Consider the hydroboration and protonation steps shown here. In each case, (a) the electrophilic atom and (b) the alkene C that acquires positive or partial positive charge is to be labeled. Whether the electrophilic atoms add to the same alkene C in each case is to be explained. Concept introduction: For the reaction of the C=C bond with H-BH 2 , the electrophile is the B of the H-BH 2 because it lacks an octet and is electron poor. A C-B bond is formed from the end of C=C that is less crowded, and a new C-H bond is formed from the end of C=C that is more sterically crowded. The partial positive charge in the transition state forms on the more substituted carbon. For the reaction of the C=C with H-Cl , the electrophile is the H of the H-Cl . A C-H bond is formed so that the C + that is produced is on the more stable tertiary carbon. In both cases, the electrophilic atom adds to the same carbon of the C=C bond. In both cases, either the partial positive charge in the transition state or the positive charge in the carbocation intermediate forms on the carbon that is more substituted.

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Chapter 12, Problem 12.10YT

Interpretation Introduction

Interpretation:

Consider the hydroboration and protonation steps shown here. In each case, (a) the electrophilic atom and (b) the alkene C that acquires positive or partial positive charge is to be labeled. Whether the electrophilic atoms add to the same alkene C in each case is to be explained.

Concept introduction:

For the reaction of the C=C bond with H-BH2, the electrophile is the B of the H-BH2 because it lacks an octet and is electron poor. A C-B bond is formed from the end of C=C that is less crowded, and a new C-H bond is formed from the end of C=C that is more sterically crowded. The partial positive charge in the transition state forms on the more substituted carbon. For the reaction of the C=C with H-Cl, the electrophile is the H of the H-Cl. A C-H bond is formed so that the C+ that is produced is on the more stable tertiary carbon. In both cases, the electrophilic atom adds to the same carbon of the C=C bond. In both cases, either the partial positive charge in the transition state or the positive charge in the carbocation intermediate forms on the carbon that is more substituted.

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