structures

Problem 19

1H NMR Spectrum

(200 MHz, CDCI3 solution)

	J		expansion
								, --		- )
				1		J~l
	I I		I I I	I		I i
	34		3.0	2.6		2.2 ppm
						-		-				TMS
										--i		1
										' - '

I

l

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

108

Problem 20

	IR Spectrum	1620
	(KBrdisc)

4000

3000

2000

1600

1200

800

V (em")

100

44

Mass Spectrum

80

"'"Q)

'"

60

c.

No significant UV

Q)

<Il

absorption above 220 nm

'"

40

.Q

'0

#,

20

Ii

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, 020 solution)

I

I

200 160 120 80 40 o 0 (ppm)

1H NMR Spectrum

(400 MHz, 020 solution)

Note: there are 3 protons which exchange with

the 020 solvent

						H20 and HOD
						in solvent
3.9		3.7 ppm		1.6	1.4 ppm

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

109

Problem 21

IR Spectrum

(KBr disc)

1600

	4000						3000	2000		1600
									V (crn'")
	100
						30					Mass Spectrum
	80	""
		co
		Q)
	60	c,													No significant UV
		Q)
		en
		co													absorption above 220 nm
	40	.c
		'0
		;f!.
	20
		40					80	120	160	200	240	280
									m/e
																.....,
	13C NMR						..........,1.'.'• ".OJ •• : ...,/.".' ......." .......				h,	I 4 .... t ,cart. WIU"M ,			"~
	Spectrum
	(100.0 MHz,
	O2°solution)

proton decoupled

200

160

120

80

40

0 o(ppm)

1H NMR Spectrum

(400 MHz, 020 solution)

Note: there are 3 protons which exchange with the 020 solvent

		expansions
i	i	J ,	i

H20 and HOD in solvent

.. I

3.2 3.0 ppm 2.2 2.0 ppm

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

110

I

1\

IR Spectrum

(liquid film)

4000				3000			2000					1600		1200		800
										V (ern")
100								M+'108						Mass Spectrum					UV Spectrum
80
	ell
	.:.:																		Amax 269 nm		(I091QE	3.2)
	<Il
60	Cl.			78
	Vl
	<Il
	ell
40	.0																		solvent: methanol
	'0
							93
20	<fi.
			j	j,			l									C7HaO
	40			80			120				160	200		240		280
										m/e
13C NMR Spectrum
(100 MHz, CDCI3 solution)
													lJJ
													W			•
																solvent
	proton decoupled
																						o(ppm)
																80					0
	200						160					120						40
1H NMR Spectrum
(400 MHz, CDCI3 solution)
			expansion

TMS

i i

7.27.0

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

III

Problem 23

IR Spectrum

(liquid film)

4000				3000	2000				1600	1200	800
							V (crn'")						UV Spectrum
100													Amax 243 nm (10910£	1.9)
				79						Mass Spectrum
													Amax 248 nm (10910£
80		""												2.1)
		0'".											Amax 252 nm (10910£
		<Il												2.2)
60		<Il
		en
		'"											Amax 258 nm (10910£
40		J:J												2.3)
		15			91
		*-											Amax 264 nm (10910£
20														2.1)
													Amax 268nm (10910£	1.9)

40

80

120

160

200

240

280

solvent: ethanol

m/e

13C NMR Spectrum
(100 MHz, CDCI3 solution)
							I		I
						129		128	127	ppm
					solvent		I	I	I	I
proton decoupled						129		128	127	ppm
200			160	120	80	40				o 0 (ppm)

1H NMR Spectrum

(400 MHz. CDCI3 solution)

expansion

Exchanges with

°2°

j

TMS

7.67.4 7.2 ppm

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

112

Problem 24

IR Spectrum

(liquid film)

0.0

4000

3000

2000

1600

1200

800

V (cm'")

100

91

Mass Spectrum

0.5

II)

80

o

-"

c:

11l

11l

II)

€

60

a.

0

UV spectrum

II)

.Cl'"

'"11l

1.0

11l

0.917 mg 110 mls

40

.Cl

'0

path length: 0.20 cm

20

'#

M+'

solvent: hexane

.n

I ,\,

170/172

C

7H 7Br

1.5

40

80

120

160

200

240

280

200

250

300

350

mle

A. (nm)

I

I

I

I

I

I

~

I

I

13C NMR Spectrum

expansion

(50.0 MHz, CDCI3 solution)

I

i

I

140

130

ppm

~

expansion

I

i

I

140

130

ppm

proton decoupled

solvent

•

I

I

I

I

I

I

I

I

I

200

160

120

80

40

o

s (ppm)

1H NMR Spectrum

(200 MHz, CDCI3 solution)

							r -
						~
											TMS
			t								I
I	I	I	I	I	I		I	I	I	I	I
10	9	8	7	6	5	4		3	2	1	0
											() (ppm)
											113

r

Problem 25

2251

IR Spectrum

(liquid film)

4000						3000			2000				1600		1200	800
											V (ern")
100
										M+" =117					Mass Spectrum
80		.><
		'"					77
		'"
60		0-
		'"
		'"
		'"
40		.0
		'0
		~
20
		40				80			120		160		200		240	280
											m/e
		I				I		I		I		I		I	I	I	r	T	T	I
	13C NMR Spectrum									expansion
									~
	(100.0 MHz, CDCI3 solution)

i

i

i

130 129 ppm

DEPT CHz'CH3t CHt

expansion

~

I

proton decoupled

do	i	i
	129	ppm	I	I	solvent
					•

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)

I ---

										TMS
							-			1
J	I	I	I	I	I	I	I	I		I
10	9	8	7	6	5	4	3	2	1	0
										s (ppm)

114

Problem 26

3290

IR Spectrum

(liquid film)

3000

2000

1600

1200

800

4000

V (cm'")

UV Spectrum

100

M+" 107

Mass Spectrum

Amax 256 nm

(log10~

2.2)

80

lIJ

""Ql

60

c-

Amax 264 nm

(log10~

2.1)

Ql

'"

lIJ

~

solvent: ethanol

40

'0

-

J, 20

oF-

~I

J

~

91

C7H g N

"

J .1.

40

80

120

160

200

240

280

role

I

I

I

I

I

I

I

I

I

I

I

I

13C

NMR Spectrum

ll"'~"'"

(100 MHz, CDCI 3 solution)

1

I

DEPT CH21CHJ CHt

129

128

127

ppm

I

ll"'~""

solvent

1

proton decoupled

I

1

I

129

128

127

ppm

I

200

160

120

80

40

0

o(ppm)

1H NMR Spectrum

Exchanges with

(400 MHz, CDCI 3 solution)

D20

expansion

1

TMS

7.6

7.4

7.2 ppm

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

115

Problem 27

IR Spectrum

(liquid film)

4000			3000		2000		1600	1200	800	0.0
						V	(om")
100			91					Mass Spectrum		0.5
80	-'"
	<lI
	Q)
60	0.				92
	Q)
	1I)
	<lI									1.0
40	.0
	'0				M+'=122
	;f?
20		I,	J ,I··						CaH100
					I					1.5

UV spectrum

5.662 mg I 10 mls path length: 1.00 cm

solvent: ethanol

		40				80		120				160			200	240	280					200				250	300				350
											m/e																A(nm)
		I		I			I
	13C NMR Spectrum							expansion
	(100.0 MHz,							i			, li-,
	CDCI3 solution)							135	130			ppm			I
		DEPT		CH2 f CH3t				CHt																	I
		!					'::lL, , ,										solvent
																		f
								135	130			ppm
		proton decoupled										,I																	-,
									,									I			,
															I	I	I							I		I
			200						160						120		80					40					0				()(ppm)
	lH NMR Spectrum														expansion											expansion
																										~.
	(400 MHz, CDCI3 solution)
	expansion														I	•
															3.9	3.8	ppm									2.9			2.8 ppm
		7.3	7.2				ppm																						Exchanges
																													with D20
																										•					TMS
	10	9				8			7			6				5	4					3				2	1				o
																															s (ppm)

116

3325

IR Spectrum

(liquid film)

4000				3000		2000	1600	1200	800
						V (crn")
100
				104				Mass Spectrum
80	III
	.><
	III
60	Co
	Ul
	Ql			77 78
	III					107
40	.Q				79
	'0					M+'=122
20	<fi.
			.1 j I.	.1.		.1			C 8 H 10O

Problem 28

0.0

0.58

	c
	€
	o
	Ul
	. Q
1.0	III
		UV spectrum
		5.815 mg/10mls
		path length: 1.00 cm
		solvent: ethanol
1.5 u	...................."'-o..J.................	...L...".................	l..o..I...	I

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

13C NMR Spectrum

(100.0 MHz, COCI3 solution)

DEPT

CH2 , CH3t

CHt

solvent

proton decoupled

I	~.

I

200

160

120

80

40

o

s(ppm)

1H NMR Spectrum

(400 MHz, COCI3 solution)

expansions

expansion

II

~ ~

li i

i

i

i

i

i

i

i

5.0

4.8

ppm

1.6

1.4 ppm

~

Exchanges

i

r -

with 02°

~

7.5

7.3

ppm

L

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)

117