structures

Problem 9

3458

		IR Spectrum
		(CCI4	solution)
4000			3000	2000	1600	1200	800
				V	(crn'")
100
						Mass Spectrum

59

80-'" to

Q>

60

0-

No significant UV

Q>

to

'"

40

.a

absorption above 220 nm

'0

M+'=118 «

*

1%)

20

,I

J

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)

proton decoupled

sOIV~.1

I

I

I

I

I

I

I

I

I

I

I

I

200

160

120

80

40

0

S (ppm)

1H NMR Spectrum

.. :

(200 MHz, CDCI3 solution)

:<

~

,;,'

Exchanges with

;:>

.

°2°

s,"

t~

S-

"

TMS

I

1

I

I

I

I

I

I

I

I

I

-.1._

10

9

8

7

6

5

4

3

2

1

0

s (ppm)

;

98

Problem 10

		IR Spectrum						1693
			(KBrdisc)
																	800
4000					3000			2000					1600		1200
										V		(cm'")
100
					56			M+'= 112								Mass Spectrum
80		"""
		0'"-
		Q)
60		Q)																		No significant UV
		VI																		absorption above 220 nm
		'"
40		.J:J
		'0
		0~
20
						,"	I,
		40					80	120				160	200		240		280

m/e

13e NMR Spectrum

(100.0 MHz, CDCI 3 solution)

proton decoupled

solvent

200 160 120 80 40 o 0 (ppm)

1H NMR Spectrum

(400 MHz, CDCI 3 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
										o(ppm)

99

Problem 11

IR Spectrum	1738
(liquid film)

4000						3000					2000		1600	1200	800
												V (crn")
100														Mass Spectrum
80			~						M+'= 84
			o,
			Ql
60			~															No significant UV
			'"													absorption above 220 nm
40			.0
			'0
20			<J.
						40			80		120	160	200	240	280
												m/e
	13C NMR Spectrum																	n
	(100.0 MHz, CDCI3 solution)
	proton decoupled																U			..
															solvent
						200					160		120		80					0 o(ppm)
																40
	1H NMR Spectrum												expansion
	(400 MHz, CDCI3 solution)

2.2	1.8 PPM		TMS

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

100

Problem 12

IR Spectrum

(Ijquidfilm)

4000		3000		2000				1600		1200	800	0.0
					V	(ern")
										Mass Spectrum		0.5
													Ql
80
	~												<J
							M+"= 156						C
	<ll
	'"												'"
	0.
60													-e	UV spectrum
	<ll												0
	III												III
	..c												..c
40	'"			127								1.0	'"	5.00 mg 110 mls
	'0	29							contains a haloQen					path length: 0.50 cm
	<t-													solvent: cyclohexane
20		II
												1.5
		40	80	120		160		200		240	280	200		250	300		350
					role										A(nm)
13C NMR Spectrum																No TMS in
(50.0 MHz, CDCI3 solution)														~'~PI'
											solvent

proton coupled	i

proton decoupled

III

L

200

160

120

80

40

0 o(ppm)

1H NMR Spectrum

(200 MHz, CDCI3 solution)

10

9

8

7

6

5

4

3

2

1

o

8 (ppm)

Problem 13

2989

IR Spectrum	689
(liquid film)

4000

3000

2000

1600

1200

800

V (cm'")

100

63

Mass Spectrum

80

-"

'"

'"

60

0-

No significant UV

VJ

'"

65

absorption above 220 nm

'"

40

.0

'0

M+'

20

*'

83

ll,

981100/102

I..

~ II

JJ

C2 H4C I2

40

80

120

160

200

240

280

m/e

I

I

I

I

I

I

I

I

I

I

I

I

13C NMR Spectrum

..,i"

(50.0 MHz, CDCI3 solution)

proton coupled

f t ... 1IIIf'-...... 'J t

'.,

• "P' 4'......'LU...'A roc

....

61·.... 1.... ,

i' "U

III •

'....

solvent

I

proton decoupled

ru

I

I

I

I

I

I

I

I

I

I

I

I

200

160

120

80

40

0 " (ppm)

1H NMR Spectrum

(200 MHz, CDCJ3 solution)

~		L expansions					~
,		,	,		,-
6.0		5.8 ppm	2.2		2.0 ppm

							=:f												~I
																			TMS
														~
I	I			I		I	I		I			I	I			I	I
10	9	8			7		6		5			4	3	2			1		0
																			s (ppm)

102

Problem 14

IR Spectrum

(liquid film)

3354

4000				3000		2000		1600	1200	800
							V (ern")
100
				45					Mass Spectrum
80	C1l
	-'"
	Q)
60	0-										No significant UV
	Vl
	Q)
	C1l										absorption above 220 nm
40	.0
	'0
	?ft.-.				M+'=60 «		1%)
20
		JIIHI		59						C3H aO
				I
	40			80		120	160	200	240	280

m/e

solvent

proton decoupled

•

200

160

120

80

40

o 0 (ppm)

1H NMR Spectrum

(200 MHz. CDCI 3 solution)

				expansions
I			I			I	,			TMS
4.5	4.0			ppm		1.5	1.0	ppm

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

103

~[

IR Spectrum

(liquid film)

I I

1\ Problem 15

~Ir>. " 0 ('r

I

4000

3000

2000

1600

1200

600

V (cm" )

100

43

Mass Spectrum

80

.><

'"

Q)

60

o,

Q)

No significant UV

1Il

'"

40

.0

absorption above 220 nm

'0

M+"

*'

20

122/124

,I

1I.

II

C3 H 7Br

40

80

120

160

200

240

260

m/e

I

I

I

I

I

I

I

I

I

I

I

r

13C NMR Spectrum

(50.0 MHz, CDCI3 solution)

DEPT

CH2 ,

CH3t

CHt

proton decoupled

solvent

I

~

I

I

I

I

I

I

,

I

I

I

,

I

200

160

120

80

40

0 s (ppm)

1H NMR Spectrum

(200 MHz, CDCI3 solution)

				expansions
		-, ,	1.\.,
			, ,	,		, ,		, I		,		~		-		TMS
		4.6	4.0	ppm	2.0			1.4		ppm
												Ill.				I
I		I	I		I			I			I	I	I	I	I	I
10		9	8		7			6		5		4	3	2	1	0
																s (ppm)

104

Problem 16

				IR Spectrum															776
				(liquid		film)					2960
																			650
4000						3000						2000				1600		1200	800
														V (ern")
100
									55									Mass Spectrum
80				~
				CD
				a.																					No significant UV
60				5l
				co		41
				.0									M+"											absorption above 220 nm
401				-'0											126/128/130 < 1%
				~
201				-
						40					80	120			160	200		240	280
														m/e
				I				I			I		I		I		I	I	I				I	I	I	r
	13CNMR Spectrum																								I
	(50.0 MHz, CDCI 3 solution)																						I		H-C-H
																						H-C-H
																									I
																							I

	proton decoupled	solvent
		•

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

1H NMR Spectrum

(200 MHz, CDCI 3 solution)

	expansions
									TMS
	I	ppm
	ppm

10 9 8 7 6 5 4 3 2 1 o

8 (ppm)

105

Problem 17

763

IR Spectrum

(liquid film)

4000

3000

2000

1600

1200

800

V (ern")

100

41

Mass Spectrum

80

-"

<ll

Ql

60

o,

121/123

No significant UV

Ql

III

M+"= 200/202/204

<ll

absorption above 220 nm

40

.0

'0

~

20

".

II IJ

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)

DEPT

CH2~

CH3t

CHt

solvent

proton decoupled

~

I

I

I

I

I

I

I

I

I

I

I

I

I

Problem 18

IR Spectrum		766
(liquid film)	2960	650

4000

3000

2000

1600

1200

800

V (cm'")

100

-

41

Mass Spectrum

80

~

Ql

60

c-

No significant UV

3l

77

<0

absorption above 220 nm

40

.c

M+-

'0

20

'#..

j

79

156/158/160

107/109

III

C3H6BrCI

,11

II

40

80

120

160

200

240

280

m/e

I

I

I

I

I

I

I

I

I

I

I

13C NMR Spectrum

I

H-C-H

(50.0 MHz, CDCI 3 solution)

I

I

I

H-C-H

H-C-H

I

I

/	solvent

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

(200 MHz, CDCI 3 solution)

				expansions									TMS
-, r ,					--------'				L
	,	, , I	, , ,		,	,	I	,	, ,	, I
4.0	3.5			ppm			2.5			2.0 ppm

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

107