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