Problem 100

UV Spectrum

? lmax 262 nm (log10s 2 .5)

solvent: ethanol

40 80 120 160 200 240 280

m/ e
| r | , | , | , | ,
l ' I 1 I I ' I . I . I .

13C NMR Spectrum

(100.0 MHz, CDCIj solution) expansion

i
-i------------------- 1—
130 125 ppm
DEPT ch 2| CH3f CHf

expansion
i
I
130 125 ppm
proton decoupled r->- solvent i

l . I . I . I , l . I . I , I , I . I , l . I

200 160 120 80 40 0 5 (ppm )

5 (ppm)

211
 Problem 101

100 r 105 Mass Spectrum UV Spectrum

80 -■ CO
- 0 ^max * 260 nm (log^s « 2.5)
60 "■ C0
- CO
O
-Q
40 7 o
-i-

00
II

-
20
II 1 II lI C 10H 14
__ 1_1_1___1_I_ 1 - 1 1 —1_1_._1_._1___1_1_I—* -«—* J * • *-- •-- *-- 1-- *
40 80 120 160 200 240 280
m/e
1 1 T..... 1 "1 1 "H..... ' 1 1 ' 1.. ' 1 1 1 1 ... i 1 i i .■
13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

DEPT CH2| CH3f C H f

1 1

solvent
proton decoupled
t
I i
.... I . 1 , 1 . 1 . .... 1 . 1 _ , 1 , 1 , 1 , 1 ,- 1 . 1 ,
200 160 120 80 40 0 5 (ppm)

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

212
 Problem 102

- 1 ........... ' 1 ------- ' ' ’ • 1 ................ ..

1.2

100
' 1 ' i 1 t t't ' 1 ' 1 ' 1 »1 ' 1 ' 1

119 Mass Spectrum 1.6 -

80
% of base peak

w \
0 \ ""
60 2.0 _ CD \
0 \ UV spectrum

40 M+*
134
2.4 \ 1
20
I „ C 10H 14
lr

........... 1-- •---1-- •-- 1-- ■-- 1-- •-- 1-- --- 1-- .-- 1-- .-- 1-- .-- 1-- 1_1_1_1_._1_1_1_1_1_._1_1_
40 80 120 160 200 240 280 200 250 300 350
m/ e X (nm)
n— ■
— i— 1— r
13C NMR Spectrum
(125.0 MHz, CDCI3 solution)

DEPT CH2i|f CH3f C H f

solvent
proton decoupled
i__
_i i 1 i 1 i 1 i 1 i 1 i 1__ 1__ 1__ 1__ 1__ 1__ 1__ 1__ 1__ 1__ 1__ 1__ 1-------
200 160 120 80 40 0 5 (ppm)

5 (ppm)

213
 Problem 103

4000 3000 2000 1600 1200 800

V (cm"1 )

UV Spectrum

?tmax 260 nm (log10s

^10 2.5)

solvent: methanol

40 80 120 160 200 240 280

m/ e
1 1 1 ■.. "1 1 1 1 1 J 1 . 1 . 1 . 1 . 1 1 I 1 I 1
13C NMR Spectrum
(50.0 MHz, CDCI3 solution)

D EPT ch 2i)i ch 3| CHf

solvent

proton decoupled 1
t . . . . 1.
1 . 1 . 1 . 1 . 1 . 1 . 1 . 1 . 1 , 1 . 1 . 1 .
200 160 120 80 40 0 s (ppm)

1H NMR Spectrum
(200 MHz, CDCI3 solution)

7.5 7.0 ppm r ..........

> TMS

_ A1 , .............- __________ ______ ____ L - _I

10 8 1 0
8 (ppm)

214
 Problem 104

4000 3000 2000 1600 1200 800

V (cm-1)

100 147 Mass Spectrum

139/141
80

60

40 M+‘
182/184
20
C11H15C|

40 80 120 160 200 240 280

m/ e
........i..... 1 ....... i”.... " r "i 1— i 1— r 1---- T .. '...... I 1 1 ' 1 ' 1....... 1.... 1 1 1 ................
13C NMR Spectrum Resolves into two
(50.0 MHz, CDCI3 solution) signals at higher field strength

D EP T ch 2| ch 3| c h |

Resolves into two

signals at higher field strength

solvent
proton decoupled ^ ^
III
I . I . I . I 1 1 * I * l 1 l * I 4____ l____1-------1-------1-------1-------1----------------
200 160 120 80 40 0 5 (ppm)

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

215
 Problem 105

4000 3000 2000 1600 1200 800

V (cm"1 )

UV Spectrum

^ max 262 nm (log10e

^10 2.5)
solvent: methanol

40 80 120 160 200 240 280

m/e
1 1 1 ' ... . 1 ■". 1 ■1 1 J T ' T • r > i 1 t 1 1 1 1 '
13C NMR Spectrum
expansion
(50.0 MHz, CDCI3 solution)

J u
1—
130 1:15 ppm

DEPT CH2| CH3| CH f

i
expansion

J L

......... I
proton decoupled
....... I _ _.
130 1:* PPm
JO
^ solvent
11
I * I .... I .i I 1 1 1- J_.. » 1 . 1 1 . 1 . 1 1 1
200 160 120 80 40 0 8 (ppm)

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

216
 Problem 106

4000 3000 2000 1600 1200 800

V (cm‘1 )

100 183/185 Mass Spectrum UV Spectrum

80:
? lmax 258 nm (log1Qs 4.2)
60
155/157
solvent: ethanol
40 M+’ = 198/200

20
C8H 7 O B r

40 80 120 160 200 240 280

m/ e
i 1 i 1 i 1 r 1 i 1 1 T J" “ 1 | 1 | I' | ' | P | 1
13C NMR Spectrum
(100.0 MHz, CDCIj solution)

1
D EP T CH2(| CH3f C H f

proton decoupled
solvent

i i 1 . 1
i . i . i . i . i . i i i . i . i j — i i . i I.....
200 160 120 80 40 0 S(PPm)

1H NMR Spectrum

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

217
 m/ e X (nm)
' 1 1 “1— 1 ” 1
1 1 1 1 T 1 1 .1..... 1 '.. 1 .1 r . | ' | 1
13C NMR Spectrum
(100.0 MHz, CDCIj solution) expansion

D EPT CH2-j[ CH3t C H f 140 135 ppm

expansion

I I
proton decoupled “r....... r------ r~
I solvent-r|n ^ PPm
............... LI
• I i l i I i I i I i I i I i I i I i I i I i I i
200 160 120 80 40 0 5 (ppm)

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

___ | l I L_ ___
1---- « T"" 1
r~ 8.0 7.8 7.6 7.4 ppm

— —*
TMS

L _ _ .. 1
---- 1 1 1 —1— J— 1------ 1 1 ------- 1
------- 1------- 1------- 1------- ! 1 1 1 1 1 1 » 1
10 9 8 7 6 5 4 3 2 1 0
6 (ppm)

218
 Problem 108

4000 3000 2000 1600 1200 800

V (cm'1 )
-1 rTT» T»"T ' I * 1' 1' 1' 1' 1

100 Mass Spectrum UV Spectrum

119
80
base peak

^max 254nm (log^c 4.3)

1
60
^max 258 nm (log^s 4.2 )
40
% of

^ max 279 nm (log1Qs 3.3)

20 ^ ~ M+' = 154/156
| C gHyO CI
A,max 290 nm (log10e 3.0)
— i—.—i—.—i—.—i—.—i—.—i—.—i—.—i—.—i—.—i—.—i—.—i . i . i . i . i .
40 80 120 160 200 240 280 solvent: hexane
m/e

I ' 1 ' I ' I 1 I 1 ■ r 1 1 1 ■ 1 ' 1 • 1 •

13C NMR Spectrum expansion
(100.0 MHz, CDCI3 solution) | !

D EP T c h 2| CH3f ch | 132 131 ppm |

expansion

I I
; (
i 1.
1 A

proton decoupled . 132 131 ppm solvent

i L I 1
..................................... ......... i . i . i ............................................... ......... . 1 .— 1— .--------------
200 160 120 80 40 0 5 (ppm)

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

— r~

_ __ j _^
8.0 7.5 7.0 ppm

I i TMS

j I 1

— i— 1— 1— 1— 1— 1— 1 . 1 . 1 1 1 , 1 , 1 . 1 . 1
10 9 8 7 6 5 4 3 2 1 0
6 (ppm)

219
 Problem 109

100 Mass Spectrum UV Spectrum

80
^max 224 nm (log10e 3.4)
60
s o l v e n t : m e th a n o l
40

20
C8H8^3
» ■ <____■ 1 ■ ■____i____I___ i____I_________L .

40 80 120 160 200 240 280

m/e

1 1 .....T 1 1 “1 1 1 1 1 ' 1 ' I ' 1 ' 1 1 1 . 1 1 1 1

,3C NMR Spectrum
( 1 0 0 M H z , C D C I 3 s o lu tio n )

D EPT c h 2( i C H 3f CH f

sol\/e n t

pro to n d e c o u p le d ,
I

------- 1----------- L 1 1
----- 1----------- ----------- 1----------- ----------- 1----- 1 ---------- 1----------- 1 J----------- 1----------- 1 _ l ------- 1 1 i 1 I 1 I 1 1 1 1

200 160 120 80 40 0 5 (ppm)

6 (ppm)

220
 Problem 110

4000 3000 2000 1600 1200 800

V (cm'1 ) UV Spectrum

100; Mass Spectrum

^max 252 nm (log10s 2 .2 )
80 ^max 257 nm (log^c 2.3)
60 ^max 262 nm (log^c 2 .2 )
40 ^ m ax 264 nm (log10s 2 .2 )

20 ^ m ax 268 nm (log108 2 .0 )

C 9 H1 0 ^ 2 s o l v e n t : eth a n o l

40 80 120 160 200 240 280

m/ e
' r 1 i T i . 1 1 | 1 , , "i r | 1
1 ... 1 1 1 1 1 '

,3C NMR Spectrum

(1 0 0 M H z , C D C I 3 s o lu tio n )
e x p a n s io n

JUl
D EP T c h 2| C H 3f c h | 1 2 8 .5 1 2 8 PPm

II so lv e n t

1 2 8 .5 1 2 8 PPm

I
*
p ro to n d e c o u p le d
I l
___ 1_____ 1_____ 1_____ 1___ 1_____ 1___ ,1___ l_....JL..._l____L___ 1___ 1_____ 1_____ 1_____ 1_____ L_ 1 1 1 1 1 1 1 1

200 160 120 80 40 0 5 (ppm)

1H NMR Spectrum
(2 0 0 M H z , C D C I 3 so lutio n)
r

e x p a n s io n

J
I , j 1 1 1
7 .5 7 .4 7 .3 ppm

J
J I
— I------- 1------- 1------- 1------- 1------- 1------- 1------- 1------- 1— j
J ^

I 1 1 . 1 >
j
1 > 1 .
TMS

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

221
 Problem 111

4000 3000 2000 1600 1200 800

V (cm'1 )

UV Spectrum

X max 270 (log10s 4.2)

solvent: methanol

40 80 120 160 200 240 280

m/e

1----1----1----1----1---- 1---- 1----1----1---- 1 I 1----1----'----1---- 1----1----'----1---- '----1---- '----1---- r

13C N M R Spectrum expansion
(100.0 MHz, CDCI3 solution)
"nr 1■—
135 130 ppm

D EPT CH2J CH3f C H f

expansion

I solvent
proton decoupled -«-------------- r_ ----
135 130 ppm

J 1- - - - - - - - 1- - - - - - - - 1- - - - - - - - 1- - - - - - - - 1- - - - - - - - 1- - - - - - - - 1- - - - - - - - 1- - - - - - - - 1- - - - - - - - 1- - - - - - - - 1- - - - - - - - 1- - - - - - - - 1- - - - - - - - 1_ _ _ _ _ I_ _ _ _ i_ _ _ _ _ I_ _ _ _ i_ _ _ _ _ I_ _ _ _ _ i_ _ _ _ _ I i 1 i

200 160 120 80 40 0 6 (ppm)

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

■"1---- -------- 1--------

L ■
—
8.0i 7.5 7.0 ppm

TMS
1
1 l i ........ -L.........1...........1 ...... 1 ........1...........1_____ L-.......1 1 ....J, 1 1 I i I J ........_.±...... I.....

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

222
 Problem 112

4000 3000 2000 1600 1200 800

V (cm"1)

UV Spectrum

^max 265 nm (log^s 2.6)

^m ax 271 nm (loginE 2 .6 )

solvent: methanol

40 80 120 160 200 240 280

m/e

200 160 120 80 40 0 5 (ppm)

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

223
 Problem 113

4000 3000 2000 1600 1200 800

V (cm'1 )

100 ; Mass Spectrum UV Spectrum

119
80
CL 3 lmax 238 nm (log1Qs 4.2)
60 0
91 M + '= 150
^max 281 nm (log^s 2 .7 )
40
solvent: methanol
20
C9 H10O 2
40 80 120 160 200 240 280
m/e

- i— ■. i ' i ' i ' i 1.... 1 " 1 _ ""1..... .1 — T... ..........1— 1 » 1 1 I 1

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

132.5 13(3.0 ppm

D EPT CH2(, CH3f CHf

expansion

1 " .I solvent
proton decoupled 132.5 13(3.0 ppm 1

..................i .......... i......... 1..... ... _________ 1 ^ . . ......

I 1. I ... . 1 1 ... 1 --1 J_.. 1 .... 1 . 1 . L . 1 . 1 1 1 _j__ l_. 1 1 1
200 160 120 80 40 0 §(ppm)

10 9 8 7 6 5 4 3 2 1 0
§ (ppm)

224
 Problem 114

4000 3000 2000 1600 1200 800

V (cm'1 )

UV Spectrum

A,max 270 nm (log10s 3.1)

^ max 282 nm (log10s 3.1)

solvent: hexane

Note: UV spectrum not changed

significantly on addition of base
40 80 120 160 200 240 280
m/e

— r 1 i 1 i 1 i '— i 1 1 1 1 1 1 ' 1 1 1 | 1 | 1
13C NMR Spectrum
(50.0 MHz, CDCI3 solution)

D EP T CH2| CH3t ch |

solvent
proton decoupled . I
__ ____ Hi. __ -
I , I , I , I , I . I , I . I , I . 1 , 1 , 1
200 160 120 80 40 0 5 (ppm)

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

225
 Problem 115

4000 3000 2000 1600 1200 800

V (cm'1)

UV Spectrum

lo9io 8 ~ 3 - 4

Note: UV spectrum changed

significantly on addition
of base

40 80 120 160 200 240 280

m/e

1H NMR Spectrum
(400 MHz, CDCI3 solution)

\ I
7.5 7.0 PPm

Exchanges
J j
with D2 O

zl
J 1 I 1 L
10 9 8 7 0
5 (ppm)

226
 Problem 116

4000 3000 2000 1600 1200 800

V (crrf1)

100
80

60

40

20

40 80 120 160 200 240 280

m/e

I 1 1 ' 1 1 1 1 1 ' 1 T 1 ' 1 "r — r..... '■ i 1 i » i •................

13C NMR Spectrum
(50.0 MHz, C D C I3 solution)

proton coupled
.- n 1 1 ,ii,

soh/ent

proton decoupled I
L . _ . ____ _
I 1 1 « 1 I 1 1 1 i 1 - .. L 1 J--- 1 1 1----- •----- 1----- 1----- 1------1----- 1----- 1-------------
200 160 120 80 40 0 5 (ppm)

1H N M R S p e c t r u m
(200 MHz, C D C I3 solution)

expansion .

I 1
l| |»ji
___fi U fK ji U\
1 1 1 1 1
7-4 7.0 6.6 ppm

J
r
TMS

1 . 1 J1
_____ J

1......... 1 _L ...... 1 1 . 1 ..1 J- 1 . 1 . 1 . 1 > 1 . 1

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

227
 Problem 117

UV Spectrum

100 : ^max 310 nm (locj'io^' 3.3)

Mass Spectrum
80 -
A.max 261 nm (log10£ 4 .3 )
■ CC
- <D 120 solvent: methanol
60 - 1
() M+’
■ C/0
-
0
03 199/201
40 7 0 ^max 262 nm (log^s 3.0)
- ss 155/157
20 184/186 A max 257 nm (log10s 3.0)
C8H10NBr
Amax 222 nm (log10£ 4.0)

40 80 120 160 200 240 280 solvent: methanol / HCI

m/e

I ..1 1 '■■■" 1 ' 1 ' 1 1— i > n. ■ i ■.. 1 1 1 1 1

13C N M R Spectrum
(50.0 MHz, CDCI3 solution)

D EPT c h 2| CH3f ch |

solvent
proton decoupled |
1 li
-------1--- 1--- 1--- 1--- 1--- 1--- 1--- 1--- 1--- 1--- 1--- 1--- 1--- 1-- l_ i 1 i 1 i 1 i 1 i
200 160 120 80 40 0 S(ppm)

1H NMR Spectrum
(200 MHz, CDCI3 solution)

expansion with
resolution enhancement

--------------- ».Ip---------------------- i
..... .....i....... i ........... .
I i i
7.5 <3.5 ppm

TMS

k . i. . I

I * I . I ■ I - I - I * I - I • I . I . I

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

228
 Problem 118

4000 3000 2000 1600 1200 800

V (cm'1)

100 : Mass Spectrum UV Spectrum

135

80 ~ jx .
■ CO
- CD^ log10s * 4
60 - CD
» (/)
- 0
cc

40 7 0

M +*
20 107
192
,l ll ., , il. i I I I . 1 C 1 2 H 16 O 2
1 . 1 . 1

40 80 120 160 200 240 280

m/e
, .. !
i r 1 1 i 1 r 1 i 1 I ■ T ~ - I ' r .. ^ T 1 1 1
13C NMR Spectrum
(50.0 MHz, CDCI3 solution)

D EP T ch2| CH3f CHf

proton decoupled solvent

I. I I ill
1 . 1 . 1 t I > I i I 1 I 1 l . I 1 I * I 1 I 1
200 160 120 80 40 0 5 (ppm)

1H NMR Spectrum
(200 MHz, CDCI3 solution)

s
TMS

i 1 L
j l_
10 8 0
8 (ppm)

229
 Problem 119

4000 3000 2000 1600 1200 800

V (cm-1)

135
100 Mass Spectrum UV Spectrum
80 -■ ±C cD
-. C Q D. A,max 262 nm (log10£ 2 .6 )
60 -■ < 0/>
-. _CQD
A,max 269 nm (log1Qs 2 .6 )
40 7 O 150

20 : 43
M + '= 192
solvent: methanol

: ii , i. u ,i ___ _ I , i C i2 h 16o 2
i . i . i ,—i—.—i—.—i—,—i—,—i—.—i—,—i—,—i—,—i—,—i—.—i—.—i—,—i—,—
40 80 120 160 200 240 280
m/e

I 1 1............... 1 1 1....... 1 1 1 | 1 | . | 1 | 1 | 1 1 1 1 1
13C NMR Spectrum
MHz, CDCI3 solution)
(100.0

DEPT CH2i|( CH3f CHf 1

expansion

Iw solvent
....r1.
proton decoupled I
149 ppm 1
I 1 1 1
----------- 1----- 1------1----- 1------1----- 1------1----- 1------1----- 1------1----- 1------1----- 1----- 1----- 1 l 1 l » l 1 l *
200 160 120 80 40 0 8 (ppm)

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

230
 Problem 120

4000 3000 2000 1600 1200 800

V (cm'1 )

UV Spectrum

A/max ~ 240 nm (l°g10s >4'°)

40 80 120 160 200 240 280

m/e

1 1 1 1 1 I 1 1 1 1 ...r 1 i " ' 1 i 1 i 1........ i ...... 1 ..i ....... ■ "‘ i 1

13C NMR Spectrum
(100.0 MHz, CDCIj solution)

D EPT CH2| CH3f C H f

_ _ ..................................................... 1

proton decoupled solvent

i 1 I .......................... .......... i 1________ i

1 . 1 . 1 ■ 1 . 1 • 1 ■ 1 • 1 ■ 1 . 1 . 1 ...-J____ ■----------
200 160 120 80 40 0 5(PPm)

1H NMR Spectrum
(400 MHz, CDCI3 solution) expansior1

8.0
I 7.Ej PPM
r----

TMS
I I
1 i 1

1 1 1 1 1 1 1 1 1 1 1
--------- ---------------- ---------------- ---------------- ---------------- ---------------- ---------------- ---------------- ---------------- ---------------- __________ __________ 1 . ................. 1 I ............... i .........- ..... 1................... 1 ............. 1 I 1 1
............ .................... .............

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

231
 Problem 121

4000 3000 2000 1600 1200 800

V (cm‘1)

UV Spectrum

X max 227 nm (log1Qs 3.9)

^max 305 nm (log^s 4.0)

solvent: methanol

40 80 120 160 200 240 280

m/ e
.... r..... 1 !" ' 'r 1 1 " ■ i • 1 1 1 ' 1— r 7 1 r 1 - ... 1 1 • ...... ■
13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

...... _ . 1
D EPT CH2i|f CH3f CH f

solvent
proton decoupled j
1 i 1
----------- 1----- 1----- 1----- 1----- 1----- 1----- 1----- 1------1----- 1----- 1----- 1----- 1----- 1----- 1----- 1 1 1 1 1 1 1 1 1
2 0 0 160 1 2 0 80 40 0 5 (ppm)

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

, 1___ —
1
8.0 7.0 ppm
---

TMS

- i

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

232
 m/ e X(nm)
■ i 1— r 1 1 1 1 ' 1 “— 1 1 1 ... 1 I..... ' 1 1 1 1 1 1 1 1................
,3C NMR Spectrurr1
(100 MHz, CDCI3 soluti on)

D EPT ch 2| ch 3| c h |

solvent

*
proton decoupled
. 1 ______________ ______
1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 — 1----- 1----- 1----- 1----- 1----- 1----- 1-------------
200 160 120 80 40 0 S(PPm)

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

233
 Problem 123

UV Spectrum

^m ax 225 nm (log^g8 4 . 2 )

^m ax 250 nm (log^c 3 . 8 )

^m ax 293 nm (log^s 3 .2 )
^m ax 330 nm (log^s 2 .6 )

solvent: methanol
40 80 120 160 200 240 280
m/e

1---- 1---- 1---- 1-------- 1— |----'— T i 1 r i 1 r

,3C NMR Spectrum
(100 MHz, CDCI3 solution)
expansion

i i i i i
134 132 ppm

D EPT CH2ijf CH3t C H f

expansion

Ju l JL
proton decoupled 134 132 ppm
X
-i 1----1----1---- 1---- 1__ i----1__ i__ i---- 1----1__ i__ i__ i__ i__ i__ i__ t i i i t i i______
200 160 120 80 40 0 S(ppm)

1H NMR Spectrum
(400 MHz, CDCL solution)

TMS
■i 11 1i 1" 1i 11
11 10 ppm

J I I 1______ 1______ i______ L

10 8 1 0
5 (ppm)

234
 Problem 124

4000 3000 2000 1600 1200 800

V (cm'1 )

UV Spectrum

^max 2 77 nm (log1Qe 4 .2)

solvent: methanol

40 80 120 160 200 240 280

m/e

I 1 1 ^ I ' I ' I T~" | ■ 1 - | 1 | 1 | '" I 1 1 ...' 1 .....

13C NMR Spectrunn
(100.0 MHz, CDCIj solijtion)

D EPT c h 2| CH3f C H f

solvent
proton decoupled
1
I i
I ■ I • I ■ I • I ■ I . I . I . I ■ I ■ I . I
200 160 120 80 40 0 S(PPrni)

expansion
1H Nl\/IR Spectrum
(400 MhHz, CDCI3 solution)

__ ,1^ ___;i[__
i i r ----r i---- i i —r
7.65 7.45 6.85 6.65 ppm

TMS

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

235
 Problem 125

UV Spectrum

log10c > 4

40 80 120 160 200 240 280

m/ e
1— >
— i— «— i— 1— i— ■
— r
13C NMR Spectrum expansion
(50.0 MHz, CDCI3 solution)

DEPT c h 2| CH3f ch | 85 80 ppm

solvent
expansion

proton decoupled 85 80 ppm

200 160 120 80 40 0 § (ppm)

10 8 0
5 (ppm)

236
 Problem 126

UV Spectrum

^m ax 235 nm (log^s 4 . 1 )

A.max 2 6 5 nm (log10£ 3 .0 )

solvent: ethanol

40 80 120 160 200 240 280

m/e

8 (ppm)

237
 m/ e X (nm)

I 1 I 1 I 1 1 1 .. 1 | 1 1 1.... 1 1 1 1 1 1 ..T 1 1 1
13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

D EPT CH2{ CH3f C H f

solvent

proton decoupled .

------ 1------- 1-------1------- 1------- 1------- 1-------1------- 1-------«------- 1-------•------- 1-------»------- 1-------1— 1 » 1 » 1 • 1 1 1 1
200 160 120 80 40 0 S(ppm)

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

238
 Problem 128

100
80

60

40

20

40 80 120 160 200 240 280

m/e

I ' I ' I ' I 1 1 ' 1 ' 1 ' 1 ' 1 1 1 1 1 1

13C NMR Spectrum
(100.0 MHz, CD3SOCD3 solution)

D EP T CH2| CH3f C H f

1— ~1- solvent

proton decoupled | |

I 1 I 1 i _j----- 1----- 1----- 1----- 1----- 1----- 1----- 1----- 1----- 1----- 1----- 1----- 1------1----- 1----- 1----- 1------1------1-------------
200 160 120 80 40 0 5 (ppm)

1H NMR Spectrum expansion

(400 MHz,CDCI3/C D 3SOCD3 solution)

expansion

mi ________________________ in___

solvent

11 1
. I___________ i________ __________
j i i i i i i i i__
10 9 8 7 6 5 4 3 2 1 0
8 (ppm)

239
 Problem 129

100 ; 120
Mass Spectrum UV Spectrum
80
^m ax 312 nm (log^s 4.3)
60
solvent: methanol
40

20
C8 H9 N O

40 80 120 160 200 240 280

m/e

1 I 1 I 1 l 1 1 i I ■ "7 I 1 1 ■ 1 T1 1 ' 1
,3C NMR Spectrum
(100 Mz, DMSO-d 6 solution)

D EPT ch2\ CH3f ch |

solvent — r n

proton decoupled | I
................... ..
1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

200 160 120 80 40 0 5 (ppm)

1H NMR Spectrum
(200 MHz, DMSO-d 6 solution)

Exchanges
with D2 O

I residual H20
in solvent

TMS

1
10 8 1 0
6 (ppm)

240
 Problem 130

4000 3000 2000 1600 1200 800

V (cm 1 )

UV Spectrum

A,max 246 nm (log10e 4.2)

■'max 280 nm (log^s 3.1)

solvent: methanol

40 80 120 160 200 240 280

m/ e
1 . 1 . 1 ’ “1 ' 1 1 T"" r 1 1 ' ”1... 1 .1 1 1 T 1 1
,3C NMR Spectrum
(100 MHz, CDCI3 solution)

D EP T c h 2| CH3f ch f

solvent

proton decoupled I jj
1
— 1----- 1----- i----- 1----- 1----- 1----- 1----- 1----- 1----- 1----- 1----- 1 —t- 1 i i » i i —1 1 1 j— 1 —1------
200 160 120 80 40 0 S(PPm)

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

241
 Problem 131

UV Spectrum

X max 250 nm (log10s 3.1)

^max 287 nm (log^s 2.2 )

solvent: chloroform

40 80 120 160 200 240 280

m/e

I 1 1 '" I 1.... 1 ' 1 ■7.....T— 7— 1...... r '.... 1 1 1 1 ..1.... 1.......r " 1

13C NMR Spectrum
(50.0 MHz, CDCI3 solution)

DEPT c h 2| CH3f ch |

solvent

proton decoupled I i i
_____________1 .
----------- 1----- «----- 1----- «----- 1----- 1----- 1----- 1----- 1----- 1----- 1----- 1----- 1----- 1----- 1----- «----- i 1 1 1 1 1 1 1
200 160 120 80 40 0 8 (ppm)

1H NMR Spectrum
(200 MHz, CDCI3 solution)

expansion

/vi,
n 1---- 1---
7.6 7.0 ppm
exchanges
with D20 on warming TMS
1

10 1 0
8 (ppm)

242
 Problem 132

4000 3000 2000 1600 1200 800

V (cm'1 )

100 UV Spectrum

80
X max 250 nm (log10e 4.1)
60
^max 285 nm (log^s 3.6)
40
solvent: ethanol
20

40 80 120 160 200 240 280

m/e

200 160 120 80 40 0 S(ppm)

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

243
 Problem 133

UV Spectrum

^ max 257 nm (log10e

*10t 4.3)
solvent: methanol

40 80 120 160 200 240 280

m/e

...! '■ I ' I • i ■ i * 1 ■ •— r 1 1 .... r r ' 1 t ...."r 1... 1 1 '

13C NMR Spectrum

(50.0 MHz, CDCI3 solution) Resolves into
two signals
at higher field

D EPT ch 2| CH3f C H f

Resolves into
two signals
solvent at higher field
proton decoupled i I
1 Hi
1 . I . I . I . I . 1 . I . I . I . I . 1 . I .

200 160 120 80 40 0 8 (ppm)

1H NMR Spectrum
(200 MHz, CDCIj solution)

expansions

V- pI [
p \
—i---- 1--- 1—
4.6 4.2 3.8 ppm

M TMS

J i L
10 8 1 0
8 (ppm)

244
 Problem 134

IR Spectrum 1730
(CHCI3 solution)

4000 3000 2000 1600 1200 800

V (cm'1 )

0.597 mg /1 0 mis
path length : 0.2 cm
solvent: ethanol

40 80 120 160 200 240 280 200 250 300 350

m/e X (nm)
, 1 I 1 I 1 I -1 1 1 1 1 1 1 n----- 1 ' 1 1 1 1
13C NMR Spectrum
(125.0 MHz, CDCIj solution)

D EP T CH2| c h 3| ch |

solvent

proton decoupled j |
...... .-......... 1
> I • I .I
I I
I L
. 1I I. I
I I
. I .I
I I
I I. I .1
I II I. II .I I
I I
. II I.______
200 160 120 80 40 0 5 (ppm)

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

245
 m/ e X (nm)

I I I I I I I I I I I I I « « ■ I i I « I »______
200 160 120 80 40 0 5 (ppm)

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

246
 m/ e X (nm)

I ' I ' I ' I ' I 1 1 1 1 , 1 ’ 1 | . | 1 | 1

13C NMR Spectrum
(50.0 MHz, CDCI3 solution)

Resolves into
two signals at higher field

D EP T CH2jf CH3t ch |

Resolves into
two signals at higher field

proton decoupled | ^ ifj- solvent

. Ill
1 « 1 1 1 «------- 1-------•-------1------- 1------- 1-------»------- 1-------•------- 1------- 1-------1-------1------- 1------- 1-------1-------1------- 1------- 1----------------
200 160 120 80 40 0 6 (ppm)

—I----- 1----- 1----- 1----- 1----- 1----- 1----- 1------ 1 i I i I i i ' i ' i i i
10 9 8 7 6 5 4 3 2 1 0
6 (ppm)

247
 m/e X (nm)

13C NMR Spectrum expansion

I 1i
CDCI3 solution)
(100.0 MHz, h |l expansion

ji '

D EPT
CH2| CH3f C H f 135
II
130 ppm 126 125 ppm

note
expansion
expansion

solvent

proton decoupled 135 130 ppm 126 125 ppm

JL
_i i i L_

200 160 120 80 40 0 5 (ppm)

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

TMS

j\Rj

10 8 1 0
8 (ppm)

248
 Problem 138

4000 3000 2000 1600 1200 800

V (cm'1 )

100
. 1. , . \ . , i , 1111111111

Mass Spectrum UV Spectrum

75
80
% of base peak

? lmax 262 nm (log10s 2.3)

60
solvent: methanol
40
91 135 M+’ = 166 (< 1%)
20
» ......I,I ... c 10 h 14o 2
--------,— i— ,— i— ,— i— ,— i— ,— i— ,— i— ,— i— ,— i— .— i— ,— i— .— i— ,— i— ,— i— ,— i— .— i— .
40 80 120 160 200 240 280
m/e
I 1 I 1 I ' I 1 I 1 I 1 " r 1 r ~i_ t ..... r 'i 1 r 1 1 1............
13C NMR Spectrum
(50.0 MHz, CDCI3 solution)

D EP T ch 2| c h 3| CHf

solvent
proton decoupled
in
I . I . I . I . I . I . I . I - I . I . I . I
200 160 120 80 40 0 5(ppm)

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

249
 Problem 139

4000 3000 2000 1600 1200 800

V (cm'1 )

UV Spectrum

? lmax 269 nm (log1Qs 2.7)

X max 263 nm (log10e 2.7)

solvent: methanol

m/ e
--------------T”.. ' I " ' l ' l ' 1 < I 1........1.......1...... T ......'........r 1 11 1 1 1 1............

13C NMR Spectrum

(50.0 MHz, CDCI3 solution)

proton coupled
.... . .. ..... ....... i,

soh✓ent

proton decoupled | |
__________ _____ ____ j _____
I , I , I . I . I . I . I . I . I . I . I . I .

200 160 120 80 40 0 5 (ppm)

1H NMR Spectrum
(200 MHz, CDCI3 solution)

expansion

1 1 1 1
2.5 2.0 1.5 ppm

TMS

1 1 1 1 1 1
1 ,,
1 • 1
__ . ... J I
1- 1 - 1---------1----------1--------- 1----------1----------1----------1----------1----------1----------1-----

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

250
 Problem 140

! \

UV spectrum

0.491 mg /1 0 mis
path length : 0.2 cm
solvent: ethanol

40 80 120 160 200 240 280 200 250 300 350

m/e X(nm)
1 ' 1 ' 1 1 1 1 1 1 ■ 1 1 1 1 r 1 1 1 1
13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

D EP T CH2(f CH3f ch|

solvent

proton decoupled I
1
--- 1--- 1___ 1___ 1___ 1___ 1___ 1___ 1___ 1___ 1___ 1___ 1___ 1___ 1___ 1_ .J_ _j___ 1___ 1___ 1___ 1___ 1___ 1___ 1___ 1_______
200 160 120 80 40 0 5 (ppm)

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

expansion

-i-------- 1-------- 1— _l 1 1----------

4.6 4.4 ppm 1.6 1.4 ppm

TMS

-i 1----- 1----- 1----- 1----- 1----- 1___ I___ i___ I___ i___ I___ i___ I___ i___ I___ i I ■
10 8 1 0
5 (ppm)

251
 m/e X (nm)
I 1 -~r -1 1 1 1 1 1 —. | . | -r | 1 | , | , , 1 1 1
13C NMR Spectrum
( 100.0 MHz, CDCI3 solution)

D EPT c h 2| CH3f C H f

solvent
proton decoupled

1
----- 1------1----- •------1----- 1------1----- 1----- 1----- 1------1----- 1------1----- 1----- 1----- 1----- 1 1 1 1 1 1 1 1 1 1
200 160 120 80 40 0 5 (ppm)

1H NMR Spectrum
(400 MHz, C D C I3 solution)

expansion

expansion
expansion

—1------ 1 r
7.8 7.6 ppm 4.4 4.2 ppm 1.4 1.2 ppmi

TMS

__ L

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

252
 Problem 142

100
80

60

40

20

40 80 120 160 200 240 280

m/e
--------- 1........1 I 1 I 1 I 1 I —1 1 ' T - ' T" ■ I 1 I 1 1 1 1 '
expansion
13C NMR Spectrum
(50.0 MHz, CDCI3 solution)
1 1 i

135 130 PPm

D EPT CH2(f CH3f C H f

expansion

!L 11 ... . 1
1
135 130 ppm

solvent
proton decoupled |
A 11
..- ....... L_ j I ... . I 1 1 .1 I 1 1. 1 I < I < I 1 I 1 I < I
200 160 120 80 40 0 8 (ppm)

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

253
 Problem 143

UV Spectrum

^max 220 nm (log^c 3.7)

^max 274 nm (log10s 3.3 )

solvent: ethanol

m/e

13C NMR Spectrum

(100.0 MHz, CDCI3 solution)

DEPT c h 2'|( CH3f ch |

solvent
proton decoupled I
j 1 i . i 1 i 1 i 1 i , i ■ 1 . i -I I L. J 1 L
200 160 120 80 40 0 8 (ppm)

8 (ppm)

254
 Problem 144

4000 3000 2000 1600 1200 800

V (cm'1 )

100 163 Mass Spectrum UV Spectrum

80 - ^
■ CD
-
.
0
Cl
? lmax 223 nm (log1Qs 3.9)
60 - 0
■ C/5
_ 0
. -Q ^max 275 nm (log^s 3.1 )
40 “ ‘o

: ^ M + '= 1 9 4 X max 281 nm (log10s 3.0 )

20 [ I 1 0 4 135
: i it i » > i
I. I. c 10h 10o 4 solvent: ethanol
i . i i i . i . i . i i i . i . i . i . a . i i i

40 80 120 160 200 240 280

m/e

....1— 1 1 1 ......1....” T" 1 1 1 1 111 1 !...... r....... 1...... T 1 ... 1 1 .... r ".. 1 1 1
13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

D EP T CH2iji CH3f C H t

solvent

proton decoupled i *
1
I . ! . I . I . I . I . I . I . I 1 1 .1.. - 1 -L----- 1----- i------------
200 160 120 80 40 0 8 (ppm)

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

255
 Problem 145

4000 3000 2000 1600 1200 800

V (crrf1 )

No significant UV
absorption above 220 nm

40 80 120 160 200 240 280

m/e

1 1 I 1 T I I I I I
13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

D EPT c h 2| CH3f C H f

solvent
proton decoupled
I
I__
J 1 L
200 160 120 80 40 0 8 (ppm)

8 (ppm)

256
 Problem 146

4000 3000 2000 1600 1200 800

V (cm'1)

100 : Mass Spectrum UV Spectrum

91
80 -
- CO
- CD ^m ax 261 nm (log1Qe 3.5)
60 -
-
CD
CO
- CO
o M + '= 92 solvent: ethanol
40 7 o

20
c 7h 8

40 80 120 160 200 240 280

m/e

I 1 I 1 I 1 I 1 I T" 1 1 1 1 1 1 1 1 1 1 1 1 1 '
13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

DEPT CH2(( CH3f C H f

solvent
proton decoupled t
.................... i
I . I . I . I . I I « I_ . I . ..J___-•___ I------.------1----- 1------1----- *------------
200 160 120 80 40 0 5 (ppm)

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

257
 Problem 147

4000 3000 2000 1600 1200 800

V (cm’1 )

No significant UV
absorption above 220 nm

40 80 120 160 200 240 280

m/e

I 1 I 1 I
13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

D EPT CH2ijf CH3t ch |

proton decoupled
solvent
i
I . I . I . I J i L
200 160 120 80 40 0 8 (ppm)

1H NMR Spectrum
(400 MHz, CDCI3 solution)

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

258
4000 3000 2000 1600 1200 800
V (cm'1 )

No significant UV
absorption above 220 nm

40 80 120 160 200 240 280

m/ e
i r r • i 1 i • i 1 r .. 1 i i > i i « i 1 1
13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

DEPT CH2i|( CH3f C H f

solvent
1
proton decoupled ^ ^

1 ■ 1 - 1 . 1 • 1 • 1 « 1 « 1 « 1 . 1 « 1 -i -L.... .
200 160 120 80 40 0 8 (ppm)

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

259
 Problem 149

4000 3000 2000 1600 1200 800

V (cm'1 )

40 80 120 160 200 240 280

m/e

i 1 i 1 r 1 1 1 f"
13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

DEPT CH2\f CH3f C h {

solvent
proton decoupled
I

8 (ppm)

260
 Problem 150

100 . Mass Spectrum

M + '= 128
80 -' 03
- CD
. CL
60 -■ CD No significant UV
C/3
_ 03
. -Q absorption above 220 nm
40 7 0
- ^8
: 0 55 83
20 , 100
1 , 113 i C 7H 12O 2
---- 1— 1— I— 1— I— 1— I— 1— I— •— I— 1— I— 1__I_____1__1__1_____1 . 1 . 1 . 1 . 1 . 1 .
40 80 120 160 200 240 280
m/ e
l 1 r 1 i 1 r
13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

D EP T c h 2| CH3f C H f

solvent

proton decoupled

5 (ppm)

261
 Problem 151

4000 3000 2000 1600 1200 800

V (cm'1 )

No significant UV
absorption above 220 nm

40 80 120 160 200 240 280

m/e

i — 1— i— « i 1 i 1 i 1 i 1 r "1 ' 1 1 1 *“
13C NMR Spectrum expansion
(100.0 MHz, CDCI3 solution)

1-------- 1------- r
DEPT c h 2J CH3f ch | 28 27 ppm

expansion

solvent
proton decoupled
1-------- 1------- 1-
I 28 27 ppm
- I ....

J 1 I . I 1 I 1 I 1 I 1 I 1 I 1 I . I 1 I 1 I 1_____
200 160 120 80 40 0 5 (ppm)

5 (ppm)

262
 Problem 152

4000 3000 2000 1600 1200 800

V (cm"1 )

No significant UV
absorption above 220 nm

40 80 120 160 200 240 280

m/e

I 1 1 1 1 ■1— r .... r " 1 •“ 1 ■ 1 1 1 ' 1 1 1 ' 1

13C NMR Spectrum
(50.0 MHz, CDCI3 solution)

D EP T CH 2| CH3t ch |

solvent

proton decoupled
1
_____ L... 1 1......j__... 1, 1 , 1 , — 1----- 1— 1 j— 1 1 1 1 1 . 1 , 1 !
200 160 120 80 40 0 5 (ppm)

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

263
 Problem 153

4000 3000 2000 1600 1200 800

V (cm'1 )

100 : 30 Mass Spectrum

80 -
■ 03
- CD

60 ~ CD No significant UV
• CO
- 03
o
absorption above 220 nm
40 7 o
56
“

20 M + ‘ = 1 0 2 (< 1% )

L 1i >iJi i i, ,1 C 5 H 14N 2
__ i___ i___ i___ _ i • i ___ 1___ 1___ ____ 1___ .___ 1___ i----- 1----- 1----- 1----- .----- L. ................................................ , .

40 80 120 160 200 240 280

m/ e
I 1 I 1 i ■ i ■ I ' 1 1 1 1 1 1 1 • 1 1 1 ■ 1
13C NMR Spectrum
r 'in n

DEPT c h 2{ CH3f ch |

solvent

proton decoupled if
1
I 1 I 1 I 1 I 1 I...._ J ___1 1 1 1 1 1 ..... 1....... 1........L ..... 1 ,, 1........1 ...... 1,.... JL.................
200 160 120 80 40 0 8 (ppm)

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

264
 Problem 154

100 : 31 Mass Spectrum

80 -
’ CO
: o- No significant UV
60 -
■<0j)
~-Q absorption above 220 nm
40 7o
-^
20 M+'
100 < 1% c 2h 3 f 3 o
^ IJ . iJ ... i
_____i_i_i_i_i_*— i— *— • * » • i — i— . i_j_1_1_1_1_1_1_1_._1_._1_._
40 80 120 160 200 240 280
m/e

...1........1 1 1 1 " 1 I 1 1 J "I 1 I 1 "1........r 1 1 1 1...... r -l 1 T

13C NMR Spectrum
(100.0 MHz, CDCI3 solution)
— — expansion
DEPT ch2| CH3f chf
1 I
1 |
V v 1
61.5 60.5 ppm

expansion

l !i

proton decoupled solvent —

i------1------1—
61.5 60.5 ppm
I
........................................................................................I________I________ I________ I________ I________ L_ J L-

200 160 120 80 40 0 8 (ppm)

10 8 1 0
8 (ppm)

265
 Problem 155

100 : 119 Mass Spectrum UV Spectrum

80 -
■
-
CO
CD
91 log10s > 5
60 “- CD
CO
-
. -Q
CO
M+‘
40 7 0 226

20
I „ l | , I C 15H 1 4 ° 2
—--L-.-- .--1--.--1--.--1--.--1--.-- --.-- --.-- --.--1--.--1--.--1--.-- --.-- --.-- --.--
L 1 1 1 1 1 1

40 80 120 160 200 240 280

m/e

i 1 r
13C NMR Spectrum
(150.0 MHz, CDCI3 solution) expansion

DEPT CH2| CHat C H f 130 129 128 ppm

expansion

130 129 128 ppm

proton decoupled
_____________solvent -rj~i

J I I I I I I L. J L-

200 160 120 80 40 0 5 (ppm)

8 (ppm)

266
 Problem 156

4000 3000 2000 1600 1200 800

V (cm'1 )

100 : 105 Mass Spectrum UV Spectrum

80 -• 00
- CD log10e > 5
. Q.
60 - 0
(/)
- CO
. _Q M+’
40 • ° 77 226
-^
20
121 n U
1 .i... i 1]__iLJ I s.l I I C 15H 1 4 ° 2
------- .— i—.— i—.— i—.—j _i_i_ --- 1------- 1---.--- 1---1--- 1
_1_1_1_1__1_1_1__ » - » ■ ! .
40 80 120 160 200 240 280
m/e

200 160 120 80 40 0 5 (ppm)

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

267
 40 80 120 160 200 240 280 200 250 300 350
m/ e A,(nm)
I 1 1. 1 1 1 1 1 1 —r 1 1 | 1 | 1 | 1 1 1 I ' I 1
expansion
13C NMR Spectrum
(75.0 MHz, CDCI3 solution)

DEPT CH2^ CH3f C H f 135 125 ppm

expansion

solvent -r-1
il 1
proton decoupled 1 --- r- T---- T.. —
T
135 125 ppm

...i_____________ L______ i
----- 1----- 1----- 1------1----- 1----- 1----- 1----- 1-----j_----- 1------1------1----- 1 l 1 l i t 1 1 1 1 * 1 1
200 160 120 80 40 0 5 (ppm)

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

268
 40 80 120 160 200 240 280 200 250 300 350
m/ e A (nm)
T ' I ' I 1 I 1 I ' 1 1 1 r..... i 1 r 1.. i .nr" i .. 1 r 1
expansion
13C NMR Spectrum
(100.0 MHz, CDCIj solution)

... f —
T
D EP T CH2-If CH3f C H f 140 13-0 ppnn

exparision

solvent

11
T........ 1 -.. T —
t
proton decoupled i i 140 13 0 pprn

I . I * l i I i I • I i l > I • l • I • I • l >
200 160 120 80 40 0 5 (ppm)

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

269
 Problem 159

4000 3000 2000 1600 1200 800

V (cm'1 )

UV Spectrum

l°9io e > 4

40 80 120 160 200 240 280

m/e

1 1----1 1 I 1 I r n 1 i 1 i 1 i n -t | , r
expansion expansion
13C NMR Spectrum
(100.0 MHz, CDCIj solution)

D EPT CH2j CHst ch | 128.7 128.4 ppm 130 120 ppm

expansion expansion
• solvent

proton decoupled

128.7 128.4 ppm 130 120 ppm

-i 1----- 1------1----- 1----- 1----- 1------1----- 1----- 1----- 1___ I___ i___ I___ i I i I ■ I i I i
200 160 120 80 40 0 S(ppm)

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

270
 Problem 160

UV Spectrum

log10s > 4

80 120 160 200 240 280

m/e

5 (ppm)

271
 Problem 161

4000 3000 2000 1600 1200 800

V (cm'1 )

40 80 120 160 200 240 280

m/e

I ...1 1 1 1 1 1 1 1 ' 1 ........r "....1 ' 1 1 1 ' ......T ” ....' 1 ' 1 ------
13C N M R S p e c tru m
(50.0 MHz, CDCI3 solution)

DEPT c h 2| CH3f ch |

solvent
proton decoupled |
1 it
----1-------•-------1-------1-------1-------•-------1-------1------1-------1-------1-------1-------1------J------ 1 L 1 1 1 1 1 1 1 1
200 160 120 80 40 0 5 (ppm)

1H NMR Spectrum
(200 MHz, CDCIj solution)

expansion

expansion scale

8.5 8.0 ppm

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

272
 Problem 162

4000 3000 2000 1600 1200 800

V (cm'1 )

100 ; 119 Mass Spectrum UV Spectrum

80
^m ax 246 nm (log^s 3.7)
60
^max 273 nm (log^c 2.6 )
40

20 Mh 191 solvent: ethanol

c 12h 17n o

40 80 120 160 200 240 280

m/e

200 160 120 80 40 0 5 (ppm)

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

273
 Problem 163

4000 3000 2000 1600 1200 800

V (cm'1 )

UV Spectrum

I max 277 nm (log^s 3.4)

solvent: methanol

40 80 120 160 200 240 280

m/e

1... 1 I 1 I ' 1 ' 1 1 1 .... 1... 1 1 1 • 1 1 r 1 1 1 1 »..

13C NMR Spectrum
(50.0 MHz, CDCI3 solution)

D EPT c h 2j c h 3| c h |

solvent
proton decoupled |
in
--------------1-------1-------1-------1-------1-------1-------1-------•------- 1-------»------- 1-------»------ 1 j— 1 1 1 1 1 1 1 1 1 1
200 160 120 80 40 0 5 (ppm)

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

274
 m/e X (nm)

13C NMR Spectrum

(50.0 MHz, CDCI3 solution)

D EPT CH2| CH3f ch|

solvent
jl expansion
expa

T------------ 1-------------T

1
175 170 165 ppm

proton decoupled
I » I I I . I L. J i I i I i L
200 160 120 80 40 0 8 (ppm)

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

275
 m/e A,(nm)
-------- I ' I ' I ' I 1 T 1 1 i | ■ | . | , | . | i | .

13C NMR Spectrum

(100.0 MHz, CDCI3 solution)

DEPT CH2| CH3f C H f

r solvent

proton decoupled

----- 1------1----- 1------1----- 1----- 1----- •----- 1----- 1------1----- «----- 1----- 1----- L i 1 i 1 i 1 i 1 i 1 i
200 160 120 80 40 0 5 (ppm)

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

276
 m/e X(nm)
I . I . I . I ■ “I 1 I 1 i ' 1 1 1 1 I T 1 1 T ..... 1
13C NMR Spectrum
(150.0 WIHz, CDCIj solution)

D EP T CH2| CH3f C H f

solvent
proton decoupled I
! I 1 1
. i . i . i . i . i . i . i . i . i . i . i . i .

200 160 120 80 40 0 S(ppm)

1H NMR Spectrum
(600 MHz, CDCI3 solution) Expansion Scale

exchanges
with D20
7.00 6.98 6.72 6.70 6.68 ppm

vertical expansion x20 TMS

_L

J ---------------- 1---------------- 1---------------- 1---------------- 1---------------- 1___________I__________ I___________I__________ I__________ I__________ I__________ I__________ I__________ I__________ L_

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

277
 Problem 167

4000 3000 2000 1600 1200 800

V (cm-1)

100 : 261/263/265 Mass Spectrum

182/184
80 -
■ CO
- CD

60 * 0
-
- C/5
CO
o 197/199 M+*
40 7 o 276/278/280
_ -o

20
C9H10 Br2
_l i I i I I L_ _l i I . I . I I ■ t I u L_

40 80 120 160 200 240 280

m/e

I 1 I ' I ' 1 ' I '1 1 T_ 1 1 T .. ' 1 ' 1 1 1 1 1 ■

13C NMR Spectrum
(50.0 MHz, CDCI3 solution)

L 1
D EP T c h 2| c h 3| ch |

solvent
proton decoupled i
.............111 .
________ I____ 1____ 1____ 1____ 1____ 1____1____ 1-------1-------1-------1-------1---------------1-------1-------.-------1-------1-------.-------.-------.____ .____ 1____ 1 ______
200 160 120 80 40 0 5 (ppm)

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

278
 Problem 168

i ■» . ■■■• ■- I - i ■« ■t • • ^* i— i i i t — i— I— i— i— •— i—
4000 3000 2000 1600 1200 800
V (cm'1)

100
80

60

40

20

m/ e
i ' i 1 r 1 ' r
13C NMR Spectrum one signal even at high field
(50.0 MHz, CDCI3 solution) I

DEPT c h 2| CH3f c h | Resolves into

two signals at higher field

solvent

proton decoupled

1____
J_ _ L J I I I I L.

200 160 120 80 40 0 5 (ppm)

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

279
 m/e A,(nm)

I I I I I 1 I 1 I 1 1 1 1 1 1 1 1 ' 1 1 1 1 1 '
13C NMR Spectrum
(150.0 MHz, CDCI3 solution)

DEPT ch 2| c H3f C H f

solvent

proton decoupled

- -L 1 ■ 1 -L 1 ■ 1 1 1 ■ .....................................................1 , 1 . 1 .
200 160 120 80 40 0 5 (ppm)

1H NMR Spectrum expansions

(600 MHz, CDCI3 solution)

Expansion Scale TMS

0 5 10 15 20 Hz

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

280
 Problem 170

4000 3000 2000 1600 1200 800

V (cm'1)

40 80 120 160 200 240 280

m/e

1 1 .
1 1 1 ' 1 1....1 1 ' 1 1 1 1 1 1 1 1 1 ' 1

13C NMR Spectrum

(50.0 MHz, CDCI3 solution)

D EP T CH2(f CH3f C H f

solvent
proton decoupled 1
I
......... ....... .............. ......I ..... J L----- . .. . 1 ______ ____
1 . 1 . 1 . 1 . 1 . 1 . 1 . 1 . 1 1 . 1 . 1 , ...
200 160 120 80 40 0 8 (ppm)

1H NMR Spectrum
(2 0 0 M H z , C D C I 3 so lutio n)
R e s o lv e s into tw o sig nals
of e q u a l intensity
a t h ig h e r field

7 .5 7 .0 p pm

TM S

_______«UUL
_1_________ I_________ I_________ I_________ L .

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

281
 Problem 171

4000 3000 2000 1600 1200 800

V (cm‘1)

40 80 120 160 200 240 280

m/e

200 160 120 80 40 0 6 (ppm)

10 8 0
6 (ppm)

282
 Problem 172

4000 3000 2000 1600 1200 800

V (cm"1 )

m/ e
i 1 i...~“r ..T " i....r * 1 T " T ....T...... r 1 ... i 1 i.. 1 i 1 i 1.............
13C NMR Spectrum
(50.0 MHz, CDCI3 solution)

DEPT CH2 | CH3| CH f

solvent

proton decoupled
1, II, 1
1 . 1 . I . I .....................................1 , 1 , 1 , 1 ,............ 1 , 1 i ...
200 160 120 80 40 0 5 (ppm)

1H NMR Spectrum
(200 MHz, CDCI3 solution)

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

283
 m/e X (n m )

200 160 120 80 40 0 8 (ppm)

1H NMR Spectrum
(100 MHz, CDCIj solution)

6H

TMS

residual CHCI3
-IH insolvent

1H
JL

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

284
 Problem 174

100 68 Mass Spectrum UV Spectrum

80
A,max 225 nm (log10s 3.9)
60
s o lv e n t: methanol
40 M+ '= 96

20
c 6 h 8o
_J I I I I I I 1 I I I I I I I I I . I ■ I * I . I . I

40 80 120 160 200 240 280

m/e

I 1 I 1 I 1 I 1 1 1 | 1 | 1 | 1 | 1 | 1 , , , .
13C NMR Spectrum
( 100.0 M H z, C D C I3 solution)

DEPT CH2| CH3f CHf 1

proton decoupled solvent

*
i ................. 1 . ____
______ I » I 1 1 1 1 *___ 1___ 1___ 1___ 1___ 1___ 1___ 1___ 1___ 1-----1-----1-----1-----1-----1-----1---- 1----------
200 160 120 80 40 0 8 (ppm)

8 (ppm)

285
 Problem 175

4000 3000 2000 1600 1200 800

V (cm‘1 )

UV Spectrum

^max 263 nm (log^s 3.9)

X max 305 nm (log10e 2.1 )

solvent: hexane

40 80 120 160 200 240 280

m/e

■............... I” 1 1 .................................................. r .. r ™...i 1_ .....r — «" 1 1 "1.......1 1 .... 1 1 1

13C NMR Spectrum expansion i
(100.0 MHz, CDCI3 solution)
i i t—i—r f T—1--1--1--1—
40 30 20 ppm

DEPT c h 2| CH3f ch |
expansion

i —i—i -r
proton decoupled 40 30 20 ppm

solve
nt 1. i____

• » 1 » 1 » 1 >----- 1---- ‘ i » > ' l i l i l i I i I i

200 160 120 80 40 0 6 (ppm)

5 (ppm)

286
 Problem 176

UV Spectrum

^max 234 nm (log^c 4.1)

solvent: ethanol

40 80 120 160 200 240 280

m/ e

6 (ppm)

287
 m/e Mnm)
' I 1 “T n— 1 1 1 1 1 r 1 ’ 1 ' 1 1 1 ' 1 1 1 1 1 1
l3C NMR Spectrum
(100 MHz, CDCI3 solution)

D EPT c h 2| c h 3| ch |

solvent
proton decoupled *

1
--- 1----- 1----- 1------1----- 1----- 1----- 1------1----- 1----- 1----- 1------1----- L-----L 1 1 1 1 1 1 1 1 1 1 1
200 160 120 80 40 0 8 (ppm)

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

288
 Problem 178

4000 3000 2000 1600 1200 800

V (cm'1)

100 UV Spectrum

80
^"max 260 nm (log^s 2.9 )
60
^max 266 nm (log^s 3.1)
40

20 X max 272 nm (log10s 3.1 )

solvent: methanol

40 80 120 160 200 240 280

m/e
I . I 1 , . I . I . I ■ I 1 I 1 I ' I 1 I 1 I 1
13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

DEPT c h 2| c h 3! C H f

solvent
proton decoupled
I
I «
I . I ■ I • I . I . I . I . I . I .....i.. ____ I____ .____ I------- .--------------
200 160 120 80 40 0 8 (ppm)

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

289
 Problem 179

4000 3000 2000 1600 1200 800

V (cm1)

100 UV Spectrum
80
^m ax = 243 nm (Iocj^qS 4.1)
60
^max = 291 nm (log1Qs 3.4)
40
solvent: ethanol
20

40 80 120 160 200 240 280

m/ e
t— ■
— r
expansion
13C NMR Spectrum
(100.0 MHz, CDCIg solution)

128 126 124 ppm

DEPT CH2j CH3f CHf expansion

128 126 124 ppm

proton decoupled
solvent I

J 1 I 1 I 1 I 1 I . I 1 I 1 I 1 I 1 I 1 I . L
200 160 120 80 40 0 5 (ppm)

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

290
 | 1i ' » ' i ' i ' | ' "i « rm
f r ' - ... 1-- ■
-- |-- --- i-- --- |-- ■
-- r » |-- r
Problem 180

IR S p e c tr u m 1751
(CHCI3 solution)

i • » * ■ • ■• » • I • ■ - ■ • ■ ■- I »_»___ 1.i * 1 ____1____L

4000 3000 2000 1600 1200 800
V (crrf1)

UV Spectrum

X max 268 nm (log10s 3.1)

A-max 275 nm (log1Qs 3.1)

s o lv e n t: ethanol

40 80 120 160 200 240 280

m/e

i ' i 1...“ i 1 i -T— r — r' I 1 I 1 I 1 I . I 1 I 1 I .

13C NMR Spectrum

(100.0 MHz, CDCI3 solution)

D EPT CH2| CH3f C H f

proton decoupled solvent

i ..................................... I_____ , 1 ______

I . I , I , I . I . I . I . I . I . I . I . I ..X.

200 160 120 80 40 0 5 (ppm)

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

291
 Problem 181

4000 3000 2000 1600 1200 800

V (cm'1)

UV Spectrum

^max 249 nm (log10s 4.1)

^ max 292 nm (log^s 3.3)

solvent: ethanol

40 80 120 160 200 240 280

m/e

13C NMR Spectrum

(100.0 MHz, CDCI3 solution)

DEPT c h 2| CH3t c h | ppm 130 125

expansion

proton decoupled
solvent
ppm 130 125

_L J I I
200 160 120 80 40 0 8 (ppm)

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

TMS

] lui. jj
10 8 1 0
8 (ppm)

292
 Problem 182

UV Spectrum

^max 265 nm (log^c 3.0)

^max 272 nm (log^s 3.1)

X-max 294 nm (log10e 1.9)

solvent: ethanol

40 80 120 160 200 240 280

m/ e

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

expansion

IT , 1 1--
3.2 3.0 ppm 2.6 2.5 ppm

T---------- 1— TMS
7.3 7.2 ppm
_JL
J 1--------- 1--------- 1--------- 1--------- 1--------- 1--------- 1--------- 1_____ 1_____ 1_____ I_____ I_____ I_____ I_____ I_____ I_____ I_____ I_____ L.
10 8 1 0
5 (ppm)

293
 Problem 183

4000 3000 2000 1600 1200 800

V (cm-1)

100 Mass Spectrum UV Spectrum

80 -■ 03
-. 0C
l M+ '= 180 ^m ax 265 nm (log^s 4.5 )
60 -■ C0/>
- 0
. £ 1£32 ^max 330 nm (log^s 4.2)
40 7 0
- 0 ^^
solvent: ethanol
20
1 ini I c 13h 8 o
» * » *— 1
— *— »— •— •— •— •— .— 1
— •— •— •— •— •— 1
— •— 1
— •— 1
— *— 1
— •— 1
— •— 1
— •— 1
— •—

40 80 120 160 200 240 280

m/e

i— ■
— i— •— i— 1— i— 1— r
13C NMR Spectrum expansion
(100.0 MHz, CDCI3 solution)

DEPT 135 125 ppm

CH2^ CH3f C H f --------------

expansion

solvent
JL
—1------ r- I
proton decoupled 135 125 ppm
_J__________________ L 1__
i
2 0 0 160 120 80 40 0 5 (ppm)

8 (ppm)

294
 Problem 184

100 45 Mass Spectrum

43
80 29

60 No significant UV
absorption above 220 nm
40
M+’ = 132 (< 1%)
89
20 87 | 117 131
c 6 h 12o 3
,1 i I I I I L_

40 80 120 160 200 240 280

m/e

1— 1— i— 1— r “i 11— r•— r 1 I I I I I I I I I [-
13C NMR Spectrum
(150.0 MHz, CDCI3 solution)

D EP T ch 2J c h 3| CHf

solvent

proton decoupled

I . I . I . I I I I I I I L_ J I I 1 I I L
200 160 120 80 40 0 5 (ppm)

6 (ppm)

295
 Problem 185

No significant UV
absorption above 220 nm

40 80 120 160 200 240 280

m/e

..I 1 I ' I 1 I ' I — 1 1 1 1 ^ 1 1 1 1 1 ' I ' I '

13C NMR Spectrum
CDCIj solution)
(100.0 MHz,

D EPT CH2| CH3f CHf

solvent

proton decoupled
| I

i I i I i I i I i I i I i I i I i I i I i I i I i
200 160 120 80 40 0 5 (ppm)

1H NMR Spectrum
(400 MHz, CDCI3 solution)

■
----

__ _ __
TMS
1

1 1 1 1 1 1 i i 1 * 1 1 1 1 I . 1 1 1 1 I
10 8 1 0
5 (ppm)

296
 Problem 186

4000 3000 2000 1600 1200 800

V (cm'1 )

No significant UV
absorption above 220 nm

40 80 120 160 200 240 280

m/e

I . I . I 1 I 1 I 1 1 ' 1 ' 1 ' “ 1-----T“ '[ 1 1 1 1 -----

13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

D EP T CH2(i CH3f ch |

solvent

*
proton decoupled
__________i i ______________ ......... .......................... 1 ..... .... _____......J__
............................................................................................................................................................... ......... < 1— <— 1— <------------
200 160 120 80 40 0 8 (PPm)

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

297
 Problem 187

No significant UV
absorption above 220 nm

40 80 120 160 200 240 280

m/ e

D EPT ch 2| CH3f CHf

solvent
proton decoupled I
JL
J i I i L -I I L. J . I I I I I I I I I I I . I L_

200 160 120 80 40 0 8 (ppm)

8 (ppm)

298
 Problem 188

UV Spectrum

^m a x 230 nm (log10s 3.6) pH 11

^ max 230 nm (log10s 4.4) pH 13

solvent: water

40 80 120 160 200 240 280

m/ e
I ' I 1 1 1 1 1 1 1 1 1 1 1 1 ' 1 1...... 1 ' 1 * 1 b
13C NMR Spectrum jon V
(100.0 MHz, CDCI3 solution) <
T~..... 1..... I .... 1 1'
35 34 ppm
1
D EP T ch 4 CH3f ch| exp;
insion

j
------ 1------ r
4 ppm
solvent 33 3
proton decoupled ^ |

1 . 1 . 1 . 1 . 1 . 1 . 1 • 1 - 1 ■ 1 . -I___ -___ 1----- i------------

200 160 120 80 40 0 8 (ppm)

1H NMR Spectrum
(400 MHz, CDCI3 solution)

expansion

T 1—
JlMJL 1
Exchanges 2.6 2.4 ppm 2.5 2.0 1.5 ppm

JL
with D2 O TMS

JL
J 1 I 1 L _i I 1 L J 1 I 1 L
10 9 8 7 6 5 4 3 2 1 0
8 (ppm)

299
 Problem 189

No significant UV
absorption above 220 nm

40 80 120 160 200 240 280

m/e

1 1 I 1 T I 1— 1— 1— ■
— 1— 1— 1— 1— 1— ■
— r
13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

D EPT CH2| CH3f C H f

solvent
proton decoupled
I
1__
1 . 1 . 1 . 1 . 1 . 1 , 1 . 1 . 1 . 1 j , L
200 160 120 80 40 0 S (ppm)

8 (ppm)

300
 Problem 190

4000 3000 2000 1600 1200 800

V (cm'1)

100
80

60

40

20

40 80 120 160 200 240 280

m/e

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 ' 1 ' 1 ' 1 ' 1 r

13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

DEPT C H 2j C H 3f C H f

solvent
proton decoupled

I ■ I ■ I ■ I » I ■ I . I . I ■ I 1 I 1 I . I 1_____
200 160 120 80 40 0 8 (ppm)

1H NMR Spectrum
(400 MHz, CDCI3 solution)

Exchanges
with D2 O

r
TMS

i
--- 1------ 1------ 1-----------1-----------1------ 1------ 1------ 1------ 1------ 1------ 1______ 1______ 1... .... ...J______ 1______ 1______ 1__ j ... ...J____ 1___ 1_
10 9 8 7 6 5 4 3 2 1 0
8 (ppm)

301
 Problem 191

4000 3000 2000 1600 1200 800

V (cm‘1)

UV Spectrum

log10e > 4.0

40 80 120 160 200 240 280

m/e

I 1 1 1 ' 1 ' 1 ... r...... .......l ■ 1 1 1 1 1 1 1 1 1 '

13C NMR Spectrunn
(50.0 MHz, CDCI3 soluldon)

D EPT ch 2(, a Hat C H f

^— solvent
proton decoupled
_________________ 1 11 ______________ j
----------- 1----- 1----- 1----- «----- 1------1----- 1----- j----- 1----- •----- 1----- 1----- 1----- 1----- 1 •— 1 1 1 1 1 1 1 1
200 160 120 80 40 0 5 (ppm)

1H NMR Spectrum
(200 MHz, CDCIj solution)

_
II
TMS

1 J I 1
I I I - 1 ■ 1 1 . 1 ■ _________ 1 1 1 ■ 1 ... .1 _ 1
10 8 1 0
5 (ppm)

302
 m/ e X(nm)
1 ... ( ( ,
1 ■ I ’ I ■ 1 I 1 • 1 1 k 1 • 1
13C NMR Spectrum
(50.0 MHz, CDCI3 solution)
expansion

i i
80 70 ppm

D EP T CH2| CH3f C H f

expansion

_luj....... .....
1 1
8(0 70 ppm
proton decoupled
1 _____
I . I . 1 . 1 • 1 . 1 i 1 i 1 • 1 j____ I____i-------1-------1-------1-------1-------------
200 160 120 80 40 0 8 (ppm)

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

303
 Problem 193

UV Spectrum

lo g 10s > 4.0

40 80 120 160 200 240 280

m/e

I 1 1 ' .....1 ■ 1 ' 1 T

1 1 r ...... r.... ' t .... ' 11' "i..... 1 1 1 1 1 1....
13C NMR Spectrum
(50.0 MHz, CDCI3 solution)
two resolved signals
at higher field

D EPT CH2(f CH3f ch| expansion

two resolved signals

iL
1 ..... 1
— at higher field solvent 8,0 70 ppm

i iii i
proton decoupled
----------- 1----- 1----- 1----- 1----- 1----- 1----- 1----- 1----- 1----- «----- 1----- 1----- 1----- 1----- 1----- 1----- 1---- 1------ 1----- 1 1 1 1 1
200 160 120 80 40 0 8 (ppm )

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

304
 Problem 194

4000 3000 2000 1600 1200 800

V (cm'1 )

100 UV Spectrum

80
lo g 10e > 4.0
60

40

20

40 80 120 160 200 240 280

m/e
I ■ I 1 I ■ I 1 I ■» i • ..i 1 i 1 i 1 1 ' '1 1 1 '
13C NMR Spectrum
(100.0 MHz, CDCI3 solution)

D EP T ch 2J CH3f ch|

r solvent

proton decoupled
_____ ______i —... L ._ ....... i
..... l . i i i i i < i i i i i . i . i i i .....i..... j ___ .___ i— .------------
200 160 120 80 40 0 5(ppm)

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

305
 Problem 195

4000 3000 2000 1600 1200 800

V (cm'1 )

100 : 121/123 Mass Spectrum

80 -
• 03 41
7 Cl

60 ” <D
• m
No significant UV
7 -Q absorption above 220 nm
40 7 o
” ■
nP
o'- M + ‘ 200/202/204
20
I hI mu II i ll
n C sH fiB r?
i • i • i . i * — i— .— i— - — i — .— «— •— i — •— i— •— i— •— i— •— i— •— i— ■— i— >— i— •—

40 80 120 160 200 240 280

m/e

13C NMR Spectrum

(100 MHz, CDCI3 solution)

solvent

proton decoupled *
I
_j i 1_______ 1_______ 1_______ 1_______ i_______ i_______ 1_______ 1_______ 1_______ i_______ 1_______ i_______ i 1 1 1 1 1 1 1 1 1 1

200 160 120 80 40 0 8 (ppm)

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

306
 Problem 196

4000 3000 2000 1600 1200 800

V (cm'1 )

No significant UV
absorption above 220 nm

40 80 120 160 200 240 280

m/ e

200 160 120 80 40 0 5(PPm)

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

307
 Problem 197

4000 3000 2000 1600 1200 800

V (cm‘1 )

No significant UV
absorption above 220 nm

40 80 120 160 200 240 280

m/e
■ I ' I 1 I ' I 1 I ' I ' 1 ' I 1 1 1 1 1 1 '........ 1 ' ..........
13C NMR Spectrum
(100.0 MHz, D20 solution)

D EPT CH2i|f CH3f c h |

proton decoupled

I . I . I . I . I . I . I . I . I , l , l , l

200 160 120 80 40 0 6 (ppm)

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

308
 Problem 198

100 : 45 Mass Spectrum

80 -
.
- CD
Q.
60 “ CD No significant UV
.
- 03
_Q 59
absorption above 220 nm
40
-^
20 M +* = 74 (< 1%)
I
I l,l,
c 4 h 10o
i . i i . i . i a

40 80 120 160 200 240 280

m/ e

13C NMR Spectrum

(50.0 MHz, CDCI3 solution)

proton coupled
ilU

solvent -a,
HI

200 160 120 80 40 0 8 (PPm)

8 (ppm)

309
 Problem 199

No significant UV
absorption above 220 nm

40 80 120 160 200 240 280

m/e

1 111 1 1 1 r" I 1 11 11 1 1 1 1 11 1 1 ".... ' ..... ..... '

3
13C N M R S p e ctru m
(125.0 MHz, CDCI solution)

DEPT 2 CH i|f CH3f CHf

1 11 1 1 1 1 11 1 1 1 1 1 111
solvent
proton decoupled

------ ------ ------ ------ ------ ------ ------ ------ ------ ------ ------ ------ ------ ------ ------ 1------ ------
200 160 120 80
_i 1

40
l 1 l • 1
0
■
8 (ppm)

8 (ppm)

310
 Problem 200

4000 3000 2000 1600 1200 800

V (cm'1 )

100 :
M+' Mass Spectrum UV Spectrum
82
80 -
r<o
-
- d log108 a 4
60 -
-
Q)
CO
- CO
o

40 7 o
-

20
c 5h 6 o
-I . I . L_

40 80 120 160 200 240 280

m/e

i 1 r ... 1 t 1 1 ....1 1 1 I 1 l 1 I 1 ... T..... 1 I..... ' I 1 1 1

13C NMR Spectrum
MHz, CDCI3 solution)
(125.0

D EPT ch 2J CH3f ch|

proton clecoupled

solvent

i
• I I I * I » 1 i 1 « 1 i 1 i 1 i 1 I ---1----- 1----- 1----- 1----- 1----- 1-------------
200 160 120 80 40 0 5(ppm)

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

311