Problem: Consider the formation of an amide from an ester.  An estimate of the overall enthalpy of this transformation using the bond dissociation energies given below is  1) 13 kcal/mol     2) – 4 kcal/mol     3) – 17 kcal/mol 4) 7 kcal/mol    5) –11 kcal/mol Bond dissociation energies (kcal/mol)  C–H                                      99 C–O                                      79 C–C                                      85 C–N                                      66 R2N–H                                 92 C=O                                    175 C=N                                    145 RO–H                                 109

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Problem Details

Consider the formation of an amide from an ester. 

An estimate of the overall enthalpy of this transformation using the bond dissociation energies given below is 

1) 13 kcal/mol     2) – 4 kcal/mol     3) – 17 kcal/mol 4) 7 kcal/mol    5) –11 kcal/mol

Bond dissociation energies (kcal/mol) 

C–H                                      99

C–O                                      79

C–C                                      85

C–N                                      66

R2N–H                                 92

C=O                                    175

C=N                                    145

RO–H                                 109

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