structures

Problem 69

IR Spectrum
(liquid film)	1714

4000					3000			2000		1600	1200	800
									V (ern")
100					45						Mass Spectrum
80	co
	-'"
	<Il	43
60	Co															No strong UV
	lJ)
	<Il
	co
40	..c														absorption above 220 nm
	'0
						M+"
20	*'
					88
			I,JI		73		~					C4 H a0 2
					.1
		40			80			120	160	200	240	280
									m/e
		I			I		I	I	I	I	I	I		I	I	I	I
13e NMR Spectrum
(50.0		MHz, COCI3 solution)

DEPT CH2 , CH 3t CHt

I j

proton decoupled											solvent J				lI
		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, COCI3 solution)
				expansions
											exchanges
~L---A-											with,0 20
						,
,		,		,	,			,									TMS
4.5		4.0		ppm	2.0	1.5		ppm			~		~
																	1
I			I	I	I			I	I		I	I			I	I	I
10		9		8	7		6		5		4	3			2	1	o
																	o(ppm)

158

Problem 70

	3410
	IR Spectrum	1705
	(liquid film)

4000

3000

2000

1600

1200

800

V (ern")

100

43

Mass Spectrum

UV Spectrum

80

cv

~

'"

60

a.

58

III

cv

'"

M+·= 116 « 1%)

solvent: hexane

40

.0

'i5

20

*'

1.1.1"

I,

I

I,

40

80

120

160

200

240

280

m/e

I

I

I

I

I

13C NMR Spectrum

-CH 3

(50.0 MHz. COCI

3

solution)

I

H-C-H

I

solvent

- CH3

C

C

I

J

I

I

I

I

I

I

I

I

I

I

I

I

200

160

120

80

40

0 () (ppm)

lH NMR Spectrum

(200 MHz, COCI3 solution)

exchanges with 0 20

						•			--	r-
						~ -					--'	TMS
						-
I	I	I	I	I	I	I	I			I	I	I
10	9	8	7	6	5	4	3		2		1	0

() (ppm)

159

Problem 71

IR Spectrum

1740

(liquid film)

4000

3000

2000

1S00

1200

800

V (em")

100

43

Mass Spectrum

80

"'"

'"

Q)

SO

0-

No significant UV

Q)

<I>

absorption above 220 nm

'"

.0

40

'0

56

M+'= 116 «

1%)

20

*'

l II

73

.1

CSH 1202

40

80

120

1S0

200

240

280

m/e

,

I

I

I

I

I

I

I

I

I

I

I

13C NMR Spectrum

(100 MHz, CDCI 3 solution)

DEPT

CH2 •

CH3t CHt

I

solvent

proton decoupled

lJ L,I

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, CDCI 3 solution)

I

20 HZ

I

11 ~J~

1/

I

I

I

3.85

ppm

1.92 ppm

0.93

ppm

expansions at 400 MHz

-

!A.

10

9

8

7

6

5

4

3

2

1

o

s (ppm)

160

Problem 72

IR Spectrum
(liquid film)	1709

4000					3000			2000		1600	1200	800
									V (crn'")
1001-							57				Mass Spectrum
80		::.:					59
		<U'"
60		Co													No significant UV
		<U
		<Jl
40		LJ'"													absorption above 220 nm
		'0		Jl~,				I
20		'#'. .
								M+'116<1%
											240	280
				40	80			120	160	200
									m/e
			I	I			I	I	I	I	I	I	I	I		I	I
13C NMR Spectrum
(100 MHz, CDCI 3 solution)

solvent

t

		proton decoupled											I
															40					o(ppm)
			200					160		120		80					0
	1H NMR Spectrum
	(400 MHz, CDCI 3 solution)																	1 -
				Exchanges with
					°2°
				Offset	---t.J			_
				_~l,----																TMS
				I	I			I									-
			13.0		12.0			11.0 ppm							-
10			9		8			7		6	5	4		3	2		1			o
																				o(ppm)

161

Problem 73

	IR Spectrum
3376	(liquid film)

4000				3000						2000		1600	1200	800
										V (em")
100
							59						Mass Spectrum
80			.><
			'"
			<ll
60			C.																No significant UV
			<ll
			l/l					73
			til
40			.c															absorption above 220 nm
			'0
20			*'							M+" '"88 «
			.I	.II	I						1%)			C5H12O
				40				80		120	160	200	240	280
										mle
			I			I			I	I	I	I	I	I		I		I		I			I
13C NMR Spectrum
(50.0 MHz, CDCI3 solution)
			DEPT CH2 , CH3t CHt
			proton decoupled											sOlvent~	I
				200						160		120		80				40					o 0 (ppm)
1H NMR Spectrum
(200 MHz, CDCI3 solution)
															Exchanges with
															°2°
															+
																								TMS
																								o		.,
										7			5							2
10				9				8				6		4	3						1
																								s (ppm)

162

Problem 74

3305

IR Spectrum

(liquid film)

4000					3000	2000			1600	1200	800
								V (crn'")
100
	f-			30						Mass Spectrum
80	~
	III
60	Co												No significant UV
	3l
	<Il												absorption above 220 nm
40	.c
	'0					M+·
	?f!..
20						101
					,L	j
			40		80	120		160	200	240	280
								m/e

13C NMR Spectrum

(50.0 MHz, COC'3 solution)

					I	WLl
					solvent
	proton decoupled
							0 o(ppm)
200			160	120	80	40
1H NMR Spectrum							2H
							exchange
(200 MHz, COCI3 solution)							with 020
							G

)

---I - -!

TMS

V

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

163

a1St

Problem 75

IR Spectrum	1740
(liquid film)

4000			3000	2000		1600	1200	800
					V (crn'")
100
							Mass Spectrum
80	""
	a>
	'"
60	0.									No significant UV
	a>
	rJl
	..c									absorption above 220 nm
40	'"			107/109
	'0
20	*"					M+'
						180/182
			80	120	160		240	280
	40					200
					m/e

13C NMR Spectrum

(50.0 MHz, CDCI3 solution)

solvent

proton decoupled

I

200

160

120

80

40

o 0 (ppm)

1H NMR Spectrum

(200 MHz, CDCI3 solution)

		~			':0	'	,',	ppm
		i	,
		4.8	4.0	ppm
												TMS
10	9	8	7	6	5		4	3	2	1		o
												o(ppm)

164

Problem 76

IR Spectrum
(liquid film)	1715

4000				3000						2000		1600		1200		800
										V (ern")
100
		43													Mass Spectrum
80		-'"
		'"
		al					75
60		c-																		No significant UV
		al
		1Il
		'"																	absorption above 220 nm
40		.0
		'0
20		<F-	il						101	M+'
						II	.j		~	I 132						CSH 120 3
				40			80			120	160	200		240		280
										m/e
		13C NMR Spectrum
		(20.0 MHz, CDCI 3 solution)															-CH3
																			I
																			H-C-H
																			I
														C-H
		proton decoupled																		-CH3
		C 1														solvent					TMS
																						L
																						0 o(ppm)
				200						160		120				80	40
1H NMR Spectrum
	(100 MHz, CDCI 3 solution)

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

165

Problem 77

			IR Spectrum
			(KBr disc)
4000						3000				2000		1600	1200	800
											V (ern")
100
								59					Mass Spectrum
80			""Q)
			m
60			Co														No significant UV
			Q)
			In
			m						83							absorption above 220 nm
40			.0
			'0							101
20			~
			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. COCI3 solution)

solvent

;'

proton decoupled

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. COCI3 solution)

	~nges								Ir -
	----.-/'--	with 0 20						V-
		I	I
		11.0	10.0 ppm
							----'	-----'		TMS
										t
I	I	I	I	I	I	I	I	I	I	I
10	9	8	7	6	5	4	3	2	1	o
										o(ppm)

166

Problem 78

IR Spectrum

1729

(KBr disc)

4000

3000

2000

1600

1200

800

V (ern")

100							69						Mass Spectrum
		41
80
		..l<					97
		<ll
		Q)
60		Q.							115
		Q)
		.Q'"
		<ll
40		'0										M+" = 160 «	1%)
		;je.
20						j					142			C7H1204
							J
				1,1							I
		40					80		120		160	200	240	280
											m/e
13C NMR Spectrum
(100 MHz, 020 solution)
		....... ".)IM!J'A .~... ~....									, ",., ....". tl:Il"l iM~""..,_
		off-resonance decoupled
													dioxan
													reference __
													67.7 ppm
		proton decoupled					I I

No significant UV

absorption above 220 nm

I

200	160	120	80	40	o s(ppm)
1H NMR Spectrum			dioxan
			reference
(100 MHz, 020 solution)
			3.7 ppm		6H
		H20 and HOD
		in solvent

I ..

Note: all labile protons exchange in the

O2°solvent

2H 2H

10 9 8 7 6 5 4 3 2 1 o

() (ppm)

167