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Date: 20-1-2020
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Date: 12-5-2016
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Date: 26-1-2020
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Table 1.1 lists the heat of combustion data for some simple cycloalkanes. These cycloalkanes do not have the same molecular formula, so the heat of combustion per each CH2 unit present in each molecule is calculated (the fourth column) to provide a useful comparison. From the data, cyclopropane and cyclobutane have significantly higher heats of combustion per CH2, while cyclohexane has the lowest heat of combustion. This indicates that cyclohexane is more stable than cyclopropane and cyclobutane, and in fact, that cyclohexane has a same relative stability as long chain alkanes that are not cyclic. What causes this difference in stability or the strain in these two small cycloalkanes?
Cycloalkane (CH2)n |
CH2 Units n |
ΔH25º kcal/mole |
ΔH25º per CH2 Unit |
Ring Strain kcal/mole |
---|---|---|---|---|
Cyclopropane | n = 3 | 468.7 | 156.2 | 27.6 |
Cyclobutane | n = 4 | 611 | 153.6 | 26.4 |
Cyclopentane | n = 5 | 741.5 | 148.3 | 6.5 |
Cyclohexane | n = 6 | 882.1 | 147.0 | 0.0 |
Cycloheptane | n = 7 | 1035.4 | 147.9 | 6.3 |
Cyclooctane | n = 8 | 1186.0 | 148.2 | 9.6 |
Cyclononane | n = 9 | 1335.0 | 148.3 | 11.7 |
Cyclodecane | n = 10 | 1481 | 148.1 | 11.0 |
CH3(CH2)mCH3 | m = large | — | 147.0 | 0.0 |
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