Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 16.SE, Problem 34MP
Using resonance structures of the intermediates, explain why bromination of biphenyl occurs at ortho and para positions rather than at meta.
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Explain using resonance structures of the intermediates (please explain and draw them out) why the bromination of phenol is faster than the bromination of phenyl ester?
Draw the benzoic acid structure and explain which products will be formed as a result of the reaction with the nitronium ion in the electrophilic aromatic displacement reaction.
Why do we have "orto" and "para" regioselectivity in bromination and nitration in electrophilic aromatic substitutions? How to explain that?
Chapter 16 Solutions
Organic Chemistry
Ch. 16.1 - Prob. 1PCh. 16.2 - Propose a mechanism for the electrophilic...Ch. 16.2 - How many products might be formed on chlorination...Ch. 16.2 - When benzene is treated with D2SŪ4. deuterium...Ch. 16.3 - Prob. 5PCh. 16.3 - What is the major monosubstitution product from...Ch. 16.3 - Identify the carboxylic acid chloride that might...Ch. 16.4 - Rank the compounds in each of the following groups...Ch. 16.4 - Predict the major products of the following...Ch. 16.4 - Prob. 10P
Ch. 16.4 - Prob. 11PCh. 16.4 - Acetanilide is less reactive than aniline toward...Ch. 16.4 - Prob. 13PCh. 16.5 - At what position would you expect electrophilic...Ch. 16.5 - Show the major product(s) from reaction of the...Ch. 16.6 - The herbicide oxyfluorfen can be prepared by...Ch. 16.7 - Treatment of p-bromotoluene with NaOH at 300°C...Ch. 16.8 - Prob. 18PCh. 16.8 - Prob. 19PCh. 16.8 - Prob. 20PCh. 16.9 - Prob. 21PCh. 16.10 - Prob. 22PCh. 16.10 - Prob. 23PCh. 16.SE - Prob. 24VCCh. 16.SE - The following molecular model of a...Ch. 16.SE - Prob. 26VCCh. 16.SE - Prob. 27VCCh. 16.SE - Aromatic iodination can be carried out with a...Ch. 16.SE - Prob. 29MPCh. 16.SE - The carbocation electrophile in a Friede1-Crafts...Ch. 16.SE - Prob. 31MPCh. 16.SE - The nitroso group, —N=O, is one of the few...Ch. 16.SE - Triphenylmethane can be prepared by reaction of...Ch. 16.SE - Using resonance structures of the intermediates,...Ch. 16.SE - Benzene and alkyl -substituted benzenes can be...Ch. 16.SE - Prob. 36MPCh. 16.SE - Hexachlorophene, a substance used in the...Ch. 16.SE - Benzenediazonium carboxylate decomposes when...Ch. 16.SE - 4-Chloropyridine undergoes reaction with...Ch. 16.SE - Propose a mechanism to account for the following...Ch. 16.SE - In the Gatterman-Kochreaction, a formyl group...Ch. 16.SE - Treatment of p-tert-butylphenol with a strong acid...Ch. 16.SE - Benzyl bromide is converted into benzaldehyde by...Ch. 16.SE - Prob. 44MPCh. 16.SE - Prob. 45MPCh. 16.SE - Prob. 46APCh. 16.SE - Prob. 47APCh. 16.SE - Prob. 48APCh. 16.SE - Predict the major monoalkylation products you...Ch. 16.SE - Name and draw the major product(s) of...Ch. 16.SE - Prob. 51APCh. 16.SE - Prob. 52APCh. 16.SE - What product(s) would you expect to obtain from...Ch. 16.SE - Prob. 54APCh. 16.SE - How would you synthesize the following substances...Ch. 16.SE - Prob. 56APCh. 16.SE - Prob. 57APCh. 16.SE - Prob. 58APCh. 16.SE - Prob. 59APCh. 16.SE - Prob. 60APCh. 16.SE - Prob. 61APCh. 16.SE - Prob. 62APCh. 16.SE - Prob. 63APCh. 16.SE - How would you synthesize the following substances...Ch. 16.SE - Prob. 65APCh. 16.SE - Prob. 66APCh. 16.SE - Draw resonance structures of the intermediate...Ch. 16.SE - Prob. 68APCh. 16.SE - p-Bromotoluene reacts with potassium amide to give...Ch. 16.SE - Prob. 70APCh. 16.SE - Prob. 71APCh. 16.SE - Prob. 72APCh. 16.SE - Use your knowledge of directing effects, along...Ch. 16.SE - Identify the reagents represented by the letters...Ch. 16.SE - Phenols (ArOH) are relatively acidic, and the...Ch. 16.SE - Prob. 76APCh. 16.SE - Prob. 77APCh. 16.SE - Melamine, used as a fire retardant and a component...
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- Explain why hydroxide ion catalyzes the reaction of piperidine with 2,4-dinitroanisole but has no effect on the reaction of piperidine with1-chloro-2,4-dinitrobenzene.arrow_forwardDraw the structure of methoxybenzene and explain which product will be formed as a result of the reaction with nitronium ion in electrophilic aromatic displacement reaction.arrow_forwardDraw resonance structures of anisole or the intermediate in the above reaction to demonstrate why the methoxy group is an o,p-directorarrow_forward
- Explain the effect of the structure of the alkyl halide on elimination through E1 and E2.arrow_forwardAssume that attached starting materials can be converted to an epoxide by this reaction. Draw the product formed (including stereochemistry) from each starting material. Why might some of these reactions be more difficult than others in yielding nucleophilic substitution products?arrow_forwardp-Fluoronitrobenzene is more reactive toward hydroxide ion than is p-chloronitrobenzene. What does this tell you about the rate-determining step for nucleophilic aromatic substitution?arrow_forward
- Rationalize the selectivity observed in the benzil reduction. Draw the transition states of the nucleophilic attack leading to either meso or racemic products and indicate why one is more stable than the other.arrow_forwardWhat two sets of reagents (each consisting of a carbonyl compound and phosphonium ylide) can be used for the synthesis of the following alkene? a. What alkyl halide is required to prepare each of the phosphonium ylides? b. What is the best set of reagents to use for the synthesis?arrow_forwardWhat is the likely mechanism of nucleophilic substitution for attached alkyl halide?arrow_forward
- a. What two sets of reagents (each consisting of a carbonyl compound and phosphonium ylide) can be used for the synthesis of the following alkene?b. What alkyl halide is required to prepare each of the phosphonium ylides?c. What is the best set of reagents to use for the synthesis?arrow_forwardDraw the structure of benzoic acid and explain which product will be formed as a result of the reaction with the nitronium ion in the electrophilic aromatic displacement reaction.arrow_forwardExplain the effect of the structure of the alkyl halide on elimination via E1 or E2.arrow_forward
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