a) Interpretation: The product expected from oxymercuration-demercuration of 1-pentene is to be given. Concept introduction: In the oxymercuration-demercuration process, in the first step, the electrophilic addition of Hg 2+ to the double bond in alkene takes place to give a mercurinium ion. In the next step the mercurinium ion reacts with water to yield an organomercury product. In the last step, NaBH 4 removes mercury from the organomercury product to give a more highly substituted alcohol, corresponding to Markovnikov regiochemistry, as the product. To give: The product expected from oxymercuration-demercuration of 1-pentene.

Question

Curved arrows are used to illustrate the flow of electrons. Using the provided structures, draw the curved arrows that epict the mechanistic steps for the proton transfer between a hydronium ion and a pi bond. Draw any missing organic structures in the empty boxes. Be sure to account for all lone-pairs and charges as well as bond-breaking and bond-making steps. 2 56°F Mostly cloudy F1 Drawing Arrows > Q Search F2 F3 F4 ▷11 H. H : CI: H + Undo Reset Done DELL

Answer 1

Question

Chapter 8.4, Problem 7P

Interpretation Introduction

a)

Interpretation:

The product expected from oxymercuration-demercuration of 1-pentene is to be given.

Concept introduction:

In the oxymercuration-demercuration process, in the first step, the electrophilic addition of Hg²⁺ to the double bond in alkene takes place to give a mercurinium ion. In the next step the mercurinium ion reacts with water to yield an organomercury product. In the last step, NaBH₄ removes mercury from the organomercury product to give a more highly substituted alcohol, corresponding to Markovnikov regiochemistry, as the product.

To give:

The product expected from oxymercuration-demercuration of 1-pentene.

Interpretation Introduction

b)

Interpretation:

The product expected from oxymercuration-demercuration of 2-methyl-2-pentene is to be given.

Concept introduction:

In the oxymercuration-demercuration process, in the first step, the electrophilic addition of Hg²⁺ to the alkene takes place to give a mercurinium ion. In the next step, the mercurinium ion reacts with water to yield an organomercury product. In the last step, reaction with NaBH₄ removes mercury from the organomercury product to give a more highly substituted alcohol, corresponding to Markovnikov regiochemistry, as the product.

To give:

The product expected from oxymercuration-demercuration of 2-methyl-2-pentene.

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