structures

Problem 119

IR Spectrum
(KBr disc)	1343
1511

4000			3000				2000							1600			1200	800
								V (em")
100							101					M+o147					Mass Spectrum							UV Spectrum
80		<tl																								> 4
		~																						10910£
		Q)
60		o,
		!/l
		Q)
		<tl
40		..0
		'0
		;ft.
20			Ih	J														CSH SN02
						.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																					1:''"'00
	(50.0 MHz. CDC'3 solution)
			CH2 f CH3t																			,		,
		DEPT			CHt																	85		80	ppm
		~
																			solventf				l:"~;oo
																			l			,		,
		proton decoupled							I						I							85		80	ppm
																,
					I		,		,								I					,				,
		I	I																	I					I				I
			200				160									120		80							40				0	s (ppm)
	1H NMR Spectrum
	(200 MHz. CDC'3 solution)
			~I																		I
																expansion
									--- r																					TMS
																			'------
												I				i	I		I
									8.25								7.75		ppm
					"---"		,							,															,
																															I
	I		I		I												I			I				I		I
10			9		8		7							6			5	4						3		2			1	o
																														s (ppm)

208

Problem 120

	IR Spectrum	1766
	(KBr disc)		1685

4000

3000

2000

1600

1200

800

V (em")

100

...

138

Mass Spectrum

UV Spectrum

80

43

Amax 235 nm (10910(; 4.1)

Q)

ttl

121

60

c-

Sol

Amax 265 nm (10910(; 3.0 )

ttl

40

..c

'0

20

<fi.

solvent:

ethanol

l

J

40

80

120

160

200

240

280

m/e

I

I

I

I

I

I

I

I

J

I

I

I

13C NMR Spectrum

(100.0 MHz, COCI3 solution)

DEPT CH2 '

CH3t

CHt

										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 Spectrum
	(400 MHz, COCI3 solution)							expansion
	exchanges						~~
~
	with 0 20
---- J J							, ,	,	, ,	,			-
		I					8.5	8.0	7.5	7.0	ppm
11.0			10.0
																	TMS
																	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)

204

Problem 121

3327

1680

IR Spectrum (nujol mull)

4000				3000			2000		1600			1200	800
								V (crn'")
100
							120					Mass Spectrum
80		""III
		(1)
60		0-
		(/)
		(1)							M+'
		III
									165
40		.0
		'0				92
		*'
20				..I..		,I,		137				C9H 11 N02
			II .I,					I
									160
			40		80		120				200	240	280
								m/e

0.0
0.5
1.0		UV spectrum
		0.172 mg /10 mls
		path length:	0.5 cm
		solvent: ethanol
1.5
200		250	300	350
		A(nm)

13C NMR Spectrum

(20.0 MHz. CDCI3 solution)

l

III

off-resonance decoupled

III

					TMS
200	160	120	80	40	o 0 (ppm)
lH NMR Spectrum					TMS
(100 MHz, CDC'3 solution)

Ii

-

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

210

Problem 122

3380	3155
IR Spectrum	1646
(KBr disc)

4000

3000

2000

1600

1200

800

V (ern")

100

121

Mass Spectrum

80

1d

\

Q)

60

Co

~

M+"

'"

40

.c

'0

165

20

80

120

160

200

240

280

40

m/e

I

I

I

I

I

I

I

I

I

I

I

I

13C NMR Spectrum

solvent

(100 MHz, CDCI3/CD 3SOCD3 solution)

C-H

C-H

solvent

I

-CH3

H-C-H

C C

I

C

proton decoupled

I I

I

I

I

I

I

I

I

I

I

I

I

I

I

200

160

120

80

40

o

0 (ppm)

lH NMR Spectrum

expansion

(400MHz,CDCI 3/CD 3SOCD3 solution)

exchange

1'''''"'

with D20 on warming

I

/I

0I

~

I

I

l----

8

7

ppm

vertical expansion

solvent

-

-

-

•

solvent -

I

I

I

I

I

I

I

I

I

I

I

10

9

8

7

6

5

4

3

2

1

o

o(ppm)

211

Problem 123

3396

3334

IR Spectrum

1662

(KBr disc)

4000

3000

2000

1600

1200

800

V (ern")

100

120

Mass Spectrum

UV Spectrum

80

"'"

Amax 312 nm (109108 4.3) \

'"

c.

Q)

60

Q)

92

M+'135

III

'"

solvent:

methanol

.n

40

'0

<!!-

20

"I.J, ,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 Mz, DMSO-d6 solution)

DEPT CH2 • CH3t CHt

proton decoupled I

		solvent ~-,
I	I		I

200

160

120

80

40

o 0 (ppm)

1H NMR Spectrum

(200 MHz, DMSO-d6 solution)

					Exchanges								, --
					with 020
			r---			•		solvent
					r -			residual	~ -,
															TMS
		----'		-	--'A						-----J				1
I
10	9	8		7	6		5	4	3		2			1	o
															o(ppm)

212

Problem 124

IR Spectrum
(KBr disc)	1684

4000						3000			2000				1600	1200	800
										V (cm'")
100
									107					Mass Spectrum		UV Spectrum
80			til
			:>(.				106									Amax 246 nm (10910£
			<IJ																4.2)
60			C.							M+" 149
			III
			<IJ													Amax 280 nm (10910£
			til																3.1)
40			.0
			'0			43
20			*'			I,.	1										solvent: methanol
															Cg H11NO
						40	80		120	160			200	240	280
										mle
													L
13C			NMR Spectrum
(100 MHz, COCI3 solution)
		DEPT				CH2 , CH3t CHt
													I		,
															solvent

proton decoupled

I

II

I

		200		160		120				80	40			0	o(ppm)
	1H NMR Spectrum									expansion
	(200 MHz, COCI3 solution)					Exchanges
						,					Jli
				~		with 020 on warming				, t ,
						, ,			,
										solvent
										residual
													I~
						7.6			7.4	7.2	ppm				TMS
			-f	I							-				1
	I	I	I		I	I			I	I	I		I	,
	10	9	8	7		6			5	4	3		2	1	o
															o(ppm)

213

Problem 125

3284

IR Spectrum

(KBr disc)

1658

4000				3000			2000			1600	1200	800
									V (cm'")
100
			43								Mass Spectrum		UV Spectrum
							108
80
	~												Amax 250nm (I0910E 3.1) \
	'"
	0.
	Q)
60	'"
	Q)												Amax 287 nm (I091OE 2.2)
	'"
40	.0									M+'
	'0								137
20	oR.	J:			i				j	179			solvent: chloroform
											C lOH13N02
										I
	40			80			120		160	200	240	280

mle

13C NMR Spectrum

(50.0 MHz, COCI3 solution)

DEPT CHz1CHat CHt

solvent

200

160

120

80

40

o 0 (ppm)

1H NMR Spectrum

(200 MHz, COCI3 solution)

expansion

	I
7.6		7.0	ppm
exchanges
with 0 20 on warming				TMS

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

214

Problem 126

	3326
	IR Spectrum	1667
	(KBrdisc)

4000

3000

2000

1600

1200

800

V (em")

100

109

Mass Spectrum

UV Spectrum

80

Ol

\

-'"

Amax 250 nm (10910E

4.1)

Co

Ql

60

<J)

M+"= 151

Ql

Amax 285 nm (10910E

Ol

3.6)

40

.0

'0

43

~

0

Ii

solvent:

ethanol

20

l

C8HgN02

40

80

120

160

200

240

280

m/e

I

I

I

I

T

T

I

I

I

I

I

I

13C NMR Spectrum

(100.0 MHz. DMSO-d6 solution)

DEPT

CH2 1CH3t

CHt

I

solvent

proton decoupled

1

I

I

I

I

	I	1	I	"I		I	I	I	I		I	1	1		I
		200		160	120				80			40			0	s (ppm)
lH NMR Spectrum							expansion
(400 MHz, DMSO-d6 solution)						Ll
					7.5		7.0	ppm	solvent residual
		exchanges								1
		with D20 on warming														TMS
10		9	8	7	6		5		4	3			2		1	o
																s (ppm)

215

Problem 127

IR Spectrum	1712
(liquid film)		1277			1254

4000			3000		2000				1600		1200		800
							V (ern")
100
						121						Mass Spectrum			UV Spectrum
80	~																	\
	'"														max	257 nm		(I091OE 4.3)
	o,														A
60	OJ
	<Jl						149
	OJ									M+"
	.n															solvent: methanol
40	'"								194
	'0
	~
20													en H140 3
	40		80		120		160		200		240		280
							m/e
13C NMR Spectrum
(50.0 MHz, CDCI3 solution)																		-- Resolves into
																		two signals
																		at higher field

-- Resolves into two signals at higher field

		200			160		120	80				40		o	a(ppm)
1H NMR Spectrum
(200 MHz, CDCI3 solution)						~_M;O",~
						I	I I I	I			I I	I
						4.6	4.2	3.8 ppm			1.6	1.2 ppm
						-				v ----
								----	rr:'						TMS
									'-J						I
10		9	8		7	6	5	4			3	2		1	o
															a(ppm)

216

Problem 128

	IR Spectrum	1730
	(CHCI3 solution)

4000						3000			2000			1600		1200		800
											V (ern")
100
									121						Mass Spectrum
80		""
		'"
		ll)
60		c.
		ll)																		UV spectrum
		.,																1.0
		'"
40		.0											M+-							0.597 mg 110 mls
		"5
		0~								134		194								path length: 0.2 em
20					I, 1.	1 ,.11 l J,					l		I			C11H1403				solvent: ethanol
									I,									1.5
		40				80			120		160	200		240		280		200		250	300			350
											m/e										A(nm)
13C NMR Spectrum
(20.0 MHz, CDCI3 solution)
													C-H
												C-H						I
																		H-C-H
																		I
																		-CH3		I
																-CH3				H-C-H
									C											I	TMS

200

160

120

80

40

o 8 (ppm)

1H NMR Spectrum

(100 MHz. CDCI3 solution)

TMS

10 9 8 7 6 5 4 3 2 1 o

8 (ppm)

217