Q)
'"
0-
60 Q)
VI
No significant UV
'"
.J:J
absorption above 220 nm
40 '0
0~

20
," I,

40 80 120 160 200 240 280

m/e

13e NMR Spectrum

(100.0 MHz, CDCI 3 solution)

proton decoupled
solvent

200 160 120 80 40 o 0 (ppm)

1H NMR Spectrum
(400 MHz, CDCI 3 solution)

TMS

I I I I I I I I I I I

10 9 8 7 6 5 4 3 2 1 0
o(ppm)

99
 Problem 11

IR Spectrum
(liquid film) 1738

4000 3000 2000 1600 1200 800

V (crn")

100 Mass Spectrum

80 ~
Ql
o, M+' = 84
60 ~ No significant UV
'"
.0
absorption above 220 nm
40 '0
<J.
20

40 80 120 160 200 240 280

m/e

13C NMR Spectrum

(100.0 MHz, CDCI 3 solution)

n
proton decoupled

200 160 120

solvent

80
U
40 0 o(ppm)
..

1H NMR Spectrum expansion

(400 MHz, CDCI 3 solution)

2.2 1.8 PPM TMS

10 9 8 7 6 5 4 3 2 1 o
o(ppm)

100
 Problem 12

IR Spectrum
(Ijquidfilm)

4000 3000 2000 1600 1200 800 0.0

V (ern")

Mass Spectrum 0.5

Ql
<J
80 ~

M+"= 156
C
'"
<ll
0. -e'"0 UV spectrum
60 <ll
III III
..c
'"
..c
127 1.0 '" 5.00 mg 110 mls
40 '0 29 path length: 0.50 cm
<t- contains a haloQen
solvent: cyclohexane
20
II
1.5
40 80 120 160 200 240 280 200 250 300 350
role A(nm)

13C NMR Spectrum No TMS in

~'~PI'
(50.0 MHz, CDCI3 solution)

solvent

proton coupled
i

proton decoupled
III L
200 160 120 80 40 0 o(ppm)

1H NMR Spectrum
(200 MHz, CDCI3 solution)

10 9 8 7 6 5 4 3 2 1 o
8 (ppm)
 Problem 13
2989

IR Spectrum
(liquid film) 689

4000 3000 2000 1600 1200 800

V (cm'")

100 63 Mass Spectrum

80 -"
''""
0-
60 '" VJ
No significant UV
'"
.0
65 absorption above 220 nm
40 '0
83 M+'
20 *' 981100/102
I.. ~ II l, JJ C2 H4 CI2
40 80 120 160 200 240 280
m/e

I I I I I I I I I I I I

13C NMR Spectrum

(50.0 MHz, CDCI 3 solution)

proton coupled
61·. . . . 1.... , i' "U III • f t ... 1IIIf'-........ 'J t ' ....
'. , • "P' 4'...... 'LU... 'A roc
. ,i" ....

solvent
proton decoupled
ru I
I I I I I I I I I I I I

200 160 120 80 40 0 " (ppm)

1H NMR Spectrum
(200 MHz, CDCJ3 solution)

L
~
expansions

, , ,
-
,
~

6.0 5.8 ppm 2.2 2.0 ppm

I I I I
=:f I I I I
~

I I
~
TMS

10 9 8 7 6 5 4 3 2 1 0
s (ppm)

102
 Problem 14

IR Spectrum
(liquid film)
3354

4000 3000 2000 1600 1200 800

V (ern")

100 45 Mass Spectrum

80 -'"
C1l
Q)
0-
60 Q)
Vl
No significant UV
C1l
.0
absorption above 220 nm
40 '0
?ft.-.
M+' =60 « 1%)
20 59
JIIHI I C 3H aO

40 80 120 160 200 240 280

m/e

solvent
proton decoupled
•

200 160 120 80 40 o 0 (ppm)

1H NMR Spectrum
(200 MHz. CDCI 3 solution)

expansions

I I I , TMS
4.5 4.0 ppm 1.5 1.0 ppm

10 9 8 7 6 5 4 3 2 1 o
o(ppm)

103
 ~[ ~I r>. " 0 ('r 1\ Problem 15

IR Spectrum
(liquid film)

I I I

4000 3000 2000 1600 1200 600

V (cm" )

100 43 Mass Spectrum

80 .><
'"
Q)
o,
60 Q)
1Il No significant UV
40
'"
.0
'0 absorption above 220 nm
M+"
20 *' 122/124

,I 1I. II C 3 H 7Br
40 80 120 160 200 240 260
m/e

I I I I I I I I I I I r
13C NMR Spectrum
(50.0 MHz, CDCI 3 solution)

DEPT CH 2 , CH 3t CHt

solvent
proton decoupled
~ I
I I I I I I , I I I , I

200 160 120 80 40 0 s (ppm)

1H NMR Spectrum
(200 MHz, CDCI 3 solution)

expansions

1.\.,
-
, , , , , , , , I , TMS
4.6 4.0 ppm 2.0 1.4 ppm ~ -
Ill. I
I I I I I I I I I I I

10 9 8 7 6 5 4 3 2 1 0
s (ppm)

104
 Problem 16

IR Spectrum
(liquid film) 776

2960
650

4000 3000 2000 1600 1200 800

V (ern")

100 Mass Spectrum

55
80 ~
CD
a.
60 5l No significant UV
co
.0 41 absorption above 220 nm
401-'0 M+" 126/128/130 < 1%
~
201-

40 80 120 160 200 240 280

m/e

I I I I I I I I I I I r
13CNMR Spectrum I
(50.0 MHz, CDCI 3 solution) I H-C-H
H-C-H
I
I

solvent
proton decoupled

•
I I I I I I I I I I I I

200 160 120 80 40 o 8 (ppm)

1H NMR Spectrum
(200 MHz, CDCI 3 solution)

expansions

TMS
I
ppm ppm

10 9 8 7 6 5 4 3 2 1 o
8 (ppm)

105
 Problem 17

763
IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800

V (ern")

100 Mass Spectrum

41
80 -"
<ll
Ql
o,
121/123 No significant UV
60 Ql
III
<ll M+"= 200/202/204
.0 absorption above 220 nm
40 '0
~
20
". II IJ

40 80 120 160 200 240 280

m/e

I I I I I I I I I I I I
13C NMR Spectrum
(100.0 MHz, CDCI3 solution) DEPT CH2~ CH3t CHt

solvent
proton decoupled ~
I

I I I I I I I I I I I I
 Problem 18

IR Spectrum 766
(liquid film) 2960
650

4000 3000 2000 1600 1200 800

V (cm'")

100 41 Mass Spectrum

-
80 ~
Ql
c-
60 3l No significant UV
.c
<0 77
M+- absorption above 220 nm
40 '0
'#... 156/158/160
20
j ,11
79
107/109
II III C3H6BrCI

40 80 120 160 200 240 280

m/e

I I I I I I I I I I I
I
13C NMR Spectrum H-C-H
I
(50.0 MHz, CDCI 3 solution) I I

H-C-H H-C-H
I I

solvent
/

proton decoupled
~.
I I I I I I I I I I I I

200 160 120 80 40 0 o(ppm)

1H NMR Spectr um
(200 MHz, CDCI 3 solution)

expansions TMS

-, r , , , , I
, , , --------'
, , I
L
, , , , I
4.0 3.5 ppm 2.5 2.0 ppm

10 9 8 7 6 5 4 3 2 1 o
o(ppm)

107
 Problem 19

1H NMR Spectrum
(200 MHz, CDCI 3 solution)

expansion

,--

J
-)

I I I I I
1
I I
J~l i
34 3.0 2.6 2.2 ppm

TMS
- - --i
1
'-'
I l

10 9 8 7 6 5 4 3 2 1 o
s (ppm)

108
 Problem 20

IR Spectrum
1620
(KBrdisc)

4000 3000 2000 1600 1200 800

V (em")

100 44 Mass Spectrum

80 "''""
Q)
c.
60 Q)
<Il
No significant UV
'"
.Q
absorption above 220 nm
40 '0
#,
20
Ii
40 80 120 160 200 240 280
m/e

I I I I I I I I I I I I
13C NMR Spectrum
(100.0 MHz, 020 solution)

I
I
200 160 120 80 40 o 0 (ppm)

1H NMR Spectrum
(400 MHz, 020 solution)
Note: there are 3 protons
which exchange with
the 020 solvent

H 20 and HOD
in solvent

3.9 3.7 ppm 1.6 1.4 ppm

10 9 8 7 6 5 4 3 2 1 o
o(ppm)

109
 Problem 21

IR Spectrum
1600
(KBr disc)

4000 3000 2000 1600

V (crn'")

100 30 Mass Spectrum

80 ""co
Q)
c,
60 Q) No significant UV
en
co
.c absorption above 220 nm
40 '0
;f!.
20

40 80 120 160 200 240 280

m/e

13C NMR
Spectrum
(100.0 MHz,
O2 ° solution)
..........,1.'.' • ".OJ •• : ...,/.".' ......." ....... h, I 4 .... t ,cart. WIU"M ,
"~ ..... ,

proton decoupled

200 160 120 80 40 0 o(ppm)

1H NMR Spectrum
(400 MHz, 020 solution)
H 2 0 and HOD
Note: there are 3 protons
which exchange with in solvent
the 020 solvent .. I

expansions

i i
J , i

3.2 3.0 ppm 2.2 2.0 ppm

10 9 8 7 6 5 4 3 2 1 0
s (ppm)

110
I1 \ Problem 22

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800

V (ern")

100 Mass Spectrum UV Spectrum

M+' 108
80 .:.:
ell
<Il
Cl.
Amax 269 nm (I091QE 3.2)
78
60 <Il
Vl
ell
.0
solvent: methanol
40 '0
<fi. 93
20 j j, l C 7H aO

40 80 120 160 200 240 280

m/e

13C NMR Spectrum

(100 MHz, CDCI 3 solution)

lJJ
proton decoupled

200 160
W 120
solvent

80
•
40 0 o(ppm)

1H NMR Spectrum
(400 MHz, CDCI 3 solution)

expansion

TMS
i i
7.2 7.0

10 9 8 7 6 5 4 3 2 1 o
o(ppm)

III
 Problem 23

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800

V (crn'") UV Spectrum

100 79 Mass Spectrum Amax 243 nm (10910£ 1.9)

80 "" Amax 248 nm (10910£ 2.1)

<Il'"
0.
Amax 252 nm (10910£ 2.2)
60 <Il
en

40 15
'"
J:J
Amax 258 nm (10910£ 2.3)
91
*-
20 Amax 264 nm (10910£ 2.1)
Amax 268nm (10910£ 1.9)
80 120 160 200 240 280 solvent: ethanol
40
m/e

13C NMR Spectrum

(100 MHz, CDCI3 solution)

I I
129 128 127 ppm

solvent
I I I I
proton decoupled 129 128 127 ppm

200 160 120 80 40 o 0 (ppm)

1H NMR Spectrum
(400 MHz. CDCI3 solution)

expansion

Exchanges with

°2°
j TMS

7.6 7.4 7.2 ppm

10 9 8 7 6 5 4 3 2 1 o
o(ppm)

112
 Problem 24

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800 0.0

V (cm'")

100 Mass Spectrum

91 0.5 II)
o
c:
80 -"
11l 11l
II)
a. €
0
60 UV spectrum
II)
'"
.Cl
'"
11l 11l
0.917 mg 110 mls
40
.Cl
'0
1.0
path length: 0.20 cm
'#
M+' solvent: hexane
20
I ,\, .n 170/172
C 7H 7Br
1.5
40 80 120 160 200 240 280 200 250 300 350
mle A. (nm)
I I I I I I I I

~
13C NMR Spectrum expansion
(50.0 MHz, CDCI3 solution)
I i I
140 130 ppm

~
expansion

I i I
140 130 ppm

proton decoupled solvent

•
I I I I I I I I I

200 160 120 80 40 o s (ppm)

1H NMR Spectrum
(200 MHz, CDCI3 solution)

r-

TMS

t I
I I I I I I I I I I I

10 9 8 7 6 5 4 3 2 1 0
() (ppm)

113
r

Problem 25

2251

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800

V (ern")

100 Mass Spectrum

M+" = 117
80 .><
'"'"
0- 77
60 '"
'"
'"
.0
40 '0
~
20

40 80 120 160 200 240 280

m/e

I I I I I I I I r T T I
expansion
13C NMR Spectrum
(100.0 MHz, CDCI 3 solution) ~
i i i
130 129 ppm

DEPT CH z' CH 3t CHt expansion

I
~
do
i i

proton decoupled 129 ppm solvent

I I •
I I I I I I I I I I I I

200 160 120 80 40 0 s (ppm)

1H NMR Spectrum
(400 MHz, CDCI 3 solution)

I---

TMS
-
1

I I I I
J I I I I I

10 9 8 7 6 5 4 3 2 1 0
s (ppm)

114
 Problem 26

3290
IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800

V (cm'")

Mass Spectrum UV Spectrum

100
M+" 107
80 ""c-
lIJ
Amax 256 nm (log10~ 2.2)
Ql

60 Ql
'"
lIJ
Amax 264 nm (log10~ 2.1)
~

40 '0 solvent: ethanol

oF- 91
-J, 20
~I ~ J
" J .1. C 7H g N

40 80 120 160 200 240 280

role
I I I I I I I I I I I I

ll"'~"'"
13C NMR Spectrum
(100 MHz, CDCI 3 solution)

1 I
129 128 127 ppm
DEPT CH 2 1CHJ CHt

I
solvent
ll"'~""
proton decoupled
1 I 1
129 128 127 ppm
I I

200 160 120 80 40 0 o(ppm)

1H NMR Spectrum
(400 MHz, CDCI 3 solution) Exchanges with
D20
expansion
1

TMS
7.6 7.4 7.2 ppm

10 9 8 7 6 5 4 3 2 1 o
s (ppm)

115
 Problem 27

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800 0.0

V (om")

100 91 Mass Spectrum 0.5

80 -'"
<lI
Q)
0.
60 Q) 92
1I)
<lI UV spectrum
.0
1.0
40 '0 M+'= 122 5.662 mg I 10 mls
;f?
path length: 1.00 cm
20
I, J ,I·· I CaH 100 solvent: ethanol

1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
I I I
13C
(100.0 MHz,
NMR Spectrum expansion

i ,
li- ,
CDCI 3 solution) 135 130 ppm
I
DEPT CH2 f CH 3t CHt
I

proton decoupled
'::lL 135
,
130
, ,
ppm
solvent
f
I
, , I I I
I
, I I -,
200 160 120 80 40 0 () (ppm)

expansion expansion
lH NMR Spectrum

~.
(400 MHz, CDCI 3 solution)

expansion

I •

3.9 3.8 ppm 2.9 2.8 ppm

7.3 7.2 ppm Exchanges

with D20
TMS
•

10 9 8 7 6 5 4 3 2 1 o
s (ppm)

116
 Problem 28

3325
IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800 0.0

V (crn")

100 104 Mass Spectrum 0.5 8

80 .>< c
III
III
Co
€o
60 Ql
Ul
Ul
.Q
III 77 78 III
.Q 107 1.0 UV spectrum
79
40 '0
<fi. M+'= 122 5.815 mg/10mls
20 path length: 1.00 cm
.1 j I. .1. .1 C 8 H 10O solvent: ethanol
1.5 u...................."'-o..J.................. ...L...".................l..o..I...I
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)
I I I I I I I I I I I
13C NMR Spectrum
(100.0 MHz, COCI 3 solution)

DEPT CH 2 , CH 3t CHt

solvent

proton decoupled
I
~.
I

200 160 120 80 40 o s (ppm)

1H NMR Spectrum
(400 MHz, COCI 3 solution) expansions

expansion
II ~ ~
l
i i i i i i i
5.0 4.8 ppm 1.6 1.4 ppm
~

Exchanges
i i i
with 02°
ppm r- ~
7.5 7.3
L TMS
---'
-'~
~ ~

I
I I I I I I I I I I I

10 9 8 7 6 5 4 3 2 1 o
s (ppm)

117
 Problem 29

IR Spectrum
(liquid film) 1715

4000 3000 2000 1600 1200 800 0.0

V (crn")

100 Mass Spectrum

43 0.5 Ql
o
80 -" c
'"
Ql
Co e'"
0
60 Ql
UJ
91 UJ
.J:J
UV spectrum

40
'"
.J:J
'0
1.0 '" solvent: cyclohexane
M+' 7.90 mg 110 mls
;ft. 134 path length: 0.50 cm
20
II ,I II I. C g H 1Q O
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)
I I I I I I I I I I I I

13C NMR Spectrum

(50.0 MHz, CDCI 3 solution)

DEPT CH2 1 CH 3t CHt

II I

proton decoupled

...-J ~ solvent
II I
I I I I I I I I I

200 160 120 80 40 0 <5 (ppm)

1H NMR Spectrum
(200 MHz, CDC'3 solution)

..-
~ ~
TMS

!1~ L

10 9 8 7 6 5 4 3 2 1 o
<5 (ppm)

118
 Problem 30

IR Spectrum
(liquid film)

1690

4000 3000 2000 1600 1200 800

V (crn'")

100 105 Mass Spectrum

77 0.5
80 ~
Q)
c-
60 ~

40
'"
.c
'0
M+" 1.0 UV spectrum
134 1.075 mg /10 mls
<;e.
path length: 0.10cm
20
solvent: ethanol
IJ 1 Cg H 1Q O
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)

13e NMR Spectrum

(20.0 MHz, CDCI 3 solution)

solvent

off-resonance decoupled

200 160 120 80 40 0 15 (ppm)

1H NMR Spectrum
(100 MHz, CDC'3 solution)

I TMS

10
~~
9
I I

8
I

7
I

6
I

5
I

4
L
I

3
J I

2
L1 0
v;

15 (ppm)

119
 Problem 31

IR Spectrum
(liquid film) 1723

4000 3000 2000 1600 1200 800

V (em")

100 Mass Spectrum

105

80 .><
'0-"
Q)

60 Q)
Vl

'"
D
40 '0 77 M+-
~ 134

L ~"
20
,II .,li J I

40 80 120 160 200 240 280

m/e

13C NMR Spectrum

(50.0 MHz, CDC'3 solution)

solvent

II

200 160 120 80 40 o 0 (ppm)

lH NMR Spectrum
(200 MHz, CDCI 3 solution)

I
9.7
i
9.5
I
3.7 3.5
I
JI
1.5
I
1.3 ppm

_~I TMS

10 9 8 7 6 5 4 3 2 1 o
s (ppm)

120
 Problem 32

IR Spectrum
(liquid film) 1686

4000 3000 2000 1600 1200 800

V (ern")

100 105 Mass Spectrum UV Spectrum 0

80 .><
<ll 77
(lJ
0- Amax 241 nm (10910£ 4.1)
60 Q)
en M+"
<ll
.0 148
40 '0 solvent: methanol
;/i. 120
20
.1. Ju ,I ,I. II I. C1QH 12O

40 80 120 160 200 240 280

m/e

I I I I I I I I I I I I

13C NMR Spectrum

(50.0 MHz. CDCI 3 solution)

~xpansion I I
proton decoupled 135 130 ppm
1 I
..---- solvent
Iii I
I I I 1 I I I 1 1 1 I I

200 160 120 80 40 o 8 (ppm)

1H NMR Spectrum
(200 MHz. CDCI 3 solution)

, ,
3.0 2.0 1.0 ppm

TMS

10 9 8 7 6 5 4 3 2 1 o
8 (ppm)

121
 Problem 33

IR Spectrum
(liquid film) 1735

4000 3000 2000 1600 1200 800

V (ern")

100 43 Mass Spectrum

57
80 "''Q"">
c,
60 Q> No significant UV
til

'"
.0 85 absorption above 220 nm
40 '0
~
20 M+' 158<1%
I J
40 80 120 160 200 240 280
m/e

I I I I I I I I r I I I

13C NMR Spectrum

(100 MHz, CDCI 3 solution)

solvent

proton decoupled

I I I.• I I
200 160 120 80 40 o 0 (ppm)

1H NMR Spectrum
(400 MHz, CDCI 3 solution)

TMS

- --
10 9 8 7 6 5 4 3 2 1 o
s (ppm)

122
 Problem 34

IR spectrum
(liquid film)

, r
1725

4000 3000 2000 1600 1200 800

V (ern")

100 31 Mass Spectrum

29 45
80 ~
4l
a. No significant UV
60 Sl
t1I
J::J
M+' absorption above 210 nm
40 0 74

20
III I J.
C3H602
40 80 120 160 200 240 280
m/e

I I I I I I I I I I I I

13C NMR Spectrum

(50,0 MHz, CDCI 3 solution)

proto" =-~""'~_~_",".1j,,~. . ~ ~Ww!\'W~1f\I' l I

proton _
decoupled

I
_ _ _ _ _ _---il...-

200
I I I

160
I I

120
I
s_"LJ
I

80
I I

40
_
I
L 0
I

o(ppm)
1H NMR Spectrum
(100 MHz, CDCI 3 solution)

TMS

expansion 4x

10 9 8 7 6 5 4 3 2 1 o
o(ppm)

123
 Problem 35

IR Spectrum
(KBr disc)
1662

4000 3000 2000 1600 1200 800

V (ern")

100 105 Mass Spectrum UV Spectrum

80 sc
til
ll)
c.
77
Amax 258 nm (Io910E 4.2)
60 ll)
VI

Amax 330 nm

,JJ
til
..0 (Io910E 2.8)
40 a
20 *' M+" Amax 388 nm (I091OE 2.2)
210
C14H1002 solvent: ethanol

40 80 120 160 200 240 280

m/e

I I I I I I I I I I I I

13C NMR Spectrum

(100 MHz, CDCI 3 solution)

I
 Problem 36

IR Spectrum
(KBr disc)

4000 3000 2000 1600 1200 800 0.0

V (ern")

100 Mass Spectrum

91 0.5 Q)
o
c
80 ..>< t'lI
t'lI
Q)
0.
-e0
60 Q)
(I)
(I)
.0
t'lI M+" t'lI
.0
162 1.0 uv spectrum
40 '0
165.3 mg 1100 mls
~
path length: 0.2 cm
20
I ,I I, C14H 14 solvent: ethanol
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)
I I I I I I I I I I I I

13C NMR Spectrum - - Resolves into

two signals at higher fielel
(50.0 MHz, CDCI 3 solution)

I
DEPT CH 2 f CHJ CHt

- - Resolves into
two signals at higher fielel

proton elecoupled solvent

I
I I I I I I I I I I I I

200 160 120 80 40 o 0 (ppm)

1H NMR Spectrum
(200 MHz, CDCI 3 solution)

TMS
_ _ _ _ _ _-----' \'-- " .....
I
------l

10 9 8 7 6 5 4 3 2 1 o
o(ppm)

125
 Problem 37

3310

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800

V (crn'")

100 91 Mass Spectrum

106
80 -'"
C1l
Ql
0..
60 Ql

'"
C1l
.0
M+'
40 0 197
<ft.
20
C 14H1SN

40 80 120 160 200 240 280

m/e

I I I I I I I I I I I I

13C NMR Spectrum

(100.0 MHz, COCI3 solution)
Jl:i ,
129
,
128
Sion

ppm

DEPT CH z 1CH 3t CHt

JL:LSion

i ,
129 128 ppm

proton decoupled
I solvent
.
I I

200 160 120 80 40 o s(ppm)

lH NMR Spectrum
(200 MHz, COCI 3 solution)
r

exchanges
°
with O2

-'~ -r TMS

I I I I I I I I I

10 9 8 7 6 5 4 3 2 1 0
s (ppm)

126
 Problem 38

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200

V (ern")

100 58 Mass Spectrum

80 -'"
.,0-<1l

60 ., III
No significant UV
<1l
.0
absorption above 220 nm
40 '0
'ffl"
20 M+" = 116
72
I

40 80 120 160 200 240 280

m/e

I I I I I I I I I I I I
13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

1
,,,100 decoupled
1----1----------------1-1
I I I 1 I
J L
1 I
_
I

o () (ppm)
200 160 120 80 40

1H NMR Spectrum
(400 MHz, CDCI3 solution)
expansion

2.4 2.2 2.0 ppm TMS

10 9 8 7 6 5 4 3 2 1 o
() (ppm)

127
 Problem 39

IR Spectrum 1713
(liquid film)

4000 3000 2000 1600 1200 800 0.0

V (ern")

100 Mass Spectrum

43 0.5 Gl
u
80 -'" co
''""
0-
-e0'"
60 '"
III
III
..c

40
'"
..c
'0
1.0 '" UV spectrum

99 104.1 mg/10 mls

oR- M+' path length: 0.2 cm
20 114
C S H 1Q 0 solvent: ethanol
.1 .1 ' I. I I
2
1.5
40 80 120 160 200 240 280 200 250 300 350
mle A. (nm)

13C NMR Spectrum

(20.0 MHz, CDCI3 solution)
I
H-C-H
I

-CH
3

JC
proton decoupled

solvent TMS

200 160 120 80 40 0 o(ppm)

1H NMR Spectrum
(100 MHz, CDCI3 solution)

TMS

10 9 8 7 6 5 4 3 2 1 o
o(ppm)

128
 Problem 40

IR Spectrum
(liquid film)
1746
1259

4000 3000 2000 1600 1200 800

V (ern")

100 Mass Spectrum

29
80 -'"
'"c-
Q)
45
60 Q)
<1l
No significant UV
'"
.0
M+'= 118 «1%) absorption above 220 nm
40 '0
*-
20
,I j C S H 100 3

40 80 120 160 200 240 280

m/e

I I I I I I I I I I I I

13C NMR Spectrum

(50.0 MHz. CDCI 3 solution)

DEPT CH2 • CH3t CHt

I
proton decoupled

200
I I I

160
I I

120
I
OOILJ
I

80
I I

40
I
L 0
I
o(ppm)
1H NMR Spectrum
(200 MHz, CDCI 3 solution)

- TMS

10 9 8 7 6 5 4 3 2 1 o
o(ppm)

129
 Problem 41

IR Spectrum
(liquid film)

4000 3000 2000 1S00 1200 800

V (cm'")

100 57 Mass Spectrum

80 .><
ell
Q)
0.
SO Q)
(J)
29 No significant UV
ell
..0
absorption above 220 nm
40 '0
;f?
74
20
,II I M+' = 130 « 1%) C S H 1003
40 80 120 1S0 200 240 280
m/e

I I I I I I I I I I I I

13C NMR Spectrum

(50.0 MHz, CDC'3 solution)

proton coupled
I j II

proton decoupled

I I I I I I I
solvent

I
III

I I
I
I
L I

200 160 120 80 40 0 o(ppm)

1H NMR Spectrum
(200 MHz, CDCI3 solution)
..

expansion
~

L1 ~
,---
, , , , TMS
2.5 2.0 1.5 ppm ----1
-
1
I I I I I I I I I I I

10 9 8 7 6 5 4 3 2 1 o
s (ppm)

130
 Problem 42

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800

V (crn'")

100 Mass Spectrum

29
80 "'"
<ll
Ql
Co
60 Ql
!Il
<ll
.0
40 (;
'if!.
20 45 M+' = 146 «1 %)
,I .I C 6H 10 04

40 80 120 160 200 240 280

m/e

I I I I I I
, I I I I I

13C NMR Spectrum

(50.0 MHz, CDCI 3 solution)
I
DEPT CH2 ' CH3t CHt

solvent
proton decoupled
I
I I I I

200 160 120 80 40 o 0 (ppm)

J
1H NMR Spectrum
(200 MHz, CDCI 3 solution)

TMS

I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)

131
 Problem 43

IR Spectrum 1742
(liquid film)

4000 3000 2000 1600 1200 800

V (em")

100 43 Mass Spectrum

80 ~
<Il
C.
60 I- 3l No significant UV
III
..c absorption above 220 nm
40 (;
86
20
I M+" = 146 « 1%)

40 80 120 160 200 240 280

m/e

13C NMR Spectrum

(50.0 MHz, CDCI 3 solution)

proton coupled

200 160 120 80 40 o 0 (ppm)

1H NMR Spectrum
(200 MHz, CDCI 3 solution)

- TMS

10 9 8 7 6 5 4 3 2 1 o
s (ppm)

132
 Problem 44

IR Spectrum
(liquid film) 1739

4000 3000 2000 1600 1200 800

V (ern")

100 115 Mass Spectrum

80 "'III"
Q)
c.
60 Q) No significant UV
UI
III
..c absorption above 220 nm
40 '0 59
'#.
87
20 I- M+" 146 < 1%
.L .I I

40 80 120 160 200 240 280

m/e

I I I I I I I I I I I I

13C NMR Spectrum

(100 MHz, CDCI 3 solution)

solvent
1
•
proton decoupled

200 160
,., .... It, t Pi" .t;

120
,J.,
80
:ih ..J....
ll ..........

40
l._.".. . o 0 (ppm)

1H NMR Spectrum
(400 MHz. CDCI 3 solution)

TMS

- -
I I I I I I : I I

10 9 8 7 6 5 4 3 2 1 o
o(ppm)

133
 Problem 45

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800

V (ern")

100 Mass Spectrum

43
80 -'"
ell
Q)
o,
60 Q) No significant UV
(/)
ell
.0 absorption above 220 nm
40 '0
20 *' 87 M+" = 146 « 1%)

40 80 120 160 200 240 280

m/e

I I I I I I I I I I I I

13C NMR Spectrum

(20.0 MHz, CDCI3 solution)
C-H
C

TMS
solvent
proton decoupled
III
j
I I I I I I I I I I I I

200 160 120 80 40 o (5 (ppm)

1H NMR Spectrum
(100 MHz, CDCI3 solution)

I~
-
~

10 9
I I

8
I

7
.il
I

6
I

5 4
I I

3
I

2
I

1
T 0
(5 (ppm)

134
 Problem 46

IR Spectrum
(liquid film)
1737

4000 3000 2000 1600 1200 800

V (ern")

100 59 Mass Spectrum

80 -'"
Cll
Ql
Q.

60 Ql No significant UV
'"
Cll
..0 115 absorption above 220 nm
40 '0 87

20 *' M+'
146
C 6 H1Q 0 4
40 80 120 160 200 240 280
mle

TMS
,
.11.
I I I I I I I I I I I

10 9 8 7 6 5 4 3 2 1 o
o(ppm)

135
 Problem 47

IR Spectrum
(liquid film) 1747

4000 3000 2000 1600 1200 800

V (ern")

100 43 Mass Spectrum

80 -'"
'Co"
Q)

60 Q)
(f)
No significant UV
'"
.D
absorption above 220 nm
40 '0 87
;f?
M+'
20 146
IJ,
59
I
I C 6 H1Q 0 4
40 80 120 160 200 240 280
mle
I I I I I I I I I I I I
13C NMR Spectrum
(50.0 MHz, CDCI 3 solution)

DEPT CH z+ CH 3t CHt
I

proton decoupled solvent m

II I
I I I I I I I I I I I

200 160 120 80 40 o 0 (ppm)

lH NMR Spectrum
(200 MHz, CDCI 3 solution)

expansions

~ r--"

I
2.5
I
L
I
1.5
I

I
J
I I
"r: ~ -"

~
5.5 4.5 ppm

I I I I I I I I I I I

10 9 8 7 6 5 4 3 2 1 o
o(ppm)

136
 Problem 48

IR Spectrum
(liquid film) 1736

4000 3000 2000 1600 1200 800

V (em")

100 Mass Spectrum

101
80 "'.,l'll"
60 .,
Q.
129
II>
No significant UV
l'll
.0
absorption above 220 nm
40 '0
0>i'!...
20 M+"
,1.1 III Il 1 174
CS H 1404
40 80 120 160 200 240 280
m/e

I I I I I , , I I I I I

13C NMR Spectrum

(50.0 MHz, CDCI 3 solution)

DEPT t CH
I
CH 2 3t CHt

I
proton decoupled

200
I I

160
I I I

120
I
solvent

80
•
[
I I

40
LL I I

0 8 (ppm)

1H NMR Spectrum
(200 MHz, CDCI 3 solution)

expansion

I---
~ ~

--'
- -
, I
4.0 2.0 ppm

TMS

I
10 9 8 7 6 5 4 3 2 1 0
8 (ppm)

137
 Problem 49

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800

V (crn'")

100 57 Mass Spectrum

80 .>t:
III
Q)
c-
60 Q)
Ul
29 No significant UV
III
.c absorption above 220 nm
40 '0 M+"=174 «1%)
?ft.
100
20
1,1 I. ~ n C aH 140 4

40 80 120 160 200 240 280

m/e

I I I I I I I I I I I I

13C NMR Spectrum

(50.0 MHz, CDCI 3 solution)

proton decoupled solvent

•
I I I I I 1 I I 1 I I I

200 160 120 80 40 o 0 (ppm)

1H NMR Spectrum
(200 MHz, CDCI 3 solution)

1_ _ _

TMS

138
 Problem 50

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800

V (ern")

100 55 Mass Spectrum

71
80 .><
70
'C."
Ql

60 Ql No significant UV

40
'"'"
.c
'0
M+' = 158 « 1%) absorption above 220 nm
<fl.
20
C aH 1403
40 80 120 160 200 240 280
m/e

I I I I I I I I I I I I

13C NMR Spectrum

(50.0 MHz. CDCJ 3 solution)

I
proton decoupled

200
I I I

160
I I

120
I
solvent

80
I
• I I
Il
40
I I

o () (ppm)

lH NMR Spectrum
(200 MHz, CDCI3 solution)

,--

k~" J
1L-JL-
I I
2.00 1.50 ppm TMS

I I I I I I I I I I I

10 9 8 7 6 5 4 3 2 1 o
() (ppm)

139