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The bond lengths of carbon–carbon, carbon–nitrogen, carbon–oxygen, and nitrogen–nitrogen single, double, and triple bonds are listed in Table 8.5. Plot bond enthalpy (Table 8.4) versus bond length for these bonds (as in Figure 8.17). (a) Is this statement true: “The longer the bond, the stronger the bond”? (b) Order the relative strengths of C – C, C – N, C – O, and N – N bonds from weakest to strongest. (c) From your graph for the carbon–carbon bond in part (a), estimate the bond enthalpy of the hypothetical CC quadruple bond.

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Casey DurganLv2
21 May 2020
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Related questions

(a) Compare the bond enthalpies (Table 8.4) of the carbon–carbon single, double, and triple bonds to deduce an average π bond contribution to the enthalpy. What fraction of a single bond does this quantity represent? (b) Make a similar comparison of nitrogen–nitrogen bonds. What do you observe? (c) Write Lewis structures of N2H4, N2H2, and N2, and determine the hybridization around nitrogen in each case. (d) Propose a reason for the large difference in your observations of parts (a) and (b).

Consider benzene (C6H6) in the gas phase. (a) Write the reaction for breaking all the bonds in C6H6(g), and use data in Appendix C to determine the enthalpy change for this reaction. (b) Write a reaction that corresponds to breaking all the carbon–carbon bonds in C6H6(g). (c) By combining your answers to parts (a) and (b) and using the average bond enthalpy for C – H from Table 8.4, calculate the average bond enthalpy for the carbon–carbon bonds in C6H6(g). (d) Compare your answer from part (c) to the values for
C – C single bonds and C C double bonds in Table 8.4. Is benzene’s C – C bond enthalpy exactly halfway between them? If not, which bond type is more similar to that of benzene, CC single or CC double bonds?

If you do not write clearly, I will not accept your answer! You must write clearly!

The structure of 1,3-butadiene is usually written as H2C=CH–CH=CH2. The average bond lengths given in Table 9.2 in your textbook are: C–C of 154 pm and C=C of 133 pm. Explain the fact that the observed value of the distance between the two central carbon atoms in 1,3-butadiene is 146 pm.

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