Chapter 6: Problem 31
When 2-pentene is treated with \(\mathrm{Cl}_{2}\) in methanol, three products are formed. Account for the formation of each product (you need not explain their relative percentages).
Chapter 6: Problem 31
When 2-pentene is treated with \(\mathrm{Cl}_{2}\) in methanol, three products are formed. Account for the formation of each product (you need not explain their relative percentages).
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Get started for freeThe 2-propenyl cation appears to be a primary carbocation, and yet it is considerably more stable than a \(1^{\circ}\) carbocation such as the 1 -propyl cation. $$ \begin{array}{lc} \mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{2}^{+} & \mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}^{+} \\ \text {2-Propenyl cation } & \text { 1-Propyl cation } \end{array} $$ How would you account for the differences in the stability of the two carbocation?
Describe the stereochemistry of the bromohydrin formed in each reaction (each reaction is stereospecific). (a) cis-3-Hexene \(+\mathrm{Br}_{2} / \mathrm{H}_{2} \mathrm{O}\) (b) trans-3-Hexene \(+\mathrm{Br}_{2} / \mathrm{H}_{2} \mathrm{O}\)
Draw the alternative chair conformations for the product formed by the addition of bromine to 4-tert-butylcyclohexene. The Gibbs free energy differences between equatorial and axial substituents on a cyclohexane ring are \(21 \mathrm{~kJ}\) ( \(4.9 \mathrm{kcal}) / \mathrm{mol}\) for tert-butyl and \(2.0-2.6 \mathrm{~kJ}(0.48-0.62 \mathrm{kcal}) / \mathrm{mol}\) for bromine. Estimate the relative percentages of the alternative chair conformations you drew in the first part of this problem.
State the number and kind of stereoisomers formed when \((R)\)-s-methyl-1-pentene is treated with these reagents. Assume that the starting alkene is enantiomerically pure and optically active. Will each product be optically active or inactive?
Predict the organic product(s) of the reaction of 2-butene with each reagent. (a) \(\mathrm{H}_{2} \mathrm{O}\left(\mathrm{H}_{2} \mathrm{SO}_{4}\right)\) (b) \(\mathrm{Br}_{2}\) (c) \(\mathrm{Cl}_{2}\) (d) \(\mathrm{Br}_{2}\) in \(\mathrm{H}_{2} \mathrm{O}\) (e) \(\mathrm{HI}\) (f) \(\mathrm{Cl}_{2}\) in \(\mathrm{H}_{2} \mathrm{O}\) (g) \(\operatorname{Hg}(\mathrm{OAc})_{2}, \mathrm{H}_{2} \mathrm{O}\) (h) product (g) \(+\mathrm{NaBH}_{4}\)
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