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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

Predict the major organic product in each of the following reactions:
The hydrolysis of p-bromotoluene with aqueous sodium hydroxide at 300°C yields M-methylphenol and p-methylphenol in a 5:4 ratio. What is the meta–para ratio for the same reaction carried out on
The herbicide trifluralin is prepared by the following sequence of reactions. Identify compound A and deduce the structure of trifluralin.
Chlorbenside is a pesticide used to control red spider mites. It is prepared by the sequence shown. Identify compounds A and B in this sequence. What is the structure of chlorbenside?
An article in the October 1998 issue of the Journal of Chemical Education (p. 1266) describes the following reaction.
A method for the generation of benzyne involves heating the diazonium salt from o-Aminobenzoic acid (benzenediazonium-2-carboxylate). Using curved arrows, show how this substance forms benzyne. What
The compound triptycene may be prepared as shown. What is compound A?
Nitro-substituted aromatic compounds that do not bear halide leaving groups react with nucleophiles according to the equation
A careful study of the reaction of 2, 4, 6-trinitroanisole with sodium methoxide revealed that two different Meisenheimer complexes were present. Suggest reasonable structures for these two complexes.
Suggest a reasonable mechanism for each of the following reactions:
Mixtures of chlorinated derivatives of biphenyl, called polychlorinated biphenyls, or PCBs, were once prepared industrially on a large scale as insulating materials in electrical equipment. As
DDT-resistant insects have the ability to convert DDT to a less toxic substance called DDE. The mass spectrum of DDE shows a cluster of peaks for the molecular ion at m/z 316, 318, 320, 322, and 324.
Write structural formulas for each of the following compounds: (a) Pyrogallol (1, 2, 3-benzenetriol) (c) 3-Nitro-1-naphthol (b) o-Benzylphenol (d) 4-Chlororesorcinol
The compound triptycene may be prepared as shown. What is compound A? Discuss.
Which is the stronger acid in each of the following pairs? Explain your reasoning. (a) Phenol or p-hydroxybenzaldehyde (b) m-Cyanophenol or p-cyanophenol (c) o-Fluorophenol or p-fluorophenol
Write a stepwise mechanism for the conversion of p-toluenesulfonic acid to p-cresol under the conditions shown in the preceding equation.
Write a stepwise mechanism for the hydrolysis of chlorobenzene under the conditions shown in Table 24.3.
Each of the following reactions has been reported in the chemical literature and gives a single organic product in high yield. Identify the product in each case. (a) 3-Benzyl-2, 6-dimethylphenol
Write chemical equations expressing each of the following: (a) Preparation of o-nitrophenyl acetate by sulfuric acid catalysis of the reaction between a phenol and a carboxylic acid anhydride. (b)
Reaction of phenol with 1, 2-epoxypropane in aqueous sodium hydroxide at 150°C gives a single product, C9H12O2, in 90% yield. Suggest a reasonable structure for this compound.
Which of the following two combinations of reactants is more appropriate for the preparation of p-nitrophenyl phenyl ether? (a) Fluorobenzene and p-nitrophenol (b) p-Fluoronitrobenzene and phenol
The mechanism of the Claisen rearrangement of other allylic ethers of phenol is analogous to that of allyl phenyl ether. What is the product of the Claisen rearrangement of C6H5OCH2CH=CHCH3?
The IUPAC rules permit the use of common names for a number of familiar phenols and aryl ethers. These common names are listed here along with their systematic names. Write the structure of each
Name each of the following compounds: Discuss.
Write a balanced chemical equation for each of the following reactions: (a) Phenol + sodium hydroxide (b) Product of part (a) + ethyl bromide (c) Product of part (a) + butyl
Which phenol in each of the following pairs is more acidic? Justify your choice. (a) 2, 4, 6-Trimethylphenol or 2, 4, 6-trinitrophenol (b) 2, 6-Dichlorophenol or 3, 5-dichlorophenol (c)
Choose the reaction in each of the following pairs that proceeds at the faster rate. Explain your reasoning. (a) Basic hydrolysis of phenyl acetate or m-nitrophenyl acetate (b) Basic hydrolysis of
Pentafluorophenol is readily prepared by heating hexafluorobenzene with potassium hydroxide in tert-butyl alcohol:
Each of the following reactions has been reported in the chemical literature and proceeds cleanly in good yield. Identify the principal organic product in each case.
A synthesis of the analgesic substance phenacetin is outlined in the following equation. What is the structure of phenacetin?
Identify compounds A through C in the synthetic sequence represented by equations (a) through (c).
Treatment of 3, 5-dimethylphenol with dilute nitric acid, followed by steam distillation of the reaction mixture, gave a compound A (C8H9NO3, mp 66°C) in 36% yield. The nonvolatile residue from the
Outline a reasonable synthesis of 4-nitrophenyl phenyl ether from chlorobenzene and phenol.
As an allergen for testing purposes, synthetic 3-pentadecylcatechol is more useful than natural poison ivy extracts (of which it is one component). A stable crystalline solid, it is efficiently
Describe a scheme for carrying out the following synthesis. (In the synthesis reported in the literature, four separate operations were required.)
In a general reaction known as the cyclohexadienone-phenol rearrangement, cyclohexadienones are converted to phenols under conditions of acid catalysis. An example is
Treatment of p-hydroxybenzoic acid with aqueous bromine leads to the evolution of carbon dioxide and the formation of 2, 4, 6-tribromophenol. Explain.
Treatment of phenol with excess aqueous bromine is actually more complicated than expected. A white precipitate forms rapidly, which on closer examination is not 2, 4, 6-tribromophenol but is instead
Treatment of 2, 4, 6-tri-tert-butylphenol with bromine in cold acetic acid gives the compound C18H29BrO in quantitative yield. The infrared spectrum of this compound contains absorptions at 1630 and
Compound A undergoes hydrolysis of its acetal function in dilute sulfuric acid to yield 1, 2- ethanediol and compound B (C6H6O2), mp 54°C. Compound B exhibits a carbonyl stretching band in the
One of the industrial processes for the preparation of phenol, discussed in Section 24.6, includes an acid-catalyzed rearrangement of cumene hydroperoxide as a key step. This reaction proceeds by way
Identify the following compounds on the basis of the information provided: (a) C9H12O: Its infrared and 1H NMR spectra are shown in Figure 24.5. (b) C9H11BrO: Its infrared and 1H NMR spectra are
One of the following esters cannot undergo the Claisen condensation. Which one? Write structural formulas for the Claisen condensation products of the other two. CH3CH2CH2CH2CO2CH2CH3
Write the structure of the Dieckmann cyclization product formed on treatment of each of the following diesters with sodium ethoxide, followed by acidification.
Give the structure of the product obtained when ethyl phenylacetate (C6H5CH2CO2CH2CH3) is treated with each of the following esters under conditions of the mixed Claisen condensation: (a) Diethyl
Write an equation for the carbon–carbon bond-forming step in the cyclization reaction just cited. Show clearly the structure of the enolate ion, and use curved arrows to represent its nucleophilic
Write appropriate chemical equations showing how you could prepare cyclopentanone from diethyl hexanedioate.
Show how you could prepare each of the following ketones from ethyl acetoacetate and any necessary organic or inorganic reagents: (a) 1-Phenyl-1, 4-pentanedione (c) 5-Hexen-2-one (b) 4-Phenyl-
Show how you could prepare each of the following carboxylic acids from diethyl malonate and any necessary organic or inorganic reagents: (a) 3-Methylpentanoic acid (c) 4-Methylhexanoic acid (b)
Ethyl acetoacetate may also be subjected to double alkylation. Show how you could prepare 3-methyl-2-butanone by double alkylation of ethyl acetoacetate.
Cyclopentyl methyl ketone has been prepared from 1, 4-dibromobutane and ethyl acetoacetate. Outline the steps in this synthesis by writing a series of equations showing starting materials, reagents,
Show, by writing a suitable sequence of reactions, how you could prepare pentobarbital from diethyl malonate (The structure of pentobarbital was shown in this section.)
Thiourea (H2NCNH2) reacts with diethyl malonate and its alkyl derivatives in the same way that urea does. Give the structure of the product obtained when thiourea is used instead of urea in the
Aryl halides react too slowly to undergo substitution by the SN2 mechanism with the sodium salt of diethyl malonate, and so the phenyl substituent of phenobarbital cannot be introduced in the way
Ethyl acetoacetate behaves similarly to diethyl malonate in its reactivity toward a, ß- unsaturated carbonyl compounds. Give the structure of the product of the following reaction sequence:
Outline efficient syntheses of each of the following compounds from readily available aldehydes, ketones, esters, and alkyl halides according to the methods described in this section:
The following questions pertain to the esters shown and their behavior under conditions of the Claisen condensation.
(a) Give the structure of the Claisen condensation product of ethyl phenylacetate (C6H5CH2COOCH2CH3). (b) What ketone would you isolate after saponification and decarboxylation of this Claisen
All the following questions concern ethyl (2-oxocyclohexane) carboxylate
Give the structure of the product formed on reaction of ethyl acetoacetate with each of the following: (a) 1-Bromopentane and sodium ethoxide (b) Saponification and decarboxylation of the product
(a) Only a small amount (less than 0.01%) of the enol form of diethyl malonate is present at equilibrium. Write a structural formula for this enol. (b) Enol forms are present to the extent of about
(a) On addition of one equivalent of methylmagnesium iodide to ethyl acetoacetate, the Grignard reagent is consumed, but the only organic product obtained after working up the reaction mixture is
Give the structure of the principal organic product of each of the following reactions:
Give the structure of the principal organic product of each of the following reactions: Discuss.
The spicy flavor of cayenne pepper is due mainly to a substance called capsaicin. The following sequence of steps was used in a 1955 synthesis of capsaicin. See if you can deduce the structure of
Show how you could prepare each of the following compounds. Use the starting material indicated along with ethyl acetoacetate or diethyl malonate and any necessary inorganic reagents. Assume also
Diphenadione inhibits the clotting of blood; that is, it is an anticoagulant. It is used to control vampire bat populations in South America by a “Trojan horse” strategy. A few bats are trapped,
Phenylbutazone is a frequently prescribed antiinflammatory drug. It is prepared by the reaction shown.
The use of epoxides as alkylating agents for diethyl malonate provides a useful route to - lactones. Write equations illustrating such a sequence for styrene oxide as the starting epoxide. Is the
Diethyl malonate is prepared commercially by hydrolysis and esterification of ethyl cyanoacetate.
The tranquilizing drug meprobamate has the structure shown.
When the compound shown was heated in refluxing hydrochloric acid for 60 hours, a product with the molecular formula C5H6O3 was isolated in 97% yield. Identify this product. Along with this product,
How many a hydrogens are there in each of the following? (a) 3, 3-Dimethyl-2-butanone (c) Benzyl methyl ketone (b) 2, 2-Dimethylpropanal (d) Cyclohexanone
Chlorination of 2-butanone yields two isomeric products, each having the molecular formula C4H7ClO, Identify these two compounds
Write the structures of the enol forms of 2-butanone that react with chlorine to give 1-chloro-2-butanone and 3-chloro-2-butanone.
Represent the reaction of chlorine with each of the enol forms of 2-butanone according to the curved arrow formalism just described.
Write structural formulas corresponding to (a) The enol form of 2, 4-dimethyl-3-pentanone (b) The enol form of acetophenone (c) The two enol forms of 2-methylcyclohexanone
Write structural formulas corresponding to
Write the structure of the enolate ion derived from each of the following B-dicarbonyl compounds. Give the three most stable resonance forms of each enolate.
After the compound shown was heated in D2O containing K2CO3 at 70°C the only signals that could be found in its 1H NMR spectrum were at δ3.9 ppm (6H) and 6.7–6.9 ppm (3H). What happened?
Is the product from the a chlorination of (R)-sec-butyl phenyl ketone with Cl2 in acetic acid chiral? Is it optically active?
Write the structure of the aldol addition product of
Write the structure of the aldol condensation product of each of the aldehydes in Problem 18.10. One of these aldehydes can undergo aldoladdition, but not aldol condensation. Which one? Why?
Outline a synthesis of 2-ethyl-1-hexanol from butanal. The carbon–carbon bond-forming potential of the aldol condensation has been extended beyond the self-condensations described in this section
Give the structure of the mixed aldol condensation product of benzaldehyde with
Commercial mesityl oxide, (CH3) 2C═CHCCH3, is often contaminated with about 10% of an isomer having the same carbon skeleton. What is a likely structure for this compound?
Acrolein (CH2═CHCH═O) reacts with sodium azide (NaN3) in aqueous acetic acid to form a compound, C3H5N3O in 71% yield. Propanal (CH3CH2CHoeO), when subjected to the same reaction
Both the conjugate addition step and the intramolecular aldol condensation step can be carried out in one synthetic operation without isolating any of the intermediates along the way. For example,
Outline two ways in which 4-methyl-2-octanone can be prepared by conjugate addition of an organocuprate to an a, B-unsaturated ketone.
(a) Write structural formulas or build molecular models for all the noncyclic aldehydes and ketones of molecular formula C4H6O. (b) Are any of these compounds stereoisomeric? (c) Are any of these
The main flavor component of the hazelnut is (2E, 5S)-5-methyl-2-hepten-4-one. Write a structural formula or build a molecular model showing its stereochemistry.
The simplest a, ß -unsaturated aldehyde Acrolein is prepared by heating glycerol with an acid catalyst. Suggest a mechanism for this reaction.
In each of the following pairs of compounds, choose the one that has the greater enol content, and write the structure of its enol form:
Give the structure of the expected organic product in the reaction of 3-phenylpropanal with each of the following: (a) Chlorine in acetic acid (b) Sodium hydroxide in ethanol, 10°C (c) Sodium
Each of the following reactions has been reported in the chemical literature. Write the structure of the product(s) formed in each case.
Show how each of the following compounds could be prepared from 3-pentanone. In most cases more than one synthetic transformation will be necessary. (a) 2-Bromo-3-pentanone (d) 3-Hexanone (b)
(a) A synthesis that begins with 3,3-dimethyl-2-butanone gives the epoxide shown. Suggest reagents appropriate for each step in the synthesis.
Using benzene, acetic anhydride and 1-propanethiol as the source of all the carbon atoms, along with any necessary inorganic reagents, outline a synthesis of the compound shown.
Show how you could prepare each of the following compounds from cyclopentanone, D2O, and any necessary organic or inorganic reagents.
(a) At present, butanal is prepared industrially by hydroformylation of propene (Section 17.4). Write a chemical equation for this industrial synthesis. (b) Before about 1970, the principal

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