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Diploma Programme

Chemistry data bookletFirst examinations 2009

4019aPrinted in the United Kingdom by Antony Rowe Ltd, Chippenham, Wiltshire

First published March 2007Revised edition published September 2008

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Diploma Programme

Chemistry data booklet

Chemistry data bookletChemistry data booklet

Contents

1. Some relevant equations 1

2. Physical constants and unit conversions 1

3. The electromagnetic spectrum 1

4. Names of the elements 2

5. The periodic table 3

6. Melting points and boiling points of the elements 4

7. First ionization energy, electron affinity and electronegativity of the 5 elements

8. Atomic and ionic radii of the elements 6

9. Covalent bond lengths 7

10. Bond enthalpies and average bond enthalpies at 298 K 7

11. Organic compounds—thermodynamic data 8

12. Enthalpies of combustion 9

13. Lattice enthalpies at 298 K (experimental and theoretical values) 10

14. Standard electrode potentials 12

15. Strengths of organic acids and bases 13

16. Acid–base indicators 14

17. Infrared data 15

18. 1H NMR data 16

19. 2-Amino acids 17

20. Structural formulas of some medicines and drugs 19

21. Structural formulas of some biological molecules 21

22. Structural formulas of some food chemistry molecules 22

23. References 24

Notes

This booklet cannot be used for paper 1 of the examination (SLP1 and HLP1), but the periodic table given on page 3 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

1. Some relevant equations

010log =I εlcI

−

=aE

RTk Ae

k A ln – ln= +aE

RTc=f λ

=PV nRT ∆ = ∆ − ∆G H T SÖ Ö Ö

q=mcΔT E=hf

2. Physical constants and unit conversionsAvogadro’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 and 1.01 × 105 Pa = 2.24 × 10–2 m3 mol–1 (= 22.4 dm3 mol–1)

Planck’s constant (h) = 6.63 × 10–34 J s

Specific 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 at 298 K

1 atm = 1.01 × 105 Pa

1 dm3 = 1 litre = 1 × 10–3 m3 = 1 × 103 cm3

3. The electromagnetic spectrum

10–16 10–14 10–12 10–10 10–8 10–6 10–4 10–2 100 102 104 106 108

γ rays X rays UV IR microwaves radio waves

wavelength / m

Energy

V I B G Y O R

wavelength / nm700400

1


Chemistry data booklet2

4. Names of the elements

Element Symbol Atomic number

Element Symbol Atomic number

actiniumaluminiumamericiumantimonyargonarsenicastatinebariumberkeliumberylliumbismuthbohriumboronbrominecadmiumcaesiumcalciumcaliforniumcarbonceriumchlorinechromiumcobaltcoppercuriumdubniumdysprosiumeinsteiniumerbiumeuropiumfermiumfluorinefranciumgadoliniumgalliumgermaniumgoldhafniumhassiumheliumholmiumhydrogenindiumiodineiridiumironkryptonlanthanumlawrenciumleadlithiumlutetiummagnesiummanganesemeitnerium

AcAl

AmSbArAsAtBaBkBeBiBhBBrCdCsCaCfCCeClCrCoCuCmDbDyEsErEuFmFFrGdGaGeAuHfHsHeHoHInIIrFeKrLaLrPbLiLuMgMnMt

891395511833855697

483

1075

35485520986

581724272996

10566996863

1009

876431327972

1082

671

495377263657

103823

711225

109

mendeleviummercurymolybdenumneodymiumneonneptuniumnickelniobiumnitrogennobeliumosmiumoxygenpalladiumphosphorusplatinumplutoniumpoloniumpotassiumpraseodymiumpromethiumprotactiniumradiumradonrheniumrhodiumrubidiumrutheniumrutherfordiumsamariumscandiumseaborgiumseleniumsiliconsilversodiumstrontiumsulfurtantalumtechnetiumtelluriumterbiumthalliumthoriumthuliumtintitaniumtungstenuraniumvanadiumxenonytterbiumyttriumzinczirconium

MdHgMoNdNeNpNiNbNNoOsOPdPPtPuPoKPrPmPaRaRnReRhRbRuRfSmScSgSeSiAgNaSrSTaTcTeTbTlThTmSnTiWUVXeYbYZnZr

101804260109328417

102768

461578948419596191888675453744

1046221

1063414471138167343526581906950227492235470393040

2



5. T

he p

erio

dic

tabl

e

12

34

56

70

11 H 1.01

2 He

4.00

23 Li

6.94

4 Be

9.01

5 B10

.81

6 C12

.01

7 N14

.01

8 O 16.0

0

9 F19

.00

10 Ne

20.1

8

311 Na

22.9

9

12 Mg

24.3

1

13 Al

26.9

2

14 Si 28.0

9

15 P30

.97

16 S32

.06

17 Cl

35.4

5

18 Ar

39.9

5

419 K 39.1

0

20 Ca

40.0

8

21 Sc 44.9

6

22 Ti 47.9

0

23 V50

.94

24 Cr

52.0

0

25 Mn

54.9

4

26 Fe 55.8

5

27 Co

58.9

3

28 Ni

58.7

1

29 Cu

63.5

5

30 Zn

65.3

8

31 Ga

69.7

4

32 Ge

72.5

9

33 As

74.9

2

34 Se 78.9

6

35 Br

79.9

1

36 Kr

83.8

0

537 Rb

85.4

7

38 Sr 87.6

2

39 Y88

.91

40 Zr

91.2

2

41 Nb

92.9

1

42 Mo

95.9

4

43 Tc 98.9

1

44 Ru

101.

07

45 Rh

102.

91

46 Pd 106.

42

47 Ag

107.

87

48 Cd

112.

41

49 In11

4.82

50 Sn11

8.69

51 Sb12

1.75

52 Te12

7.60

53 I12

6.90

54 Xe

131.

30

655 C

s13

2.91

56 Ba

137.

33

57

†L

a13

8.91

72 Hf

178.

49

73 Ta18

0.95

74 W18

3.85

75 Re

186.

21

76 Os

190.

23

77 Ir19

2.22

78 Pt19

5.09

79 Au

196.

97

80 Hg

200.

59

81 Tl

204.

37

82 Pb 207.

19

83 Bi

208.

98

84 Po 210

85 At

209.

99

86 Rn

222.

02

787 Fr

223.

02

88 Ra

226.

03

8

9 ‡

Ac

227.

03

104

Rf

260

105

Db

262.

11

106

Sg26

6.12

107

Bh

264.

12

108

Hs

269.

13

109

Mt

268.

13

†

58 Ce

140.

12

59 Pr14

0.91

60 Nd

144.

24

61 Pm 144.

91

62 Sm 150.

35

63 Eu

151.

96

64 Gd

157.

25

65 Tb

158.

93

66 Dy

162.

50

67 Ho

164.

93

68 Er

167.

26

69 Tm

168.

93

70 Yb

173.

04

71 Lu

174.

97

‡90 Th

232.

04

91 Pa23

1.04

92 U23

8.03

93 Np

239.

05

94 Pu 239.

05

95 Am

243.

06

96 Cm

247.

07

97 Bk

247.

07

98 Cf

252.

08

99 Es

254.

09

100

Fm 253.

09

101

Md

257.

10

102

No

255.

09

103

Lr

257

Ato

mic

num

ber

Ele

men

tR

elat

ive

atom

ic m

ass

3



6. M

eltin

g p

oint

s an

d b

oilin

g p

oint

s of

the

elem

ents

14 H 20

1 He 4

454

Li

1615

1551 Be

3243

2573 B 2823

3925 C 5100

63 N 77

55 O 90

53 F 85

25 Ne

27

371

Na

1156

922

Mg

1380

933

Al

2740

1683 Si 2628

317 P 553

392 S 718

172

Cl

238

84 Ar

87

336 K 10

33

1112 Ca

1757

1814 Sc 3104

1933 Ti 3560

2163 V 3653

2130 Cr

2943

1517

Mn

2235

1808 Fe 3023

1768 Co

3143

1728 Ni

3003

1356 Cu

2840

693

Zn

1180

303

Ga

2676

1210 Ge

3103

1090 As

886

490

Se 958

266

Br

332

116

Kr

121

312

Rb

959

1042 Sr 1657

1795 Y 3611

2125 Zr

4650

2740 Nb

5015

2883

Mo

5833

2445 Tc 5150

2583 Ru

4173

2239 Rh

4000

1827 Pd 3243

1235 Ag

2485

594

Cd

1038

429

In 2353

505

Sn 2543

904

Sb 2023

723

Te 1263

387 I 457

161

Xe

166

302

Cs

942

998

Ba

1913

1194 La

3730

2500 Hf

4875

3269 Ta 5700

3683 W 5933

3453 Re

5900

2973 Os

5570

2683 Ir 4403

2045 Pt 4100

1337 Au

3353

234

Hg

630

577

Tl

1730

601

Pb 2013

544

Bi

1833

527

Po 1235

575

At

610

202

Rn

211

300

Fr 950

973

Ra

1413

1323 Ac

3473

Mel

ting

poin

t / K

Ele

men

tB

oilin

g po

int /

K

4



7. F

irst i

oniz

atio

n en

ergy

, ele

ctro

n af

finit

y an

d el

ectr

oneg

ativ

ity

of th

e el

emen

ts

1312

–

73

H 2.2

237

2

He

520

–

60

Li

1.0

900

Be

1.6

801

–27

B 2.0

1086

–1

22

C 2.6

1402

N 3.0

1314

–1

41

+798

O 3.4

1681

–3

28

F 4.0

208

1

Ne

496

–

53

Na

0.9

738

Mg

1.3

578

–42

Al

1.6

789

–

134

Si 1.9

1012

–

72

P 2.2

1000

–2

00+6

40

S 2.6

1251

–34

9

Cl

3.2

152

1

Ar

419

–48

K 0.8

590

–2

Ca

1.0

631

–18

Sc 1.4

658

–8

Ti 1.5

650

–

51

V 1.6

653

–64

Cr

1.7

717

Mn

1.6

759

–

15

Fe 1.8

758

–

64

Co

1.9

737

–

112

Ni

1.9

746

–

119

Cu

1.9

906

Zn

1.7

579

–41

Ga

1.8

762

–

119

Ge

2.0

947

–79

As

2.2

941

–

195

Se 2.6

1140

–32

5

Br

3.0

135

1

Kr

403

47

Rb

0.8

550

–5

Sr 1.0

616

-30

Y 1.2

660

–41

Zr

1.3

664

–86

Nb

1.6

685

–72

M

o2.

2

702

–

53

Tc 2.1

711

–

101

Ru

2.2

720

–

110

Rh

2.3

805

–

54

Pd

2.2

731

–

126

Ag

1.9

868

Cd

1.7

558

–29

In 1.8

709

–

107

Sn 2.0

834

–

101

Sb 2.1

869

–

190

Te 2.1

1008

–29

5

I 2.7

1170

Xe

376

–46

Cs

0.8

503

–14

Ba

0.9

538

–

45

La

1.1

680

Hf

1.3

761

–31

T

a 1.5

770

–79

W

1.7

760

–14

R

e 1.9

840

–

106

Os

2.2

880

–

151

Ir

2.2

870

– 2

05

Pt 2.2

890

–

223

Au

2.4

1007

Hg

1.9

589

–19

Tl

1.8

716

–35

Pb 1.8

703

–91

Bi

1.9

812

–

183

Po 2.0

–

270

At

2.2

103

7

Rn

393

–44

Fr 0.7

509

–

10

Ra

0.9

499

–3

4

Ac

1.1

Firs

t ion

izat

ion

ener

gy /

El

ectro

n af

finity

/ kJ

mol

–1

kJ m

ol–1

2nd

EA /

kJ m

ol –

1

Ele

men

t

Elec

trone

gativ

ity

5



8. A

tom

ic a

nd io

nic

radi

i of t

he e

lem

ents

30

H

154

(1–)

H

e

152

Li

68 (1

+)

112

Be

30 (2

+)

88

B

16 (3

+)

77

C

260

(4–)

70

N

171

(3–)

66

O

146

(2–)

64

F

133

(1–)

Ne

186

Na

98 (1

+)

160

Mg

65 (2

+)

143

Al

45 (3

+)

11

7

Si42

(4+)

271

(4–)

110

P

212

(3–)

104

S

190

(2–)

99

Cl

181

(1–)

Ar

231

K

133

(1+)

197

Ca

94 (2

+)

16

0

Sc

81 (3

+)

146

Ti90

(2+)

68 (4

+)

131

V

88

(2+)

125

Cr

63

(3+)

129

Mn

80 (2

+)

60 (4

+)

126

Fe76

(2+)

64

(3+)

125

Co

74 (2

+)

63 (3

+)

124

Ni

72 (2

+)

128

Cu

96 (1

+)

69 (2

+)

133

Zn

74 (2

+)

141

Ga

62 (3

+)

122

Ge

53 (4

+)

27

2 (4

–)

121

As

222

(3–)

117

Se

202

(2–)

114

Br

196

(1–)

Kr

244

Rb

148

(1+)

215

Sr

110

(2+)

18

0

Y

93 (3

+)

15

7

Zr

80 (4

+)

1

41

Nb

72 (3

+)64

(5+)

13

6

Mo

68 (4

+)

13

5

Tc65

(4+)

37 (7

+)

133

Ru

68 (3

+)62

(4+)

13

4

Rh

67 (3

+)60

(4+)

138

Pd86

(2+)

62 (4

+)

144

Ag

126

(1+)

149

Cd

97 (2

+)

166

In

81 (3

+)

162

Sn11

2 (2

+)

71 (4

+)

141

Sb

245

(3–)

137

Te

222

(2–)

133

I

219

(1–)

Xe

262

Cs

167

(1+)

217

Ba

134

(2+)

188

La

115

(3+)

1

57

Hf

76 (4

+)

143

Ta64

(5+)

72 (6

+)

137

W66

(4+)

42

(6+)

13

7

Re

63 (4

+)38

(7+)

134

Os

63 (4

+)39

(8+)

13

5

Ir68

(3+)

63 (4

+)

138

Pt80

(2+)

63 (4

+)

144

Au

137

(1+)

85

(3+)

152

Hg

127

(1+)

11

0 (2

+)

171

Tl

150

(1+)

93 (3

+)

175

Pb12

0 (2

+)

84 (4

+)

170

Bi

120

(3+)

76

(5+)

140

Po94

(4+)

67 (6

+)

140

At

62 (7

+)

Rn

270

Fr18

0 (1

+)

220

Ra

148

(2+)

188

Ac

112

(3+)

Ato

mic

ra

dius

/ 10

–12 m

Ele

men

t

Ioni

cra

dius

/ 10

–12 m

6



9. Covalent bond lengthsBond Bond length / nm Bond Bond length / nm

H–HC–CC=CC≡CC C (in benzene)Si–SiN–NN=NN≡NP–P O–OO=OS–S S=SF–FCl–ClBr–BrI–I

0.0740.1540.1340.1200.1400.235 0.1450.1200.1100.2210.1480.1210.2050.1890.1420.1990.2280.267

C–HSi–HN–HP–HO–HS–HF–HCl–HBr–HI–H

C–OC=OC–NC=NC≡NC–FC–ClC–BrC–I

Si–O

0.1080.1480.1010.1440.0960.1340.0920.1270.1410.161

0.1430.1200.1470.1300.1160.1380.1770.1940.214

0.161

10. Bond enthalpies and average bond enthalpies at 298 KBond ΔH / kJ mol–1 Bond ΔH / kJ mol–1

H–HC–CC=CC≡CC C (benzene)Si–SiN–NN=NN≡NP–PO–OO=OS–SF–FCl–ClBr–BrI–I

436347612838505226158410945198144498266158243193151

C–HSi–HN–HP–HO–HS–HF–HCl–HBr–HI–H

C–OC=OC–NC=NC≡NC–FC–ClC–BrC–ISi–O

413318391321464364568432366298

358746286615887467346290228466

7



11. Organic compounds—thermodynamic data

Substance Formula State f∆H Ö /

kJ mol–1f∆GÖ /

kJ mol–1S Ö /

J K–1 mol–1

methaneethanepropanebutanepentanehexaneethenepropenebut-1-enecis-but-2-enetrans-but-2-eneethynepropynebuta-1,3-dienecyclohexanebenzenemethylbenzeneethylbenzenephenylethenechloromethanedichloromethanetrichloromethanebromomethaneiodomethanechloroethanebromoethanechlorobenzenemethanolethanolphenolmethanalethanalpropanonemethanoic acidethanoic acidbenzoic acidmethylamine

CH4C2H6C3H8C4H10C5H12C6H14C2H4C3H6C4H8C4H8C4H8C2H2C3H4C4H6C6H12C6H6C6H5CH3C6H5CH2CH3C6H5CHCH2CH3ClCH2Cl2CHCl3CH3BrCH3IC2H5ClC2H5BrC6H5ClCH3OHC2H5OHC6H5OHHCHOCH3CHO(CH3)2COHCOOHCH3COOHC6H5COOHCH3NH2

ggggllgggggggglllllgllglgllllsgglllsg

–75–85

–105–127–173–199

5220

0*–8

–12228187110

–1564912

–13104–82

–124–135–37–16

–137–91

11–239–277–165–109–191–248–425–485–385–23

–51–33–23–16–9–46875726663

20919415227

125111120203–57–63–71–26

13–53

94–166–175–48

–113–128–155–361–390–245

32

186230270310261296220267306301296201248279204173320255345235178202246163

240161

219160

129160

243

* (–0.4)

8



12. E

ntha

lpie

s of

com

bust

ion

The

valu

es o

f the

mol

ar e

ntha

lpy

of c

ombu

stio

n c

()

H∆

in th

e fo

llow

ing

tabl

e re

fer t

o a

tem

pera

ture

of 2

98 K

and

a p

ress

ure

of 1

.01

× 10

5 Pa

(1 a

tm).

Subs

tanc

eFo

rmul

aSt

ate

cH∆

/ k

J m

ol–1

Subs

tanc

eFo

rmul

aSt

ate

cH∆

/ k

J m

ol–1

hydr

ogen

sulfu

rca

rbon

(gra

phite

)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

ech

loro

etha

nebr

omoe

than

eio

doet

hane

(chl

orom

ethy

l)ben

zene

trich

loro

met

hane

met

hano

let

hano

l

H2

S C CO

CH

4C

2H6

C3H

8C

4H10

C5H

12C

6H14

C8H

18C

6H12

C2H

4C

4H6

C2H

2C

6H6

C6H

5CH

3C

10H

8C

2H5C

lC

2H5B

rC

2H5I

C6H

5CH

2Cl

CH

Cl 3

CH

3OH

C2H

5OH

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

–286

–297

–394

–283

–890

–156

0–2

219

–287

7–3

509

–416

3–5

470

–392

0–1

411

–254

1–1

301

–326

7–3

910

–515

6–1

413

–142

5–1

467

–370

9–4

74–7

26–1

367

prop

an-1

-ol

buta

n-1-

olcy

cloh

exan

olph

enol

etho

xyet

hane

met

hana

let

hana

lbe

nzal

dehy

depr

opan

one

pent

an-3

-one

phen

ylet

hano

nem

etha

noic

aci

det

hano

ic a

cid

benz

oic

acid

etha

nedi

oic

acid

ethy

l eth

anoa

teet

hana

mid

em

ethy

lam

ine

ethy

lam

ine

phen

ylam

ine

nitro

benz

ene

urea

gluc

ose

sucr

ose

C3H

7OH

C4H

9OH

C6H

11O

HC

6H5O

H(C

2H5)

2OH

CH

OC

H3C

HO

C6H

5CH

O(C

H3)

2CO

(C2H

5)2C

OC

H3C

OC

6H5

HC

OO

HC

H3C

OO

HC

6H5C

OO

H(C

OO

H) 2

CH

3CO

OC

2H5

CH

3CO

NH

2C

H3N

H2

C2H

5NH

2C

6H5N

H2

C6H

5NO

2C

O(N

H2)

2C

6H12

O6

C12

H22

O11

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

–202

1–2

676

–372

7–3

053

–272

4–5

71–1

167

–352

5–1

817

–310

0–4

149

–254

–874

–322

7–2

43–2

238

–118

5–1

085

–174

0–3

393

–308

8–6

32–2

803

–564

0

9



13. Lattice enthalpies at 298 K (experimental and theoretical values)

The lattice enthalpy values lattice( )∆H Ö given relate to the endothermic process for a solid crystal breaking into gaseous ions.

For example, for an alkali metal halide:

MX(s) → M+(g) + X–(g)

Experimental valuesThe data in these two tables are experimental values obtained by means of a suitable Born–Haber cycle.

Alkali metal halides

lattice∆H Ö/ kJ mol–1

F Cl Br I

LiNaKRbCs

1049930829795759

864790720695670

820754691668647

764705650632613

Other substances lattice∆H Ö / kJ mol–1 Other substances lattice∆H Ö / kJ mol–1

CaF2BeCl2MgCl2CaCl2SrCl2BaCl2MgOCaOSrOBaO

2651303325402271217020693791340132233054

CuCl2AgFAgClAgBrAgI

2824974918905892

10



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

Alkali metal halides

lattice∆H Ö / kJ mol–1

F Cl Br I

LiNaKRbCs

1030910808774744

834769701680657

788732671651632

730682632617600

Other substances lattice∆H Ö / kJ mol–1

Other substances lattice∆H Ö / kJ mol–1

CaF2MgOCaOSrOBaO

26403795341432173029

AgFAgClAgBrAgI

953910897881

11



14. Standard electrode potentials

Oxidized species Reduced species E Ö / V

Li+(aq) + e– Li(s) –3.04

K+(aq) + e– K(s) –2.93

Ca2+(aq) + 2e– Ca(s) –2.87

Na+(aq) + e– Na(s) –2.71

Mg2+(aq) + 2e– Mg(s) –2.37

Al3+(aq) + 3e– Al(s) –1.66

Mn2+(aq) + 2e– Mn(s) –1.19

H2O(l) + e– ½H2(g) + OH–(aq) –0.83

Zn2+(aq) + 2e– Zn(s) –0.76

Fe2+(aq) + 2e– Fe(s) –0.45

Ni2+(aq) + 2e– Ni(s) –0.26

Sn2+(aq) + 2e– Sn(s) –0.14

Pb2+(aq) + 2e– Pb(s) –0.13

H+(aq) + e– ½H2(g) 0.00

Cu2+(aq) + e– Cu+(aq) +0.15

SO42–(aq) + 4H+(aq) + 2e– H2SO3(aq) + H2O(l) +0.17

Cu2+(aq) + 2e– Cu(s) +0.34

½O2(g) + H2O(l) + 2e– 2OH–(aq) +0.40

Cu+(aq) + e– Cu(s) +0.52

½I2(s) + e– I–(aq) +0.54

Fe3+(aq) + e– Fe2+(aq) +0.77

Ag+(aq) + e– Ag(s) +0.80

½Br2(l) + e– Br–(aq) +1.07

½O2(g) + 2H+(aq) + 2e– H2O(l) +1.23

Cr2O72–(aq) + 14H+(aq) + 6e– 2Cr3+(aq) + 7H2O(l) +1.33

½Cl2(g) + e– Cl–(aq) +1.36

MnO4–(aq) + 8H+(aq) + 5e– Mn2+(aq) + 4H2O(l) +1.51

½F2(g) + e– F–(aq) +2.87

12



15. Strengths of organic acids and basesThe 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

methanoicethanoicpropanoicbutanoic2-methylpropanoicpentanoic2,2-dimethylpropanoicbenzoicphenylethanoic

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

3.754.764.874.834.844.835.034.204.31

Halogenated carboxylic acids

Name Formula pKa

chloroethanoicdichloroethanoictrichloroethanoicfluoroethanoicbromoethanoiciodoethanoic

CH2ClCOOHCHCl2COOHCCl3COOHCH2FCOOHCH2BrCOOHCH2ICOOH

2.871.350.662.592.903.18

Phenols

Name Formula pKa

phenol2-nitrophenol3-nitrophenol4-nitrophenol2,4-dinitrophenol2,4,6-trinitrophenol

C6H5OHO2NC6H4OHO2NC6H4OHO2NC6H4OH(O2N)2C6H3OH(O2N)3C6H2OH

9.997.238.367.154.070.42

13



Alcohols

Name Formula pKa

methanolethanol

CH3OHC2H5OH

15.515.5

Amines

Name Formula pKb

ammoniamethylamineethylaminedimethylaminetrimethylaminediethylaminetriethylaminephenylamine

NH3CH3NH2CH3CH2NH2(CH3)2NH(CH3)3N(C2H5)2NH(C2H5)3NC6H5NH2

4.753.343.353.274.203.163.259.13

16. Acid–base indicators

Indicator pKa pH range Colour change

Acid Alkali

methyl orangebromophenol bluebromocresol greenmethyl redbromothymol bluephenol redphenolphthalein

3.464.104.905.007.308.009.50

3.2–4.43.0–4.63.8–5.44.8–6.06.0–7.66.6–8.08.2–10.0

redyellowyellowredyellowyellowcolourless

yellowblueblueyellowblueredpink

14



17. Infrared dataCharacteristic ranges for infrared absorption due to stretching vibrations in organic molecules.

Bond Organic molecules Wavenumber / cm–1

C–I

C–Br

C–Cl

C–F

C–O

C=C

C=O

C≡C

O–H

C–H

O–H

N–H

iodoalkanes

bromoalkanes

chloroalkanes

fluoroalkanes

alcohols, esters, ethers

alkenes

aldehydes, ketones, carboxylic acids and esters

alkynes

hydrogen bonding in carboxylic acids

alkanes, alkenes, arenes

hydrogen bonding in alcohols and phenols

primary amines

490–620

500–600

600–800

1000–1400

1050–1410

1610–1680

1700–1750

2100–2260

2500–3300

2850–3100

3200–3600

3300–3500

15



18. 1H NMR dataTypical proton chemical shift values (δ) 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 Chemical shift / ppm

CH3 0.9–1.0

CH2 R 1.3–1.4

CHR2 1.4–1.6

C

O

RO CH22.0–2.5

CR CH2

O2.2–2.7

CH3 2.5–3.5

C C H 1.8–3.1

CH2 Hal 3.5–4.4

O CH2R 3.3–3.7

C

O

R O CH23.8–4.1

C

O

R O H9.0–13.0

R O H 4.0–12.0

HC CH2 4.5–6.0

OH 4.0–12.0

H 6.9–9.0

C

O

HR9.4–10.0

16



19. 2-Amino acids

Common name Symbol Structural formulapH of isoelectric

point

alanine AlaH2N CH

CH3

COOH6.0

arginine Arg

H2N CH

CH2 CH2 CH2 NH C

NH

NH2

COOH

10.8

asparagine Asn

H2N CH

CH2

COOH

C

O

NH2 5.4

aspartic acid AspH2N CH

CH2

COOH

COOH2.8

cysteine CysH2N CH

CH2

COOH

SH5.1

glutamic acid GluH2N CH

CH2

COOH

CH2 COOH3.2

glutamine Gln

H2N CH

CH2

COOH

CH2 C

O

NH2 5.7

glycine Gly H2N CH2 COOH 6.0

histidine His

H2N CH

CH2

N

N

COOH

H

7.6

isoleucine IleH2N CH

CHH3C

COOH

CH2 CH3 6.0

leucine Leu

H2N CH

CH2CHH3C CH3

COOH

6.0

lysine Lys

H2N CH

CH2

COOH

CH2 CH2 CH2 NH2 9.7

17



Common name Symbol Structural formulapH of isoelectric

point

methionine MetH2N CH

CH2 CH2 S CH3

COOH

H2N CH

CH2 CH2 S CH3

COOH5.7

phenylalanine Phe

H2N CH

CH2

COOH

5.5

proline Pro HN

COOH

6.3

serine SerH2N CH

CH2

COOH

OH5.7

threonine ThrH2N CH

CH

COOH

H3C OH5.6

tryptophan Trp

H2N CH

CH2

N

COOH

H

5.9

tyrosine Tyr

H2N CH

CH2

OH

COOH

5.7

valine ValH2N CH

CH

COOH

CH3H3C6.0

18



20. Structural formulas of some medicines and drugs

COH

O

O

CH3C O

OH

NH C

O

CH3CH3C COOH

H

H2C C

CH3

H

CH3

aspirin paracetamol (acetaminophen) ibuprofen

O

OH

OH

N

H2C CH2

H3C

O

OH

O

N

H2C CH2

H3C

CH3

O

O

O

N

H2C CH2

H3C

C

CCH3

O

CH3

O

morphine codeine diamorphine (heroin)

CH2CH

CH3

NH2

HO

HO CH

OH

CH2N

CH3

H

N

N N

N

O

O

H3C

CH3

CH3

amphetamine epinephrine (adrenaline) caffeine

N

N

CH3 NO

S CH3CH3

CHO

O

HNC

R

O

N

N

H3C O

Cl

nicotine penicillin(general structure) diazepam (Valium®)

19



N

NO

O2N

H

nitrazepam (Mogadon®)

N

NH

N

N

O

H2NCH2

O

CH2H2C

OH

NH

indole

acyclovir

N

O OH3C

OO

CH3

NH

N

CH3

CN

O

CH2H3C

CH2H3C

cocaine lysergic acid diethylamide (LSD)

F3C

O CH2CH2

NH2+

CH3

Cl_

fluoxetine hydrochloride (Prozac®)

CH3

O

OH

H3CCH3

CH2CH2

CH2CH2

CH3

N

O

ONH

O

O

thalidomide

tetrahydrocannabinol (THC)

_

NH

PO O

O

H

CH2 CH2

N+ H

H3C CH3H3CO

H3CO

OCH3

CH2CH2

NH2

mescaline

PtCl

Cl

NH3

NH3

cisplatin

psilocybin

20



21. Structural formulas of some biological molecules

O

O

CH2OH

HO

H

OHH

H

OH

H

OCH2OH

H

H

OHH

OH

HOH

H

H

O

O

CH2OHH

H

OHH

HO

OH

H

OCH2 H

CH2OHH

OH H

HO

H HO

lactose sucrose

CH3

CH3

CH3

CHCH

C

CH3

CHCH

CHC

CH3

CHCH2

OH

retinol (vitamin A)

O

O

OH

OHHC

CH2HO

HO

ascorbic acid (vitamin C)

HO

CH3

CH3

HC

H3C CH2CH2

CH2CH

CH3

CH3

cholesterol

HCCH

CH3

HC

H3C CH2CH2

CH2CH

CH3

CH3

CH2

HO

vitamin D

HO

CH3OH

O

CH3C

CH3

H3CO

O

CH3OH

CH3

estradiol progesterone testosterone

21



HO

HO CH

OH

CH2N

H

CH3OI

I

I

IHO CH2CH C

OH

O

NH2

epinephrine (adrenaline) thyroxine

N

HCN

C

CC

NCH

N

NH2

H

N

CN

C

CC

NCH

N

O

HH2N

HN

CN

CH

CHC

NH2

O

H

adenine guanine cytosine

N

CN

CH

CHC

O

O

H

HN

CN

CH

CC

O

O

H

H CH3

uracil thymine

22. Structural formulas of some food chemistry molecules

Natural pigmentsAnthocyanins

O

R

OH

RO

OH

O glucose

O

R

OH

RHO

OH

O glucose

+

quinoidal base (blue) flavylium cation (red)

22



Carotenes

CH3

CHCH

C

CH3

CHCH

CHC

CH3

CHCH

CHCH

C

CH3

CHCH

CHC

CH3

CHCH

H3C

H3C CH3

CH3H3C

α-carotene

CH3

CHCH

C

CH3

CHCH

CHC

CH3

CHCH

CHCH

C

CH3

CHCH

CHC

CH3

CHCH

H3C

H3C CH3

CH3H3C

β-carotene

Porphyrins

N

HC

N

CH

NN

Fe

CH3

H3C

CH

H2C

H3C

H2CCH2

OHO

CH3

CH2H2C

HOO

CHH2C

N

HC

N

CH

NN

Mg

RHCCH2

H3C

H3CHH2C H

CH2CO

O

C20H39

CH2CH3

HC

O O

CH3

O

R=CH3 (Chlorophyll a)R=CHO (Chlorophyll b)

CH3

heme B chlorophyll

Preservatives

OH

OCH3

CCH3

CH3CH3

OH

C

CH3

CH3

CH3

OCH3

OH

CH3

C CCH3

CH3

H3C

H3CCH3

CH3

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

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

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

23



Fatty acids

Fatty acid Formula

Octanoic acid CH3(CH2)6COOH

Lauric acid CH3(CH2)10COOH

Stearic acid CH3(CH2)16COOH

Oleic acid CH3(CH2)7CH═CH(CH2)7COOH

Linoleic acid CH3(CH2)4(CH═CHCH2)2(CH2)6COOH

Linolenic acid CH3CH2(CH═CHCH2)3(CH2)6COOH

23. ReferencesThe data in tables 4–16 can be found in the following three sources.

Lide, DR. 2008. CRC Handbook of Chemistry and Physics. Boca Raton, USA. CRC Press. Copyright 2008 by CRC Handbook of Chemistry and Physics. David R Lide. Reproduced by permission from Taylor and Francis Group, LLC, a division of Informa plc.

NVON. 2007. Binas. English Edition. Groningen, The Netherlands. Wolters–Noordhoff.

Royal Society of Chemistry. 2002. Royal Society of Chemistry Electronic Data Book CD-Rom. London, UK. Reproduced by permission of The Royal Society of Chemistry.

For tables 17 and 18, in addition to the sources above, the data were informed by the following.

Aylward, G and Findlay, T. 2002. SI Chemical Data. 5th Edition. Queensland, Australia. John Wiley & Sons.

Clugston, M and Flemming, R. 2000. Advanced Chemistry. Oxford, UK. Oxford University Press.

Morrison, RT and Boyd, RN. 1987. Organic Chemistry. 5th Edition. Boston, Massachusetts, USA. Allyn and Bacon, Inc.

24

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