Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 16.SE, Problem 69AP
p-Bromotoluene reacts with potassium amide to give a mixture of m-and p-methylaniline. Explain.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
In an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?
Treatment of Compound E with sodium amide and then methyl iodide does not produce the desired product F but instead forms Compound G. Explain this observation.
Explain how benzaldehyde and dimedone reacts with each other, and then with the aminotriazole to form compound 1a in the presence of an acid catalyst. Provide a detailed reaction mechanism and explanation.
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...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Explain the following observation. Ethyl 3-phenylpropanoate (C6H5CH2CH2CO2CH2CH3) reacts with electrophiles to afford ortho- and para-disubstituted arenes, but ethyl 3-phenylprop-2-enoate (C6H5CH= CHCO2CH2CH3) reacts with electrophiles to afford meta-disubstituted arenes.arrow_forwardIn an aqueous solution containing sodium bicarbonate, aniline reacts quickly with bromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions, however, and the yields (mostly m-nitroaniline) are poor.Explain why nitration of aniline is so sluggish and why it gives mostly metasubstitution.arrow_forwardSuggest reasonable explanations for each of the following: A. The rate of saponification of ethyl p-nitrobenzoate is 200 times faster than that of ethyl p-methoxybenzoate. B. The rate of saponification of methyl acetate, CH3CCO2CH3 is 50 times greater than that for isopropylacetate.arrow_forward
- When 2-methylcyclohexanone is treated with pyrrolidine, two isomeric enamines areformed.Why is enamine A with the less substituted double bond the thermodynamicallyfavored product? (You will find it helpful to examine the models of these twoenamines.)arrow_forwarda. Provide the structure of the hydrate of cyclopentanone. b. Provide the major organic product which results when pentanal is subjected to the following sequence of steps: 1. PhMgBr; 2. H3O+; 3. PCC.arrow_forwardExplain this observation: Ethyl 3-phenylpropanoate (C6H5CH2CH2CO2CH2CH3) reacts with electrophiles to afford ortho- and para-disubstituted arenes, but ethyl 3-phenylprop-2-enoate (C6H5CH=CHCO2CH2CH3) reacts with electrophiles to afford meta- disubstituted arenes.arrow_forward
- Acid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?arrow_forwardWhen pyrrole is added to a dilute solution of D2SO4 in D2O, 2-deuteriopyrrole is formed. Propose a mechanism to account for the formation of this compound.arrow_forward(a) Give a plausible explanation for each one of the following :(i) There are two – NH2 groups in semicarbazide. However, only one such group is involved in the formation of semicarbazones.(ii) Cyclohexanone forms cyanohydrin in good yield but 2, 4, 6-trimethylcyclohexanone does not.(b) An organic compound with molecular formula C9H10O forms 2, 4, – DNP derivative, reduces Tollens’ reagent and undergoes Cannizzaro’s reaction. On vigorous oxidation it gives 1, 2-benzene-di- carboxylic acid. Identify the compound.arrow_forward
- Depending on the reaction conditions, two different imines of formula C8H9N mightbe formed by the reaction of benzaldehyde with methylamine. Explain, and give thestructures of the two imines.arrow_forwardArrange the compounds in order of INCREASING reactivity towards bromination. I. Toluene, Nitrobenzene, Iodobenzene, Acetanilide II. Phenol, Acetophenone, Anisole, Chlorobenzene III. Aniline, Benzaldehyde, Benzonitrile, Benzenesulfonic acidarrow_forwardExplain this observation: Ethyl 3-phenylpropanoate(C6H5CH2CH2CO2CH2CH3 ) reacts with electrophiles to afford ortho- and para-disubstituted arenes, but ethyl 3-phenylprop-2-enoate (C6H5CH=CHCO2CH2CH3) reacts with electrophiles to afford metadisubstituted arenes.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License