Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
2nd Edition
ISBN: 9780393655551
Author: KARTY, Joel
Publisher: W. W. Norton & Company
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Chapter 7, Problem 7.13P
Interpretation Introduction

(a)

Interpretation:

The product for the given nucleophilic addition step with appropriate curved arrows is to be drawn.

Concept introduction:

In the nucleophilic addition step, the nucleophile adds to the polar π bond. The nucleophile is relatively electron rich, and the polar π bond is relatively electron poor. Thus, the curved arrow drawn from the nucleophile to the polar π bond represents the flow of electrons from an electron rich site to an electron poor site. The first curved arrow is drawn from the negatively charged atom of the nucleophile to the less electronegative atom of the polar π bond, and the second curved arrow is drawn from the less electronegative atom to the double bonded more electronegative atom. The atom bonded to metal acts as a nucleophile.

Interpretation Introduction

(b)

Interpretation:

The product for the given nucleophilic addition step with appropriate curved arrows is to be drawn.

Concept introduction:

In the nucleophilic addition step, the nucleophile adds to the polar π bond. The nucleophile is relatively electron rich, and the polar π bond is relatively electron poor. Thus, the curved arrow drawn from the nucleophile to the polar π bond represents the flow of electrons from an electron rich site to an electron poor site. The first curved arrow is drawn from the negatively charged atom of the nucleophile to the less electronegative atom of the polar π bond, and the second curved arrow is drawn from the less electronegative atom to the double bonded more electronegative atom. The atom bonded to metal acts as a nucleophile.

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Help please. Draw the curved arrow notation and products for the each elementary step described by the sequence shown here.Note that the products of each step should be used as the reactants in the next step, and you may need to draw in additional reagents as directed. Remember to click on each box to see step-specific instructions. Draw H3CH2C–, and then add the curved arrow notation showing a nucleophilic addition.
Bonus Question: If you deemed the previous reaction to be unsuccessfull, propose a reaction or synthesis that would successfully produce the desired ether product (shown again to the side). You may use any reaction you know of.
Draw the complete, detailed mechanism for the following reaction.

Chapter 7 Solutions

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)

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