structures

Problem 59

IR Spectrum

(liquid film)

4000				3000		2000					1600	1200	800
								V	(em")
100
							105					Mass Spectrum		UV Spectrum
80		"'"												Amax 261 nm	(109101': 2.7)
		'"e-
60		Ql
		IJl
		Ql												Amax 269 nm
		'"													2.5 )
															(109101':
40		J:>
		'0
		'$.												solvent: methanol
20
					I
				I		I
				40	80	120			160		200	240	280
								m/e

13C NMR Spectrum

(100.0 MHz, CDCI3 solution)

I	I

	proton decoupled			solvent
				I		I
		160	120			o 0 (ppm)
200				80	40
1H NMR Spectrum
(400 MHz, CDCI3 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)

"

~~,

J.

,.<;

.:."

.

:1_,:

."{

':

t

t

I

t

.L

J; .

4000

3000

2000

1600

1200

800

V (ern")

100

Mass Spectrum

UV Spectrum

105

80

-'"

Amax 270 nm (10910£

<1l

2.6)

0-

60

Ql

VI

Ql

<1l

solvent:

methanol

40

.Q

'0

~

Q .

20

I

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

~

(100.0 MHz. CDCI3 solution)

expan:JL

i

I

I

135

130

ppm

CH2 , CH3 + CH +

I

I

i

I

I

DEPT

24

20

ppm

"''"jill

'~":JL

proton decoupled

I

I

I

III

solvent I

i

i

i

I

I

135

130

ppm

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

'~Jl

+

'~":Jl

r --

TMS

i

i

ppm

6.8

6.6

----{

2.2

2.0

ppm

-

I

I

I

I

I

I

I

I

I

I

I

I

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							119								Mass Spectrum		0.5
																				III
80																				<J
		.><																		c:
																				€'"
		Gl
		<1l
60		a.																		0
		III																		.0
		Gl																		III		UV spectrum
																				'"
40		.'"0									M+'						1.0
																					1.032 mg 110 mls
		'0								134
		*"																				path length: 1.00 cm
20						1																solvent: cyclohexane
				I Ii	J. J.. L		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)
														1
																					III
		off-resonance decoupled

lL

solvent

j

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

(100 MHz, CDCI3 solution)

			-r-					J		1
								------1
										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)

150

Problem 62

IR Spectrum	802
(liquid film)

4000					3000		2000						1600	1200	800
										V (crn'")
100
									119					Mass Spectrum
80			~
			III
60			c-							M+"
			~
										134
			.c
401			'"
			-0
			"#..
20						.t"
				I II	1, "L [I		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, CDCI3 solution)

J

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, CDCI3 solution)

													TMS
													I
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	274 nm			(109101':		2.3)
		'"					M+'= 134
60		a.															max
		Ul
		Ql															Amax 277 nm
		'"																			(109101':		2.3)
40		.t:J
		'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'3solution)

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	"'"Q)										A
	III											278 nm	(109		8	2.4)
	0.													10
60	Q)										max
											Amax 274 nm (109108
	'"															2.4)
	III						M+'
40	.0
	'0						162				Amax 270 nm		(109108			2.5)
20	c!?:
												solvent: methanol
			80	120	160			200	240	280
	40

m/e

13C NMR Spectrum

(50.0 MHz, CDCI3 solution)

proton coupled

I

solvent

200 160 120 80 40 o 3 (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	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

""Q)

Amax 232 nm (log lO E

'"

3.4)

60

c..

Vl

Q)

Amax 248 nm (log 10E

40

.'"0

3.5)

'0

Amax 265 nm (log lO E 3.4)

;f<.

20

II

I

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

1:1, , , , ,

(100.0 MHz, CDCI3 solution)

DEPT

CHA CH3t

CHt

15

13 ppm

solvent

[I, , , , i

proton decoupled

II

I

•

15

13 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,

JL

~

2.7

2.6

ppm

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
			'"		43
			Q)				M+"
60			Co
			Q)				59							No significant UV
			If)
			'"
40			.0											absorption above 210 nm
			'0
			~
201		-
					40		80	120	160	200	240	280
									m/e

13C NMR Spectrum

(50.0 MHz. COCI3 solution)

proton coupled

rol~oll L

proton decoupled

~~4jP~""."~1".(i""_~~~"'~

200	160	120	80	40	0 () (ppm)
1H NMR Spectrum
(200 MHz. COCI3 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,

No significant UV

60

~

ctl

absorption above 220 nm

40

.1:J

'0

~

M+" = 104 «

1%)

20

45

61

C4HS03

. 76

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, COCI3 solution)

I

solvent

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

1H NMR Spectrum

(200 MHz. COCI3 solution)

					expansions										exchanges
															with 0 20
															t
			4.0		3.6	ppm
4.4								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)
60		c-												No significant UV
		II)
		lJ)
		III												absorption above 220 nm
40		.D
		'0
20		'ifl.				I	M+'
				UJ~J			113
						86
		40			80		120		160	200	240	280
									m/e
							I					I

13C NMR Spectrum

(50.0 MHz. CDCI3 solution)

DEPT CH2 f CHat CHt

I

	L	I	solvent
proton decoupled			•