Cambridge International Advanced Subsidiary and Advanced Level in Chemistry (9701)

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1 Cambridge International Advanced Subsidiary and Advanced Level in Chemistry (9701) For use from 2016 in all papers for the above syllabus, except practical examinations. CSTxxx **

2 Contents: Tables of Chemical Data Page no. 1 Important values, constants and standards 3 2 Ionisation energies (1 st, 2 nd, 3 rd and 4 th ) of selected elements in kj mol Bond energies 5 4 Standard electrode potential and redox potentials, E at 298K (25 C) 7 5 Atomic and ionic radii 10 6 Typical proton ( 1 H) chemical shift values (δ) relative to TMS = Typical carbon ( 13 C) chemical shift values (δ) relative to TMS = Characteristic infra-red absorption frequencies for some selected bonds 14 9 The orientating effect of groups in aromatic substitution reactions Names, structures and abbreviations of some amino acids The Periodic Table of Elements 17 2

3 1 Important values, constants and standards molar gas constant R = 8.31 J K 1 mol 1 the Faraday constant F = C mol 1 the Avogadro constant L = mol 1 the Planck constant h = J s speed of light in a vacuum c = m s 1 rest mass of proton, H 1 1 m p = kg rest mass of neutron, n 0 1 m n = kg rest mass of electron, 0 e 1 m e = kg electronic charge e = C molar volume of gas V m = 22.4 dm 3 mol 1 at s.t.p. V m = 24.0 dm 3 mol 1 under room conditions (where s.t.p. is expressed as 101 kpa, approximately, and 273 K [0 C]) ionic product of water K w = mol 2 dm 6 (at 298 K [25 C]) specific heat capacity of water = 4.18 kj kg 1 K 1 (= 4.18 J g 1 K 1 ) 3

4 2 Ionisation energies (1st, 2nd, 3rd and 4th) of selected elements, in kj mol 1 Proton number First Second Third Fourth H He Li Be B C N O F Ne Na Mg Al Si P S Cl Ar K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Br Rb Sr Ag I Cs Ba

5 3 Bond Energies 3(a) Bond energies in diatomic molecules (these are exact values) Homonuclear Heteronuclear Bond Energy / kj mol 1 Bond Energy / kj mol 1 H H 436 H F 562 D D 442 H Cl 431 N N 944 H Br 366 O=O 496 H I 299 P P 485 C O 1077 S=S 425 F F 158 Cl Cl 242 Br Br 193 I I 151 5

6 3(b) Bond energies in polyatomic molecules (these are average values) Homonuclear Heteronuclear Bond Energy / kj mol 1 Bond Energy / kj mol 1 C C 350 C H 410 C=C 610 C Cl 340 C C 840 C Br 280 C. C (benzene) 520 C I 240 N N 160 C N 305 N=N 410 C=N 610 O O 150 C N 890 Si Si 222 C O 360 P P 200 C=O 740 S S 264 C=O in CO N H 390 N Cl 310 O H 460 Si Cl 359 Si H 320 Si O (in SiO 2 (s)) 460 Si=O (in SiO 2 (g)) 640 P H 320 P Cl 330 P O 340 P=O 540 S H 347 S Cl 250 S O 360 S=O 500 6

7 4 Standard electrode potential and redox potentials, E at 298 K (25 o C) For ease of reference, two tables are given: (a) an extended list in alphabetical order; (b) a shorter list in decreasing order of magnitude, i.e. a redox series. (a) E in alphabetical order Electrode reaction E / V Ag + + e Ag Al e Al 1.66 Ba e Ba 2.90 Br 2 + 2e 2Br Ca e Ca 2.87 Cl 2 + 2e 2Cl HOCl + 2H + + 2e Cl 2 + 2H 2 O Cl O + H 2 O + 2e Cl + 2OH Co e Co 0.28 Co 3+ + e Co [Co(NH 3 ) 6 ] e Co + 6NH Cr e Cr 0.91 Cr e Cr 0.74 Cr 3+ + e Cr Cr 2 O H + + 6e 2Cr H 2 O Cu + + e Cu Cu e Cu Cu 2+ + e Cu [Cu(NH 3 ) 4 ] e Cu + 4NH F 2 + 2e 2F Fe e Fe 0.44 Fe e Fe 0.04 Fe 3+ + e Fe [Fe(CN) 6 ] 3 + e [Fe(CN) 6 ] Fe(OH) 3 + e Fe(OH) 2 + OH H + + 2e H H 2 O + 2e H 2 + 2OH 0.83 I 2 + 2e 2I K + + e K 2.92 Li + + e Li 3.04 Mg e Mg 2.38 Mn e Mn 1.18 Mn 3+ + e Mn MnO 2 + 4H + + 2e Mn H 2 O MnO 4 + e 2 MnO MnO 4 + 4H + + 3e MnO 2 + 2H 2 O MnO 4 + 8H + + 5e Mn H 2 O NO 3 + 2H + + e NO 2 + H 2 O NO 3 + 3H + + 2e HNO 2 + H 2 O NO H + + 8e NH H 2 O

8 Electrode reaction E / V Na + + e Na 2.71 Ni e Ni 0.25 [Ni(NH 3 ) 6 ] e Ni + 6NH H 2 O 2 + 2H + + 2e 2H 2 O HO 2 + H 2 O + 2e 3OH O 2 + 4H + + 4e 2H 2 O O 2 + 2H 2 O + 4e 4OH O 2 + 2H + + 2e H 2 O O 2 + H 2 O + 2e HO 2 + OH 0.08 Pb e Pb 0.13 Pb e Pb PbO 2 + 4H + + 2e Pb H 2 O SO H + + 2e SO 2 + 2H 2 O S 2 O e 2 2SO S 4 O e 2 2S 2 O Sn e Sn 0.14 Sn e Sn V e V 1.20 V 3+ + e V VO H + + e V 3+ + H 2 O VO H + + e VO 2+ + H 2 O VO 3 + 4H + + e VO H 2 O Zn e Zn 0.76 All ionic states refer to aqueous ions but other state symbols have been omitted. 8

9 (b) E in decreasing order of oxidising power (a selection only see also the extended alphabetical list on the previous pages) Electrode reaction E / V F 2 + 2e 2F S 2 O e 2 2SO H 2 O 2 + 2H + + 2e 2H 2 O MnO 4 + 8H + + 5e Mn H 2 O PbO 2 + 4H + + 2e Pb H 2 O Cl 2 + 2e 2Cl Cr 2 O H + + 6e 2Cr H 2 O O 2 + 4H + + 4e 2H 2 O Br 2 + 2e 2Br ClO + H 2 O + 2e Cl + 2OH NO H + + 8e NH H 2 O NO 3 + 2H + + e NO 2 + H 2 O Ag + + e Ag Fe 3+ + e Fe I 2 + 2e 2I O 2 + 2H 2 O + 4e 4OH Cu e Cu SO H + + 2e SO 2 + 2H 2 O Sn e Sn S 4 O e 2 2S 2 O H + + 2e H Pb e Pb 0.13 Sn e Sn 0.14 Fe e Fe 0.44 Zn e Zn H 2 O + 2e H 2 + 2OH 0.83 V e V 1.20 Mg e Mg 2.38 Ca e Ca 2.87 K + + e K

10 5 Atomic and ionic radii (a) Period 1 atomic / nm ionic / nm single covalent H H van der Waals He (b) Period 2 atomic / nm ionic / nm metallic Li Li Be Be single covalent B B C C C N N O O F F van der Waals Ne (c) Period 3 atomic / nm ionic / nm metallic Na Na Mg Mg Al Al single covalent Si Si P P S S Cl Cl van der Waals Ar (d) Group 2 atomic / nm ionic / nm metallic Be Be Mg Mg Ca Ca Sr Sr Ba Ba Ra Ra

11 (e) Group 14 atomic / nm ionic / nm single covalent C C Si Si Ge Ge metallic Sn Sn Pb Pb (f) Group 17 atomic / nm ionic / nm single covalent F F Cl Cl Br Br I I At (g) First row transition elements atomic / nm ionic / nm metallic Sc Sc Ti Ti Ti V V V Cr Cr Cr Mn Mn Mn Fe Fe Fe Co Co Co Ni Ni Ni Cu Cu Zn Zn

12 6 Typical proton ( 1 H) chemical shift values (δ) relative to TMS = 0 type of proton environment of proton example structures chemical shift range (δ) alkane CH 3, CH 2, >CH alkyl next to C=O CH 3 C=O, CH 2 C=O, >CHC=O alkyl next to aromatic ring alkyl next to electronegative atom CH 3 Ar, CH 2 Ar, >CHAr CH 3 O, CH 2 O, CH 2 Cl, >CHBr CH attached to alkyne CH attached to alkene =CH 2, =CH attached to aromatic ring H O aldehyde R C H alcohol ROH O-H (see note below) phenol OH O carboxylic acid R C O H alkyl amine RNH N-H (see note below) aryl amine NH O R C amide N H Note: δ values for O-H and N-H protons can vary depending on solvent and concentration 12

13 7 Typical carbon ( 13 C) chemical shift values (δ) relative to TMS = 0 hybridisation of the carbon atom environment of carbon atom example structures chemical shift range (δ) sp 3 alkyl CH 3, CH 2, CH< 050 sp 3 next to alkene/arene CH 2 C=C, CH sp 3 next to carbonyl/carboxyl CH 2 COR, CH 2 CO 2 R 2550 sp 3 next to nitrogen CH 2 NH 2, CH 2 NR 2, CH 2 NHCO 3065 sp 3 next to chlorine (-CH 2 -Br and -CH 2 -I are in the same range as alkyl) CH 2 Cl 3060 sp 3 next to oxygen CH 2 OH, CH 2 OCO 5070 C C sp 2 alkene or arene >C=C<, C C C C sp 2 carboxyl RCO 2 H, RCO 2 R sp 2 carbonyl RCHO, RCOR sp alkyne RC C 6585 sp nitrile RC N

14 8 Characteristic infra-red absorption frequencies for some selected bonds bond functional groups containing the bond absorption range (in wavenumbers) /cm 1 appearance of peak (s = strong, w = weak) CO alcohols, ethers, esters s C=C aromatic compounds, alkenes w unless conjugated C=O amides, ketones and aldehydes esters, s s s C C alkynes w unless conjugated C N nitriles w CH alkanes, CH 2 H alkenes/arenes, =CH s w NH amines, amides w OH carboxylic acids, RCO 2 H Hbonded alcohol, ROH free alcohol, ROH s and very broad s s and sharp 14

15 9 The orientating effect of groups in aromatic substitution reactions. The position of the incoming group, Y, is determined by the nature of the group, X, already bonded to the ring, and not by the nature of the incoming group Y. X X Y + Y + H + X- groups that direct the incoming Y group to the 2- or 4- positions X- groups that direct the incoming Y group to the 3- position NH 2, NHR or NR 2 NO 2 OH or OR NH 3 NHCOR CH 3, alkyl Cl CN CHO, COR CO 2 H, CO 2 R 15

16 10 Names, structures and abbreviations of some amino acids structure of side chain R- in name 3-letter abbreviation 1-letter symbol R CH NH 2 CO 2 H alanine Ala A CH 3 aspartic acid Asp D HO 2 CCH 2 cysteine Cys C HSCH 2 glutamic acid Glu E HO 2 CCH 2 CH 2 glycine Gly G H lysine Lys K H 2 NCH 2 CH 2 CH 2 CH 2 phenylalanine Phe F CH 2 serine Ser S HOCH 2 tyrosine Tyr Y HO CH 2 valine Val V CH 3 CH CH 3 16

17 17 The Periodic Table of Elements Group Key 1 H hydrogen He helium Li lithium Be beryllium 9.0 atomic number atomic symbol name relative atomic mass 5 B boron C carbon N nitrogen O oxygen F fluorine Ne neon Na sodium Mg magnesium Al aluminium Si silicon P phosphorus S sulfur Cl chlorine Ar argon K potassium Ca calcium Sc scandium Ti titanium V vanadium Cr chromium Mn manganese Fe iron Co cobalt Ni nickel Cu copper Zn zinc Ga gallium Ge germanium As arsenic Se selenium Br bromine Kr krypton Rb rubidium Sr strontium Y yttrium Zr zirconium Nb niobium Mo molybdenum Tc technetium 44 Ru ruthenium Rh rhodium Pd palladium Ag silver Cd cadmium In indium Sn tin Sb antimony Te tellurium I iodine Xe xenon Cs caesium Ba barium lanthanoids 72 Hf hafnium Ta tantalum W tungsten Re rhenium Os osmium Ir iridium Pt platinum Au gold Hg mercury Tl thallium Pb lead Bi bismuth Po polonium 85 At astatine 86 Rn radon 87 Fr francium 88 Ra radium actinoids 104 Rf rutherfordium 105 Db dubnium 106 Sg seaborgium 107 Bh bohrium 108 Hs hassium 109 Mt meitnerium 110 Ds darmstadtium 111 Rg roentgenium 112 Cr copernicium 114 Fl flerovium 116 Lv livermorium lanthanoids 57 La lanthanum Ce cerium Pr praseodymium Nd neodymium Pm promethium 62 Sm samarium Eu europium Gd gadolinium Tb terbium Dy dysprosium Ho holmium Er erbium Tm thulium Yb ytterbium Lu lutetium actinoids 89 Ac actinium 90 Th thorium Pa protactinium U uranium Np neptunium 94 Pu plutonium 95 Am americium 96 Cm curium 97 Bk berkelium 98 Cf californium 99 Es einsteinium 100 Fm fermium 101 Md mendelevium 102 No nobelium 103 Lr lawrencium

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