Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 19.10C, Problem 19.13P
Interpretation Introduction
Interpretation:
The mechanism for the reaction of methoxide ion with
Concept introduction:
The reactions in which a nucleophile replaces a leaving group (for example, halide) on an
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We have considered nucleophilic aromatic substitution of pyridine at the 2-positionand 3-position but not at the 4-position. Complete the three possible cases by showingthe mechanism for the reaction of methoxide ion with 4-chloropyridine. Show how theintermediate is stabilized by delocalization of the charge onto the nitrogen atom
Pyridine reacts with hydroxide by nucleophilic aromatic substitution. Complete the mechanism by drawing curved arrows, the structure of the charged intermediate, and the structure of the major uncharged product.
All non‑bonding electrons must be shown, including those associated with charges.
Show the mechanism by which aromaticity is restored following electrophilic attack on benzene
Chapter 19 Solutions
Organic Chemistry (9th Edition)
Ch. 19.2A - Prob. 19.1PCh. 19.2B - Prob. 19.2PCh. 19.2B - Give correct names for the following amines:Ch. 19.3 - Prob. 19.4PCh. 19.4 - Prob. 19.5PCh. 19.6 - Rank each set of compounds in order of increasing...Ch. 19.8A - Prob. 19.7PCh. 19.8C - Prob. 19.8PCh. 19.8C - Prob. 19.9PCh. 19.8D - a. Show how fragmentation occurs to give the base...
Ch. 19.10B - Propose a mechanism for nitration of pyridine at...Ch. 19.10B - Prob. 19.12PCh. 19.10C - Prob. 19.13PCh. 19.10C - Prob. 19.14PCh. 19.11 - Propose a mechanism to show the individual...Ch. 19.11 - Prob. 19.16PCh. 19.12 - Give the products expected from the following...Ch. 19.13 - Prob. 19.18PCh. 19.13 - Prob. 19.19PCh. 19.14 - Prob. 19.20PCh. 19.15 - Prob. 19.21PCh. 19.15 - Prob. 19.22PCh. 19.16 - Prob. 19.23PCh. 19.17 - Prob. 19.24PCh. 19.17 - Prob. 19.25PCh. 19.18 - Prob. 19.26PCh. 19.19 - Prob. 19.27PCh. 19.20A - Addition of one equivalent of ammonia to...Ch. 19.20A - Prob. 19.29PCh. 19.20B - Show how you would accomplish the following...Ch. 19.20C - Prob. 19.31PCh. 19 - For each compound, 1. classify the...Ch. 19 - Prob. 19.33SPCh. 19 - Within each structure, rank the indicated...Ch. 19 - In each pair of compounds, select the stronger...Ch. 19 - Which of the following compounds are capable of...Ch. 19 - Complete the following proposed acid-base...Ch. 19 - Predict the products of the following reactions:...Ch. 19 - Prob. 19.39SPCh. 19 - Show how m-toluidine can be converted to the...Ch. 19 - The mass spectrum of tert-butylamine follows shows...Ch. 19 - Prob. 19.42SPCh. 19 - The following drugs are synthesized using the...Ch. 19 - Prob. 19.44SPCh. 19 - Synthesize from benzene. (Hint: All of these...Ch. 19 - Propose mechanisms for the following reactions.Ch. 19 - Prob. 19.47SPCh. 19 - Prob. 19.48SPCh. 19 - Prob. 19.49SPCh. 19 - Show how you can synthesize the following...Ch. 19 - Prob. 19.51SPCh. 19 - The alkaloid coniine has been isolated from...Ch. 19 - A chemist is summoned to an abandoned...Ch. 19 - Pyrrole undergoes electrophilic aromatic...Ch. 19 - Prob. 19.55SPCh. 19 - Prob. 19.56SPCh. 19 - An unknown compound shows a weak molecular ion at...Ch. 19 - A compound of formula C11H16N2 gives the IR,...Ch. 19 - (A true story.) A drug user responded to an ad...Ch. 19 - Prob. 19.60SPCh. 19 - Prob. 19.61SPCh. 19 - Prob. 19.62SPCh. 19 - Prob. 19.63SPCh. 19 - Prob. 19.64SPCh. 19 - Prob. 19.65SP
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- Complete these electrophilic aromatic substitution reactions. Where you predict meta substitution, show only the meta product. Where you predict ortho-para substitution, show both products.arrow_forwardpropose a retrosynthesis, and a way in which this diene can be synthesizedarrow_forwardThe Mannich reaction can take many forms, including reactions where aromatic heterocycles are employed. Provide mechanisms for the reactions in the following sequence.arrow_forward
- Strong support for the mechanism of the nucleophilic aromatic substitutionreaction that proceeds through a benzyne intermediate comes from the reaction shown here, in which bromobenzene is treated with KNH2 in the presence of cyclopentadiene. A product that is isolated has the formula C11H10. Draw the structure of that product and explain how it validates the production of a benzyne intermediate.arrow_forwardLike other strong nucleophiles, triphenylphosphine attacks and opens epoxides. The initial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses to an alkene and triphenylphosphine oxide. Show how this sequence might be used to convert cis-cyclooctene to trans-cyclooctene.arrow_forwardWhen benzene is treated with I2 in the presence of CuCl2, iodination of the ring is achieved with modest yields. It is believed that CuCl2 interacts with I2 to generate I+, which is an excellent electrophile. The aromatic ring then reacts with I+ in an electrophilic aromatic substitution reaction. Draw a mechanism for the reaction between benzene and I+.For the mechanism, draw the curved arrows as needed. Include lone pairs and charges in your answer. Do not draw out any hydrogen explicitly in your products. Do not use abbreviations such as Me or Ph.arrow_forward
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