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Using the table of bond dissociation enthalpies, calculate AH for the reaction A

ID: 509159 • Letter: U

Question

Using the table of bond dissociation enthalpies, calculate AH for the reaction A. (Use the entries for propene and propenyl halides for the calculation of cyclohexene and cyclohexenyl halides, respectively. Pay attention to the algebraic sign of your answer Table of bond dissociation enthalpies C-H bond BDE (kJ/mol) C-X bond BDE (kJ/mol) X2 and HXbonds BDE (kJ/mol) CH3-H CH3-Br 301 Cl-Cl 439 247 Br-Br C2H5-H C2H5-Br 301 192 422 (CH3)2CH-Br 309 LI (CH3)2CH-H 414 151 (CH3) 3C-H 405 (CH3)3 C-Br 305 H-Cl 431 CH2 CHCH2-H 372 CH2 CEICH2-Br 247 H-Br 368 CH2-CH-H 464 H-I 297 Br H Br HBr AH kJ/mol

Explanation / Answer

For the first propagation step

one allylic C-H bond is broken so energy required = +372 kJ

one H-Br bond is formed = -368 kJ

Thus DElta H of the reaction = +372 -368

= +4 kJ

Endothermic reaction.

second propagation step

one allyl C -Br bond formed = -247 kJ

one Br-Br bond is broken = +192 kJ

thus delta H of the reaction = -247-192

= -55 kJ

Thus the first step of propagation (endothermic reaction) is the rate determining step.

The total delta H of the reaction = sum of delta H of both the steps

= +4 -51 KJ

= -47 kJ