The “plastic” explosive C-4, often used in action movies, contains the molecule cyclotrimethylenetrinitramine, which is often called RDX (for Royal Demolition eXplosive):
(a) Complete the Lewis structure for the molecule by adding unshared electron pairs where they are needed. (b) Does the Lewis structure you drew in part (a) have any resonance structures? If so, how many? (c) The molecule causes an explosion by decomposing into CO(g), N2(g), and H2O(g). Write a balanced equation for the decomposition reaction. (d) With reference to Table, which is the weakest type of bond in the molecule?
Table Average Bond Enthalpies(kJ/mol)
Single Bonds | |||||||
C–H | 413 | N–H | 391 | O–H | 463 | F–F | 155 |
C–C | 348 | N–N | 163 | O—O | 146 |
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C–N | 293 | N–O | 201 | O–F | 190 | Cl–F | 253 |
C–O | 358 | N–F | 272 | O–Cl | 203 | Cl–Cl | 242 |
C–F | 485 | N–Cl | 200 | O–l | 234 |
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C–Cl | 328 | N–Br | 243 | Br–F | 237 |
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C–Br | 276 | S–H | 339 | Br–Cl | 218 |
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C–l | 240 | H–H | 436 | S–F | 327 | Br–Br | 193 |
C–S | 259 | H–F | 567 | S–Cl | 253 |
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H–Cl | 431 | S—Br | 218 | I–Cl | 208 |
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Si–H | 323 | H–Br | 366 | S—S | 266 | I–Br | 175 |
Si–Si | 226 | H–l | 299 | I–l | 151 |
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Si–C | 301 |
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Si–O | 368 |
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Si–Cl | 464 |
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Multiple Bonds | |||||||
C=C | 614 | N=N | 418 | O=O | 495 |
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C≡C | 839 | N≡N | 941 |
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C=N | 615 | N=O | 607 | S=O | 523 |
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C≡N | 891 | S=S | 418 |
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C=O | 799 |
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C≡O | 1072 |
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, (e) Use average bond enthalpies to estimate the enthalpy change when 5.0 g of RDX decomposes.
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