The reagents and experimental conditions to carry out the synthesis of procaine from the given three compoubds has to be shown. Concept introduction: Acid-catalyzed ring-opening of epoxide : The epoxide ring is protonated and the nucleophile attack depends on the electronic or steric effect (nature of epoxide). Base catalyzed ring opening of epoxide: The nucleophile will attack at the less substituted position under basic conditions and then the alkoxide ion gets proton from alcohol which form the product.

Question

Kumada Coupling: 1. m-Diisobutylbenzene below could hypothetically be synthesized by Friedel-Crafts reaction. Write out the reaction with a mechanism and give two reasons why you would NOT get the desired product. Draw the reaction (NOT a mechanism) for a Kumada coupling to produce the molecule above from m-dichlorobenzene. Calculate the theoretical yield for the reaction in question 2 using 1.5 g of p-dichlorobenzene and 3.0 mL isobutyl bromide. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?

Answer 1

Question

Chapter 18, Problem 18.42P

Interpretation Introduction

Interpretation:

The reagents and experimental conditions to carry out the synthesis of procaine from the given three compoubds has to be shown.

Concept introduction:

Acid-catalyzed ring-opening of epoxide: The epoxide ring is protonated and the nucleophile attack depends on the electronic or steric effect (nature of epoxide).

Base catalyzed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions and then the alkoxide ion gets proton from alcohol which form the product.

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