structures

Problem 49

IR Spectrum

(liquid film)

4000

3000

2000

1600

1200

800

V (crn'")

100

57

Mass Spectrum

80

III

.>t:

Q)

60

c-

29

No significant UV

Q)

Ul

III

absorption above 220 nm

40

.c

'0

M+"=174 «1%)

?ft.

100

20

~ n

CaH 1404

1,1

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)

l

proton decoupled

solvent

•

I

I

I

I

I

1

I

I

1

I

I

I

200

160

120

80

40

o 0 (ppm)

1H NMR Spectrum

(200 MHz, CDCI3 solution)

1___

TMS

1

138

Problem 50

IR Spectrum

(liquid film)

4000				3000				2000		1600	1200	800
								V (ern")
100				55		71					Mass Spectrum
80
	.><				70
	'"
	Ql
60	C.														No significant UV
	Ql
	'"							M+'= 158 «	1%)
	.c													absorption above 220 nm
40	'"
	'0
20	<fl.
												CaH1403
	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. CDCJ 3 solution)

											I
I	I	I	I	I	I	I	I	•	I	IIlI I
	proton decoupled						solvent
	200		160		120		80			40	o () (ppm)

lH NMR Spectrum

(200 MHz, CDCI3 solution)

	k~"			J
			1L-JL-
	I	I
	2.00	1.50 ppm

, --

TMS

I

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

139

Problem 51

IR Spectrum

(nujol mull)

4000

3000

2000

1600

1200

800

0.0

V

(cm'")

100

Mass Spectrum

0.5

Q)

o

80

"'"

M+"

c:

€'"

Q)

234/236/238

60

c.'"

0

III

III

UV spectrum

.0

Q)

155/157

'"

.0

40

'"

1.0

a 15.07mg/10ml

'0

20

<f-

C 6 H 4 Br2

!! 0.302 mg/10ml

I II

path length:

0.5 cm

,L

solvent: ethanol

80

120

160

200

240

280

250

300

40

350

m/e

A(nm)

I

I

I

I

I

I

I

I

I

I

I

I

13C NMR Spectrum

(20,0 MHz,CDC'3solution)

off-resonance decoupled

I	II
	solvent

proton decoupled

I

I

I

I

I

I

I

I

I

I

I

I

I

200

160

120

80

40

o o(ppm)

1H NMR Spectrum

(100 MHz, CDCI3 solution)

TMS

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

140

Problem 52

IR Spectrum

(nujol mull)

4000		3000		2000			1600	1200	800
					V (ern")
100
						152		Mass Spectrum			UV Spectrum
80	-""								C12H8Br2		Amax 264 nm (109101:: 4.5)
	l\'l
	c-
60	Q)
	en
	Q)
	l\'l	76							M+"
40	.Q										solvent: methanol
	15								310/312/314
20	"*	11
			,,-.II	L
	40	80		120	160		200	240	280
					m/e

13C NMR Spectrum

(50.0 MHz, CDCI3 solution)

C-H C-H

C

C

solvent

proton decoupled

200

160

120

80

40

o 0 (ppm)

1H NMR Spectrum

(200 MHz, CDCI3 solution)

								expansion
					1 I	I I i		iii
				8.0		7.5		7.0	ppm
													TMS
10	9	8	7	6		5		4	3		2	1	o
													o(ppm)

141

Problem 53

IR Spectrum
(liquid film)	696

4000

3000

2000

1600

1200

800

V (em")

100

125/127

Mass Spectrum

80

"""

'"

Ql

60

a.

rn

Ql

'"

40

.0

'0

20

*"

M+·

J,I,h ,L"

.l J.

160/162/164

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

(50.0 MHz, CDCI3 solution)

I

proton decoupled

I

SOlve:

I

I

I

I

I

I

I

I

I

I

I

I

I

200

160

120

80

40

o o(ppm)

1H NMR Spectrum

(200 MHz, CDCI3 solution)

expansion

									V	-,
						I		I		I			TMS
						B.O		7.5		7.0	6.5	ppm
			V										1
I	I	I		I	I		I		I	I	I	I	1-
10	9	8	7		6		5	4		3	2	1	0
													o(ppm)

142

Problem 54

IR Spectrum

(liquid film)

4000	3000	2000	1600	1200	800
		V (em")

100

80 ~

Q)'"

a.

60 Q)

III

.'"0

40 '0

~

o .

20

I

121	Mass Spectrum

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			~pao']l
(100.0 MHz, CDCI	3	solution)

, , ,

130 128 ppm

DEPT CH2 , CH3 t CHt

I

~~-Jl1

, , ,

130 128 ppm

proton decoupled

I

solvent,

I .

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

Jl

7.6 7.4 ppm

					J			-				TMS
			.1		I							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)

143

Problem 55

	IR Spectrum
	(KB'r disc)
3400	1720

4000						3000					2000		1600					1200					800
												V (em")
100
											105			183						Mass Spectrum									UV Spectrum
80			.><																										Amax 253 nm (10910E
			III																															2.6)
			Q.
60			'"
			fF)
			'"																										Amax 259 nm (10910E
			III																															2.7)
40			.0													M+" =228 « 1%)
			'0																										Amax 264 nm (l0910E
			~																															2.5)
20												IL I
							,I.
																							C14H1203								solvent: ethanol
						40		80			120	160	200							240			280
												m/e
			I				I			I	I	I					I				I			I			I				I
	13C NMR Spectrum
	(100 MHz, COCI3 solution)
																	i		i
															130			128			ppm
																	j[''"''OO
																									solvent
			proton decoupled													,		,		,				I"j'..-J
										I		I				130		128			ppm
						200					160		120										80						40		0			S (ppm)
		1H NMR Spectrum
		(400MHz, CDCI3 solution)																						expansion
			Exchanges																		JlJl, ,
				with D20
				+																7.7			7.6			7.5		ppm
				~								Exchanges
			,	,		,		ppm				with 020																						TMS
	14.5			14.0		13.5
												+
								~				----r-																						1
		I				I				I		I		I						I				I				I		I		I
10						9		8				7	6							5			4					3	2		1			0
																																		S (ppm)

144

Problem 56

IR Spectrum

(KBrdisc)

3461

3326

4000

3000

2000

1600

1200

800

V (cm-1 )

100

UV Spectrum

Mass Spectrum

80

""III

M+"

110

Amax 225 nm

(loglOE

3.5)

Ql

A

60

0.

27S nm

(log E

3.4)

Ql

en

max

lO

III

Amax 283 nm

40

.Q

(log10E

3.3)

'0

20

"#.,

I

CSHS0

solvent: methanol

J

.Ii

I

2

40

80

120

160

200

240

280

m/e

I

I

I

I

I

I

I

I

I

I

I

T

13C

NMR Spectrum

11

(100 MHz, CDCI3 solution)

D~:IIl~:L.C;,3'~~4~':!"'I1l~.~'.'Ill

~ _ll/l¥"lWJt#...lIIlfIIlIlI.W1...~~-.-..."......

II"," 'Ifi

$' ,....

1M.'nWl....... ...

....-.ll'IoollI.........t 1IWII

r- '"">----

solvent

proton decoupled

I

200

160

120

80

40

0 o(ppm)

1H NMR Spectrum

(400 MHz. CDCI3 solution)

1rr--r-

expansion

Exchanges with

						0:0	~vIN~
			-		S 0'90						'						TMS
															i
														680		ppm
												I
10	9	8	7		6	5	4		3					2		1	0

8 (ppm)

145

Problem 57

IR Spectrum

(CCI4 solution)

I I I I I

4000					3000	2000					1600	1200	800
									V (ern")
100											M+- =168	Mass Spectrum		UV Spectrum
80		"'"<IJ
		co							153					Amax 267 nm (Io910E 2.8)
60		a.
		III
		<IJ
		co
40		.0												solvent: ethanol
		'0
20		*-			~Ijl'~J I	l			I			C9H1203
		40			80	120			160		200	240	280
									m/e
	13C NMR Spectrum
	(100.0 MHz, CDCI3 solution)
			__J"--------J"-------

proton decoupled

200 160 120 80 40 o 0 (ppm)

1H NMR Spectrum

(200 MHz, CDCI3 solution)

expansion

,,

7.0

6.4 ppm

ppm

TMS

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

146

Problem 58

IR Spectrum

(liquid film)

4000			3000		2000			1600	1200	800
						V (cm'")
100				105		M+'			Mass Spectrum
80	.:s:.
	1Il'"					120
60	c-
	en
	1Il
	'"
40	.c
	'0
20	*'	'III	1	~I I,						C9H12
	40			80	120		160	200	240	280

mle

0.0
0.5		1Il
		<J
		c:
		'"
		-e
		o
		en
		.c
1.0		'"			UV spectrum
				5.875 mg 110 mls
				path length: 1.00 cm
1.5				solvent: ethanol
	200		250	300		350

A(nm)

I I I I I I I I I I

13C NMR Spectrum

(20.0 MHz, CDCI3 solution)

I

I

off-resonance decoupled

proton decoupled

I

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

lH NMR Spectrum

(100 MHz, CDCI3 solution)

s

				L									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)

147