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Chemistry

First examinations 2009

Diploma Programme

Data booklet

Diploma Programme

Chemistry
Data booklet

First examinations 2009

International Baccalaureate Organization


Buenos Aires

Cardiff

Geneva

New York

Singapore

Diploma Programme
Chemistrydata booklet

Published March 2007


International Baccalaureate Organization
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United Kingdom
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International Baccalaureate Organization 2007
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4019a

Contents
1.

Some relevant equations

2.

Physical constants

3.

Fundamental particles

4.

Names of the first 103 elements

5.

The periodic table

6.

Melting points and boiling points of the elements

7.

First ionization energy, electron affinity and electronegativity of the


elements

8.

Atomic and ionic radii of the elements

9.

Covalent bond lengths

10

10.

Average bond enthalpies at 298 K

11

11.

Organic compoundsthermodynamic data

12

12.

Enthalpies of combustion

14

13.

Lattice enthalpies at 298 K (experimental and theoretical values)

16

14.

Standard electrode potentials

18

15.

Strengths of organic acids and bases

20

16.

Acidbase indicators

22

17.

Infrared data

23

18.

H NMR data

24

19.

2-Amino acids

26

20.

Structural formulas of some important medicines and drugs

29

21.

Structural formulas of some important biological molecules

32

22.

Structural formulas of some important food chemistry molecules

35

Notes
This booklet cannot be used for paper 1 of the examination (SLP1 and HLP1), but the periodic table given on
page 4 will be available as part of these examination papers. Clean copies of this booklet must be made
available to candidates for papers 2 and 3 (SLP2, SLP3, HLP2 and HLP3).

Chemistry data booklet

1. Some relevant equations


t1 =
2

0.693
k

log10

Ea

ln k =

k = Ae RT

E = hf

I0
= lc
I
Ea
+ ln A
RT

PV = nRT

G = H T S

International Baccalaureate Organization 2007

Chemistry data booklet

2. Physical constants
Avogadros constant (L) = 6.02 1023 mol1
Gas constant (R) = 8.31 J K1 mol1
Molar volume of an ideal gas at 273 K and 1.01 105 Pa = 2.24 102 m3 mol1 (= 22.4 dm3 mol1)
Plancks constant (h) = 6.63 1034 J s
Specific heat capacity of water = 4.18 kJ kg1 K1 (= 4.18 J g1 K1)
Ionic product constant for water (Kw) = 1.00 1014 mol2 dm6 at 298 K
1 atm = 1.01 105 Pa
1 dm3 = 1 litre = 1 103 m3 = 1 103 cm3

International Baccalaureate Organization 2007

Chemistry data booklet

3. Fundamental particles
Proton

Neutron

Electron

Mass (kg)

1.672648 1027

1.674954 1027

9.109534 1031

Charge (C)

1.602189 1019

1.602189 1019

International Baccalaureate Organization 2007

Chemistry data booklet

4. Names of the first 103 elements


Symbol

Atomic
number

Element

Symbol

Atomic
number

actinium

Ac

89

fluorine

aluminium

Al

13

francium

Fr

87

americium

Am

95

gadolinium

Gd

64

antimony

Sb

51

gallium

Ga

31

argon

Ar

18

germanium

Ge

32

arsenic

As

33

gold

Au

79

astatine

At

85

hafnium

Hf

72

barium

Ba

56

helium

He

berkelium

Bk

97

holmium

Ho

67

beryllium

Be

hydrogen

bismuth

Bi

83

indium

In

49

boron

iodine

53

bromine

Br

35

iridium

Ir

77

cadmium

Cd

48

iron

Fe

26

caesium

Cs

55

krypton

Kr

36

calcium

Ca

20

lanthanum

La

57

californium

Cf

98

lawrencium

Lr

103

carbon

lead

Pb

82

cerium

Ce

58

lithium

Li

chlorine

Cl

17

lutetium

Lu

71

chromium

Cr

24

magnesium

Mg

12

cobalt

Co

27

manganese

Mn

25

copper

Cu

29

mendelevium

Md

101

curium

Cm

96

mercury

Hg

80

dysprosium

Dy

66

molybdenum

Mo

42

einsteinium

Es

99

neodymium

Nd

60

erbium

Er

68

neon

Ne

10

europium

Eu

63

neptunium

Np

93

fermium

Fm

100

nickel

Ni

28

Element

International Baccalaureate Organization 2007

Names of the first 103 elements

Element

Symbol

Atomic
number

Element

Symbol

Atomic
number

niobium

Nb

41

silicon

Si

14

nitrogen

silver

Ag

47

nobelium

No

102

sodium

Na

11

osmium

Os

76

strontium

Sr

38

oxygen

sulfur

16

palladium

Pd

46

tantalum

Ta

73

phosphorus

15

technetium

Tc

43

platinum

Pt

78

tellurium

Te

52

plutonium

Pu

94

terbium

Tb

65

polonium

Po

84

thallium

Tl

81

potassium

19

thorium

Th

90

praseodymium

Pr

59

thulium

Tm

69

promethium

Pm

61

tin

Sn

50

protactinium

Pa

91

titanium

Ti

22

radium

Ra

88

tungsten

74

radon

Rn

86

uranium

92

rhenium

Re

75

vanadium

23

rhodium

Rh

45

xenon

Xe

54

rubidium

Rb

37

ytterbium

Yb

70

ruthenium

Ru

44

yttrium

39

samarium

Sm

62

zinc

Zn

30

scandium

Sc

21

zirconium

Zr

40

selenium

Se

34

International Baccalaureate Organization 2007

Chemistry data booklet

5. The periodic table


1

0
2

He

Atomic number

1.01
3

Li

Be

6.94
11

4.00

Element

10

Ne

9.01

10.81

12.01

14.01

16.00

19.00

20.18

12

13

14

15

16

17

18

Atomic mass

Na

Mg

Al

Si

Cl

Ar

22.99

24.31

26.98

28.09

30.97

32.06

35.45

39.95

19

20

21

22

23

24

25

26

27

28

29

30

31

32

33

34

35

36

Ca

Sc

Ti

Cr

Mn

Fe

Co

Ni

Cu

Zn

Ga

Ge

As

Se

Br

Kr

39.10

40.08

44.96

47.90

50.94

52.00

54.94

55.85

58.93

58.71

63.55

65.37

69.72

72.59

74.92

78.96

79.90

83.80

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37

38

39

40

41

42

43

44

45

46

47

48

49

50

51

52

53

54

Rb

Sr

Zr

Nb

Mo

Tc

Ru

Rh

Pd

Ag

Cd

In

Sn

Sb

Te

Xe

85.47

87.62

88.91

91.22

92.91

95.94

98.91

101.07

102.91

106.42

107.87

112.40

114.82

118.69

121.75

127.60

126.90

131.30

55

56

72

73

74

75

76

77

78

79

80

81

82

83

84

85

86

Cs

Ba

La

Hf

Ta

Re

Os

Ir

Pt

Au

Hg

Tl

Pb

Bi

Po

At

Rn

132.91

137.34

138.91

178.49

180.95

183.85

186.21

190.21

192.22

195.09

196.97

200.59

204.37

207.19

208.98

(210)

(210)

(222)

58

59

60

61

62

63

64

65

66

67

68

69

70

71

57

87

88

Fr

Ra

Ac

89

(223)

(226)

(227)

Ce

Pr

Nd

Pm

Sm

Eu

Gd

Tb

Dy

Ho

Er

Tm

Yb

Lu

140.12

140.91

144.24

146.92

150.35

151.96

157.25

158.92

162.50

164.93

167.26

168.93

173.04

174.97

90

91

92

93

94

95

96

97

98

99

100

101

102

103

Th

Pa

Np

Pu

Am

Cm

Bk

Cf

Es

Fm

Md

No

Lr

232.04

231.04

238.03

(237)

(244)

(243)

(247)

(247)

(251)

(254)

(257)

(258)

(259)

(260)

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Chemistry data booklet

6. Melting points and boiling points of the elements


14

Melting point (K)

Element

He

20
454

Boiling point (K)

1551

2573

4100

63

55

54

25

Li

Be

Ne

1600

3243

3931

5100

77

90

85

27

371

922

936

1683

317

392

172

84

Na

Mg

Al

Si

Cl

Ar

1156

1363

337

1112

1814

1933

1973

2130

1517

1808

1768

1726

1357

693

2740

2628

553

718

239

87

303

1211

1090

490

266

117

Ca

Sc

Ti

Cr

Mn

Fe

Co

Ni

Cu

Zn

Ga

Ge

As

Se

Br

Kr

1047

1757

3104

3560

3650

2755

2235

3023

3143

3005

2840

1180

2676

3103

886

958

332

121

312

1042

1780

2125

2741

2890

2445

2583

2239

1825

1235

594

429

505

904

723

387

161

Rb

Sr

Zr

Nb

Mo

Tc

Ru

Rh

Pd

Ag

Cd

In

Sn

Sb

Te

Xe

961

1657

3611

4650

5015

4885

5150

4173

4000

3413

2485

1038

2353

2543

2023

1263

458

166

302

983

1194

2503

3269

3680

3453

3327

2683

2045

1338

234

577

601

545

527

575

202

Cs

Ba

La

Hf

Ta

Re

Os

Ir

Pt

Au

Hg

Tl

Pb

Bi

Po

At

Rn

952

2023

3730

5470

5698

5930

5900

5300

4403

4100

3080

630

1730

2013

1833

1235

610

211

300

973

1320

Fr

Ra

Ac

950

1413

3470

Chemistry data booklet


8

7. First ionization energy, electron affinity and electronegativity of the elements


1310

72

First ionization
energy
(kJ mol 1)

H
2.1
519

52 900

Li

He
799 29

Element
Be

1.0
494

2370

Electron affinity
(kJ mol 1)

1.5

2.5

3.0

786 180

1060 70

Si

Al

1.2
590

2.0
577 47

Mg

0.9
418

1400 3

Electronegativity

71 736

Na

1090 120

1.5
632

661

648

653

716

762

757

736

745

908

577

1.8
762

1310 142 1680 348 2080


(O +844)

3.5

4.0

Cl

1140 342 1350

Ca

Sc

Ti

Cr

Mn

Fe

Co

Ni

Cu

Zn

Ga

Ge

As

Se

Br

1.0

1.3

1.5

1.6

1.6

1.5

1.8

1.8

1.8

1.9

1.6

1.6

1.8

2.0

2.4

2.8

548

636

669

653

694

699

724

745

803

732

866

556

707

833

870

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Sr

Zr

Nb

Mo

Tc

Ru

Rh

Pd

Ag

Cd

In

Sn

Sb

Te

0.8

1.0

1.2

1.4

1.6

1.8

1.9

2.2

2.2

2.2

1.9

1.7

1.7

1.8

1.9

2.1

2.5

540

502

Cs

Ba

0.7
381

0.9
510

531

760

770

762

841

887

866

891

1010

590

716

703

812

920

Hf

Ta

Re

Os

Ir

Pt

Au

Hg

Tl

Pb

Bi

Po

At

1.1

1.3

1.5

1.7

1.9

2.2

2.2

2.2

2.4

1.9

1.8

1.8

1.9

2.0

2.2

Fr

Ra

Ac

0.7

0.9

1.1

Xe
1040

La
669

Kr

1010 314 1170

Rb
376

Ar

3.0

2.5
941

0.8
402

Ne

1000 200 1260 364 1520


(S +532)

2.1
966

Rn

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Chemistry data booklet

8. Atomic and ionic radii of the elements


Atomic
radius
(1012 m)

30

H
154 (1)
152

Element
112

Li

Be

68 (1+)

30 (2+)

186

He

88

Ionic
radius
(1012 m)

16 (3+)

160

143

Na

Mg

Al

98 (1+)

65 (2+)

45 (3+)

231

K
133 (1+)
244

Rb
148 (1+)
262

Cs
167 (1+)
270

Fr

197

160

146

131

125

129

126

125

124

128

133

141

77

C
260 (4)
117

Si
42 (4+)
271 (4)
122

Ca

Sc

Ti

Cr

Mn

Fe

Co

Ni

Cu

Zn

Ga

Ge

94 (2+)

81 (3+)

90 (2+)
68 (4+)

88 (2+)
59 (5+)

63 (3+)

80 (2+)
60 (4+)

76 (2+)
64 (3+)

74 (2+)
63 (3+)

72 (2+)

96 (1+)
69 (2+)

74 (2+)

62 (3+)

53 (4+)
272 (4)

215

Sr
110 (2+)
217

Ba
34 (2+)
220

Ra

180

Y
93 (3+)
188

La
115 (3+)
200

Ac

157

Zr
80 (4+)

141

Nb
70 (5+)

157

Hf
81 (4+)

135

Tc

68 (4+)
143

Ta
73 (5+)

136

Mo
137

W
68 (4+)

137

Re

133

134

Ru

Rh

65 (4+)

86 (2+)

134

135

Os

Ir

67 (4+)

66 (4+)

138

Pd

144

Ag
126 (1+)

138

Pt

144

Au
137 (1+)
85 (3+)

149

166

Cd

In

97 (2+)

81 (3+)

152

Hg
127 (1+)
110 (2+)

171

Tl
95 (3+)

162

Sn
112 (2+)
71 (4+)
175

Pb
120 (2+)
84 (4+)

70

N
171 (3)
110

P
212 (3)
121

As
222 (3)
141

Sb
245 (3)
170

Bi
120 (3+)

66

O
146 (2)

58

F
133 (1)

104

S
190 (2)
117

Se
202 (2)
137

Te
222 (2)
140

Po

Ne
99

Cl

Ar

181 (1)
114

Br

Kr

196 (1)
133

Xe

219 (1)
140

At

Rn

Chemistry data booklet

9. Covalent bond lengths


Bond

Bond length (nm)

Bond

Bond length (nm)

HH

0.074

CH

0.109

CC

0.154

SiH

0.146

C=C

0.134

NH

0.101

CC

0.120

PH

0.142

CC (in benzene)

0.139

OH

0.096

SiSi

0.235

SH

0.135

NN

0.146

FH

0.092

N=N

0.120

ClH

0.128

NN

0.110

BrH

0.141

PP (P4)

0.221

IH

0.160

OO

0.148

CO

0.143

O=O

0.121

C=O

0.122

SS (S8)

0.207

CO (in phenol)

0.136

S=S

0.188

CN

0.147

FF

0.142

C=N

0.127

ClCl

0.199

CN

0.116

BrBr

0.228

CN (in phenylamine)

0.135

II

0.267

CF

0.138

CCl

0.177

CCl (in chlorobenzene)

0.169

CBr

0.193

CI

0.214

SiO

0.150

10

International Baccalaureate Organization 2007

Chemistry data booklet

10. Average bond enthalpies at 298 K


Bond

H (kJ mol1)

Bond

H (kJ mol1)

HH

436

CH

412

DD

442

SiH

318

CC

348

NH

388

C=C

612

PH

322

CC

837

OH

463

CC (benzene)

518

SH

338

SiSi

226

FH

562

GeGe

188

ClH

431

SnSn

151

BrH

366

NN

163

IH

299

N=N

409

CO

360

NN

944

C=O

743

PP

172

CN

305

OO

146

C=N

613

O=O

496

CN

890

SS

264

CF

484

FF

158

CCl

338

ClCl

242

CBr

276

BrBr

193

CI

238

II

151

SiO

374

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11

Chemistry data booklet

11. Organic compoundsthermodynamic data


H f

G f

(kJ mol1)

(kJ mol1)

(J K1 mol1)

Substance

Formula

methane

CH4

75

51

186

ethane

C2H6

85

33

230

propane

C3H8

104

24

270

butane

C4H10

125

16

310

pentane

C5H12

173

261

hexane

C6H14

199

296

ethene

C2H4

52

68

219

propene

C3H6

20

63

267

but-1-ene

C4H8

72

307

cis-but-2-ene

C4H8

67

301

trans-but-2-ene

C4H8

10

64

296

ethyne

C2H2

227

209

201

propyne

C3H4

185

194

248

buta-1,3-diene

C4H6

112

152

279

cyclohexane

C6H12

156

27

204

benzene

C6H6

83

130

269

benzene

C6H6

49

125

173

methylbenzene

C6H5CH3

12

111

320

ethylbenzene

C6H5CH2CH3

13

120

255

phenylethene

C6H5CHCH2

104

202

345

chloromethane

CH3Cl

82

59

234

dichloromethane

CH2Cl2

117

63

179

trichloromethane

CHCl3

132

72

203

bromomethane

CH3Br

36

26

246

tribromomethane

CHBr3

20

222

iodomethane

CH3I

20

163

triiodomethane

CHI3

141

chloroethane

C2H5Cl

105

53

276

bromoethane

C2H5Br

85

12

State

International Baccalaureate Organization 2007

Organic compoundsthermodynamic data

H f

G f

(kJ mol1)

(kJ mol1)

(J K1 mol1)

31

52

264

166

80

208

C6H5Cl

11

94

314

methanol

CH3OH

201

162

238

methanol

CH3OH

239

166

127

ethanol

C2H5OH

235

169

282

ethanol

C2H5OH

278

175

161

phenol

C6H5OH

163

51

146

methanal

HCHO

116

110

219

ethanal

CH3CHO

166

134

266

propanone

(CH3)2CO

216

152

295

methanoic acid

HCOOH

409

346

129

ethanoic acid

CH3COOH

487

392

160

benzoic acid

C6H5COOH

385

245

167

ethyl ethanoate

CH3COOC2H5

481

ethanamide

CH3CONH2

320

methylamine

CH3NH2

28

28

242

ethylamine

C2H5NH2

49

37

285

urea

CO(NH2)2

333

47

105

Substance

Formula

iodoethane

C2H5I

31

chloroethene

C2H3Cl

1,2-dichloroethane

CH2ClCH2Cl

chlorobenzene

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State

13

Chemistry data booklet


14

12. Enthalpies of combustion


The values of the molar enthalpy of combustion (H c ) in the following table refer to a temperature of 298 K and a pressure of 1.01 105 Pa (1 atm).
State

H c (kJ mol1)

H2

sulfur

carbon (graphite)

Substance

Formula

hydrogen

H c

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Substance

Formula

State

286

propan-1-ol

C3H7OH

2010

297

butan-1-ol

C4H9OH

2673

394

phenylmethanol

C6H5CH2OH

4056

carbon (diamond)

395

cyclohexanol

C6H11OH

3727

carbon monoxide

CO

283

phenol

C6H5OH

3064

methane

CH4

890

ethoxyethane

(C2H5)2O

2727

ethane

C2H6

1560

methanal

HCHO

561

propane

C3H8

2220

ethanal

CH3CHO

1167

butane

C4H10

2877

benzaldehyde

C6H5CHO

3520

pentane

C5H12

3509

propanone

(CH3)2CO

1786

hexane

C6H14

4194

pentan-3-one

(C2H5)2CO

3078

octane

C8H18

5512

phenylethanone

CH3COC6H5

4138

cyclohexane

C6H12

3924

diphenylmethanone

(C6H5)2CO

6512

ethene

C2H4

1409

methanoic acid

HCOOH

263

buta-1,3-diene

C4H6

2542

ethanoic acid

CH3COOH

876

ethyne

C2H2

1299

benzoic acid

C6H5COOH

3227

benzene

C6H6

3267

ethanedioic acid

(COOH)2

246

methylbenzene

C6H5CH3

3909

ethyl ethanoate

CH3COOC2H5

2246

(kJ mol1)

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State

H c (kJ mol1)

C10H8

anthracene

C14H10

chloroethane

Substance

Formula

naphthalene

State

H c

Substance

Formula

5157

ethanamide

CH3CONH2

1182

7114

benzamide

C6H5CONH2

3546

C2H5Cl

1413

methylamine

CH3NH2

1072

bromoethane

C2H5Br

1425

ethylamine

C2H5NH2

1709

iodoethane

C2H5I

1466

phenylamine

C6H5NH2

3397

(chloromethyl)benzene

C6H5CH2Cl

3709

nitrobenzene

C6H5NO2

3094

trichloromethane

CHCl3

373

urea

CO(NH2)2

634

methanol

CH3OH

715

glucose

C6H12O6

2816

ethanol

C2H5OH

1371

sucrose

C12H22O11

5644

(kJ mol1)

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Chemistry data booklet

13. Lattice enthalpies at 298 K (experimental and theoretical


values)

The lattice enthalpy values (H lattice


) given relate to the endothermic process

MX(s) M+(g) + X(g)


in which the gaseous ions of a crystal are separated to an infinite distance from each other.

Experimental values
The data in these two tables are experimental values obtained by means of a suitable
BornHaber cycle.

H lattice

Alkali metal halides

(kJ mol1)

Cl

Br

Li

1022

846

800

744

Na

902

771

733

684

801

701

670

629

Rb

767

675

647

609

Cs

716

645

619

585

Other substances

H lattice

(kJ mol1)

Other substances

H lattice

(kJ mol1)

CaF2

2602

MgS

3238

BeCl2

3006

CaS

2966

MgCl2

2493

SrS

2779

CaCl2

2237

BaS

2643

SrCl2

2112

CuCl

976

BaCl2

2018

AgF

955

MgO

3889

AgCl

905

CaO

3513

AgBr

890

SrO

3310

AgI

876

BaO

3152

NH4Cl

640

16

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Lattice enthalpies at 298 K (experimental and theoretical values)

Theoretical values
These two tables contain lattice enthalpies calculated from electrostatic principles on the
basis of a purely ionic model for the crystal.

H lattice

Alkali metal halides

(kJ mol1)

Cl

Br

Li

1004

833

787

728

Na

891

766

732

686

795

690

665

632

Rb

761

674

644

607

Cs

728

636

611

582

Other substances

H lattice

(kJ mol1)

Other substances

H lattice

(kJ mol1)

CaF2

2611

AgF

870

MgO

3929

AgCl

770

CaO

3477

AgBr

758

SrO

3205

AgI

736

BaO

3042

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Chemistry data booklet

14. Standard electrode potentials


Reduced species

E (V)

Li+(aq) + e

Li(s)

3.03

K+(aq) + e

K(s)

2.92

Ca2+(aq) + 2e

Ca(s)

2.87

Na+(aq) + e

Na(s)

2.71

Mg2+(aq) + 2e

Mg(s)

2.36

Al3+(aq) + 3e

Al(s)

1.66

Mn2+(aq) + 2e

Mn(s)

1.18

H2(g) + OH(aq)

0.83

Zn2+(aq) + 2e

Zn(s)

0.76

Fe2+(aq) + 2e

Fe(s)

0.44

Ni2+(aq) + 2e

Ni(s)

0.23

Sn2+(aq) + 2e

Sn(s)

0.14

Pb2+(aq) + 2e

Pb(s)

0.13

Oxidized species

H2O(l) + e

H+(aq) + e

H2(g)

0.00

Cu2+(aq) + e

Cu+(aq)

+0.15

H2SO3(aq) + H2O(l)

+0.17

Cu(s)

+0.34

2OH(aq)

+0.40

Cu(s)

+0.52

SO42(aq) + 4H+(aq) + 2e
Cu2+(aq) + 2e
O2(g) + H2O(l) + 2e
Cu+(aq) + e

18

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Standard electrode potentials

Reduced species

E (V)

I(aq)

+0.54

Fe3+(aq) + e

Fe2+(aq)

+0.77

Ag+(aq) + e

Ag(s)

+0.80

Br2(l) + e

Br(aq)

+1.09

O2(g) + 2H+(aq) + 2e

H2O(l)

+1.23

2Cr3+(aq) + 7H2O(l)

+1.33

Cl(aq)

+1.36

Mn2+(aq) + 4H2O(l)

+1.51

F(aq)

+2.87

Oxidized species

I2(s) + e

Cr2O72(aq) + 14H+(aq) + 6e
Cl2(g) + e
MnO4(aq) + 8H+(aq) + 5e
F2(g) + e

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Chemistry data booklet

15. Strengths of organic acids and bases


The acid strengths in the following tables are given in terms of pKa values, where
pKa = log10 Ka.
The dissociation constant, Ka, values are for aqueous solutions at 298 K. Base strengths are
given in terms of pKb values.

Carboxylic acids
Name

Formula

pKa

methanoic

HCOOH

3.75

ethanoic

CH3COOH

4.76

propanoic

CH3CH2COOH

4.87

butanoic

CH3(CH2)2COOH

4.82

2-methylpropanoic

(CH3)2CHCOOH

4.85

pentanoic

CH3(CH2)3COOH

4.86

2,2-dimethylpropanoic

(CH3)3CCOOH

5.05

benzoic

C6H5COOH

4.20

phenylethanoic

C6H5CH2COOH

4.31

Halogenated carboxylic acids


Name

Formula

pKa

chloroethanoic

CH2ClCOOH

2.86

dichloroethanoic

CHCl2COOH

1.29

trichloroethanoic

CCl3COOH

0.65

fluoroethanoic

CH2FCOOH

2.66

bromoethanoic

CH2BrCOOH

2.90

iodoethanoic

CH2ICOOH

3.17

20

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Strengths of organic acids and bases

Phenols
Name

Formula

pKa

phenol

C6H5OH

10.00

2-nitrophenol

O2NC6H4OH

7.21

3-nitrophenol

O2NC6H4OH

8.35

4-nitrophenol

O2NC6H4OH

7.15

2,4-dinitrophenol

(O2N)2C6H3OH

4.01

2,4,6-trinitrophenol

(O2N)3C6H2OH

0.42

Name

Formula

pKa

methanol

CH3OH

15.5

ethanol

C2H5OH

16.0

Name

Formula

pKb

ammonia

NH3

4.75

methylamine

CH3NH2

3.36

ethylamine

CH3CH2NH2

3.27

dimethylamine

(CH3)2NH

3.28

trimethylamine

(CH3)3N

4.20

diethylamine

(C2H5)2NH

3.07

triethylamine

(C2H5)3N

3.36

phenylamine

C6H5NH2

9.38

Alcohols

Amines

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Chemistry data booklet

16. Acidbase indicators


Colour change
Indicator

pKa

pH range

Acid

Alkali

methyl orange

3.7

3.14.4

red

yellow

bromophenol blue

4.0

3.04.6

yellow

blue

bromocresol green

4.7

3.85.4

yellow

blue

methyl red

5.1

4.26.3

red

yellow

bromothymol blue

7.0

6.07.6

yellow

blue

phenol red

7.9

6.88.4

yellow

red

phenolphthalein

9.3

8.310.0

colourless

red

22

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Chemistry data booklet

17. Infrared data


Characteristic ranges for infrared absorption due to stretching vibrations in organic
molecules.
Bond

Organic molecules

Wavenumber (cm1)

CI

iodoalkanes

490620

CBr

bromoalkanes

500600

CCl

chloroalkanes

600800

CF

fluoroalkanes

10001400

CO

alcohols, esters, ethers

10501410

C=C

alkenes

16101680

C=O

aldehydes, ketones, acids, esters

17001750

CC

alkynes

21002260

OH

hydrogen bonded in acids

25003300

CH

alkanes, alkenes, arenes

28503100

OH

hydrogen bonded in alcohols, phenols

32003600

NH

primary amines

33003500

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Chemistry data booklet

18. 1H NMR data


Typical proton chemical shift values () relative to tetramethylsilane (TMS) = 0.

R represents an alkyl group, and Hal represents F, Cl, Br, or I.


These values may vary in different solvents and conditions.
Type of proton

R
R

Chemical shift (ppm)

0.91.0

CH3
R

CH2

1.31.4
1.41.6

R3CH

2.02.5

H 3C
C

2.22.7

CH3

2.53.5

1.83.1

Hal

3.54.4

CH2

CH3

O
R

3.84.1
O

CH2R

O
R

24

9.013.0

3.33.7

4.012.0

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Type of proton

RHC

CH2

H NMR data

Chemical shift (ppm)

4.56.0

OH

4.012.0

6.99.0

O
R

9.410.0

C
H

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25

Chemistry data booklet

19. 2-Amino acids


Common name

alanine

Symbol

Ala

pH of isoelectric
point

Structural formula
H2N

CH

COOH

6.0
CH3

H2N

arginine

Arg

CH

COOH

CH2

CH2

NH

CH2

NH2

10.8

NH

H2N

asparagine

Asn

CH
CH2

COOH
C

5.4

NH2

aspartic acid

Asp

H2N

CH

2.8
CH2

cysteine

Cys

H2N

H2N

glutamine

Gln

COOH
COOH

CH

COOH

CH2

SH

CH

COOH

CH2

CH2

5.1

NH2

5.7

glutamic acid

glycine

26

Glu

Gly

H2N

H2N

CH

COOH

CH2

CH2

CH2

COOH

3.2
COOH

6.0

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2-Amino acids

Common name

Symbol

pH of isoelectric
point

Structural formula
H2N

CH

COOH
H

histidine

CH2

His

7.6

isoleucine

Ile

H 2N
CH3

H2N

leucine

Leu

H2N

Lys

H2N

methionine

Met

H2N

phenylalanine

proline

serine

Phe

Pro

Ser

CH

CH2

CH

COOH

6.0
CH3

6.0

CH

CH3

CH

COOH

CH2

CH2

CH

COOH

CH2

CH2

CH

H
N

H2N

9.7
CH2

CH2

NH2

5.7
S

CH3

COOH

5.5

CH2

H2N

threonine

COOH

CH2
CH3

lysine

CH

COOH

6.3

CH

COOH

CH2

OH

5.7

CH

COOH

CH

OH

Thr

5.6
CH3

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2-Amino acids

Common name

Symbol

H2N

tryptophan

pH of isoelectric
point

Structural formula
CH

COOH

CH2

Trp

5.9
N
H

H2N

tyrosine

Tyr

OH

CH

COOH

CH

CH3

Val

5.7

6.0
CH3

28

COOH

CH2

H2N

valine

CH

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Chemistry data booklet

20. Structural formulas of some important medicines and


drugs
CH3

OH

CH2

OH
O

CH3

CH3

CH3

NHCOCH 3

COOH

aspirin

paracetamol
(acetaminophen)

ibuprofen

CH2

CH3

OH
CH2

CH2

CH3

CH2

OH
CH2

CH2

CH3

OCCH3

O
OCCH3

OCH3

OH

morphine

codeine

heroin

O
H3C

OH

CH2

CH

NH2

HO

CH

CH2

NH

CH3

CH3
HO

CH3

CH3

amphetamine

epinephrine (adrenaline)

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caffeine

29

Structural formulas of some important medicines and drugs

CH3

O
R

NH

CH3
CH3

Cl

CH3

OH

nicotine

diazepam (Valium)

penicillin

CH3

O
N

HN
N

O2N

H2 N
HO

nitrazepam (Mogadon)

N
H

N
CH2
CH2

CH2
O

acyclovir

indole

CH3
O
O

N
CH3

CH3

cocaine

30

H3 C
H3 C

CH2
NH

N
CH2
O

lysergic acid diethylamide (LSD)

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Structural formulas of some important medicines and drugs

O
NH2

CH2CH3
O

CH2CH2

F 3C

CH2CH3

CH 2

CH 2

NH 2 + Cl CH 2

fluoxetine hydrochloride (Prozac)

procaine

CH3

CH3
OH

NH

H3C
O

H3C

CH2

CH2

CH2

CH2

CH3

CH2
N

H 2C

CH2

CH3

CH3

CH3

tetrahydrocannabinol (THC)

lidocaine

H
O
O

CH 3O

CH 2

CH 2

NH 2

CH 3

O
CH 2

Pt

N+
CH 2

NH3

Cl

CH 3

CH 3O

OCH 3

Cl

NH3

N
H

psilocybine

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mescaline

cisplatin

31

Chemistry data booklet

21. Structural formulas of some important biological


molecules

HO

OH

CH2OH

CH2OH

CH2OH

H
4
OH
3

OH

HO OH

OH

OH

HOCH2

H
3

OH

lactose

O H CH2OH
4

OH

sucrose

O
C
HO

HO

HO

CH2OH

retinol (vitamin A)

H3C

CH2

CH
CH3

ascorbic acid (vitamin C)

CH3

CH2
CH2

H3 C

CH

CH2

CH
CH3

CH3

CH3

CH2
CH2

CH
CH3

CH3

CH2
HO

HO

cholesterol

32

vitamin D

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Structural formulas of some important biological molecules

CH3

CH3

OH

CH3

CH3

OH

CH3
H3C

HO

estradiol

progesterone

OH
HO

testosterone

CH

CH2

NH

CH3

HO

HO

thyroxine

NH2

HN

CH
HC

NH2

C
C
N

H2N C

N
H

adenine

CH
C
N

O
C

HN

CH

CH
N
H

cytosine

CH

N
H

guanine

HN

COOH

NH2

epinephrine (adrenaline)

CH

CH2

CH
N
H

uracil

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CH3

CH
N
H

thymine

33

Structural formulas of some important biological molecules

CH2

CH

CH2
CH2

HO

CH2

CH2

CH3

CH3

CH3

CH2
CH2

CH

CH

CH3

CH3

H3C

CH

CH2

N
Fe
N
O

CH3

HOOC

CH2

CH2

CH2

CH2

COOH

the heme group from cytochrome oxidase

NH2
N

P
O

O
O

P
O

CH2
O

OH OH

adenosine triphosphate (ATP)

34

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Chemistry data booklet

22. Structural formulas of some important food chemistry


molecules

Some anthocyanins

quinoidal base (blue)

flavylium cation (red)

chalcone (colourless)

carbinol pseudo-base (colourless)

NH

Fe
N

myoglobin

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HN

porphyrin

35

Structural formulas of some important food chemistry molecules

chlorophyll

Some preservatives
OH

OH
C(CH3)3

C(CH3)3
O
CH3

2-tert-butyl-4hydroxyanisole (2-BHA)

36

O
CH3

3-tert-butyl-4hydroxyanisole (3-BHA)

3,5-di-tert-butyl-4hydroxytoluene (BHT)

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Structural formulas of some important food chemistry molecules

OH

OH
HO

HO

OH

OH
C

C3H7

COOC3H7

tert-butylhydroquinone
(TBHQ)

2,4,5trihydroxybutyrophenone
(THBP)

propyl gallate (PG)

Some of the carotenes

alpha-carotene

beta-carotene

HO

lutein

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37

Structural formulas of some important food chemistry molecules

HO
O

astaxanthin

Some fatty acids


Fatty acid

Formula

Octanoic acid

CH3(CH2)6COOH

Lauric acid

CH3(CH2)10COOH

Stearic acid

CH3(CH2)14COOH

Palmitic acid

CH3(CH2)14COOH

Oleic acid

CH3(CH2)7CHCH(CH2)7COOH

Linoleic acid

CH3(CH2)4(CHCHCH2)2(CH2)6COOH

Linolenic acid

CH3CH2(CHCHCH2)3(CH2)6COOH

38

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