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chemistry
organic chemistry
Questions and Answers of
Organic Chemistry
What is the pH of a 0.050 M solution of formic acid, pKa = 3.75?
Sodium bicarbonate, NaHCO3, is the sodium salt of carbonic acid (H2CO3), pKa = 6.37. Which of the substances shown in Problem 2.43 will react with sodium bicarbonate?
Assume that you have two unlabeled bottles, one of the following which contains phenol (pKa = 9.9) and one of which contains acetic acid (pKa = 4.76). In light of your answer to Problem 2.51, suggest
Identify the acids and bases in the followingreactions:
Which of the following pairs represent resonance structures?
Draw as many resonance structures as you can for the following species. Adding appropriate formal charger to each: (a) Nitromethane, (b) Ozone, (c) Diazomethane,
Carbocations, ions that contain a trivalent, positively charged carbon atom, react with water to give alcohols. How can you account for the fact that the following carbocation gives a mixture of two
We?ll see that organic molecules can be classified according to the functional groups they contain, where a functional group is a collection of atoms with a characteristics chemical reactivity. Use
Phenol, C6H5OH, is a stronger acid then methanol, CH3OH, even though both contains an O ? H bond. Draw the structures of the anions resulting from loss of H+ from phenol and methanol, and use
Monobromination of toluene gives a mixture of three bromotoluene products. Draw and name them.
How many products might be formed on chlorination of o-xylene (o-dimethyl-benzene), m-xylene, and p-xylene?
When benzene is treated with D2SO4, deuterium slowly replaces all six hydrogen’s in the aromatic ring. Explain.
Which of the following alkyl halides would you expect to undergo Friedel-Crafts reaction without rearrangement? Explain.(a) CH3CH2Cl(b) CH3CH2CH (Cl) CH3(c) CH3CH2CH2Cl(d) (CH3) CCH2Cl(e)
What is the major mono-substitution product from the Friedel-Crafts reaction of benzene with 1-chloro-2-methylpropane in the presence of AlCl3?
Identify the carboxylic acid chloride that might be used in a Friedel-Crafts acylation reaction to prepare each of the followingacylbenzenes:
Write resonance structures for nitrobenzene to show the electron-withdrawing resonance effect of the nitro group.
Write resonance structures for chlorobenzene to show the electron-donating resonance effect of the chloro group.
Predict the major products of the following reactions:(a) Nitration of Bromobenzene(b) Bromination of nitrobenzene(c) Chlorination of phenol(d) Bromination of aniline
Rank the compounds in each group in order of their reactivity to electrophilic substitution:(a) Nitrobenzene, phenol, toluene, benzene(b) Phenol, benzene, chlorobenzene, benzoic acid(c) Benzene,
Use Figure to explain why Friedel-Crafts alkylation’s often poly-substitution but Friedel-Crafts acylations do not.
An electrostatic potential map of (trifluoromethyl) benzene, C6H5CF3, is shown. Would you expect (trifluoromethyl) benzene to be more reactive or less reactive than toluene toward electrophilic
Acetanilide is less reactive than aniline toward electrophilic substitution.Explain.
Draw resonance structures for the intermediates from reaction of an electrophile at the ortho, Meta and Para positions of nitrobenzene. Which intermediates are most stable?
At what position would you expect electrophilic substitution to occur in each of the followingsubstances?
Show the major product(s) from reaction of the following substances with (i) CH3CH2Cl, AlCl3 and (ii) HNO3,H2SO4
The herbicide oxyfluorfen can be prepared by reaction between a phenol and an aryl fluoride. Propose amechanism.
Treatment of p-bromotoluene with NaOH at 300 oC yields mixture of two products but treatment of m-bromotoluene with NaOH yields a mixture of three products. Explain.
What aromatic products would you obtain from the KMnO4 oxidation of the followingsubstances?
Refer to Table 5.3 for quantitative idea of the stability of a benzyl radical. How much more stable (in kJ/mol) is the benzyl radical than a primary alkyl radical? How does a benzyl radical compare
Styrene, the simplest alkenylbenzene, is prepared commercially for use in plastics manufacture by catalytic dehydrogenation of ethylbenzene. How might you prepare styrene from benzene using reactions
How would you prepare diphenylmethane, (Ph) 2Ch2, from benzene and an acid chloride?
Propose syntheses of the following substances from benzene:(a) m-Chloronitrobenzene(b) m-Chloroethylbenzene(c) 4-Chloro-1-nitro-2-propylbenzene(d) 3-Bromo-2-methylbenzenesulfonic acid
In planning synthesis, it?s as important to know what not do as to know what to do. As written, the following reaction schemes have flaws in them. What is wrong with each?
Draw the product from reaction of each of the following substances with (i) Br2, FeBr3 and (ii) CH3COCl,AlCl3.
The following molecular model of a dimethyl-substituted biphenyl represents the lowest-energy conformation of the molecule. Why are the two benzene rings tilted at a 63o angle to each other rather
How would you synthesize the following compound starting from benzene? More than one step isneeded.
The following compound can?t be synthesized using the methods discussed in this chapter. Why not?
Identify each of the following groups as an activator or deactivator and as and o,p-director orm-director.
Predict the major product(s) of nitration of the following substances. Which react faster than benzene and which slower?(a) Bromobenzene(b) Benzonitrile(c) Benzoic acid(d) Nitrobenzene(e)
Rank the compounds in each group according to their reactivity toward electrophilic substitution.(a) Chlorobenzene, o-dichlorobenzene, benzene(b) p-Bromonitrobenzene, nitrobenzene, phenol(c)
A Predict the major mono-alkylation products you would expect to obtain from reaction of the following substances with chloromethane arid AlCl3:(a) Bromobenzene (b) m-Bromo-phenol(c)
Name and draw the major product(s) of electrophilic chlorination of the following compounds:(a) in-Nitro phenol(b) o-Xylene(c) p-Nitro benzoic acid(d) p-Bromo benzenesulfonic acid
Predict the major product(s) you would obtain from sulfonation of the following compounds:(a) Fluor benzene(b) Br-Bromo phenol(c) m-Dichlorobenzene(d) 2, 4-Dibromophenol
Rank the following aromatic compounds in the expected order of their reactivity toward Friedel—Crafts alkylation. Which compounds are un-reactive?(a) Bromobenzene(b) Toluene(c) Phenol(d) Aniline(e)
What product(s) would you expect to obtain from the followingreactions?
Predict the major product(s) of the followingreactions:
Aromatic iodination can be carried out with a number of reagents, including iodine mono chloride, ICI. What is the direction of polarization of ICI? Propose a mechanism for the iodination of an
The sulfonation of an aromatic ring with SO3 and H2SO4 is reversible. That is, heating benzenesulfonic add with H2SO4 yields benzene. Show the mechanism of the de-sulfonation reaction. What is the
The carbocation electrophile in a Friedel—Crafts reaction can be generated in ways other than by reaction of an alkyl chloride with A1Cl3. For example, reaction of benzene with 2-methylpropene in
The N, N, N-trimethyl ammonium group, —N (CH3)3, is one of the few groups that is a meta-directing deactivator yet has no electron-withdrawing resonance effect. Explain.
The nitroso group, —N = O, is one of the few non-halogens that is an ortho- and Para-directing deactivator. Explain by drawing resonance structures of the carbocation intermediates in ortho, Meta
Using resonance structures of the intermediates, explain why bromination of biphenyl occurs at ortho and Para positions rather than at Meta.
At what position and on what ring do you expect nitration of 4-bromo- biphenyl to occur? Explain, using resonance structures of the potentialintermediates.
Electrophilic substitution on 3-phenylpropanenitrile occurs at the ortho and Para positions, but reaction with 3-phenylpropenenitrile occurs at the meta position. Explain using resonance structures
Addition of HBr to 1-phenyipropene yields only (1-bromopropyl) benzene. Propose a mechanism for the reaction, and explain why none of the other regioisomer isproduced.
Triphenylmethane can be prepared by reaction of benzene and chloroform in the presence of A1Cl3. Propose a mechanism for thereaction.
At what position, and on what ring, would you expect the following sub stances to undergo electrophilicsubstitution?
At what position, and on what ring, would you expect bromination of benzanilide to occur? Explain by drawing resonance structures of theintermediates.
Would you expect the Friedel—Crafts reaction of benzene with (R)-2-chloro- butane to yield optically active or racemic product explain.
How would you synthesize the following substances starting from benzene or phenol? Assume that ortho- and Para-substitution products can be separated.(a) o-Bromobenzoic acid(b) p-Methoxytoluene(c) 2,
Starting with benzene as your only source of aromatic compounds, how would you synthesize the following substances? Assume that you can separate ortho and Para isomers if necessary.(a) p-Chloro
Starting with either benzene or toluene, how would you synthesize the following substances? Assume that ortho and Para isomers can be separated.(a) 2-Brorno-4-nitrotoluene(b) 1, 3,
As written, the following syntheses have flaws. What is wrong witheach?
How would you synthesize the following substances starting frombenzene?
The compound MON-0585 is a nontoxic, biodegradable larvicide that is highly selective against mosquito larvae. Synthesize MON-0585 using either benzene or phenol as a source of the aromaticrings.
Hexachlorophene, a substance used in the manufacture of germicidal soaps, is prepared by reaction of 2, 4, 5-trichiorophenol with formaldehyde in the presence of concentrated sulfuric acid. Propose a
Benzenediazonium carboxylate decomposes when heated to yield N2, C02, and a reactive substance that can't be isolated. When Benzenediazonium carboxylate is heated in the presence of furan, the
Phenylboronic acid, C6H5B (OH)2, is nitrated to give 15% ortho-substitution product and 85% meta. Explain the meta-directing effect of the —B (OH)2 group.
Draw resonance structures of the intermediate carbocations in the bromination of naphthalene, and account for the fact that naphthalene undergoes electrophilic substitution at C1 rather than C2.
Propose a mechanism for the reaction of 1-chioroanthraquinone with methoxide ion to give the substitution product 1-methoxyanthraquinone. Use curved arrows to show the electron flow in eachstep.
4-Chloropyridine undergoes reaction with dim ethylamine to yield 4-dimethylaminopyridine. Propose a mechanism for thereaction.
P-Bromotoluene reacts with potassium amide to give a mixture of m- and p-methyl aniline. Explain.
Propose a mechanism to account for the reaction of benzene with 2, 2, 5, 5- tetra methyl tetra hydrofuran.
Propose a mechanism to account for the following reaction:
In the Gatterman-Koch reaction, a formyl group (?CHO) is introduced directly onto a benzene ring. For example, reaction of toluene with CO and HCl in the presence of mixed CuCl/AlCl3 gives
Treatment of p-tert-butyl phenol with a strong acid such as H2SO4 yields phenol and 2-methyipropene. Propose a mechanism.
Benzene and alkyl-substituted benzenes can be hydroxylated by reaction with H2O2 in the presence of an acidic catalyst. What is the structure of the reactive electrophile? Propose a mechanism for
How would you synthesize the following compounds from benzene? Assume that ortho and Para isomers can beseparated.
You know the mechanism of HBr addition to alkenes, and you know the effects of various substituent groups on aromatic substitution. Use this knowledge to predict which of the following two alkenes
Benzyl bromide is converted into benzaldehyde by heating in dimethyl sulfoxide. Propose a structure for the intermediate, and show the mechanisms of the two steps in thereaction.
Use your knowledge of directing effects, along with the following data, to deduce the directions of the dipole moments in aniline andBromobenzene.
Identify the reagents represented by the letters a?c in the following scheme:
Phenols (ArOH) are relatively acidic, and the presence of a substituent group on the aromatic ring has a large effect. The PKa of un-substituted phenol, for example, is 9.89, while that of p-nitro
Would you expect p-methyl phenol to be more acidic or less acidic than un-substituted phenol? Explain.
Name the following ethers:
Why do you suppose only symmetrical ethers are prepared by the sulfuric acid-catalyzed dehydration procedure? What product(s) would you expect if ethanol and 1-propanol were allowed to react
How would you prepare the following ethers using a Williamson synthesis?(a) Methyl propyl ether(b) Anisole (methyl phenyl ether)(c) Benzyl isopropyl ether(d) Ethyl 2, 2-dimethylpropyl ether
Review the mechanism of oxymercuration shown in figure, and then write the mechanism of the alkoxy mercuration reaction of 1-methylcyclopentene with ethanol. Use curved arrows to show the electron
How would you prepare the following ethers? Use whichever method you think is more appropriate, the Williamson synthesis or the alkoxy mercuration reaction.(a) Butyl cyclohexyl ether(b) Benzyl ethyl
Rank the following halides in order of their reactivity in the Williamson synthesis:(a) Bromo ethane, 2-bromopropane, bromo benzene(b) Chloro ethane, bromo ethane, 1-iodopropene
Predict the products of the following reactions:
Write the mechanism of the acid-catalyzed cleavage of tert-butyl cyclohexyl ether to yield Cyclohexanol and 2-methylpropene.
Why are HI and HBr more effective than HCI in cleaving ethers?
What product would you expect from Claisen rearrangement of 2-butenyl phenylether?
Reaction of cis-2-butene with m-chloroperoxybenzoic acid yields an epoxide different from obtained by reaction of the trans isomer. Explain.
Predict the major product of each of the following reactions:
How would you prepare the following diols?
Predict the major product of the following reactions:
15-Crown-5 and 12-crown-4 ethers complex Na + and Li +, respectively. Make models of these crown ethers, and compare the sized of the cavities.
Name the followingcompounds:
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