Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 17, Problem 52P
Suggest a synthesis of ibuprofen (Section 5.11) from benzene, employing chloromethylation as one step. Chloromethylation is a special case of the Friedel–Crafts reaction in which a mixture of HCHO and HCL, in the presence of
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Acid-catalyzed dehydration of neopentyl alcohol, (CH3)3CCH2OH, yields 2-methyl-2- butene as the major product. Outline a mechanism showing all steps in its formation.
(a) The Friedel-Crafts reaction of benzene with 2-chloro-3-methylbutane in the presence of
AlCl3 occurs with a carbocation rearrangement. Give mechanistic explanation and the
product formed.
(b) Predict the product(s) will be formed from the following reactions:
(i) Bromination of p-methylbenzoic acid
(ii) Sulphonation of m-bromoanisole
(iii) Friedel-craft acylation of o-bromonitrobenzene
Give reasons for the following:
(i) p-nitrophenol is more acidic than p-methylphenol.
(ii) Bond length of C—O bond in phenol is shorter than that in methanol.
(iii) (CH3)3C—Br on reaction with sodium methoxide (Na+ _OCH3) gives alkene as the main product and not an ether.
Chapter 17 Solutions
Organic Chemistry
Ch. 17 - Practice Problem 17.1 Give an IUPAC systematic...Ch. 17 - Prob. 2PPCh. 17 - PRACTICE PROBLEM
17.3 Which acid of each pair...Ch. 17 - Practice Problem 17.3 Write structural formulas...Ch. 17 - Practice Problem 17.4
Show how each of the...Ch. 17 - Practice Problem 17.5
Show how you could prepare...Ch. 17 - Practice Problem 17.6
(a) Which of the carboxylic...Ch. 17 - Prob. 8PPCh. 17 - Prob. 9PPCh. 17 - Practice Problem 17.9
Esters can also be...
Ch. 17 - Prob. 11PPCh. 17 - Prob. 12PPCh. 17 - Practice Problem 17.12
What products would you...Ch. 17 - Practice Problem 17.13 (a) Provide the reagents...Ch. 17 - Prob. 15PPCh. 17 - Practice Problem 17.15 Using decarboxylation...Ch. 17 - Practice Problem 17.16 Diacyl peroxides, ,...Ch. 17 - Prob. 18PCh. 17 - Give an IUPAC systematic or common name for each...Ch. 17 - Prob. 20PCh. 17 - Prob. 21PCh. 17 - 17.21 What major organic product would you expect...Ch. 17 - Prob. 23PCh. 17 - Prob. 24PCh. 17 - Prob. 25PCh. 17 - Prob. 26PCh. 17 - 17.26 What products would you expect to obtain...Ch. 17 - Write structural formulas for the major organic...Ch. 17 - 17.28 Indicate reagents that would accomplish each...Ch. 17 - Write structural formulas for the major organic...Ch. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - Prob. 33PCh. 17 - 17.33 On heating,...Ch. 17 - Prob. 35PCh. 17 - Prob. 36PCh. 17 - 17.36 Show how pentanoic acid can be prepared from...Ch. 17 - 17.37 The active ingredient of the insect...Ch. 17 - Prob. 39PCh. 17 - Prob. 40PCh. 17 - Give stereochemical formulas for compounds AQ:...Ch. 17 - 17.41 -Glyceraldehyde can be transformed into...Ch. 17 - Prob. 43PCh. 17 - 17.44 Cantharidin is a powerful vesicant that can...Ch. 17 - Prob. 45PCh. 17 - 17.44 Given here are the NMR spectra and carbonyl...Ch. 17 - Compound X (C7H12O4) is insoluble in aqueous...Ch. 17 - 17.45 Compound Y dissolves slowly when warmed...Ch. 17 - Prob. 49PCh. 17 - Prob. 50PCh. 17 - 17.52 Starting with 1-naphthol, suggest an...Ch. 17 - Suggest a synthesis of ibuprofen (Section 5.11)...Ch. 17 - Prob. 53PCh. 17 - Prob. 54PCh. 17 - Prob. 1LGPCh. 17 - Prob. 2LGPCh. 17 - Prob. 3LGPCh. 17 - Prob. 4LGPCh. 17 - Prob. 1QCh. 17 - 17.2 Which of the following would yield...Ch. 17 - 17.3 Which reagent would serve as the basis for a...Ch. 17 - Prob. 4QCh. 17 - Complete the following synthesis.Ch. 17 - 17.6 Which of these acids would undergo...
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- (i) 1-Octanol can be synthesized via a reaction sequence that involves the reaction of the Schwartz's reagent Zr(n5-Cp)2(H)CI with stoichiometric quantities of 1-heptene followed by the reaction with reagent I, acidic work-up and subsequent reduction with reagent J. Give the names of reagents I and J. (ii) 1-Octanol can also be prepared from the reaction of the Schwartz's reagent with cis-2-hexene followed by reaction with reagents K and L and subsequent acidic work-up. Give the name of reagent K and give the chemical structure of reagent L. Give a detailed reaction mechanism.arrow_forwardIn two parts, outline the Electrophilic aromatic substitution for the nitration of benzene using nitric acid and sulfuric acid: A) In part I, using the curved arrow formalism, outline a mechanism for the formation of the nitronium ion, NO2+ starting from nitric acid, HNO3 and sulfuric acid, H2SO4. Do not forget to show all of the formal charges for each atom that is not zero in this mechanism. B) Starting from the nitronium ion that you generated in part “a” from above, outline the Electrophilic Aromatic Substitution of this ion with benzene.arrow_forward4) Aromatic compounds are among the most abundant and versatile in nature. From a synthetic point of view, these compounds, despite their stabilities, are quite useful and can undergo reactions under special conditions and by specific mechanisms, such as the Electrophilic Aromatic Substitution (SAE) and the Nucleophilic Aromatic Substitution (SNAr). Based on this, please answer the following items: (b) How would you prepare the following compounds starting from benzene? Explain the second in a different wayarrow_forward
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