Chapter 8: Problem 23
Using the table of bond dissociation enthalpies (Appendix 3), estimate the BDE of each indicated bond in cyclohexene.
Chapter 8: Problem 23
Using the table of bond dissociation enthalpies (Appendix 3), estimate the BDE of each indicated bond in cyclohexene.
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Get started for freeThere are three constitutional isomers with the molecular formula \(\mathrm{C}_{5} \mathrm{H}_{12}\). When treated with chlorine at \(300^{\circ} \mathrm{C}\), isomer A gives a mixture of four monochlorination products. Under the same conditions, isomer B gives a mixture of three monochlorination products and isomer \(C\) gives only one monochlorination product. From this information, assign structural formulas to isomers \(A, B\), and \(C\).
Write a pair of chain propagation steps for the radical bromination of propane to give 1-bromopropane. Then calculate \(\Delta H^{0}\) for each propagation step and for the overall reaction.
Name and draw structural formulas for all monochlorination products formed by treatment of 2 -methylpropane with \(\mathrm{Cl}_{2}\). Predict the major product based on the regioselectivity of the reaction of \(\mathrm{Cl}_{2}\) with alkanes.
The boiling point of methylcyclohexane \(\left(\mathrm{C}_{7} \mathrm{H}_{14}, \mathrm{MW} 98.2\right)\) is \(101^{\circ} \mathrm{C}\). The boiling point of perfluoromethylcyclohexane \(\left(\mathrm{C}_{7} \mathrm{~F}_{14}, \mathrm{MW} 350\right)\) is \(76^{\circ} \mathrm{C}\). Account for the fact that although the molecular weight of perfluoromethylcyclohexane is over three times that of methylcyclohexane, its boiling point is lower than that of methylcyclohexane.
The first chain propagation step of all radical halogenation reactions we considered in Section 8.5B was abstraction of hydrogen by the halogen atom to give an alkyl radical and HX, as for example $$ \mathrm{CH}_{3} \mathrm{CH}_{3}+\cdot \stackrel{\ddot{B r}}{*}: \longrightarrow \mathrm{CH}_{3} \mathrm{CH}_{2}^{*}+\underset{*}{\mathrm{HBr}}: $$ (a) Propose a second chain propagation step. Remember that a characteristic of chain propagation steps is that they add to the observed reaction. (b) Calculate the heat of reaction, \(\Delta H^{0}\), for each propagation step. (c) Compare the energetics and relative rates of the set of chain propagation steps in Section \(8.5 \mathrm{~B}\) with the set proposed here.
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