structures

Problem 99

IR Spectrum

1718

(liquid film)

4000

3000

2000

1600

1200

800

V (ern")

100

43

119

Mass Spectrum

UV Spectrum

80

,

Amax 262 nm

"'"

'"

(

I091OE 2.5)

a.

(l)

60

"'

(l)

.c

40

'"

M+"

solvent: methanol

'0

176

~

20

II

L ,.I.""jll

161

I

C 12 H16 0

I.

I

I.

40

80

120

160

200

240

280

m/e

I

I

I

I

I

I

I

I

I

I

I

I

13e NMR Spectrum

lL~";oo

(50.0 MHz, CDC'3solution)

I

I

1

130

125

ppm

DEPT

CH2 t CH3 t

CH t

lc";oo

I

.'	I	I

I	I			I I
130	125 ppm	•	solvent
		II

proton decoupled

I

I

I

I

I

J

I

I

I

I

I

I

200

160

120

80

40

o 0 (ppm)

1H NMR Spectrum

(200 MHz, CDCI3 solution)

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

188

Problem 100

1693

IR Spectrum

(CCI4 solution)

4000

3000

2000

1600

1200

800

V (crn'")

100
80	ltJ
	~
	Ol
60	c-
	(fl
	Ol
	ltJ
	.a

400

f1!..

20

1 Il

183/185

Mass Spectrum

UV Spectrum

155/157

M+" = 198/200	solvent: ethanol

11 CaH 70Br

	40	80	120	160	200	240	2ao
				m r e
I	I	I	I	I	I	I	I	I	I	I	I

13C NMR Spectrum

(100.0 MHz, COCI3 solution)

DEPT CH2 , CH3+	CH+
proton decoupled			solvent
I	I	II	.

I

I	I	I	I	I	I	I	I	I	I	I	I
	200		160		120		80		40		0 () (ppm)

1H NMR Spectrum

(200 MHz, COCI3 solution)

						expansion
					JJL				-
					7.8	7.2	ppm
				~								I
												TMS
I	I	I		I		I	I	I			I
10	9	8	7		6	5	4	3	2		1	0

() (ppm)

Problem 101

IR Spectrum

(liquid film)

,

UV spectrum

0.104 mg/10 mls path length: 1.00 cm solvent: ethanol

250 300 350

A(nm)

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

13C NMR Spectrum

(20.0 MHz, CDCI3 solution)

C-H C-H

-CH 3

C

CC

l

TMS

proton decoupled

I I

I

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, CDCI3 solution)

3H

		2H		2H
												TMS
		1
					U							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)

190

Problem 102

IR Spectrum

1773 1738

875

(liquid film)

4000

3000

2000

1600

1200

800

V (crn'")

100

119

Mass Spectrum

UV Spectrum ,

80

"'"

Amax 254 nm (10910£

""

4.3)

a.

Q)

60

Q)

91

'"

Amax 258 nm

40

.""0

(10910£

4.2 )

'0

Amax 279 nm

20

*'

M+" = 1541156

CSH 70CI

(10910£

3.3)

.,1]

I,

Amax

290 nm (10910£

3.0)

40

80

120

160

200

240

280

solvent: hexane

m/e

I

I

I

I

I

I

I

I

I

I

I

I

13C NMR Spectrum

l=~;OOL

(100.0 MHz, CDC'3 solution)

DEPT

CH2 t CH3t

,

,

I

CHt

132

131

ppm

,

i

i

proton decoupled

I

r.132 131 ppm

.----J

I

I

solvent

I

I

I

I

I

I

I

I

I

I

I

I

200

160

120

80

40

0

o(ppm)

1H NMR Spectrum

(400 MHz, CDCI3 solution)

expansion

, . -

II

-- '

,

,

,

I

8.0

7.5

7.0 ppm

I

TMS

I

I

I

I

I

I

I

I

I

I

I

10

9

8

7

6

5

4

3

2

1

o

o(ppm)

191

			3500-2500													Problem 103
			IR Spectrum							1688
				(KBrdisc)
4000					3000		2000					1600		1200	800
								V (em")
100
							135				M+- 152			Mass Spectrum		UV Spectrum
80			""Ql
			'"
60			c-
			rJ)
			Ql
			.0													solvent: methanol
40			'"
			'0
20			oft.
					III .111 •.1,,1 I
				I			.1"
			40		80		120			160		200		240	280
							m/e

13C NMR Spectrum

(100 MHz, COCI3 solution)

	DEPT CH2 1CHat	CHt		I	I
				LJ
							solvent
						1
						1
	proton decoupled
	200	160			120	80		40	0 o(ppm)
	1H NMR Spectrum
	(200 MHz, CDCI3 solution)			expansion

exchanges with 0 20

~

~

I I

13.012.0 r-r-rr:

----1

I I I

	JL		JL
	I I I		I I I
8.1		8.0	7.0	6.9 ppm			I --
	,---
								TMS
.--1				-				I
I		I				I	I	I

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

192

Problem 104

IR Spectrum	1743
(liquid film)
	1229

4000				3000				2000				1600	1200	800
										V (ern")					UV Spectrum
100															Amax 252 nm
									108				Mass Spectrum			Q0910E		2.2)
80	-'"														Amax 257 nm (i0		9 10E	2.3)
	<Il
	Q)					91
60	c.			43											Amax 262 nm (I0910E			2.2)
	Q)
	U>
	<Il														Amax 264 nm (I0910E
40	.0										M+" 150							2.2)
	'15
	~														Amax 268 nm
	o .															(I091OE		2.0)
20				.I	,l ,I			rJ						CgH100 2
			.I			1,1.									solvent: ethanol
				40		80		120		160		200	240	280
										m/e
13C NMR Spectrum
(100 MHz, CDCI 3 solution)									expansion
								1L

I I

128.5128 ppm

						¥,;'ppmI				,
										solvent
proton decoupled								I		I
	200					160		120		80	40		o		0 (ppm)
1H NMR Spectrum
(200 MHz, CDCI3 solution)
expansion
												~
					,				----
I	, I			I
	~\
					ppm
7.5	7.4			7.3
															TMS
					--.J			-			-
															I
I					I		I	I	I	I	I	I
10	9				8	7		6	5	4	3	2	1		o
															o(ppm)

193

Problem 105

IR Spectrum (nujol mull)

1670

4000						3000			2000				1600				1200	800
										V (cm")
100
									135								Mass Spectrum					UV Spectrum
80			-"
			co																			Amax 270 (I091O E			4.2)
			a.
			Q)
60			Q)								M+"
			'"co								150											solvent: methanol
40			.0
			'0
20			*			..J		J	107
				I	I n,	Jt..			I									Cg H1Q 0 2
					40		80		120	160			200				240	280
										m/e
		13C NMR Spectrum
		(15.0 MHz, CDCI 3 solution)
									l									solvent
						I														J	. k		, l
		off-resonance decoupled					",,"0,,10at 130ppm				l
										,-													l		TMS
	proton decoupled					I			I																I
					200				160				120					80				40			o 0 (ppm)

1H NMR Spectrum

(100 MHz, CDC'3 solution)

3H

3H

		2H	2H
		U	~							TMS
										L
I	I	I	. ,	I	I	I	I	I	I	I
10	9	8	7	6	5	4	3	2	1	0
										o(ppm)

194

Problem 106

IR Spectrum
(liquid film)	1760

4000

3000

2000

1600

1200

800

V (crn'")

100

108

Mass Spectrum

UV Spectrum

80

ttl

\

.><

Amax 265 nm (109101>

2.6)

Co

60

<I)

VJ

<I)

Amax 271

ttl

107

nm (109101>

2.6 )

40

.Q

'0

~

M+'= 150

solvent:

methanol

20

I~

I

J,

I

40

80

120

160

200

240

280

m/e

I

I

I

I

I

I

I

I

I

I

13e NMR Spectrum

.~'"~

(100.0 MHz, CDCI3 solution)

DEPT

CH2 t CH3t

CHt

,

,

,

,

I

24

20

ppm

"~"':L

,

,

,

,

I

proton decoupled

I

I

I

solvent

24

20

ppm

I

I

I

I

I

I

I

I

I

I

I

I

I

200

160

120

80

40

0

3 (ppm)

1H NMR Spectrum

(400 MHz. CDCI3 solution)

expansion		-

~~

7.27.0 ppm

J	-	TMS
d		I

I I I I I I I I I

10 9 8 7 6 5 4 3 2 1 0

3 (ppm)

195

Problem 107

	IR Spectrum	1724
	(liquid film)

4000

3000

2000

1600

1200

800

V (cm-1 )

100

119

Mass Spectrum

UV Spectrum

80

.><

Amax 238 nm (109101':

l'll

4.2) \

Ql

60

a.

Ql

Amax 281 nm (109101':

VI

91

2.7)

l'll

40

.Cl

'0

;f!.

solvent:

methanol

20

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

.,

JL"":'"', ,

(100.0 MHz, CDCI3 solution)

I

I

132.5

130.0

ppm

DEPT

CH2 •

CH3t CHt

~~~slon

proton decoupled

,

,

,

solvent

132.5

130.0

ppm

I

I

I-.-J

I

I

I

I

I

I

I

I

I

I

I

I

200

160

120

80

40

0

() (ppm)

1H NMR Spectrum

(400 MHz, CDCI3 solution)

expansion

If

L

JL

8.0 7.9

7.3

7.2

ppm

-

TMS

I

I

I

I

I

I

I

I

I

I

I

I

I

I

10

9

8

7

6

5

4

3

2

1

0

() (ppm)

196

Problem 108

	IR Spectrum
3352	(liquid film)

4000				3000					2000					1600	1200	800
											V (cm'")
100
															Mass Spectrum				UV Spectrum
80	""III												M+"								\
												138							Amax 270 nm				3.1)
	Ql																				(109108
60	c,
	Ql								121
	III																					8
	'"																		Amax 282 nm		(10 9 10		3.1)
40	.J::J
	'0
	~																			solvent: hexane
20
																C8H100 2			Note: UV spectrum not changed
																				significantly on addition of base
	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)

I

DEPT

CH2 , CH3t

CHt

I

I

I

I

I

IUI

I

I

LJI

I

I

I

proton decoupled

solvent

I

I

200

160

120

80

40

o s(ppm)

1H NMR Spectrum

(200 MHz. CDCI3 solution)

__ exchanges	TMS
with D20

10 9 8 7 6 5 4 3 2 1 o

() (ppm)

197