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
 Problem 51

IR Spectrum
(nujol mull)

4000 3000 2000 1600 1200 800 0.0

V (cm'")

100 Mass Spectrum

0.5 Q)
o
c:
80 "''"" M+"
Q) €'"
c. 234/236/238 0
III
60 Q)
III
155/157
.0 UV spectrum
'"
.0
1.0 '"
40 '0 a 15.07mg/10ml
<f- !! 0.302 mg/10ml
20 C 6 H 4 Br2 path length: 0.5 cm
I I ,L solvent: ethanol

40 80 120 160 200 240 280 250 300 350

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

13C NMR Spectrum

(20,0 MHz, CDC'3 solution)

off-resonance decoupled
I solvent
II

proton decoupled
I

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

200 160 120 80 40 o o(ppm)

1H NMR Spectrum
(100 MHz, CDCI3 solution)

TMS

I I I I I I I I I I

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

140
 Problem 52

IR Spectrum
(nujol mull)

4000 3000 2000 1600 1200 800

V (ern")

100 152 Mass Spectrum UV Spectrum

80 -""
l\'l
C12H8Br2
Q)
c- Amax 264 nm (1 09 10 1:: 4.5)
60 Q)
en
l\'l
.Q 76 M+" solvent: methanol
40 15 310/312/314

20 "*
11 ,,-.II L

40 80 120 160 200 240 280

m/e

13C NMR Spectrum

(50.0 MHz, CDCI 3 solution)
C-H C-H

C C solvent

proton decoupled

200 160 120 80 40 o 0 (ppm)

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

expansion

1 I I I i iii

8.0 7.5 7.0 ppm

TMS

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

141
 Problem 53

IR Spectrum
(liquid film) 696

4000 3000 2000 1600 1200 800

V (em")

100 125/127 Mass Spectrum

80 """
'a.Q"l
60 rnQl

'"
.0
40 '0
*" M+·
20 160/162/164
J,I,h ,L" .l J. 1.1.

40 80 120 160 200 240 280

m/e

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

13C NMR Spectrum

(50.0 MHz, CDCI 3 solution)

proton decoupled
I
SOlve: I
I I I I I I I I I I I I

200 160 120 80 40 o o(ppm)

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

expansion

V -,
I I I
B.O 7.5 7.0 6.5 ppm TMS

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

142
 Problem 54

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800

V (em")

100 121 Mass Spectrum

80 ~

'a."
Q)

60 Q)
III

'"
.0
40 '0
o~ .

20
I I

40 80 120 160 200 240 280

m/e

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

~pao']l
13C NMR Spectrum
(100.0 MHz, CDCI 3 solution)

, , ,
130 128 ppm
t CHt
DEPT CH 2 , CH 3
I
~~-Jl1

proton decoupled
,
130 128 ppm
, ,

I I
,.
solvent

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

200 160 120 80 40 0 o(ppm)

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

expansion

Jl
7.6 7.4 ppm

.1
JI -
TMS

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)

143
 Problem 55

IR Spectrum
(KB'r disc)
3400 1720

4000 3000 2000 1600 1200 800

V (em")

100 105 Mass Spectrum

183 UV Spectrum
80 .><
III

'"
Q. Amax 253 nm (10910E 2.6)
60 '" fF)
III

40 '0
.0
M+" =228 « 1%)
Amax 259 nm (10910E 2.7)
~

20
Amax 264 nm (l0910E 2.5)
,I. IL I C14H1203 solvent: ethanol

40 80 120 160 200 240 280

m/e

I I I I I I I I I I
13C NMR Spectrum
(100 MHz, COCI 3 solution)

i i

130 128 ppm

j[''"' OO solvent
, , ,
proton decoupled
I I
130 128 ppm I "j'..-J

200 160 120 80 40 0 S (ppm)

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

Exchanges
with D20

~
+
Exchanges
JlJl
,
7.7 7.6
,
7.5 ppm

, , , with 020
TMS
14.5 14.0 13.5 ppm
+
~ ----r- 1
I I I I I I I I I I

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

144
 Problem 56

IR Spectrum
(KBrdisc)

3461
3326

4000 3000 2000 1600 1200 800

V (cm-1 )

100 UV Spectrum
Mass Spectrum
M+" 110
80 ""III
Ql
Amax 225 nm (loglOE 3.5)

60
0.
Ql
en
Amax 27S nm (log lOE 3.4)
III

40
.Q

'0 Amax 283 nm (log 10 E 3.3)

"#.,
20
solvent: methanol
J .Ii I I C SHS 0 2

40 80 120 160 200 240 280

m/e

13C NMR Spectrum

I

(100 MHz, CDCI 3 solution)

I I I

11I I I I I I T

D~:IIl~:L.C;,3'~~4~': !"'I1l~.~' .'Ill $' ,.... ~

1M.'n.......
Wl ... ~~-.-...".
lIIlfIIlIlI.W1_. ..
_ll/l¥"lWJt#... ..... 1IWI
....-.ll'IoollI_.........
II"," t 'Ifi

r- '"">---- solvent

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

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

1rr--r-
Exchanges with

0:0 ~vIN~

-
S ' 0'90 '
I
i
680 ppm
TMS

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

145
 Problem 57

IR Spectrum
(CCI4 solution)
I I I I I

4000 3000 2000 1600 1200 800

V (ern")

100 Mass Spectrum UV Spectrum

M+- =168
80 "'co"
<IJ
a. 153 Amax 267 nm (Io910E 2.8)
60 <IJ III
co
.0
solvent: ethanol
40 '0
*-
20
~Ij l'~J I l I C9H1203

40 80 120 160 200 240 280

m/e

13C NMR Spectrum

(100.0 MHz, CDCI3 solution)

_ _J"--------J"-------
proton decoupled

200 160 120 80 40 o 0 (ppm)

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

, ,
7.0 6.4 ppm ppm

TMS

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

146
 Problem 58

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800 0.0

V (cm'")

100 Mass Spectrum

105 0.5 1Il

80 .:s:. M+' <J

c:
'"c-
1Il
120 -eo'"
en
60 1Il
en .c

40
'"
.c
'0
1.0 '" UV spectrum
*' 5.875 mg 110 mls
20
'I II 1 ~I I, C 9H12
1.5
path length: 1.00 cm
solvent: ethanol

40 80 120 160 200 240 280 200 250 300 350

mle A(nm)
I I I I I I I I I I

13C NMR Spectrum

(20.0 MHz, CDCI3 solution)

off-resonance decoupled
I I

proton decoupled
I
I I I I I I I I I I I I

200 160 120 80 40 o 0 (ppm)

lH NMR Spectrum
(100 MHz, CDCI3 solution)

s
I I I I
L I I I I I I
TMS
I
I

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

147
 Problem 59

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800

V (em")

100 105 Mass Spectrum UV Spectrum

80 "'"
'e-" Ql
Amax 261 nm (109101': 2.7)
60 Ql
IJl

'"
J:> Amax 269 nm (109101': 2.5 )
40 '0
'$.
solvent: methanol
20
I I I

40 80 120 160 200 240 280

m/e

13C NMR Spectrum

(100.0 MHz, CDCI 3 solution)

I I

solvent
proton decoupled

I I
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 L

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

148
 Problem 60

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800

V (ern")

100 105 Mass Spectrum UV Spectrum

80 -'"
<1l
Ql
0- Amax 270 nm (109
10
£ 2.6)
60 Ql
VI
<1l
.Q
solvent: methanol
40 '0
~.
Q

20
I I I l
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) expan:JL
i I I
135 130 ppm
I I i I I
DEPT CH 2 , CH 3 + CH + 24 20 ppm

" proton decoupled

"''"jill I I I
I
'~":JL i i i I I
135 130 ppm
III solvent 24 20 ppm

I I I I I I I I I I

200 160 120 80 40 0 8 (ppm)

1H NMR Spectrum
(400 MHz, CDCI 3 solution)
resolves into 2 peaks
~~, at higher field
J.
,.<;
.:."

. +
:1_,:

."{
': '~Jl '~":Jl
t r--

t i

6.8
i

6.6 ppm 2.2 2.0 ppm

TMS

I ----{ - I
tL
. I I I I I I I I I I I
J.;
10 9 8 7 6 5 4 3 2 1 0
8 (ppm)

149
 Problem 61

IR Spectrum
(KBrdisc)

4000 3000 2000 1600 1200 800 0.0

V (crn'")

100 Mass Spectrum

119 0.5 III
<J
c:
80 .><
€0'"
<1l
Gl
a.
60 Gl
III
III
.0
UV spectrum
'"
.0 M+' 1.0 '"
40 '0 134 1.032 mg 110 mls
path length: 1.00 cm
*"
20 solvent: cyclohexane
I Ii J. J.. L 1 IJ C 10 H 14
1.5
40 80 120 160 200 240 280 200 250 300 350
off-resonance decoupled
m/e A(nm)
I I I I I I I I I I I I
13C NMR Spectrum
(20.0 MHz, CDCI3 solution)

off-resonance decoupled
1 III

proton decoupled

I I I I I
lL I I
solvent

I I I I
TMS
j
I

200 160 120 80 40 0 o(ppm) •

1H NMR Spectrum
(100 MHz, CDCI3 solution)

-r-
------1
TMS

I I I I I I
J 1I
I I I I

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

150
 Problem 62

IR Spectrum 802
(liquid film)

4000 3000 2000 1600 1200 800

V (crn'")

100 119 Mass Spectrum

80 ~
III
c-
60 ~
M+"
134
'"
.c
401-0
"#..
20
I II 1, "L [I .t" 1,1

40 80 120 160 200 240 280

m/e

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

13C NMR Spectrum

(50.0 MHz, CDCI 3 solution)

solvent
proton decoupled
II 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

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

151
 Problem 63

IR Spectrum
(liquid film)

4000 3000 2000 1600

V (em")

100 119 Mass Spectrum UV Spectrum

80 ""'"
Ql
a. M+' = 134 Amax 274 nm (109101': 2.3)
60 Ql
Ul

'"
.t:J Amax 277 nm (109101': 2.3)
40 '0
'#.
solvent: cyclohexane
20
I I " 1,1

40 80 120 160 200 240 280

m/e

13e NMR Spectrum expansion

(100.0 MHz, CDCI3 solution) ~

~
expansion

i i

140 130 ppm , ,

20 15 ppm

J
expansion

solvent , ,
I 20 15

200 160 120 80 40 0 () (ppm)

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

expansion

lr
I-- -= , , , TMS
- 2.2 2.0 ppm
- 1
I I I I I I I I I I

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

152
 Problem 64

IR Spectrum
(KBr disc)

4000 3000 2000 1600 1200 800

V (em")

100 147 Mass Spectrum UV Spectrum

80 "'III"
Q)
0. Amax 278 nm (109 10 8 2.4)
60 Q)

'"
III
.0 M+' Amax 274 nm (109108 2.4)
40 '0 162
c!?: Amax 270 nm (109108 2.5)
20
solvent: methanol

40 80 120 160 200 240 280

m/e

13C NMR Spectrum

(50.0 MHz, CDCI 3 solution)

proton coupled

solvent

200 160 120 80 40 o 3 (ppm)

1H NMR Spectrum
(200 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
3 (ppm)

15:
aus .

Problem 65

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 800

V (ern")

100 121 Mass Spectrum UV Spectrum

80 ""
'c.." Q)
Amax 232 nm (log lO E 3.4)
60 Vl Q)

'"
.0 Amax 248 nm (log 10E 3.5)
40 '0

20
;f<.
Amax 265 nm (log lO E 3.4)
I II I solvent: isooctane

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)

DEPT CHA CH 3t CHt

1:1
, , , ,
15 13
,
ppm

proton decoupled
II
solvent

•
I
[I
, , , ,
15 13
i

ppm

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

200 160 120 80 40 0 (5 (ppm) .~

lH NMR Spectrum
(400 MHz, CDC'J solution)
expansion expansion expansion

JL
,
2.7 2.6 ppm
JL
1.85 1.75 ppm
~
1.3 1.2 ppm

TMS

A L

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

154
 Problem 66

3348 IR Spectrum
(KBr disc)

4000 3000 2000 1600 1200 800

V (ern")

100 Mass Spectrum

80 -" 44
'"Co
Q) 43
M+"
60 Q)
If)
59 No significant UV
'"
.0
40 '0 absorption above 210 nm
~
201-

40 80 120 160 200 240 280

m/e

13C NMR Spectrum

(50.0 MHz. COCI3 solution)

proton coupled

proton decoupled
rol~oll L
~~4jP~""."~1".(i""_~~~ "'~
200 160 120 80 40 0 () (ppm)

1H NMR Spectrum
(200 MHz. COCI 3 solution)
exchanges
with 0 20 on warming

/ TMS

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

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

155
 Problem 67

IR Spectrum
(liquid film)

4000 3000 2000 1600 1200 SOO

V (cm'")

100 31 Mass Spectrum

SOI-~
<Il
c,
60 ~ No significant UV
ctl
.1:J
absorption above 220 nm
40 '0
~
45 61 M+" = 104 « 1%)
20
. 76 C4H S03
1,1 ,I

40 SO 120 160 200 240 2S0

m/e

I I I I I I I I f I I I

13C NMR Spectrum

(50.0 MHz, COCI 3 solution)

• j.
solvent
proton decoupled

I I I I I I I

200 160 120 80 40 o 0 (ppm)

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

expansions exchanges
with 0 20
t
4.4 4.0 3.6 ppm 1.4 1.2 ppm
TMS

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

156
 Problem 68
2266

IR Spectrum
(liquid film) 1749

4000 3000 2000 1600 1200 800

V (cm")

100 68 Mass Spectrum

80 .><
III
II)
c-
60 II)
lJ)
No significant UV
III
.D absorption above 220 nm
40 '0
'ifl. M+'

J~J
20 86
113
U I

40 80 120 160 200 240 280

m/e

I I

13C NMR Spectrum

(50.0 MHz. CDCI 3 solution)

DEPT CH 2 f CHat CHt

I

solvent
proton decoupled
L I •
 Problem 69

IR Spectrum
(liquid film)
1714

4000 3000 2000 1600 1200 800

V (ern")

100 45 Mass Spectrum

80 -'"
co
<Il 43
Co
60 <Il
lJ)
No strong UV
co
..c absorption above 220 nm
40 '0
M+"
20 *' 88
73
I,JI .1 ~ C4 H a0 2
40 80 120 160 200 240 280
m/e

I I I I I I I I I I I I
13e NMR Spectrum
(50.0 MHz, COCI 3 solution)

DEPT CH 2 , CH 3t CHt Ij

proton decoupled

I
I
I

200
I

160
I I

120
I I
solvent

80
J I I

40
l I I

0 o(ppm)

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

expansions

~L---A-
, , ,
ppm
, , ,
, exchanges
with 0 20

TMS

~
4.5 4.0 2.0 1.5 ppm ~

1
I I I I I I I I I I I

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

158
 Problem 70

3410

IR Spectrum
(liquid film) 1705

4000 3000 2000 1600 1200 800

V (ern")

100 Mass Spectrum UV Spectrum

43
80 ~

'"a.cv
60 cv
III
58
'"
.0 M+· = 116 « 1%) solvent: hexane
40 'i5
20 *'
1.1.1" I, I I,

40 80 120 160 200 240 280

m/e

I I I I I

13C NMR Spectrum

(50.0 MHz. COCI 3 solution)
-CH 3

I
H-C-H
I

solvent
- CH 3

C
C

I J
I I I I I I I I I I I I

200 160 120 80 40 0 () (ppm)

lH NMR Spectrum
(200 MHz, COCI 3 solution)

exchanges
with 0 20

•
~ -
- -
r-

--' TMS

I I I I I I
- I I I I I

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

159