Pushing Electrons
Pushing Electrons
4th Edition
ISBN: 9781133951889
Author: Weeks, Daniel P.
Publisher: Cengage Learning
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Chapter 3, Problem 32EQ
Interpretation Introduction

Interpretation:

The products of protonation on the epoxide oxygen by hydronium ion are to be written.

Concept Introduction:

The simultaneous making and breaking of sigma bonds occurs also between a neutral nucleophile or base with pushable electrons and a positively charged species that can act as a receptor.

Pushing Electrons, Chapter 3, Problem 32EQ

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Hydration of aldehydes and ketones can be catalyzed by acid or base. Bases catalyze hydration by: protonating the carbonyl oxygen making the carbonyl group more electrophilic employing hydroxide ion, which is a better nucleophile than water making the carbonyl group less electrophilic shifting the equilibrium position of the reaction to favor products
H3C CH3 H3C NA C→XT Br Br₂ CH₂Cl₂ H3C Electrophilic addition of bromine, Br₂, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH₂Cl₂. CH3 Br In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br CH3 H3C CH3
please complete the reaction
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