structures

Problem 109

IR Spectrum	1085
(CHCI3 solution)

4000

3000

2000

1600

1200

800

V (cm'")

100

107

Mass Spectrum

UV Spectrum

80

~

'"a.

60

Ql

VI

Ql

.0

Note: UV spectrum changed

40

'"

'0

significantly on addition

oR-

20

of base

III,

40

80

120

160

200

240

280

m/e

,

,

I

I

I

I

I

I

I

I

I

I

13C NMR Spectrum

(100.0 MHz, CDCI 3 solution)

DEPT

CH2 • CH3t

CHt

I

I

I

I

I

I

I

solvent

I

,

,

proton decoupled

'. I I

I

I

I

I

200

160

120

80

40

o s(ppm)

1H NMR Spectrum

(400 MHz, CDCI3 solution)

Exchanges

with D20

J II 7.5
				7.0		"-
			.	,			II-
						ppm
. I						-	-		TMS
								1

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

198

2209

IR Spectrum

(nujol mull)

4000		3000		2000	1600		1200	800
				V (crn'")
100
					145		Mass Spectrum
80	"'"ro
	Q)
60	Co
	III
	Q)			102
	ro
40	.Q				M+"
	'0
20	*				146
	40	80		120	160	200	240	280
				m/e

13C NMR Spectrum

(50.0 MHz, CDCI 3 solution)

proton coupled

Problem 110

,

Problem 111

IR Spectrum

(KBrdisc)

4000				3000		2000		1600		1200	800
							V (crn'")
100
										Mass Spectrum
80		~				120
		Ql
60		a.								M+"
		~
										199/201
		'"
40		.Q
		'0
20
				80		120	160	200		240	280
		40

m/e

UV Spectrum

Amax 310 nm (I091OE 3.3)

Amax 261 nm	(I091OE 4.3)
		\
solvent: methanol
Amax 262 nm (lo910E		3.0)
A 257 nm	(Io91OE	3.0)
max
Amax 222 nm	(Io91OE	4.0)

solvent: methanol 1HCI

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

13C NMR Spectrum

(50.0 MHz, CDCI3 solution)

solvent

proton decoupled

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, CDCI3 solution)

expansion with resolution enhancement

	I	I
7.5	6.5	ppm

									-			TMS
			~		II							L
I	I	I		I		I	I	I	I	I	I	I
10	9	8	7		6		5	4	3	2	1	0
												o(ppm)

200

Problem 112

1666

IR Spectrum

(liquid film)

4000					3000		2000			1600			1200	800
								V (crn'")
100
									135				Mass Spectrum			UV Spectrum
80			~
			4l
60			0-
			~
			'"
401			.0
			-'0
			t/!.-,								M+"
20							107
						j I				192
							I
					d.
					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, CDCI3 solution)

proton decoupled

solvent

I

I

I

I

I

•

I

I

I

I

I

I

I

I

I

I

I

200

160

120

80

40

0 o(ppm)

1H NMR Spectrum

(200 MHz, CDCI3 solution)

expansion

I	I	I	I
8.0	7.5	7.0	6.5 ppm

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

201

Problem 113

IR Spectrum

(liquid film)		1766
					1200
4000	3000	2000		1600		800
			V (cm-1 )

100
80	-«l"
	C1l
60	o,
	rn
	C1l
	«l
	.&J
40	'0
	~	43
20
		,II

	135	Mass Spectrum	UV Spectrum
			Amax 262 nm (109101>	\
				2.6)
	150		Amax 269 nm (109101>	2.6)
	I	M+"= 192	solvent: methanol
I I		C12H1602

40

80

120

160

200

240

280

m/e

I

I

I

I

I

I

I

I

I

I

I

I

13e NMR Spectrum

(100.0 MHz, CDCI3 solution)

DEPT

CH2 •

CH3t

CHt

I

"~:L

solvent

proton decoupled

I

I

•I

I

I

I

I

150

149 ppm

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, CDCI3 solution)

expansion

U

			-r-r	7.4	7.2	ppm
													I
									-		-		TMS
10	9	8	7	6	5	4		3	2		1		0
													o(ppm)

202

Problem 114

IR Spectrum	1729
(liquid film)

4000		3000	2000	1600	1200	800
			V (crn'")
100
				177	Mass Spectrum		UV Spectrum

\

80""t1l

'"c.

60

l/J

'"

t1l

40

.0

M+" =192

'0

135

0~

20

I I

ill

I ,I

I,

I

40

80

120

160

200

240

280

m/e

I

I

I

I

I

I

I

I

I

I

I

1

13C NMR Spectrum

(100.0 MHz, CDCI 3 solution)

DEPT

CHz1CH

3' CH'

I

proton decoupled

solvent

I

I

I

I

I

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, CDC'3solution)

expansion

U,

I

8.0

7.5

PPM

If

-

TMS

I

•

1

I

I

I

I

I

I

I

I

I

I

I

10

9

8

7

6

5

4

3

2

1

0

o(ppm)

Problem 115

	IR Spectrum	1514
		1338
	(CHCI3 solution)

4000				3000			2000				1600	1200	800
									V (em")
100
									M+'= 153			Mass Spectrum		UV Spectrum
80		""					123							Amax 227 nm
		III													(Io910E	3.9)
		a.
		Ql
60		U>
		Ql												Amax 305 nm
		III														4.0)
40		..c													(Io910E
		'0
		'if!.												solvent: methanol
20				~	II		l						C7 H 7N03
			I IIII						I
		40		80			120		160		200	240	280
									m/e
											UL...-_
	13C NMR Spectrum
	(100.0 MHz, CDCI3 solution)

solvent

proton decoupled

			200			160	120			80		40	0	S (ppm)
1H NMR Spectrum					J,			L
(400 MHz, CDCI3 solution)							expansion
					,..-	8.0	7.0	ppm
							r-
			-							-				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)

204

Problem 116

	l-
-		f-		r-r-:			V
										'----					TMS
							I		i		i
	I					8.4			8.2		8.0 ppm
I
10.5	10 ppm	-
	~
		' --
10	9	8			7	6			5	4		3	2	1	0

() (ppm)

205

Problem 117

IR Spectrum	1699
(KBr disc)

4000						3000				2000				1600	1200	800
											V (ern")
100
											121				Mass Spectrum		UV Spectrum
80		""l1l															"'max225 nm	(I091QE	4.2)
		Q)
60		c,
		Q)															"'max250 nm (I091QE		3.8)
		en
		l1l
40		.c								104
		15															"'max293 nm	(I0910E	3.2)
		<f.								l
20				I~
					1							M+" 151 < 1%					"'max330 nm (I091QE		2.6)
																	solvent: methanol
					40	80				120		160		200	240	280

m/e

13C NMR Spectrum

(100 MHz, CDCI3 solution)

134 132 ppm

proton decoupled				solvent - .
				134		132	ppm
200		160	120	80		40		o 0 (ppm)

1H NMR Spectrum

(400 MHz, CDCI3 solution)

expansion

TMS

I

8.0

ppm

I

11

10 ppm

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

206

Problem 118

	IR Spectrum	1698
	(liquid film)

4000					3000					2000					1600		1200
											V (cm'")
100
																				Mass Spectrum							UV Spectrum
80				"'"
				'"																						A. max 277 nm (10910£ 4.2 )
				a:>
60				0.
				en
				a:>
				.J:J																									solvent:		methanol
				'"
40				a				92		107
				~
20						j I ,I		I,		l
					40		80			120	160				200					240	280
											mle
				I		I		I		I				I			I			I		I		I			I				r
		13C NMR Spectrum
		(100.0 MHz, CDC'3 solution)
						I																			I
		DEPT			CH2 1CH3t		CHt								LJI
				I		I		I		I				I						I		I		I			I		I		I
		proton decoupled ~																			solvent
										I											1			!
																						I
					200					160					120						80					40					0	8 (ppm)
															J_					~
	1H NMR Spectrum																	expansion
		(400 MHz. CDCI 3 solution)
										J J					, ,		, ,			, ,	,	,
															7.65		7.45			6.85	6.65 ppm
				S
																																TMS
10					9		8				7				6					5	4			3				2			1	o
																																8 (ppm)

207