Chapter 8: Problem 4
Write a pair of chain propagation steps for the radical bromination of propane to give 1-bromopropane, and calculate \(\Delta H^{\circ}\) for each propagation step and for the overall reaction.
Chapter 8: Problem 4
Write a pair of chain propagation steps for the radical bromination of propane to give 1-bromopropane, and calculate \(\Delta H^{\circ}\) for each propagation step and for the overall reaction.
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Get started for freeWater and dichloromethane are insoluble in each other. When each is added to a test tube, two layers form. Which layer is water and which is dichloromethane?
An important use of radical-chain reactions is in the polymerization of ethylene and substituted ethylene monomers such as propene, vinyl chloride (the synthesis of which was discussed in Section \(7.6\) along with its use in the synthesis of poly(vinyl chloride), \((\mathrm{PVC}))\), and styrene. The reaction for the formation of PVC, where \(n\) is the number of repeating units and is very large, follows. (a) Give a mechanism for this reaction (see Chapter 29). (b) Give a similar mechanism for the formation of poly(styrene) from styrene. Which end of the styrene double bond would you expect R- to attack? Why?
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 \(\left(\mathrm{C}_{7} \mathrm{~F}_{14}\right.\), MW 350) 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.
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 major product formed when methylenecyclohexane is treated with NBS in dichloromethane is 1-(bromomethyl)-cyclohexene. Account for the formation of this product.
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