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chemistry
organic chemistry
Questions and Answers of
Organic Chemistry
2-Butene-1-thiol is one component of shunk spray. How would you synthesize this substance from methyl 2-butenoate? From 1,3-butadiene
The 1H NMR spectrum shown is that of an ether with the formula C4H8O. Propose astructure.
Give IUPAC name for the following compounds (reddish brown =Br):
Show the product, including stereochemistry that would result from reaction of the following epoxide with HBr.
Show the product, including stereochemistry, of the following reaction:
Treatment of the following alkene with a peroxyacid yields an epoxide different from that obtained by reaction with aqueous Br2 followed by base treatment. Propose structures for the two epoxides,
Draw structures corresponding to the following IUPAC names:(a) Ethyl 1-ethylpropyl ether(b) Di (p-chlorophenyl) ether(c) 3, 4-Dimethoxybenzoic acid(d) Cyclopentyloxycyclohexanc(e)
Give IUPAC names for the followingstructures:
Predict the products of the following ether cleavagereactions:
How would you prepare the following ethers?
How would you prepare the following compounds from 1-phenylethanol?(a) Methyl 1-phenyl ethyl ether(b) Phenylepoxyethane(c) tert-Butyl 1-phenylethyl ether(d) 1-Phenylethanethiol
Predict the products of the following reactions:
How would you carry out the following transformations? More than one step may berequired.
What product would you expect from cleavage of tetra hydro furan with HI?
How could you prepare benzyl phenyl ether from benzene and phenol? More than one step is required.
When 2-methyl-2, 5-pentanediol is treated with sulfuric acid, dehydration occurs and 2, 2-dimethyltetrahydrofuran is formed. Suggest a mechanism for this reaction. Which of the two oxygen atoms is
Write the mechanism of the hydrolysis of cis-5, 6-epoxydecane by reaction with aqueous acid. What is the stereochemistry of the product, assuming normal backside SN2 attack?
What is the stereochemistry of the product from acid-catalyzed hydrolysis of trans-5, 6-epoxvdecane? How does the product differ from that formed in Problem 18.33?
Methyl aryl ethers, such as anisole, are cleaved to iodomethane and a phenoxide ion by treatment with LiI in hot DMF. Propose a mechanism for this reaction.
Tert-Butyl ethers can be prepared by the reaction of an alcohol with 2-methyipropene in the presence of an acid catalyst. Propose a mechanism for this reaction.
Meerwein?s reagent, triethyloxonium tetra-fluoroborate, is a powerful ethylating agent that converts alcohols into ethyl ethers at neutral pH. Show the reaction of Meerwein?s reagent with
Safrole, a substance isolated from oil of sassafras, is used as a perfumery agent. Propose a synthesis of safrole from catechol (1,2-benzenediol).
Epoxides are reduced by treatment with lithium aluminum hydride to yield alcohols. Propose a mechanism for thisreaction.
Show the structure and stereochemistry of the alcohol that would result if 1, 2-epoxycyclohexane (Problem 18.39) were reduced with lithium aluminum deuteride, LiAID4.
Acid-catalyzed hydrolysis of a 1, 2-epoxycyclohexane produces a trans-diaxial 1, 2—diol. What product would you expect to obtain from acidic hydrolysis of cis-3-tert-butyl-1, 2-epoxycyclohexane?
Grignard reagents react with oxetane, a four-membered cyclic ether, to yield primary alcohols, but the reaction is much slower than the corresponding reaction with ethylene oxide. Suggest a reason
Treatment of trans-2-chlorocyclohcxanol with NaOH yields 1, 2-epoxycyclo- hexane, but reaction of the cis isomer under the same conditions yields Cyclohexanone. Propose mechanisms for both reactions,
Ethers undergo an acid-catalyzed cleavage reaction when treated with the Lewis acid BBr3 at room temperature. Propose a mechanism for thereaction.
The Zeisel method is an analytical procedure for determining the number of methoxyl groups in a compound. A weighed amount of the compound is heated with concentrated HI, ether cleavage occurs, and
Disparlure, C19H38O, is a sex attractant released by the female gypsy moth, Lymantria dispar. The 1H NMR spectrum of disparlure shows a large absorption in the alkane region, 1 to 2 δ, and a triplet
How would you synthesize racemic disparlure (Problem 18.46) from corn- pounds having ten or fewer carbons?
Treatment of 1, 1-diphenyl- 1, 2-epoxyethane with aqueous acid yields diphenylacetaldehyde as the major product. Propose a mechanism for the reaction.
How would you prepare o-hydroxyphenyl-acetaldehyde from phenol? More than one step is required.
Imagine that you have treated (2R, 3R)-2, 3-epoxy-3-methylpentane with aqueous acid to carry out a ring-opening reaction. (a) Draw the epoxide, showing stereochemistry. (b) Draw and name the product,
Identify the reagents a?c in the following scheme:
Fluoxetine, a heavily prescribed antidepressant marketed under the name Prozac, can be prepared by a route that begins with reaction between a phenol and an alkyl chloride. (a) The rate of the
The herbicide acifluorfen can be prepared by a route that begins with reaction between a phenol and an aryl fluoride. Propose a mechanism.
The red fox (Vulpes) uses a chemical communication system based on scent marks in urine. Recent work has shown one component of fox urine to be a sulfide. Mass spectral analysis of the pure
Anethole, C10H12O, a major constituent of the oil of anise, has the 1H NMR spectrum shown. On oxidation with Na2Cr2O7, Anethole yields p-methoxybenzoic acid. What is the structure of Anethole? Assign
How would you synthesize Anethole (Problem 18.55) from phenol?
Aldehydes and ketones undergo acid-catalyzed reaction with alcohols to yield hemiacetals, compounds that have one alcohol-like oxygen and one ether-like oxygen bonded to the same carbon. Further
We saw in Section 17.4 that ketones react with NaBH4 to yield alcohols. We?ll also see in Section 22.3 that ketones react with Br2 to yield a-bromo ketones. Perhaps surprisingly, treatment with NaBH4
Give IUPAC name for the following compounds:
Draw structures corresponding to the following IUPAC name:(a) (Z)-2-Ethyl-2-buten-1-o1(b) 3-Cyclohexen-1-o1(c) trans-3-Chlorocycloheptanol(d) 1, 4-Pentanediol(e) 2, 6-Dimethylphenol(f)
The following data for isomeric four-carbon alcohols show that there is a decrease in boiling point with increasing substitution of the OH-bearing carbon. How might you account for this
Rank the following substances in order of increasing acidity:(a) (CH3)2CHOH, HC ≡ CH, (CF3)2CHOH, CH4OH(b) Phenol, p-methyl phenol, p-(trifluoromethyl) phenol(c) Benzyl alcohol, phenol, p-hydroxy
P-Nitro benzyl alcohol is more acidic than benzyl alcohol but p-methoxy benzyl alcohol is less acidic. Explain.
Predict the products of the following reactions:
What reagent would you use to accomplish each of the following reactions?
What carbonyl compounds give the following alcohols on reduction with LiAlH4? Show allpossibilities.
Show the products obtained from addition of methyl magnesium bromide to the following compounds:(a) Cyclopentanone(b) Benzophenone (diphenyl ketone)(c) 3-Hexanone
Use a Grignard reaction to prepare the following alcohols:(a) 2-Methyl-2-propanol(b) 1-Methylcyclohexanol(c) 3-Methyl-3-pentanol(d) 2-Phenyl-2-butanol(e) Benzyl alcohol(f) 4-Methyl-1-pentanol
Use the reaction of a Grignard reagent with a carbonyl compound to synthesize the following compound:
How would you carry out the following transformation, a step used in the commercial synthesis of(S)-ibuprofen?
What product(s) would you expect from dehydration of the following alcohols with POCl3 in pyridine? Indicate the major product in eachcase?
What alcohols would give the following products on oxidation?
What products would you expect from oxidation of the following compounds with CrO3 in aqueous acid with pyridinium chlorochromate?(a) 1-Hexanol(b) 2-Hexanol(c) Hexanol
TMS ethers can be removed by treatment with fluoride ion as well as be acid-catalyzed hydrolysis. Propose a mechanism for the reaction of cyclohexyl TMS ether with LiF. Fluorotrimethyisilane is a
Show the mechanism of the reaction of p-methaylphenol with 2-methylpropene and H3PO4 catalyst to yield the food additive BHT.
Assume that you need to prepare 5-cholesten-3-one from cholesterol. How could you use IR spectroscopy to tell whether the reaction was successful? What differences would you look for in the IR
When the 1HNMR spectrum of an alcohol is run in dimethyl sulfoxide (DMSO) solvent rather than in chloroform, exchange of the O—H proton is slow and spin—spin splitting is seen between the O—H
Give IUPAC names for the following compounds:
Draw the structure of the carbonyl compound(s) from which each of the following alcohols might have been prepared, and show the products you would obtain by treatment of each alcohol with (i) Na
Predict the product from reaction of the following substance (reddish brown = Br) with: (a) PBr3 (b) Aqueous H2SO4 (c) SOCl2 (d) PCC (e) Br2,FeBr3
Predict the product from reaction of the following substance with: (a) NaBH4 then H3O+ (b) LiAlH4 then H3O+ (c) CH3CH2 MgBr; then H3O+
Name and assign R or S stereochemistry to the product(s) you would obtain by reaction of the following substance with ethyl magnesium bromide. Is the product chiral? Is it optically active? Explain.
Give IUPAC names for the following compounds:
Draw and name the eight isomeric alcohols with formula C5H12O.
Which of the eight alcohols you identified in problem react with CrO3 in aqueous acid? Show the products you would expect from each reaction.
Named bombykol, the sex pheromone secreted by the female silkworm moth has the formula C16H280 and the systematic name (10E, 12Z)-10, 12-hexadecadien-1-ol. Draw bombykol showing correct geometry for
Carvacrol is a naturally occurring substance isolated from oregano, thyme, and marjoram. What is its IUPAC name?
What products would you obtain from reaction of 1-penlanol with the following reagents?(a) PBr3(b) SOCl2(c) CrO3, H20, H2SO4(d) PCC
How would you prepare the following compounds from 2-phenylethanol? More than one step may be required.(a) Styrene (PhCH = CH2(b) Phenyl acetaldehyde (PhCH2CHO)(c) Phenyl acetic acid (PhCH2CO2H)(d)
How would you prepare the following compounds from 1-phenylethanol? More than one step may be required.(a) Acetophenone (PhCOCH3)(b) Benzyl alcohol(c) m-Bromobenzoic acid(d) 2-Phenyl-2-propanol
What Grignard reagent and what carbonyl compound might you start with to prepare the following alcohols?
What carbonyl compounds would you reduce to prepare the following alcohols? List all possibilities.
How would you carry out the following transformations?
What carbonyl compounds might you start with to prepare the following compounds by Grignard reaction? List all possibilities. (a) 2-Methyl-2-propanol (b) 1-Ethylcyclohexanol (c)
Evidence for the intermediate carbocations in the acid-catalyzed dehydration of alcohols comes from the observation that rearrangements sometimes occur. Propose a mechanism to account for the
Acid-catalyzed dehydration of 2, 2-dimethylcyclohexanol yields a mixture of 1, 2-dimethylcyclohexene and isopropylidenecyclopentane. Propose a mechanism to account for the formation of bothproducts.
Epoxide?s react with Grignard reagents to yield alcohols propose a mechanism.
How would you prepare the following substances from Cyclopentanol? More than one step may be required. (a) Cyclopentanone (b) Cyclopentane (c) 1-Methylcyclopentanol (d) Trans-2-Methylcyclopentanol
What products would you expect to obtain from reaction of 1-methylcyclo-hexanol with the following reagents?(a) HBr(b) NaH(c) H2SO4(d) Na2Cr2O7
Treatment of the following epoxide with aqueous acid produces a carbocation intermediate that reacts with water to give a diol product. Show the structure of the carbocation, and propose a mechanism
Benzoquinone is an excellent dienophile in the Diels—Alder reaction. What product would you expect from reaction of Benzoquinone with 1 equivalent of 1, 3-butadiene from reaction with 2 equivalents
Rank the following substituted phenols in order of increasing acidity, and explain your answer:
Benzyl chloride can be converted into benzaldehyde by treatment with nitro methane and base. The reaction involves initial conversion of nitro methane into its anion, followed by SN2 reaction of the
Reduction of 2-butanone with NaBH4 yields 2-butanol. Is the product chiral is it optically active? Explain.
Reaction of (S)-3-methyl-2-pentanone with methyl magnesium bromide followed by acidification yields 2, 3-dlmethyl-2-pentanol. What is the stereo chemistry of the product? Is the product optically
Testosterone is one of the most important male steroid hormones. When testosterone is dehydrated by treatment with acid, rearrangement occurs to yield the product shown. Propose a mechanism to
Starting from testosterone (Problem 17.48), how would you prepare the followingsubstances?
Compound A, C10H18O, undergoes reaction with dilute H2SO4 at 25 °C to yield a mixture of two alkenes, C10H16. The major alkene product, B, gives only Cyclopentanone after ozone treatment followed by
Dehydration of trans-2-methylcyclopentanol with POCl3 in pyridine yields predominantly 3-methylcyclopentene. Is the stereochemistry of this dehydration syn or anti? Can you suggest a reason for
How would you synthesize the following alcohols, starting with benzene and other alcohols of six or fewer carbons as your only organic reagents?
2, 3-Dimethyl-2, 3-butanediol has the common name pinacol. On heating with aqueous add, pinacol rearranges to pinacolone, 3, 3-dimethyl-2-hutanone. Suggest a mechanism for this reaction.
As a rule, axial alcohols oxidize somewhat faster than equatorial alcohols. Which would you expect to oxidize faster, cis-4-tert-butylcyclohexanol or trans-4-tert-butylcyclohexanol? Draw the more
Propose a synthesis of bicyclohexylidene, starting from Cyclohexanone as the only source of carbon.
A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate:
Identify the reagents a?f in the following scheme:
Galactose, a constituent of the disaccharide lactose found in dairy products, is metabolized by a pathway that includes the isomerization of UDP-galactose to UDP-glucose, where UDP = uridylyl
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