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Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 24.SE, Problem 34MP
The diazotization of aniline first involves the formation of NO+ (nitrosonium ion) by the dehydration of nitrous acid with sulfuric acid. The aniline nitrogen then acts as a nucleophile and eventually loses water. Propose a mechanism for the formation of the dizaonium salt of aniline. Use curved arrows to show all electron movement.
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1- Convert Aniline to Diazonium Salt
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3- Convert Aniline to carboxylic acid
b) The Wolf-Kishner reduction is a reaction used in Organic Chemistry to convert
carbonyl functionalities into methylene group. The reaction was used to convert
an aldehyde or ketone to an alkane using hydrazine, base and thermal conditions.
The mechanism begins with the attack of hydrazine of the aldehyde or ketone.
Stage 1: The reaction of aldehyde/ketone with hydrazine to produce hydrazine
Stage 2: Reaction with the base and heat to convert hydrozone to alkane
Write the mechanism of the reaction.
H3C
OH
OH
H+
CH3
Esters can be synthesized by an acid-catalyzed nucleophilic acyl substitution between an alcohol and a carboxylic acid; this process is called the Fischer
esterification reaction. Because the alcohol oxygen is a poor nucleophile, the carbonyl carbon is made a better electrophile by protonation of the
carbonyl oxygen. The steps of the synthesis are all reversible. The reaction is generally driven to completion by using an excess of the liquid alcohol as a
solvent, or by distilling off the product as it forms.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
CIX
10-4
H₂O
CH3
H₂O
CH3
Chapter 24 Solutions
Organic Chemistry
Ch. 24.1 - Name the following compounds:Ch. 24.1 - Prob. 2PCh. 24.1 - Prob. 3PCh. 24.3 - Prob. 4PCh. 24.3 - The benzylammonium ion (C6H5CH2NH3+) has pKa =...Ch. 24.4 - Prob. 6PCh. 24.5 - Prob. 7PCh. 24.6 - Prob. 8PCh. 24.6 - Prob. 9PCh. 24.6 - Show two methods for the synthesis of dopamine, a...
Ch. 24.6 - Prob. 11PCh. 24.6 - Prob. 12PCh. 24.6 - Prob. 13PCh. 24.7 - Prob. 14PCh. 24.7 - Prob. 15PCh. 24.8 - Prob. 16PCh. 24.8 - Propose syntheses of the following compounds from...Ch. 24.8 - How would you prepare the following compounds from...Ch. 24.8 - Prob. 19PCh. 24.9 - Draw an orbital picture of thiazole. Assume that...Ch. 24.9 - Prob. 21PCh. 24.9 - Prob. 22PCh. 24.9 - Which nitrogen atom in the hallucinogenic indole...Ch. 24.9 - Prob. 24PCh. 24.10 - Prob. 25PCh. 24.SE - Name the following amines, and identify each as...Ch. 24.SE - The following compound contains three nitrogen...Ch. 24.SE - Name the following amine, including R, S...Ch. 24.SE - Prob. 29VCCh. 24.SE - Predict the product(s) for each reaction below and...Ch. 24.SE - Predict the product(s) and provide the complete...Ch. 24.SE - Prob. 32MPCh. 24.SE - Predict the product(s) and provide the mechanism...Ch. 24.SE - The diazotization of aniline first involves the...Ch. 24.SE - Prob. 35MPCh. 24.SE - Prob. 36MPCh. 24.SE - Prob. 37MPCh. 24.SE - Prob. 38MPCh. 24.SE - Choline, a component of the phospholipids in cell...Ch. 24.SE - Prob. 40MPCh. 24.SE - -Amino acids can be prepared by the Strecker...Ch. 24.SE - Prob. 42MPCh. 24.SE - Prob. 43MPCh. 24.SE - Prob. 44MPCh. 24.SE - Propose a mechanism for the following reaction:Ch. 24.SE - Prob. 46MPCh. 24.SE - Name the following compounds:Ch. 24.SE - Prob. 48APCh. 24.SE - Prob. 49APCh. 24.SE - Prob. 50APCh. 24.SE - Histamine, whose release in the body triggers...Ch. 24.SE - Prob. 52APCh. 24.SE - Prob. 53APCh. 24.SE - Prob. 54APCh. 24.SE - Prob. 55APCh. 24.SE - Prob. 56APCh. 24.SE - Prob. 57APCh. 24.SE - Prob. 58APCh. 24.SE - Prob. 59APCh. 24.SE - Prob. 60APCh. 24.SE - Show the products from reaction of p-bromoaniline...Ch. 24.SE - Prob. 62APCh. 24.SE - How would you prepare the following compounds from...Ch. 24.SE - Prob. 64APCh. 24.SE - Phenacetin, a substance formerly used in...Ch. 24.SE - Prob. 66APCh. 24.SE - Draw the structure of the amine that produced the...Ch. 24.SE - Fill in the missing reagents a-e in the following...Ch. 24.SE - Prob. 69APCh. 24.SE - Prob. 70APCh. 24.SE - Deduce the structure of the compound with formula...Ch. 24.SE - Prob. 72APCh. 24.SE - Prob. 73APCh. 24.SE - Prob. 74APCh. 24.SE - Prob. 75APCh. 24.SE - Prob. 76APCh. 24.SE - Propose a structure for the product with formula...Ch. 24.SE - Prob. 78APCh. 24.SE - Prob. 79APCh. 24.SE - Prob. 80APCh. 24.SE - Prob. 81APCh. 24.SE - Prob. 82APCh. 24.SE - Prob. 83APCh. 24.SE - Prob. 84AP
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