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nINTERNATIONAL BACCALAUREATE ORGANIZATION

CHEMISTRY DATA BOOKLET

March 2003

To be used in the teaching and examination ofDiploma Programme chemistry

Valid for examination sessions from May 2003

Chemistry Data BookletFirst published August 2001

Reprinted with minor corrections March 2003

© International Baccalaureate Organization 2001

Organisation du Baccalauréat InternationalRoute des Morillons 15

Grand-Saconnex, GenèveCH-1218

SWITZERLAND

Notes

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

Contents

1. Some Relevant Equations 2

2. Physical Constants 2

3. Fundamental Particles 2

4. Names of the First 103 Elements 3

5. The Periodic Table 4

6. Melting Points and Boiling Points of the Elements 5

7. First Ionization Energy, Electron Affinity and Electronegativity of the Elements 6

8. Atomic and Ionic Radii of the Elements 7

9. Covalent Bond Lengths 8

10. Average Bond Enthalpies at 298 K 8

11. Organic Compounds—Thermodynamic Data 9

12. Ellingham Diagram 10

13. Enthalpies of Combustion 11

14. Lattice Enthalpies at 298 K (Experimental and Theoretical Values) 12

15. Standard Electrode Potentials 13

16. Strengths of Organic Acids and Bases 14

17. Acid–base Indicators 15

18. Infrared Data 16

19. 1H NMR Data 17

20. 2-amino Acids 18

21. Structural Formulas of Some Important Medicines and Drugs 20

22. Structural Formulas of Some Important Biological Molecules 22

1. Some Relevant Equations

or[ ] [ ] kto

A A e−=[ ][ ]

oln =A

ktA

aERTk Ae−

= ln lnaEk ART

= − +

IlogI

o lc10 = ∈12

0.693tk

=

PV PVT T1 1 2 2

1 2

=G H T S∆ = ∆ − ∆0 0 0

E mc2=E hf=

2. Physical Constants

Avogadro’s constant (L) = 6.02 × 1023 mol-1

Gas constant (R) = 8.31 J K-1 mol-1

Molar volume of an ideal gas at 273 K, 1.01 × 105 Pa = 2.24 × 10-2 m3 mol-1 (22.4 dm3 mol-1)Speed of light in a vacuum (c) = 3.00 × 108 m s-1

Planck constant (h) = 6.63 × 10-34 J sSpecific heat capacity of water = 4.18 kJ kg-1 K-1 ( = 4.18 J g-1 K-1)Ionic product constant for water (Kw) = 1.00 × 10-14 mol2 dm-6 at 298 K(1 atm = 1.01 × 105 Pa)(1 dm3 = 1 litre = 1 × 10-3 m3 = 1 × 103 cm3)

3. Fundamental Particles

9.109534 × 10-31

1.602189 × 10-19

1.674954 × 10-27

0

1.672648 × 10-27

1.602189 × 10-19

Mass/kg

Charge/C

ElectronNeutronProton

2 IB Diploma Programme: Chemistry Data Booklet, March 2003

4. Names of the First 103 Elements

804260109328417

102768

46157894841959619188867545374462213414471138167343526581906950227492235470393040

HgMoNdNeNpNiNbN

NoOsOPdPPtPuPoKPrPmPaRaRnReRhRbRuSmScSeSiAgNaSrS

TaTcTeTbTlThTmSnTiWUVXeYbYZnZr

mercurymolybdenumneodymiumneonneptuniumnickelniobiumnitrogennobeliumosmiumoxygenpalladiumphosphorusplatinumplutoniumpoloniumpotassiumpraseodymiumpromethiumprotactiniumradiumradonrheniumrhodiumrubidiumrutheniumsamariumscandiumseleniumsiliconsilversodiumstrontiumsulfurtantalumtechnetiumtelluriumterbiumthalliumthoriumthuliumtintitaniumtungstenuraniumvanadiumxenonytterbiumyttriumzinczirconium

8913955118338556974

835

35485520986

58172427299666996863

1009

8764313279722

671

495377263657

103823

711225

101

AcAlAmSbArAsAtBaBkBeBiBBrCdCsCaCfCCeClCrCoCuCmDyEsErEuFmFFrGdGaGeAuHfHeHoHInIIrFeKrLaLrPbLiLuMgMnMd

actiniumaluminiumamericiumantimonyargonarsenicastatinebariumberkeliumberylliumbismuthboronbrominecadmiumcaesiumcalciumcaliforniumcarbonceriumchlorinechromiumcobaltcoppercuriumdysprosiumeinsteiniumerbiumeuropiumfermiumfluorinefranciumgadoliniumgalliumgermaniumgoldhafniumheliumholmiumhydrogenindiumiodineiridiumironkryptonlanthanumlawrenciumleadlithiumlutetiummagnesiummanganesemendelevium

AtomicNumber

SymbolElementAtomicNumber

SymbolElement

IB Diploma Programme: Chemistry Data Booklet, March 2003 3

1

2

3

4

5

6

7

0

5. T

he P

erio

dic

Tab

le

103

Lr

(260

)

102

No

(259

)

101

Md

(258

)

100

Fm (257

)

99 Es

(254

)

98 Cf

(251

)

97 Bk

(247

)

96 Cm

(247

)

95 Am

(243

)

94 Pu (244

)

93 Np

(237

)

92 U23

8.03

91 Pa23

1.04

90 Th

232.

04

‡

71 Lu

174.

97

70 Yb

173.

04

69 Tm

168.

93

68 Er

167.

26

67 Ho

164.

93

66 Dy

162.

50

65 Tb

158.

92

64 Gd

157.

25

63 Eu

151.

96

62 Sm 150.

35

61 Pm 146.

92

60 Nd

144.

24

59 Pr14

0.91

58 Ce

140.

12

†

8

9 ‡

Ac

(227

)

88 Ra

(226

)

87 Fr (223

)

86 Rn

(222

)

85 At

(210

)

84 Po (210

)

83 Bi

208.

98

82 Pb20

7.19

81 Tl

204.

37

80 Hg

200.

59

79 Au

196.

97

78 Pt19

5.09

77 Ir19

2.22

76 Os

190.

21

75 Re

186.

21

74 W18

3.85

73 Ta

180.

95

72 Hf

178.

49

57

†L

a13

8.91

56 Ba

137.

34

55 Cs

132.

91

54 Xe

131.

30

53 I12

6.90

52 Te

127.

60

51 Sb12

1.75

50 Sn11

8.69

49 In11

4.82

48 Cd

112.

40

47 Ag

107.

87

46 Pd10

6.42

45 Rh

102.

91

44 Ru

101.

07

43 Tc

98.9

1

42 Mo

95.9

4

41 Nb

92.9

1

40 Zr

91.2

2

39 Y88

.91

38 Sr 87.6

2

37 Rb

85.4

7

36 Kr

83.8

0

35 Br

79.9

0

34 Se 78.9

6

33 As

74.9

2

32 Ge

72.5

9

31 Ga

69.7

2

30 Zn

65.3

7

29 Cu

63.5

5

28 Ni

58.7

1

27 Co

58.9

3

26 Fe 55.8

5

25 Mn

54.9

4

24 Cr

52.0

0

23 V50

.94

22 Ti

47.9

0

21 Sc 44.9

6

20 Ca

40.0

8

19 K39

.10

18 Ar

39.9

5

17 Cl

35.4

5

16 S32

.06

15 P30

.97

14 Si 28.0

9

13 Al

26.9

8

12 Mg

24.3

1

11 Na

22.9

9

10 Ne

20.1

8

9 F19

.00

8 O16

.00

7 N14

.01

6 C12

.01

5 B10

.81

4 Be

9.01

3 Li

6.94

2 He

4.00

Ato

mic

Num

ber

Ele

men

t

Ato

mic

Mas

s

1 H 1.01

IB D

iplo

ma

Prog

ram

me

Che

mis

try

Dat

a Bo

okle

t, A

ugus

t 200

14


6. M

eltin

g Po

ints

and

Boi

ling

Poin

ts o

f the

Ele

men

ts

132

0

Ac

3470

97

3

Ra

1413

300

Fr 95

0

202

R

n

211

575

At

610

527 Po 1235

545 Bi

1833

601

Pb 2013

577 Tl

1730

234

Hg

630

1338 Au

3080

204

5

Pt

410

0

2683

Ir 4403

3327

Os

5300

3453 Re

5900

3680

W 5930

326

9 Ta

5698

2503

Hf

5470

119

4 La

3730

98

3

Ba

2023

302

C

s

952

161

Xe

166

387

I 458

723 Te

1263

904

Sb 2023

505 Sn 2543

429

In 2353

594

Cd

1038

1235 Ag

2485

182

5

P

d

341

3

223

9

Rh

4000

25

83

Ru

4173

2445 Tc

5150

289

0

Mo

4885

274

1

N

b

5015

212

5

Zr

4650

1780 Y 3611

104

2

Sr 1657

31

2

Rb

961

117 Kr

121

266

Br

332

490 Se 958

889

As

1211 Ge

3103

303

Ga

2676

693 Zn

1180

1357

Cu

2840

1726 Ni

3005

1768

Co

3143

1808

Fe 3023

1

517

Mn

2235

2

130

Cr

2755

1

973

V 3650

1

933

Ti

3560

1

814

Sc 3104

1112

Ca

1757

33

7

K 1047

84

Ar

87

172

Cl

239

392

S 718

317

P 553

16

83

Si 2628

936

Al

2740

9

22

M

g

1363

371

Na

115

6

25

Ne

27

54

F 85

55

O 90

6

3

N 77

4

100

C

5100

2

573

B 3931

1

551

B

e

3243

454

Li

1600

1

He 4

M.p

t/K

Ele

men

t

B.p

t/K

1

4

H 20

Dip

lom

a Pr

ogra

mm

e: C

hem

istr

y D

ata

Book

let,

Mar

ch 2

003


7. F

irst

Ioni

zatio

n E

nerg

y, E

lect

ron

Aff

inity

and

Ele

ctro

nega

tivity

of t

he E

lem

ents

669

Ac

1.1

510

Ra

0.9

381

Fr 0.7

104

0

Rn

920

At

2.2

812

Po 2.0

703

Bi

1.9

716

Pb 1.8

590

Tl

1.8

101

0

Hg

1.9

891

Au

2.4

866

Pt 2.2

887

Ir 2.2

841

Os

2.2

762

R

e 1.9

770

W 1.

7

760

T

a1.

5

531

Hf

1.3

540

La

1.1

502

Ba

0.9

376

Cs

0.7

117

0

Xe

1010

-31

4

I 2.5

870

Te

2.1

833

Sb 1.9

707

Sn 1.8

556

In 1.7

866

Cd

1.7

732

Ag

1.9

803

Pd

2.2

745

Rh

2.2

724

Ru

2.2

699

Tc

1.9

694

M

o1.

8

653

Nb

1.6

669

Zr

1.4

636

Y 1.2

548

Sr 1.0

402

Rb

0.8

135

0

Kr

1140

-34

2

Br

2.8

941

Se 2.4

966

As

2.0

762

Ge

1.8

577

Ga

1.6

908

Zn

1.6

745

Cu

1.9

736

Ni

1.8

757

Co

1.8

762

Fe 1.8

716

Mn

1.5

653

Cr

1.6

648

V 1.6

661

Ti

1.5

632

Sc 1.3

590

Ca

1.0

418

K 0.8

152

0

Ar

1260

-36

4

Cl

3.0

1000

-200

(S- +

532)

S 2.5

1060

-70

P 2.1

786

-180

Si 1.8

577

-4

7

Al

1.5

736

Mg

1.2

494

-7

1

Na

0.9

208

0

Ne

1680

-34

8

F 4.0

1310

-142

(O- +

844)

O 3.5

1400

-3

N 3.0

1090

-120

C 2.5

799

-2

9

B 2.0

Ele

men

t

Elec

trone

gativ

ity

900

Be

1.5

519

-5

2

Li

1.0

237

0

He

Elec

tron

affin

ity /

kJ m

ol -1

Firs

t ion

izat

ion

ene

rgy

/ kJ m

ol -1

1310

-72

H 2.1

IB D

iplo

ma

Prog

ram

me

Che

mis

try

Dat

a Bo

okle

t, A

ugus

t 200

16


8. A

tom

ic a

nd Io

nic

Rad

ii of

the

Ele

men

ts

200

Ac

220

Ra

270

Fr

Rn

140

At

140

Po

170

Bi

120

(3+)

175

Pb12

0 (2

+)

84 (4

+)

171

Tl

95 (3

+)

152

Hg

127

(1+)

110

(2+)

144

Au

137

(1+)

85

(3+)

138

Pt

135

Ir

66 (4

+)

134

Os

67 (4

+)

137

Re

137

W

68 (4

+)

143

Ta

73 (5

+)

157

Hf

81 (4

+)

188

La

115

(3+)

217

Ba

34 (2

+)

262

Cs

167

(1+)

Xe

133

I

219

(1-)

137

Te

222

(2-)

141

Sb

245

(3-)

162

Sn11

2 (2

+)71

(4+)

166

In

81 (3

+)

149

Cd

97 (2

+)

144

Ag

126

(1+)

138

Pd

134

Rh

86 (2

+)

133

Ru

65 (4

+)

135

Tc

136

Mo

68 (4

+)

141

Nb

70 (5

+)

157

Zr

80

(4+)

180

Y

93

(3+)

215

Sr

110

(2+)

244

Rb

148

(1+)

Kr

114

Br

196

(1-)

117

Se

202

(2-)

121

As

222

(3-)

122

Ge

53 (4

+)27

2 (4

-)

141

Ga

62

(3+)

133

Zn

74 (2

+)

128

Cu

96

(1+)

69

(2+)

124

Ni

72

(2+)

125

Co

74 (2

+)

63 (3

+)

126

Fe76

(2+)

6

4 (3

+)

129

Mn

80 (2

+)

60 (4

+)

125

Cr

63

(3+)

131

V 8

8 (2

+)

59

(5+)

146

Ti

90 (2

+)68

(4+)

160

Sc

81

(3+)

197

Ca

94

(2+)

231

K

133

(1+)

Ar

99

Cl

181

(1-)

104

S

190

(2-)

110

P

212

(3-)

11

7 Si

42 (4

+)27

1 (4

-)

143

Al

45 (3

+)

160

Mg

65

(2+)

186

Na

98

(1+)

Ne

58

F

133

(1-)

66

O

146

(2-)

70

N

171

(3-)

77

C

260

(4-)

88

B

16 (3

+)

Ele

men

t

Ioni

cra

dius

/10

-12 m

112

Be

30

(2+)

152

Li

68

(1+)

He

Ato

mic

ra

dius

/ 10

-12 m

30

H 1

54 (1

-)

Dip

lom

a Pr

ogra

mm

e: C

hem

istr

y D

ata

Book

let,

Mar

ch 2

003


9. Covalent Bond Lengths

0.1090.1460.1010.1420.0960.1350.0920.1280.1410.160

0.1430.1220.1360.1470.1270.1160.1350.1380.1770.1690.1930.214

0.150

C–H Si–H N–H P–H O–H S–H F–H Cl–H Br–H I–H

C–O C=O C–O (in phenol) C–N C=N ChN C–N (in phenylamine) C–F C–Cl C–Cl (in chlorobenzene) C–Br C–I

Si–O

0.0740.1540.1340.1200.1390.2350.1460.1200.1100.2210.1480.1210.2070.1880.1420.1990.2280.267

H–H C–C C=C ChC C–C (in benzene) Si–Si N–N N=N NhN P–P (P4) O–O O=O S–S (S8) S=S F–F Cl–Cl Br–Br I–I

Bond length/nm

BondBond length/nm

Bond

10. Average Bond Enthalpies at 298 K

412318388322463338562431366299

360743305613890484338276238

374

C–H Si–H N–H P–H O–H S–H F–H Cl–H Br–H I–H

C–O C=O C–N C=N ChN C–F C–Cl C–Br C–I

Si–O

436442348612837518226188151163409944172146496264158242193151

H–H D–D C–C C=C ChC C–C (benzene) Si–Si Ge–Ge Sn–Sn N–N N=N NhN P–P O–O O=O S–S F–F Cl–Cl Br–Br I–I

∆H / kJ mol-1 Bond∆H / kJ mol-1 Bond


11. Organic Compounds—Thermodynamic Data

186230270310348387219267307301296201248279204269173320360345234179203246222163

276

264208314238127282161146219266295129160167

242285105

-51-33-24-16-80

6863726764

20919415227

130125122131214-59-63-72-263

20

-53

52-8099

-162-166-169-175-51

-110-134-152-346-392-245

2837-47

-75-85

-104-125-146-16752201-6

-10227185112-15683495030

148-82

-117-132-36-20-8

141-105-85-3131

-16652

-201-239-235-278-163-116-166-216-409-487-385-481-320-28-49

-333

gggggggggggggglglggggllgllsgllglgglglsgggllslsggs

CH4

C2H6

C3H8

C4H10

C5H12

C6H14

C2H4

C3H6

C4H8 C4H8 C4H8

C2H2

C3H4

C4H6 C6H12 C6H6

C6H6

C6H5CH3

C6H5CH2CH3

C6H5CHCH2

CH3ClCH2Cl2

CHCl3

CH3BrCHBr3

CH3ICHI3

C2H5ClC2H5BrC2H5IC2H3ClCH2ClCH2ClC6H5ClCH3OHCH3OHC2H5OHC2H5OHC6H5OHHCHOCH3CHO(CH3)2COHCOOHCH3COOHC6H5COOHCH3COOC2H5

CH3CONH2

CH3NH2

C2H5NH2

CO(NH2)2

methaneethanepropanebutanepentanehexaneethenepropenebut-1-enecis-but-2-enetrans-but-2-eneethynepropynebuta-1,3-dienecyclohexanebenzene benzene methylbenzeneethylbenzenephenylethenechloromethanedichloromethanetrichloromethanebromomethanetribromomethaneiodomethanetriiodomethanechloroethanebromoethaneiodoethanechloroethene1,2-dichloroethanechlorobenzenemethanol methanol ethanol ethanol phenolmethanalethanalpropanonemethanoic acidethanoic acidbenzoic acidethyl ethanoateethanamidemethylamineethylamineurea

S0 / J K-1 mol-1∆Gf0 / kJ mol-1∆Hf

0 / kJ mol-1State FormulaSubstance


12. Ellingham Diagram

Standard Gibbs free energy changes of formation, ∆G0f , for oxides given per mole of oxygen gas

as a function of temperature.

0

– 200

– 400

– 600

– 800

– 1000

– 1200

500 1000 1500 2000 2500

Ag

Hg

C

Pb

Fe

CO

Zn

Cr

Ti

Al

Mg

Ca

Pb

4Ag+O 2Ag Od2

2

2Hg+O 2HgO

d2

2Pb+O 2PbOd2

2Fe+O 2FeOd 2

2Zn+O 2ZnO

d2

Cr+O Cr Od2

232

3–

43–

Al+O Al Od

2

232

3–

43–

2Mg+O 2MgO

d2

2Ca+O 2CaO

d2

Ti+O TiOd

2

2

2C+O 2COd 2

2CO+O 2COd2

2

C

Temperature / K


f / kJmolG −1∆ 0

2 2C O CO+ →

13. E

ntha

lpie

s of C

ombu

stio

nTh

e va

lues

of t

he m

olar

ent

halp

y of

com

bust

ion

in

the

follo

win

g ta

ble

refe

r to

a te

mpe

ratu

re o

f 298

K a

nd a

pre

ssur

e of

1.0

1 ×

105 P

a (1

atm

).

-201

0-2

673

-405

6-3

727

-306

4-2

727

-561

-116

7-3

520

-178

6-3

078

-413

8-6

512

-263

-876

-322

7-2

46-2

246

-118

2-3

546

-107

2-1

709

-339

7-3

094

-634

-281

6-5

644

1 1 l s s l g l l l l s s l l s s l s s g g l l s s s

C3H

7OH

C4H

9OH

C6H

5CH

2OH

C6H

11O

HC

6H5O

H(C

2H5) 2

OH

CH

OC

H3C

HO

C6H

5CH

O(C

H3) 2

CO

(C2H

5) 2C

OC

H3C

OC 6

H5

(C6H

5) 2C

OH

CO

OH

CH

3CO

OH

C6H

5CO

OH

(CO

OH

) 2C

H3C

OO

C2H

5

CH

3CO

NH

2

C6H

5CO

NH

2

CH

3NH

2

C2H

5NH

2

C6H

5NH

2

C6H

5NO

2

CO

(NH

2) 2C

6H12

O6

C12

H22

O11

prop

an-1

-ol

buta

n-1-

olph

enyl

met

hano

lcy

cloh

exan

olph

enol

etho

xyet

hane

met

hana

let

hana

lbe

nzal

dehy

depr

opan

one

pent

an-3

-one

phen

ylet

hano

nedi

phen

ylm

etha

none

met

hano

ic a

cid

etha

noic

aci

dbe

nzoi

c ac

idet

hane

dioi

c ac

idet

hyl e

than

oate

etha

nam

ide

benz

amid

em

ethy

lam

ine

ethy

lam

ine

phen

ylam

ine

nitro

benz

ene

urea

gluc

ose

sucr

ose

-286

-297

-394

-395

-283

-890

-156

0-2

220

-287

7-3

509

-419

4-5

512

-392

4-1

409

-254

2-1

299

-327

3-3

909

-515

7-7

114

-132

5-1

425

-149

0-3

709

-373

-715

-137

1

g s s s g g g g g g l l l l g g g l l s s g g l l l l

H2

S C C CO

CH

4

C2H

6

C3H

8

C4H

10

C5H

12

C6H

14

C8H

18

C6H

12

C2H

4

C4H

6

C2H

2

C6H

6

C6H

5CH

3

C10

H8

C14

H10

C2H

5Cl

C2H

5Br

C2H

5IC

6H5C

H2C

lC

HC

l 3C

H3O

HC

2H5O

H

hydr

ogen

sulfu

r ca

rbon

(gra

phite

)ca

rbon

(dia

mon

d)ca

rbon

mon

oxid

em

etha

neet

hane

prop

ane

buta

nepe

ntan

ehe

xane

octa

necy

cloh

exan

eet

hene

buta

-1,3

-die

neet

hyne

benz

ene

met

hylb

enze

nena

phth

alen

ean

thra

cene

chlo

roet

hane

brom

oeth

ane

iodo

etha

ne(c

hlor

omet

hyl)b

enze

netri

chlo

rom

etha

nem

etha

nol

etha

nol

/ kJ

mol

-1c

H∆0

Stat

e F

orm

ula

Sub

stan

ce /

kJ m

ol-1

cH∆

0St

ate

For

mul

a S

ubst

ance

IB D

iplo

ma

Prog

ram

me:

Che

mis

try

Dat

a Bo

okle

t, M

arch

200

311


c(

)H∆

0

14. Lattice Enthalpies at 298 K (Experimental and Theoretical Values)

The lattice enthalpy values given relate to the endothermic processlattice( )H∆ 0

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 Born–Haber cycle.

744684629609585

800733670647619

846771701675645

1022902801767716

Li Na K Rb Cs

IBrClF

/ kJ mol-1latticeH∆ 0Alkali metal halides

3238296627792643976955905890876640

MgS CaS SrS BaS CuCl AgF AgCl AgBr AgI NH4Cl

2602300624932237211220183889351333103152

CaF2

BeCl2

MgCl2

CaCl2

SrCl2

BaCl2

MgO CaO SrO BaO

/ kJ mol-1latticeH∆ 0Other substances/ kJ mol-1

latticeH∆ 0Other substances

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

728686632607582

787732665644611

833766690674636

1004891795761728

Li Na K Rb Cs

IBrClF

/ kJ mol-1latticeH∆ 0Alkali metal halides

870770758736

AgF AgCl AgBr AgI

26113929347732053042

CaF2

MgO CaO SrO BaO

/ kJ mol-1latticeH∆ 0Other substances/ kJ mol-1

latticeH∆ 0Other substances


MX(s) M (g) X (g)+ −→ +

15. Standard Electrode Potentials

+2.87F-(aq)l½F2 (g) + e- +1.51Mn2+(aq) + 4H2O(l)lMnO4

-(aq) + 8H+(aq) + 5e-

+1.36Cl-(aq)l½Cl2(g) + e-

+1.332Cr3+(aq) + 7H2O(l) lCr2O72-(aq) + 14H+(aq) + 6e-

+1.23H2O(l)l½O2(g) + 2H+(aq) + 2e-

+1.09Br-(aq)l½Br2 (l) + e- +0.80Ag(s)lAg+(aq) + e- +0.77Fe2+(aq)lFe3+(aq) + e- +0.54I-(aq)l½I2(s) + e- +0.52Cu(s)lCu+(aq) + e- +0.402OH-(aq)l½O2(g) + H2O(l) + 2e- +0.34Cu(s)lCu2+(aq) + 2e-

+0.17H2SO3(aq) + H2O(l)lSO42-(aq) + 4H+(aq) + 2e-

+0.15Cu+(s)lCu2+(aq) + e-

0.00½H2(g)lH+(aq) + e-

-0.13Pb(s)lPb2+(aq) + 2e- -0.14Sn(s)lSn2+(aq) + 2e-

-0.23Ni(s)lNi2+(aq) + 2e- -0.44Fe(s)lFe2+(aq) + 2e- -0.76Zn(s)lZn2+(aq) + 2e-

-0.83½H2(g) + OH-(aq)lH2O(l) + e-

-1.18Mn(s) lMn2+(aq) + 2e-

-1.66Al(s)lAl3+(aq) + 3e-

-2.36Mg(s)lMg2+(aq) + 2e-

-2.71Na(s) lNa+(aq) + e-

-2.87Ca(s)lCa2+(aq) + 2e-

-2.92K(s)lK+(aq) + e-

-3.03Li(s)lLi+(aq) + e-

E0 / VOxidized species l Reduced species


16. 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 interms of pKb values.

Carboxylic Acids

3.754.764.874.824.854.865.054.204.31

HCOOHCH3COOHCH3CH2COOHCH3(CH2)2COOH(CH3)2CHCOOHCH3(CH2)3COOH(CH3)3CCOOHC6H5COOHC6H5CH2COOH

methanoic ethanoic propanoic butanoic 2-methylpropanoic pentanoic 2,2-dimethylpropanoic benzoic phenylethanoic

pKa Formula Name

Halogenated Carboxylic Acids

2.861.290.652.662.903.17

CH2ClCOOHCHCl2COOHCCl3COOHCH2FCOOHCH2BrCOOHCH2ICOOH

chloroethanoic dichloroethanoic trichloroethanoic fluoroethanoic bromoethanoic iodoethanoic

pKa Formula Name

Phenols

10.007.218.357.154.010.42

C6H5OHO2NC6H4OHO2NC6H4OHO2NC6H4OH(O2N)2C6H3OH(O2N)3C6H2OH

phenol 2-nitrophenol 3-nitrophenol 4-nitrophenol 2,4-dinitrophenol 2,4,6-trinitrophenol

pKaFormula Name

Alcohols

15.516 (approximately)

CH3OHC2H5OH

methanol ethanol

pKaFormula Name


Amines

4.753.363.273.284.203.073.369.38

NH3

CH3NH2

CH3CH2NH2

(CH3)2NH(CH3)3N(C2H5)2NH(C2H5)3NC6H5NH2

ammonia methylamine ethylamine dimethylamine trimethylamine diethylamine triethylamine phenylamine

pKbFormula Name

17. Acid–base Indicators

yellowblueblueyellowblueredred

redyellowyellowredyellowyellowcolourless

3.1–4.43.0–4.63.8–5.44.2–6.36.0–7.66.8–8.48.3–10.0

3.74.04.75.17.07.99.3

methyl orange bromophenol blue bromocresol green methyl red bromothymol blue phenol red phenolphthalein

AlkaliAcidpH rangepKa Indicator

Colour change


18. Infrared Data

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

700 to 800

1000 to 1300

1610 to 1680

1680 to 1750

2070 to 2250

2500 to 3300

2840 to 3095

3230 to 3550

3350 to 3500

halogenoalkanes

alcohols, ethers, esters

alkenes

aldehydes, ketones, acids, esters

alkynes

“hydrogen bonded” in acids

alkanes, alkenes, arenes

“hydrogen bonded” in alcohols, phenols

primary amines

C–Cl

C–O

C=C

C=O

ChC

O–H

C–H

O–H

N–H

Wavenumber / cm-1Organic moleculesBond


19. 1H NMR DataTypical proton chemical shift values (δ) relative to TMS = 0.(These values can vary slightly in different solvents.)

11.5R C

O

O H

9.7R C

O

H

7.3H

7OH

4.9–5.9RHC CH2

0.5–6.5 (can vary considerably underdifferent conditions)

R O H

4.0–4.2O C

O

CH3

4.1

R O CH3

R C O CH2R

O

3.8R O CH3

3.2–3.7R CH2 Hal

2.6R C C H

2.3CH3

2.1O

C

CH3R

2.0CH3 C

O

OR

2 R3CH1.3R CH2 R

0.9R CH3

Chemical shift/ppmType of proton


20. 2-amino Acids

6.0H2N CH

CH

COOH

CH3 CH2 CH3

Ileisoleucine

7.6H2N CH COOH

CH2

N

NHHishistidine

6.0H2N CH2 COOHGlyglycine

3.2H2N CH COOH

CH2 CH2 COOHGluglutamic acid

5.7H2N CH COOH

CH2 CH2 C NH2

O

Glnglutamine

5.1H2N CH COOH

CH2 SHCyscysteine

2.8H2N CH COOH

CH2 COOHAspaspartic acid

5.4H2N CH COOH

CH2 C NH2

O

Asnasparagine

10.8H2N CH COOH

CH2 CH2 CH2 NH C NH2

NH

Argarginine

6.0H2N CH COOH

CH3

Alaalanine

pH of isoelectricpoint

Structural formulaSymbolCommon name


6.0H2N CH COOH

CH CH3CH3

Valvaline

5.7H2N CH COOH

CH2 OHTyrtyrosine

5.9H2N CH COOH

CH2

NH

Trptryptophan

5.6H2N CH COOH

CH OHCH3

Thrthreonine

5.7H2N CH COOH

CH2 OHSerserine

6.3N

COOHHProproline

5.5H2N CH COOH

CH2

Phephenylalanine

5.7H2N CH COOH

CH2 CH2 S CH3

Metmethionine

9.7H2N CH

CH2

COOH

CH2 CH2 CH2 NH2

Lyslysine

6.0H2N CH

CH2

COOH

CH CH3CH3

Leuleucine

pH of isoelectricpoint

Structural formulaSymbolCommon name


21. Structural Formulas of Some Important Medicines and Drugs

aspirin paracetamol (acetaminophen) ibuprofen

morphine codeine heroin

amphetamine adrenaline caffeine nicotine

penicillin diazepam (valium®) nitrazepam (mogadon®)


O

COH

CCH3

O

O

CH2

C

C

CH3

H

CH3

COOH

H

CH3

OH

NHCOCH3

OH

N

OH

CH2CH3

O

CH2

N

N

CH3

OCCH3

N

OCCH3

CH2CH3

O

CH2

O

OO

OH

N

OCH3

CH2CH3

O

CH2

R C

O

NH

NO

S

CH3

CH3

C O

OH

N

N N

N

O

O

H3C

CH3

CH3

Cl N

NO

CH3

HO

HO CH

OH

NH CH3CH2CH2

CH3

NH2CH

O2N N

NO

CH3

cocaine acyclovir

cisplatin Lidocaine lysergic acid diethylamide (LSD)

mescaline

psilocybin

procaine

tetrahydrocannabinol (THC)

fluoxetine hydrochloride (prozac) indole


O

F3C

CH2

CH2NH2

+ Cl-

CH3

Pt

Cl

NH3

NH3

Cl

O

O

NCH3

OCH3

N

HN

O

N

N

CH2

O

H2N

CH2CH2

HO

CH3

NH

CH3

C CH2

NCH2H2C

CH3CH3

ON

CH2N

CH3

CH3

CH2

O

NH

CH3

CH3O

CH3O

OCH3

CH2CH2

NH2

O

N

CH2CH2

N+

H

CH3

CH3H

P OO -O

H

NH2 C O CH2CH2 N

CH2CH3

CH2CH3

O

CH3

O CH2

CH2CH2

CH2CH3

OH

H3C

H3C

NH

22. Structural Formulas of Some Important Biological Molecules

lactose sucrose

ascorbic acid (vitamin C)

oestradiol progesterone testosterone


C

CC

C

C

C

C

C

C

C

OH

C

H2C

H2C

C

C CH3

CH3

H H H H

H2

CH3 CH3 CH3

H H H2

retinol (vitamin A)

O

H

OH

OH

H

H

CH2OH

H

HOO

H

OH

OH

HOH

HH

CH2OH

H

O

H

1

2

1

23

4

OH

H

OH

OH

H

H

CH2OH

HO

H

OH

H1

2

O

O

HOCH2

1 2

3 4CH2OH

H

H

HO

CH3

CH3

CH

HO

H3C CH2

CH2

CH2

CH

CH3

CH3

CH3

CH

HO

H3C CH2

CH2

CH2

CH

CH3

CH2

CH3

C

O

C

C

C

C

CH2OH

HO

HO

H

HO H

O

CH3 OH

HO O

CH3 OH

CH3

CH3 C

H3C

O

O

CH3

cholesterol

vitamin D

adrenaline thyroxine

adenine guanine cytosine uracil thymine

adenosine triphosphate (ATP)

The haem group from cytochrome oxidase


HO

HO CH

OH

CH2 NH CH3

I

HO

I

O

I

I

CH2 CH COOH

NH2

N

CN

C

CC

N

CH

N

O

H

H

H2N

N

CN

CH

CHC

H

O

NH2

N

CN

CH

CHC

H

O

H

O

N

CN

CH

CC

H

O

H

O

CH3N

HCN

C

CC

N

CH

N

NH2

H

O

OHOH

CH2OPOPOP

OOO

O–O–O–

N

N N

N

NH2

O–

Fe

N

N N

N

CH3

CH2CH2

C

H3C

CH2 CH3

CH

CH2HOOC

O

H

CH2

CH2 COOH

CH2

HO

CH2CH

CCH2

CH2

CH

CCH2

CH2

CH

C

CH3

CH3CH3 CH3

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