Organic Chemistry - Standalone book
Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 13, Problem 60DSP
Interpretation Introduction

Interpretation:

The methylanilines, which can be formed by the reaction of p-bromotoluene

with sodium amide in ammonia, are to be determined.

Concept introduction:

Aryl halides, in the presence of a strong base, undergo substitution via elimination-addition mechanism.

In the first step, the base abstracts a proton attached to the ring carbon atom which is adjacent to the halogen. The proton and the halogen from adjacent carbon atoms are eliminated, and triple bond is created. This intermediate formed is benzyne.

The nucleophile then adds to any one of the triple bonded carbon atoms.

If the ring has a substituent other than halogen, the position of the nucleophile with respect to the substituent can be at two different sites, thus producing two different isomers.

In the overall reaction, the halogen is substituted by the nucleophile in product, and in the other product, the nucleophile gets attached to an adjacent carbon atom.

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> You are trying to decide if there is a single reagent you can add that will make the following synthesis possible without any other major side products: 1. ☑ CI 2. H3O+ O Draw the missing reagent X you think will make this synthesis work in the drawing area below. If there is no reagent that will make your desired product in good yield or without complications, just check the box under the drawing area and leave it blank. Click and drag to start drawing a structure. Explanation Check ? DO 18 Ar B © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility
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Consider a solution of 0.00304 moles of 4-nitrobenzoic acid (pKa = 3.442) dissolved in 25 mL water and titrated with 0.0991 M NaOH. Calculate the pH at the equivalence point

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Organic Chemistry - Standalone book

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