Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 16.SE, Problem 28MP
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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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- Ethylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis.arrow_forwardOne frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (l) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a carboxylate ion; and (2) reaction of the carboxylate ion with CH3N2+. (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2?arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forward
- Synthesize p-nitrobenzoic acid from benzene.arrow_forwardBisphenol A is made on a large scale by a condensation of phenol with acetone. Suggest an appropriate catalyst, and propose a mechanism for this reaction.arrow_forwardSelect the best answer. Briefly explain the selection. A mechanism is an acceptable explanation.arrow_forward
- Dihydropyran is synthesized by treating tetrahydrofurfuryl alcohol with an arenesul- fonic acid, ARSO,H. Propose a mechanism for this conversion. ARSO,H OH + H,O Tetrahydrofurfuryl Dihydropyran alcoholarrow_forwardReaction of phenol with acetone in the presence of an acid catalyst gives a compound known as bisphenol A, which is used in the production of epoxy and polycarbonate resins Propose a mechanism for the formation of bisphenol A. OH H;PO, + H,O НО HO Phenol Acetone Bisphenol Aarrow_forwardThe following compounds undergo electrophilic aromatic substitution EXCEPTarrow_forward
- The reaction of methylpropene with HBr, under radical conditions, gives two intermediates. Propose a mechanism for the formation of the two products. Propose a mechanism for the following reaction and use electronic factors to account for the formation of a major product: CH2 CH2Br N-Bromosuccinimide (NBS) ho, CCI4 Draw the structure of an antioxidant, Vitamin E free radical and use resonance structures o account for its stability.arrow_forwardSuggest a step by step mechanism for this reaction.arrow_forwardWhen 3-methyl-1-butene reacts with HBr, two alkyl halides are formed: 2-bromo-3-methylbutane and 2-bromo-2-methylbutane. Propose a mechanism that explains the formation of these two products.arrow_forward
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