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