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chemistry
organic chemistry
Questions and Answers of
Organic Chemistry
Give the products, if any, of each of the following reactions: a. Benzonitrile + methyl chloride + AlCl3 b. Aniline + 3Br2 c. Benzoic acid + CH3CH2Cl + AlCl3 d. Benzene + 2 CH3Cl + AlCl3
When N,N-dimethylaniline is nitrated, some meta-nitro-N,N-dimethylaniline is formed. Why does the meta isomer form?
Show how each of the following compounds can be synthesized from benzene: a. p-chloroaniline b. m-chloroaniline c. p-nitrobenzoic acid d. m-nitrobenzoic acid e. m-bromopropylbenzene f.
Give the major product(s) of each of the following reactions: a. Nitration of p-fluoroanisole b. Chlorination of o-benzenedicarboxylic acid c. Bromination of p-chlorobenzoic acid
When phenol is treated with Br2, a mixture of monobromo-, dibromo-, and tribromophenols is obtained. Design a synthesis that would convert phenol primarily to orthobromophenol.
Draw structures of the following compounds: a. Para-toluidine b. Meta-cresol c. Para-xylene d. Ortho-chlorobenzenesulfonic acid
Explain why a diazonium group on a benzene ring cannot be used to direct an incoming substituent to the meta position.
Write the sequence of steps involved in the conversion of benzene into benzenediazonium chloride.
Show how the following compounds could be synthesized from benzene: a. m-dibromobenzene b. m-bromophenol c. o-chlorophenol d. m-nitrotoluene e. p-methylbenzonitrile f. m-chlorobenzaldehyde
In the mechanism for electrophilic aromatic substitution with a diazonium ion as the electrophile, why does nucleophilic attack occur on the terminal nitrogen atom of the diazonium ion rather than on
Give the structure of the activated benzene ring and the diazonium ion used in the synthesis of the following compounds: a. Butter yellow b. Methyl orange
What products would be formed from the reaction of isopropylamine with sodium nitrite and aqueous HCl?
Diazomethane can be used to convert a carboxylic acid into a methyl ester. Propose a mechanism for this reaction.
Draw resonance contributors for the carbanion that would be formed if meta-chloronitrobenzene could react with hydroxide ion. Why doesn't it react?
Draw the structure of each of the following compounds: a. m-chlorotoluene b. p-bromophenol c. o-nitroaniline d. m-chlorobenzonitrile e. 2-bromo-4-iodophenol f. m-dichlorobenzene g.
Show how each of the following compounds could be synthesized from benzene: a. o-nitrophenol b. p-nitroaniline c. p-bromoanisole
Starting with benzene, show how meta-aminoanisole could be prepared via a synthesis that a. Involves a benzyne intermediate b. Does not involve a benzyne intermediate
Give the products that would be obtained from the reaction of the following compounds with sodium amide in liquid ammonia:
Use the resonance contributors of naphthalene to predict whether all the carbon-carbon bonds have the same length, as they do in benzene.
Draw the resonance contributors for the carbocation intermediates obtained from electrophilic aromatic substitution at the 1-position and the 2-position of naphthalene. Use the resonance contributors
Give the products that would be obtained from the reaction of the following compounds with Cl2:a.b. c. d.
Draw the structure of each of the following compounds: a. m-ethylphenol b. p-nitrobenzenesulfonic acid c. (E)-2-phenyl-2-pentene d. o-bromoaniline e. 2-chloroanthracene f. m-chlorostyrene g.
Name the following compounds:a.b. c. d. e. f. g. h. i.
Provide the necessary reagents next to the arrows.
The pKa values of a few ortho-, meta-, and para-substituted benzoic acids are shown here:The relative pKa values depend on the substituent. For chloro-substituted benzoic acids, the ortho isomer is
Correct the following incorrect names: a. 2,4,6-tribromobenzene b. 3-hydroxynitrobenzene c. para-methylbromobenzene d. 1,6-dichlorobenzene
Give the product(s) of each of the following reactions: a. Benzoic acid + HNO3/H2SO4 b. Isopropylbenzene + cyclohexene + HF c. Naphthalene + acetyl chloride + AlCl3 followed by H2O d. o-methylaniline
Rank the following anions in order of decreasing basicity:
The compound with the following 1HNMR spectrum is known to be highly reactive toward electrophilic aromatic substitution. Identify the compound.
Show how the following compounds could be synthesized from benzene: a. m-chlorobenzenesulfonic acid b. m-chloroethylbenzene c. benzyl alcohol d. m-bromobenzonitrile e. 1-phenylpentane f.
For each of the groups of substituted benzenes, indicatea. The one that would be the most reactive in an electrophilic aromatic substitution reactionb. The one that would be the least reactive in an
Arrange the following groups of compounds in order of decreasing reactivity toward electrophilic aromatic substitution: a. Benzene, ethylbenzene, chlorobenzene, nitrobenzene, anisole b.
Give the products of the following reactions:a.b. c. d. e. f.
For each of the statements in Column I, choose a substituent from Column II that fits the description for the compound at the right:Column Ia. Z donates electrons inductively, but does not donate or
For each of the following compounds, indicate the ring carbon that would be nitrated if the compound were treated with HNO3/H2SO4:a.b. c. d. e. f. g. h. i. j. k. l.
Show how the following compounds could be synthesized from benzene: a. N,N,N-trimethylanilinium iodide b. benzyl methyl ether c. p-benzylchlorobenzene d. 2-methyl-4-nitrophenol e. p-nitroaniline f.
Give the product of each of the following reactions:(a)(b) (c) (d)
Which of the following compounds will react with HBr more rapidly?
Give the product(s) obtained from the reaction of each of the following compounds with Br2/FeBr3:a.b. c. d.
Which would react more rapidly with Cl2 + FeCl3, m-xylene or p-xylene? Explain.
What products would be obtained from the reaction of the following compounds with Na2Cr2O7 + H+ + ?a.b. c.
A student had prepared three ethyl-substituted benzaldehydes, but had neglected to label them. The premed student at the next bench said that they could be identified by brominating a sample of each
Explain, using resonance contributors for the intermediate carbocation, why a phenyl group is an ortho-para director.
When heated with an acidic solution of sodium dichromate, compound A forms benzoic acid. Identify compound A from its 1H NMR spectrum.
Describe two synthetic routes for the preparation of p-methoxyaniline with benzene as the starting material.
Which is a more stable intermediate?a.b.
If phenol is allowed to sit in D2O that contains a small amount of D2SO4, what products would be formed?
Show how the following compounds could be prepared from benzene: a. Benzaldehyde b. Styrene c. 1-bromo-2-phenylethane d. 2-phenyl-1-ethanol e. Aniline f. Benzoic acid
Show how the following compounds could be prepared from benzene:a.b. c.
An unknown compound reacts with ethyl chloride and aluminum trichloride to form a compound that has the following 1H NMR spectrum. Give the structure of the compound.
How could you distinguish among the following compounds, usinga. Their infrared spectra?b. Their 1H NMR spectra?
The following tertiary alkyl bromides undergo an SN1 reaction in aqueous acetone to form the corresponding tertiary alcohols. List the alkyl bromides in order of decreasing reactivity.
p-Fluoronitrobenzene is more reactive than p-chloronitrobenzene toward hydroxide ion. What does this tell you about the rate-determining step for nucleophilic aromatic substitution?
a. Explain why the following reaction leads to the products shown:b. What product would be obtained from the following reaction?
Describe how mescaline could be synthesized from benzene. The structure of mescaline is given on p. 622.
Propose a mechanism for the following reaction that explains why the configuration of the asymmetric carbon in the reactant is retained in the product:
Explain why hydroxide ion catalyzes the reaction of piperidine with 2,4-dinitroanisole, but has no effect on the reaction of piperidine with 1-chloro-2,4-dinitrobenzene.
For each of the following substituents, indicate whether it donates electrons inductively,withdraws electrons inductively, donates electrons by resonance, or withdraws electronsby resonance
List the members of the following sets of compounds in order of decreasing reactivity toward electrophilic aromatic substitution: a. Benzene, phenol, toluene, nitrobenzene, bromobenzene b.
Explain why the halo-substituted benzenes have the relative reactivities shown in Table 16.1.
Although excess amine is necessary in the reaction of an acyl chloride with an amine, explain why it is not necessary to use excess alcohol in the reaction of an acyl chloride with an alcohol.
Write the mechanism for the following reactions: a. The reaction of acetyl chloride with water to form acetic acid b. The reaction of acetyl bromide with methylamine to form N-methylacetamide
Starting with acetyl chloride, what nucleophile would you use to make each of the following compounds?a.b. c. d. e. f.
a. Propose a mechanism for the reaction of acetic anhydride with water. b. How does this mechanism differ from the mechanism for the reaction of acetic anhydride with an alcohol?
We have seen that acid anhydrides react with alcohols, water, and amines. In which one of these three reactions does the tetrahedral intermediate not have to lose a proton before it eliminates the
Write a mechanism for the following reactions: a. The noncatalyzed hydrolysis of methyl propionate b. The aminolysis of phenyl formate, using methylamine
a. State three factors that contribute to the fact that the noncatalyzed hydrolysis of an ester is a slow reaction. b. Which is faster, hydrolysis of an ester or aminolysis of the same ester?
Referring to the mechanism for the acid-catalyzed hydrolysis of methyl acetate: a. What species could be represented by HB+? b. What species could be represented by :B? c. What species is HB+ most
Name the following compounds:a. CH3CH2CH2C¡Nb.c. d. e. f. g. h. i.
Referring to the mechanism for the acid-catalyzed hydrolysis of methyl acetate, write the mechanism-showing all the curved arrows-for the acid-catalyzed reaction of acetic acid and methanol to form
Write the mechanism for the acid-catalyzed transesterification reaction of methyl acetate with ethanol.
a. What species other than an acid can be used to increase the rate of a transesterification reaction that converts methyl acetate to propyl acetate? b. Explain why the rate of aminolysis of an ester
If butanoic acid and 18O labeled methanol are allowed to react under acidic conditions, what compounds will be labeled when the reaction has reached equilibrium?
Using an alcohol for one method and an alkyl halide for the other, show two ways to make each of the following esters: a. Methyl butyrate (odor of apples) b. Propyl acetate (odor of pears) c. Ethyl
Propose a mechanism for the following reaction. (Number the carbons to help you see where they end up in the product.)
a. Which of the following reactions would lead to the formation of an amide?1.2. 3. 4. 5. 6. b. For those reactions that do form amides, what could you do to improve either the rate of amide
Write a structure for each of the following compounds: a. phenyl acetate b. γ-caprolactam c. butanenitrile d. N-benzylethanamide e. γ-caproic acid f. ethyl 2-chloropentanoate g.
Propose a mechanism for the reaction of an amide with thionyl chloride to form a nitrile.
List the following amides in order of decreasing reactivity toward acid-catalyzed hydrolysis:
What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines? a. Pentylamine b. Isohexylamine c. Benzylamine d. Cyclohexylamine
Primary amines can also be prepared by the reaction of an alkyl halide with azide ion, followed by catalytic hydrogenation. What advantage do this method and the Gabriel synthesis have over the
Which alkyl halides form the following carboxylic acids after reacting with sodium cyanide and the product heated in an acidic aqueous solution? a. Butyric acid b. Isovaleric acid c.
Design a synthesis for each of the following compounds, using an intramolecular reaction:a.b. c. d. e. f.
a. Propose a mechanism for the formation of succinic anhydride in the presence of acetic anhydride. b. How does acetic anhydride help in the formation of succinic anhydride?
What products would you expect to obtain from the following reactions? a. Phosgene + excess diethylamine b. Malonic acid + 2 acetyl chloride c. Methyl carbamate + methylamine d. Urea + water e. Urea
Write a structure for each of the following compounds: a. N,N-dimethylhexanamide b. 3,3-dimethylhexanamide c. Cyclohexanecarbonyl chloride d. Propanenitrile e. Propionyl bromide f. Sodium acetate g.
Name the following compounds:a.b. c. d. e. f. g. h. i. j.
Which is longer, the carbon-oxygen single bond in a carboxylic acid or the carbon-oxygen bond in an alcohol? Why?
What products would be formed from the reaction of benzoyl chloride with the following reagents? a. Sodium acetate b. water c. dimethylamine d. Aqueous HCl e. Aqueous NaOH f. Cyclohexanol g.
a. List the following esters in order of decreasing reactivity in the first step of a nucleophilic acyl substitution reaction (formation of the tetrahedral intermediate):b. List the same esters in
a. Which compound would you expect to have a higher dipole moment, methyl acetate or butanone?b. Which would you expect to have a higher boiling point?
How could you use 1H NMR spectroscopy to distinguish among the following esters?
If propionyl chloride is added to one equivalent of methylamine, only a 50% yield of N methylpropanamide is obtained. If, however, the acyl chloride is added to two equivalents of methylamine, the
a. When a carboxylic acid is dissolved in isotopically labeled water (H2O18), the label is incorporated into both oxygens of the acid. Propose a mechanism to account for this.b. If a carboxylic acid
What reagents would you use to convert methyl propanoate into the following compounds? a. Isopropyl propanoate b. Sodium propanoate c. N-ethylpropanamide d. Propanoic acid
compound with molecular formula C5H10O2 gives the following IR spectrum. When it undergoes acid-catalyzed hydrolysis, the compound with the following 1H NMR spectrum is formed. Identify the compounds.
Aspartame, the sweetener used in the commercial products NutraSweet® and Equal® is 160 times sweeter than sucrose. What products would be obtained if aspartame were hydrolyzed completely in
There are three carbon-oxygen bonds in methyl acetate. a. What are their relative lengths? b. What are the relative infrared (IR) stretching frequencies of these bonds?
1,4-Diazabicyclo[2.2.2]octane (abbreviated DABCO) is a tertiary amine that catalyzes transesterification reactions. Propose a mechanism to show how it does this.
Identify the major and minor products of the following reaction:
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