structures

Problem 29

IR Spectrum

(liquid film)	1715

4000					3000		2000			1600	1200	800
							V (crn")
100					43						Mass Spectrum
80		-"
		'"
		Ql
60		Co				91
		UJ
		Ql
		'"
40		.J:J
		'0					M+'
20		;ft.					134
												Cg H 1Q O
				II	,I	II	I.
		40				80	120		160	200	240	280
							m/e

0.0

0.5

Ql

o c

e'"

0

UJ

.J:J

1.0 '"

1.5

UV spectrum

solvent: cyclohexane 7.90 mg 110 mls path length: 0.50 cm

200

250

300

350

A. (nm)

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

13C NMR Spectrum

(50.0 MHz, CDCI3 solution)

DEPT CH2 1CH3t CHt

II

I

r

proton decoupled

~

solvent

I

...-J

II

I

I

I

I

I

I

I

I

I

200

160

120

80

40

0

<5

(ppm)

1H NMR Spectrum

(200 MHz, CDC'3solution)

								..-
			~									TMS
									~
			!1~									L
10	9	8	7		6	5	4	3	2		1	o
											<5	(ppm)

118

Problem 30

IR Spectrum

(liquid film)

1690

4000			3000				2000				1600	1200	800
									V	(crn'")
100
			77				105					Mass Spectrum		0.5
80
	~
	Q)
60	c-
	~															UV spectrum
	.c								M+"					1.0
40	'"
	'0								134							1.075 mg /10 mls
	<;e.
20																path length: 0.10cm
									1				Cg H 1Q O			solvent: ethanol
				IJ										1.5
	40		80				120			160	200	240	280	200	250	300	350
									m/e							A(nm)

13e NMR Spectrum

(20.0 MHz, CDCI3 solution)

solvent

off-resonance decoupled

200	160	120	80	40	0	15	(ppm)
1H NMR Spectrum				I
(100 MHz, CDC'3 solution)
							TMS

		~~						L	J		L			v;
	I	I	I	I	I	I	I	I		I
	10	9	8	7	6	5	4	3		2	1		0
											15		(ppm)

119

Problem 31

IR Spectrum
(liquid film)	1723

4000				3000				2000			1600	1200	800
									V (em")
100
								105				Mass Spectrum
80	.><
	'"
	Q)
60	0-
	Q)
	Vl
	'"
40	D								M+-
	'0			77
20	~		,II	L ~" .,li			J	134
									I
								120	160		200	240	280
				40	80
									m/e

13C NMR Spectrum

(50.0 MHz, CDC'3 solution)

solvent

										II
					160			120					40				o
		200								80								0 (ppm)
lH NMR Spectrum
(200 MHz, CDCI 3 solution)							I	i	I	I		J
												I	I
							9.7	9.5	3.7	3.5		1.5	1.3		ppm
										_~I								TMS
10		9		8	7		6		5	4		3			2		1	o
																		s (ppm)

120

Problem 32

		IR Spectrum
		(liquid film)									1686
4000					3000				2000		1600			1200	800
									V (ern")
100
									105					Mass Spectrum				UV Spectrum 0
80		.><						77										Amax 241 nm
		(lJ
		<ll																		(10910£ 4.1)
60		0-
		Q)									M+"
		en
		<ll									148
40		.0																	solvent: methanol
		'0							120
		;/i.
									II
20				.1. Ju											C1QH12O
						,I		,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
	(50.0 MHz. CDCI3 solution)

proton decoupled

1

		~xpansion		I	I
		135	130 ppm
					I
I			..---- solvent
			Iii

I	I	I	1	I	I	I	1	1	1	I	I
	200		160		120		80		40		o 8 (ppm)

1H NMR Spectrum

(200 MHz. CDCI3 solution)

,	,
3.0	2.0	1.0	ppm

TMS

10 9 8 7 6 5 4 3 2 1 o

8 (ppm)

121

Problem 33

			IR Spectrum								1735
			(liquid film)
4000						3000				2000		1600		1200	800
											V (ern")
100
														Mass Spectrum
			43
80			"'"				57
			'"
			Q>
60			c,															No significant UV
			Q>
			til
			.0					85										absorption above 220 nm
40			'"
			'0
			~
20										J	M+'158<1%
							I
			40					80		120	160	200		240	280

m/e

I

I

I

I

I

I

I

I

r

I I I

13C NMR Spectrum

(100 MHz, CDCI 3 solution)

solvent

proton decoupled		•
I
	I	I.	I

I

200

160

120

80

40

o 0 (ppm)

1H NMR Spectrum

(400 MHz, CDCI3 solution)

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

122

Problem 34

IR spectrum (liquid film)

, r

1725

4000

3000

2000

1600

1200

800

V (ern")

100

29

31

45

Mass Spectrum

80

~

4l

No significant UV

60

a.

Sl

t1I

M+'

absorption above 210 nm

40

J::J

0

74

20

C3H 602

I

J.

III

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, CDCI 3 solution)

l

=-~""'~_~_",".1j,,~

proto"

......~~~Ww!\'W~1f\I'

proton _______decoupled

---il...-

s_"LJ

__

I

I

I

I

I

I

I

I

I

I

L

I

I

200

160

120

80

40

0 o(ppm)

1H NMR Spectrum

(100 MHz, CDCI 3 solution)

TMS

expansion 4x

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

123

Problem 35

IR Spectrum

(KBr disc)

1662

4000

3000

2000

1600

1200

800

V

(ern")

100

105

Mass Spectrum

UV Spectrum

80

til

sc

Amax 258 nm

(Io910E

4.2)

c.

ll)

60

ll)

77

VI

til

,JJ

Amax 330 nm

(Io910E

2.8)

..0

40

a

20

*'

M+"

Amax 388 nm

(I091OE

2.2)

210

C14H1002

solvent: ethanol

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 MHz, CDCI3 solution)

I

Problem 36

IR Spectrum

(KBr disc)

4000				3000			2000		1600			1200	800			0.0
								V (ern")
100							91					Mass Spectrum				0.5		Q)
																		o
80			..><															c
			t'lI															t'lI
			Q)															-e
60			0.														0
			(I)														.0
			Q)															(I)
			t'lI						M+"							1.0		t'lI			uv spectrum
40			.0						162
			'0																		165.3 mg 1100 mls
			~
																					path length:			0.2 cm
20
				I	,I								C14H 14								solvent: ethanol
									I,
																1.5
				40	80		120	160	200			240	280				200			250	300			350
								m/e													A. (nm)
			I	I		I	I	I		I		I	I			I		I		I			I
	13C NMR Spectrum										Resolves into
										--
	(50.0 MHz, CDCI3 solution)										two signals at higher fielel
										I
				DEPT	CH2 f CHJ CHt
										--	Resolves into
											two signals at higher fielel

proton elecoupled

I

solvent

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
______-----'		\' --		"		.....		------Il

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

125

Problem 37

3310

IR Spectrum

(liquid film)

4000					3000						2000					1600		1200			800
													V	(crn'")
100									91		106									Mass Spectrum
80			-'"
			C1l
			Ql
60			0..
			Ql														M+'
			C1l
40			.'"0													197
			0
20			<ft.
																				C14H1SN
					40				80		120			160		200				240	280
													m/e
			I			I				I		I			I			I		I	I				I	I	I	I
	13C NMR Spectrum																	Jl:i, ,
	(100.0 MHz, COCI3 solution)																				Sion
																		129		128	ppm
			DEPT			CHz1CH3t					CHt
																		JL:LSion
																			i	,
																		129		128	ppm
			proton decoupled												I						solvent .
			I																									I
					200						160					120					80					40		o s(ppm)
	lH NMR Spectrum												r
	(200 MHz, COCI3 solution)

								exchanges
								with O2	°	l
								-r
										TMS
			-'~
I	I	I			I	I	I	I	I	I
10	9	8	7	6	5	4	3	2	1	0
										s (ppm)

126

Problem 38

IR Spectrum

(liquid film)

4000			3000					2000		1600	1200
									V (ern")
100
						58					Mass Spectrum
80		-'"
		.,
		<1l
		0-													No significant UV
60		.,
		III
		<1l												absorption above 220 nm
40		.0
		'0
20		'ffl"						M+" = 116
						72
						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)

,,,100 decoupled

J

1 1 ----	1 ----------------			1 - 1 L	_
	I	I I	1 I	1 I	I
200	160	120	80	40	o () (ppm)

1H NMR Spectrum

(400 MHz, CDCI3 solution)

expansion

						TMS
	2.4 2.2 2.0 ppm
						I

10 9 8 7 6 5 4 3 2 1 o

() (ppm)

127