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 16, Problem 55P
Interpretation Introduction

Interpretation:

The reactants of the given reactions are to be deduced.

Concept introduction:

Ketones and alkenes react with meta chloro perbenzoic acid to form esters and epoxides, the reaction is named as Baeyer Villiger oxidation. If a ketone is cyclic then it forms lactones.

The Grignard reagent or RMgX is a reagent that can be prepared from an alkyl halide and magnesium in the ether. It adds on the alkyl group to the carbonyl moiety and converts the aldehydes or ketones into alcohols. Cyanide reacts with RMgX to form ketones. It reacts with carbon dioxide to form carboxylic acid.

Wittig reagent or alkyl phosphonium ylide, in presence of base, reacts with carbonyl to form an alkene.

Alcohols can be converted to ethers by the reaction of an alkyl halide with sodium hydride.

Alcohols can be converted to alkyl halides by their reaction with mesyl chloride.

Alkyl halides react with potassium cyanide to form nitriles.

Carbonyl compound reacts with hydrazine and KOH to form alkane, via hydrazone formation. This is named as Wolff Kishner reduction.

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Write equations showing how to prepare each of the following from benzene or toluene and any necessary organic or inorganic reagents. If an ortho, para mixture is formed in any step of your synthesis, assume that you can separate the two isomers. (a) Isopropylbenzene (b) p-Isopropylbenzenesulfonic acid (c) 2-Bromo-2-phenylpropane (d) 4-tert-Butyl-2-nitrotoluene (e) m-Chloroacetophenone (f) p-Chloroacetophenone (g) 3-Bromo-4-methylacetophenone (h) 2-Bromo-4-ethyltoluene (i) 3-Bromo-5-nitrobenzoic acid (j) 2-Bromo-4-nitrobenzoic acid (k) 1-Phenyloctane (l) 1-Phenyl-1-octene (m) 1-Phenyl-1-octyne (n) 1,4-Di-tert-butyl-1,4-cyclohexadiene
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Chapter 16 Solutions

Organic Chemistry

Ch. 16 - Prob. 11PPCh. 16 - Practice Problem 16.12 What product would be...Ch. 16 - Prob. 13PPCh. 16 - Practice Problem 16.14 Dihydropyran reacts readily...Ch. 16 - Practice Problem 16.15 Show how you might use...Ch. 16 - Practice Problem 16.16 (a) Show how you might...Ch. 16 - Practice Problem 16.17 In addition to...Ch. 16 - Practice Problem 16.18 Triphenylphosphine can be...Ch. 16 - Prob. 19PPCh. 16 - PRACTICE PROBLEM 16.20 Give the structure of the...Ch. 16 - PRACTICE PROBLEM 16.21 What would be the major...Ch. 16 - Prob. 22PCh. 16 - 16.23 Write structural formulas for the products...Ch. 16 - Give structural formulas for the products formed...Ch. 16 - 16.25 What products would be obtained when...Ch. 16 - Predict the major organic product from each of the...Ch. 16 - 16.27 Predict the major product from each of the...Ch. 16 - 16.28 Predict the major product from each of the...Ch. 16 - Prob. 29PCh. 16 - 16.30 Write detailed mechanisms for each of the...Ch. 16 - Prob. 31PCh. 16 - Prob. 32PCh. 16 - Show how you would convert benzaldehyde into each...Ch. 16 - 16.34 Show how ethyl phenyl ketone could be...Ch. 16 - Show how benzaldehyde could be synthesized from...Ch. 16 - Give structures for compounds AE. Cyclohexanol...Ch. 16 - Prob. 37PCh. 16 - Prob. 38PCh. 16 - Prob. 39PCh. 16 - Prob. 40PCh. 16 - Prob. 41PCh. 16 - Prob. 42PCh. 16 - 16.43 The structure of the sex pheromone...Ch. 16 - Provide reagents that would accomplish each of the...Ch. 16 - Write a detailed mechanism for the following...Ch. 16 - Prob. 46PCh. 16 - Dutch elm disease is caused by a fungus...Ch. 16 - Prob. 48PCh. 16 - Compounds W and X are isomers; they have the...Ch. 16 - Compounds Y and Z are isomers with the molecular...Ch. 16 - Compound A (C9H18O) forms a phenylhydrazone, but...Ch. 16 - Compound B (C8H12O2) shows a strong carbonyl...Ch. 16 - Prob. 53PCh. 16 - Prob. 54PCh. 16 - Prob. 55PCh. 16 - (a) What would be the frequencies of the two...Ch. 16 - Prob. 57PCh. 16 - Prob. LGP
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