Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 20, Problem 12PP
Interpretation Introduction

Interpretation:

The synthesis of mtoluidine from toluene and the synthesis of mchlorotoludine, mbromotoludine, miodotoludine, mtolunitrile, and mtoluic acid are to be shown.

Concept introduction:

舧 Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.

舧 Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.

舧 Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

舧 Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.

舧 Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.

舧 The reaction in which hydrogen is added to the compound in the presence of catalyst is known as hydrogenation.

舧 The number of moles of hydrogen absorbed will be equal to the number of double bonds.

舧 The reaction in which a halide group is removed to form an alkene is called dehydrohalogenation.

舧 This reaction in which CO2 is removed from alkene molecules is called decarboxylation reaction.

舧 Acetylation refers to the process of introducing an acetyl group into a compound. A reaction involving te replacement of the hydrogen atom of a hydroxyl or amine group with an acetyl group. Acetic anhydride is commonly used as an acetylating agent.

舧 Piperidine is a heterocyclic amine containing six membered rings, which contains five methyl groups and one nitrogen atom.

舧 Nitrous acid (HNO2) is produced by the reaction of strong hydrochloric acid (HCl) and aqueous sodium nitrite (NaNO2) at a low temperature.

舧 Nitrous acid is used to make diazonium salts from amines.

舧 The reaction of primary aryl amine with nitrous acid gives arenediazonium salt.

舧 The nitro compounds formed by direct nitration reaction undergo reduction to give primary aryl amine.

舧 The diazonium group is easily replaced by another group.

舧 In Sandmeyer reaction, arenediazonium salt reacts with cuprous bromide, cuprous cyanide, and cuprous chloride, and the replacement of diazonium group by Br >, CN >, Cl takes place.

舧 The replacement of diazonium group by I takes place when arenediazonium salt reacts with potassium iodide.

舧 The replacement of diazonium group by H takes place when arenediazonium salt reacts with hypophosphorus acid H3PO2 >.

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Chapter 20 Solutions

Organic Chemistry

Ch. 20 - Practice Problem 20.11 In the preceding examples...Ch. 20 - Prob. 12PPCh. 20 - Prob. 13PPCh. 20 - Practice Problem 20.14 Outline a synthesis of...Ch. 20 - Prob. 15PPCh. 20 - Prob. 16PPCh. 20 - Prob. 17PPCh. 20 - Prob. 18PPCh. 20 - Prob. 19PCh. 20 - 20.20 Give common or systematic names for each of...Ch. 20 - Which is the most basic nitrogen in each compound?...Ch. 20 - Prob. 22PCh. 20 - Prob. 23PCh. 20 - Show how you might synthesize each of the...Ch. 20 - Prob. 25PCh. 20 - 20.26 Provide the major organic product from each...Ch. 20 - Prob. 27PCh. 20 - 20.28 What products would you expect to be formed...Ch. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - Prob. 31PCh. 20 - Write equations for simple chemical rests or state...Ch. 20 - Prob. 33PCh. 20 - Explain the following, including mention of key...Ch. 20 - 20.35 Provide a detailed mechanism for each of the...Ch. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - 20.40 Give structures for compounds R-W: Ch. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Diethylpropion (shown here) is a compound used in...Ch. 20 - Prob. 44PCh. 20 - 20.45 Compound W is soluble in dilute aqueous HCI...Ch. 20 - 20.46 Propose structures for compounds X, Y, and...Ch. 20 - Compound A(C10H15N) is soluble in dilute HCI. The...Ch. 20 - Prob. 48PCh. 20 - Prob. 49PCh. 20 - For each of the following, identify the product...Ch. 20 - 20.51 Develop a synthesis for the following...Ch. 20 - 20.52 When phenyl isochiocyanatc, , is reduced...Ch. 20 - Prob. 53PCh. 20 - 20.54 Propose a mechanism that can explain the...Ch. 20 - When acetone is treated with anhydrous ammonia in...Ch. 20 - Prob. 56P
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