Chapter 5 - Instructor Supplemental Solutions to Problems 2010 Roberts and Company Publishers Chapter 5 Addition Reactions of Alkenes Solutions to

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Instructor Supplemental Solutions to Problems © 2010 Roberts and Company Publishers Chapter 5 Addition Reactions of Alkenes Solutions to In-Text Problems 5.1 (a) The iodine is the electrophile, because it adds to the carbon of the double bond with fewer alkyl substituents. This result does seem to fit the electronegativity pattern for electrophilic addition, as nitrogen is considerably more electronegative than iodine. 5.2 (b) The reaction of Br 2 with 2-methyl-1-hexene follows the pattern in Eqs. 5.12 and 5.13 of the text. 5.4 The reaction of bromide ion as a nucleophile at the bromine of the bromonium ion would give a species that violates the octet rule. As we’ll learn, atoms in periods beyond the third can have more than an octet of electrons, and a structure such as this is not impossible. However, the octet rule can still be used as a guide to reactivity. A reaction of the bromide ion at the carbon of the bromonium ion gives a much more stable structure. 5.5 (b) In this part and in part (d), the double bond is symmetrically placed in the molecule; so, regioselectivity is not an issue. (d)
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INSTRUCTOR SUPPLEMENTAL SOLUTIONS TO PROBLEMS • CHAPTER 5 2 5.6 When 3-methyl-1-butene undergoes acid-catalyzed hydration, rearrangement occurs because carbocation intermediates are involved. (See the solution to Problem 4.35.) Oxymercuration–reduction gives addition without rearrangement because the intermediate is a cyclic mercurinium ion, which does not rearrange. 5.7 (b) 5.8 (b) In this part and in part (d), the double bond is symmetrically placed in the molecule; so, regioselectivity is not an issue. (d) 5.9 The products of hydroboration–oxidation are the same as the ones in parts (b) and (d) of Problem 5.5. In both, the alkene is symmetrical; consequently, regioselectivity has no meaning. In part (c), the carbons of the double bond have the same number of alkyl substituents; consequently, there is no reason to expect significant regioselectivity. However, the relative amounts of the products in each case could be different. 5.10 (b) 5.12 (a) Because cis- 2-butene is a symmetrical alkene, it reacts to give the same product in either oxymercuration- reduction or hydroboration-oxidation.
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INSTRUCTOR SUPPLEMENTAL SOLUTIONS TO PROBLEMS • CHAPTER 5 3 (b) Because 1-methylcyclohexene has different numbers of alkyl branches at the carbons of its double bond, it gives different products in the two reactions.
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This note was uploaded on 02/13/2010 for the course EGR 012 taught by Professor Witfield during the Spring '10 term at Aarhus Universitet.

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Chapter 5 - Instructor Supplemental Solutions to Problems 2010 Roberts and Company Publishers Chapter 5 Addition Reactions of Alkenes Solutions to

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