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10+ - P1 PBU/OVY JWCL234-10 P2 PBU/OVY QC PBU/OVY T1 PBU...

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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-10 JWCL234-Solomons-v1 December 11, 2009 16:44 CONFIRMING PAGES 10 RADICAL REACTIONS SOLUTIONS TO PROBLEMS 10.1 (a) H H ( DH ° = 436) 2 H F 2( DH ° = 570) F F ( DH ° = 159) + + 595 kJ mol 1 is required for bond cleavage 1140 kJ mol 1 is evolved in formation of the bonds in 2 mol of HF H = + 595 1140 = − 545 kJ mol 1 (b) CH 3 H CH 3 F ( DH ° = 440) ( DH ° = 461) F F ( DH ° = 159) + H F ( DH ° = 570) + + 599 kJ mol 1 is required for bond cleavage 1031 kJ mol 1 is evolved in bond formation H = + 599 1031 = − 432 kJ mol 1 (c) CH 3 H CH 3 Cl ( DH ° = 440) ( DH ° = 352) Cl Cl ( DH ° = 243) + H Cl ( DH ° = 432) + + 683 kJ mol 1 is required for bond cleavage 784 kJ mol 1 is evolved in bond formation H = + 683 784 = − 101 kJ mol 1 (d) CH 3 H CH 3 Br ( DH ° = 440) ( DH ° = 293) Br Br ( DH ° = 193) + H Br ( DH ° = 366) + + 633 kJ mol 1 is required for bond cleavage 659 kJ mol 1 is evolved in bond formation H = + 633 659 = − 26 kJ mol 1 182
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-10 JWCL234-Solomons-v1 December 11, 2009 16:44 CONFIRMING PAGES RADICAL REACTIONS 183 (e) CH 3 H ( DH ° = 440) CH 3 I ( DH ° = 240) I I ( DH ° = 151) + H I ( DH ° = 29 8 ) + + 591 kJ mol 1 is required for bond cleavage 538 kJ mol 1 is evolved in bond formation H = + 591 538 = + 53 kJ mol 1 (f) CH 3 CH 2 H ( DH ° = 421) CH 3 CH 2 Cl ( DH ° = 353) Cl Cl ( DH ° = 243) + H Cl ( DH ° = 432) + + 664 kJ mol 1 is required for bond cleavage 785 kJ mol 1 is evolved in bond formation H = + 664 785 = − 121 kJ mol 1 (g) Cl Cl Cl ( DH °= 243) ( DH °= 413) ( DH °= 355) + H Cl ( DH ° = 432) + H + 656 kJ mol 1 is required for bond cleavage 787 kJ mol 1 is evolved in bond formation H = + 656 787 = − 131 kJ mol 1 (h) Cl Cl H ( DH ° = 349) Cl Cl H ( DH ° = 243) ( DH ° = 400) ( DH ° = 432) + + + 643 kJ mol 1 is required for bond cleavage 781 kJ mol 1 is evolved in bond formation H = + 643 781 = − 138 kJ mol 1 10.2 3 ° 2 ° 1 ° Methyl > > CH 3 > > > > 10.3 The compounds all have different boiling points. They could, therefore, be separated by careful fractional distillation. Or, because the compounds have different vapor pressures, they could easily be separated by gas chromatography. GC/MS (gas chromatography/mass spectrometry) could be used to separate the compounds as well as provide structural infor- mation from their mass spectra.
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-10 JWCL234-Solomons-v1 December 11, 2009 16:44 CONFIRMING PAGES 184 RADICAL REACTIONS 10.4 Their mass spectra would show contributions from the naturally occurring 35 Cl and 37 Cl isotopes. The natural abundance of 35 Cl is approximately 75% and that of 37 Cl is ap- proximately 25%. Thus, for CH 3 C1, containing only one chlorine atom, there will be an M . + peak and an M . + + 2 peak in roughly a 3 : 1 (0.75 : 0.25) ratio of intensities. For CH 2 Cl 2 there will be M . + , M . + + 2, and M . + + 4 peaks in roughly a 9 : 6 : 1 ratio, respectively.
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