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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

Compounds L and M have the molecular formula C7H14, Compounds L and M are optically inactive, are nonresolvable, and are diastereomers of each other. Catalytic hydrogenation of either L or M yields
How many stereoisomers are possible for 4-methyl-2-hexene, and how many fractions would you obtain if you distilled the mixture?
Propose structures for compounds E-H. Compound E has the molecular formula C5H8 and is optically active. On catalytic hydrogenation E yields F. Compound F has the molecular formula C5H10, is
Consider the interconversion of cis-2-butene and trans-2-butene.(a) What is the value of ∆Ho for the reaction cis-2-butene : trans-2-butene?(b) Assume ∆Ho ≅ ∆Go. What minimum value of DG‡
(a) Partial dehydrohalogenation of either (1R, 2R)-1,2-dibromo-1,2-diphenylethane or (1S, 2S)-1,2-dibromo-1,2-diphenylethane enantiomers (or a race mate of the two) produces
(a) Using reactions studied in this chapter, show steps by which this alkyne could be converted to the seven-membered ring homolog of the product obtained in Problem 7.44(b).(b) Could the homologous
Predict the structures of compounds A, B, and C: A is an unbranched C6 alkyne that is also a primary alcohol. B is obtained from A by use of hydrogen and nickel boride catalyst or dissolving metal
Predict the major product formed when 2-bromobutane is subjected to dehydrobromination using sodium ethoxide in ethanol at 55oC.
List the alkenes that would be formed when each of the following alkyl halides is subjected to dehydrohalogenation with potassium ethoxide in ethanol and use Zaitsev's rule to predict the major
Consider a simple molecule such as ethyl bromide and show with Newman projection formulas how the anti coplanar transition state would be favored over the syn coplanar one.
(a) Outline a likely mechanism for the solvomercuration step of the ether synthesis just shown. (b) Show how you would use solvomercuration-demercuration to prepare tertbutyl methyl ether. (c) Why
Specify the alkene needed for synthesis of each of the following alkylboranes by hydroboration:(a)(b) (c) (d) Show the stereochemistry involved in the hydroboration of 1-methylcyclohexene.
Treating a hindered alkene such as 2-methyl-2-butene with BH3: THF leads to the for- mation of a dialkylborane instead of a trialkylborane. When 2 mol of 2-methyl-2-butene is added to 1 mol of BH3,
Specify the appropriate alkene and reagents for synthesis of each of the following alcohols by hydroboration-oxidation.(a)(b) (c) (d) (e) (f)
Starting with any needed alkene (or cycloalkene) and assuming you have deuterioacetic acid (CH3CO2D) available, outline syntheses of the following deuterium-labeled compounds.(a) (CH3)2CHCH2CH2D(b)
Write a mechanism to explain the following reaction.(As a racemic mixture)
In one industrial synthesis of ethanol, ethene is first dissolved in 95% sulfuric acid. In a second step water is added and the mixture is heated. Outline the reactions involved.
What products would you expect from each of the following reactions?(a)(b) (c)
Starting with cyclohexene and using any other needed reagents, outline a synthesis of 7, 7-dibromobicyclo [4.1.0] heptane.
Treating cyclohexene with 1, 1-diiodoethane and a zinc-copper couple leads to two isomeric products. What are their structures?
Outline mechanisms for the following addition reactions:(a)(b) (c)
Specify the alkene and reagents needed to synthesize each of the following diols.(a)(b) (Recemic) (c) (Recemic)
Predict the products of the following ozonolysis reactions.(a)(b) (c)
Write the structures of the alkenes that would yield the following carbonyl compoundsWhen treated with ozone and then with dimethyl sulfide.(a)(b) (2 Mol is produced from 1 mol of alkene) (c)
Alkenes are more reactive than alkynes toward addition of electrophilic reagents (i.e., Br2, Cl2, or HCl). Yet when alkynes are treated with one molar equivalent of these same electrophilic reagents,
A, B, and C are alkynes. Elucidate their structures and that of D using the following reaction roadmap.
How would you modify the procedure given in Solved Problem 8.8 so as to synthesize aracemic form of (3R,4R)- and (3S,4S)-3,4-dibromohexane?In problem 8.8
Write structural formulas for the products that form when 1-butene reacts with each of the following reagents: (a) HI (b) H2, Pt (c) Dilute H2SO4, warm (d) Cold concentrated H2SO4 (e) Cold
Repeat Exercise 8.26 using 1-methylcyclopentene instead of 1-butene. In Exercise 8.26 (a) HI (b) H2, Pt (c) Dilute H2SO4, warm (d) Cold concentrated H2SO4 (e) Cold concentrated H2SO4, then H2O and
Write structures for the major organic products from the following reactions. Show stereoisomers where applicable.(a)(b) (c) (d) (e)
Give the structure of the products that you would expect from the reaction of 1-butyne with: (a) One molar equivalent of Br2 (b) One molar equivalent of HBr (c) Two molar equivalents of HBr (d) H2
Provide mechanistic explanations for the following observations:(a)(b)
Give the structure of the products you would expect from the reaction (if any) of 2-butyne with: (a) One molar equivalent of HBr (b) Two molar equivalents of HBr (c) One molar equivalent of Br2 (d)
Write structures for the major organic products from the following reactions. Show stereoisomers where applicable.(a)(b) (c) (d)
Show how 1-butyne could be synthesized from each of the following: (a) 1-Butene (b) 1-Chlorobutane (c) 1-Chloro-1-butene (d) 1, 1-Dichlorobutane (e) Ethyne and ethyl bromide
Starting with 2-methylpropene (isobutylene) and using any other needed reagents, outline a synthesis of each of the following:(a)(b) (c) (d)
Write a three-dimensional formula for the product formed when 1-methylcyclohexene is treated with each of the following reagents. In each case, designate the location of deuterium or tritium
Write a mechanism that accounts for the formation of ethyl isopropyl ether in the following reaction.
When, in separate reactions, 2-methylpropene, propene, and ethene are allowed to react with HI under the same conditions (i.e., identical concentration and temperature), 2-methylpropene is found to
Propose a mechanism that accounts for the following reaction.
When 3, 3-dimethyl-2-butanol is treated with concentrated HI, a rearrangement takes place. Which alkyl iodide would you expect from the reaction? (Show the mechanism by which it is formed.)
Write stereochemical formulas for all of the products that you would expect from each of the following reactions. (You may find models helpful.)(a)(b) (c) (d)
(a) Write a mechanism for the following reaction.(b) What general conditions would you use to ensure a good yield of the product? (c) What general conditions would you use to carry out the reverse
Give (R, S) designations for each different compound given as an answer to Problem 8.39.In Problem 8.39(a)(b) (c) (d)
In one industrial synthesis of ethanol, ethene is first dissolved in 95% sulfuric acid. In a second step water is added and the mixture is heated. Outline the reactions involved. Discuss.
The reaction of bromine with cyclohexene involves anti addition, which generates, initially, the diaxial conformation of the addition product that then undergoes a ring flip to the diequatorial
Propose a mechanism that explains formation of the products from the following reaction, including the distribution of the products as major and minor.
Internal alkynes can be isomerized to terminal alkynes on treatment with NaNH2. The process is much less successful when NaOH is used. Why is there this difference?
Write a mechanism that explains the following reaction.
Write a mechanism for the following reaction.
Write a mechanism that explains formation of the products shown in the following reaction.
Myrcene, a fragrant compound found in bayberry wax, has the formula C10H16 and is known not to contain any triple bonds.(a) What is the index of hydrogen deficiency of myrcene? When treated with
Farnesene (below) is a compound found in the waxy coating of apples.(a) Give the structure and IUPAC name of the product formed when farnesene is allowed to react with excess hydrogen in the presence
Write structural formulas for the products that would be formed when geranial, a component of lemongrass oil, is treated with ozone and then with dimethyl sulfide (Me2S).Geranial
Limonene is a compound found in orange oil and lemon oil. When limonene is treated with excess hydrogen and a platinum catalyst, the product of the reaction is 1-isopropyl-4-methylcyclohexane. When
Pheromones (Section 4.7) are substances secreted by animals that produce a specific behavioral response in other members of the same species. Pheromones are effective at very low concentrations and
Synthesize the following compound starting with ethyne and 1-bromopentane as your only organic reagents (except for solvents) and using any needed inorganic compounds.
Predict features of their IR spectra that you could use to distinguish between the members of the following pairs of compounds. You may find the IR chart in the endpapers of the book and Table 2.1
Deduce the structures of compounds A, B, and C, which all have the formula C6H10. As you read the information that follows, draw reaction flowcharts (roadmaps) like those in Problems 8.24 and 8.52.In
Ricinoleic acid, a compound that can be isolated from castor oil, has the structure CH3(CH2)5CHOHCH2CH==CH(CH2)7CO2H. (a) How many stereoisomers of this structure are possible? (b) Write these
There are two dicarboxylic acids with the general formula HO2CCH==CHCO2H. One dicarboxylic acid is called maleic acid; the other is called fumaric acid. When treated with OsO4, followed by
Use your answers to the preceding problem to predict the stereochemical outcome of the addition of bromine to maleic acid and to fumaric acid. (a) Which dicarboxylic acid would add bromine to yield a
Outline all steps in a mechanism showing how 2, 3-dimethyl-2-butanol is formed in the acid-catalyzed hydration of 3, 3-dimethyl-1-butene.
Alkyl halides add to alkenes in the presence of AlCl3; yields are the highest when tertiary halides are used. Predict the outcome of the reaction of tert-pentyl chloride (1-chloro-2,
Explain the stereochemical results observed in this catalytic hydrogenation. (You may find it helpful to build hand-held molecular models.)
Make a reaction flowchart (roadmap diagram), as in previous problems, to organize the information provided to solve this problem. An optically active compound A (assume that it is dextrorotatory) has
A naturally occurring antibiotic called mycomycin has the structure shown here. Mycomycin is optically active. Explain this by writing structures for the enantiomeric forms of
An optically active compound D has the molecular formula C6H10 and shows a peak at about 3300 cm-1 in its IR spectrum. On catalytic hydrogenation D yields E (C6H14). Compound E is optically inactive
(a) Based on the following information, draw three-dimensional formulas for A, B, and C. Reaction of cyclopentene with bromine in water gives A, Reaction of A with aqueus NaOH (1 equivalent, cold)
Propose a mechanism that explains the following transformation.
Triethylamine, (C2H5)3N, like all amines, has a nitrogen atom with an unshared pair of electrons. Dichlorocarbene also has an unshared pair of electrons. Both can be represented as shown below. Draw
The following order of reactivity is observed when the following alkenes are subjected to acid-catalyzed hydration: (CH3)2C==CH2 > CH3CH==CH2 > CH2==CH2 Explain this order of reactivity.
Write a mechanism for the following reaction.
Write the structure of the appropriate alkene and specify the reagents needed for synthesis of the following alcohols by oxymercuration-demercuration:(a)(b) (c)
In what chemical shift ranges would you expect to find the proton NMR signals of ethyl acetate (CH3CO2CH2CH3)?
Propose a structure for each of the compounds whose spectra are shown in Fig. 9.22, and account for the splitting pattern of each signal.
What is the dihedral angle and expected coupling constant between the labeled protons in each of the following molecules?(a)(b)
Draw the most stable chair conformation of 1-bromo-2-chlorocyclohexane, if the coupling constant between hydrogens on C1 and C2 was found to be 7.8 Hz (J1,2 = 7.8 Hz).
Explain how you could distinguish between the following two compounds using NMR coupling constants. (These compounds are derived from glucose, by a reaction we shall study in Chapters 16 and 22.)A B
Carry out an analysis like that shown in Fig. 9.26 and show how many peaks the signal from (b) would be split into if Jab = 2Jbc and if Jab = Jbc. (Hint: In both cases peaks will fall on top of peaks
Compounds A, B, and C are isomers with the formula C5H11Br. Their broadband proton-decoupled 13C NMR spectra are given in Fig. 9.32. Information from the DEPT 13C NMR spectra is given near each peak.
In contrast to 2-methylbutane and neopentane, the mass spectrum of 3-methylpentane (not given) has a peak of very low relative abundance at - 15. It has a peak of very high relative abundance at -
Propose structures and fragmentation mechanisms corresponding to ions with m/z 57 and 41 in the mass spectrum of 4-methyl-1-hexene.
Match the mass spectra in Figs. 9.40 and 9.41 to the corresponding compounds shown below. Explain your answer.Butyl isopropyl ether Butyl propyl ether
What compound with molecular formula C3H6CI2 is consistent with the 1H NMR Spectrum shown in Fig. 9.7? Interpret the data by assigning each aspect of the spectrum to the structure you propose. (In
What are the expected ratios of thePeaks for the following compounds? (a) (b)
Given the mass spectrum in Figure 9.44 and the fact that the 1H NMR spectrum for this compound consists of only a large doublet and a small septet, what is the structure of the compound? Explain your
How many 1H NMR signals (not peaks) would you predict for each of the following compounds? (Consider all protons that would be chemical shift nonequivalent.)(a)(b) (c) (d) (e) (f) (g) (h) (i)
How many 13C NMR signals would you predict for each of the compounds shown in Problem 9.22?
Propose a structure for an alcohol with molecular formula C5H12 O that has the 1H NMR spectrum given in Fig. 9.46. Assign the chemical shifts and splitting patterns to specific aspects of the
Propose structures for the compounds G and H whose 1H NMR spectra are shown in Figs. 9.47 and 9.48.
Assume that in a certain 1H NMR spectrum you find two peaks of roughly equal intensity. You are not certain whether these two peaks are singlets arising from uncoupled protons at different chemical
Propose structures for compounds O and P that are consistent with the following information.
Compound Q has the molecular formula C7H8. The broad-band proton decoupled 13C spectrum of Q has signals at d 50 (CH), 85 (CH2), and 144 (CH). On catalytic hydrogenation Q is converted to R (C7H12).
Explain in detail how you would distinguish between the following sets of compounds using the indicated method of spectroscopy.(a) 1H NMR(b) 13C and 1H NMR(c) 13C NMR
Using the method of Section 9.8A, determine the number of expected signals for the following compounds.(a)(b) (c)
Compound S (C8H16) reacts with one mole of bromine to form a compound with molecular formula C8H16Br2. The broadband proton-decoupled 13C spectrum of S is given in Fig. 9.49. Propose a structure for
A compound with molecular formula C4H8O has a strong IR absorption at 1730 cm-1. Its mass spectrum includes key peaks at m/z 44 (the base peak) and m/z 29. Propose a structure for the compound and
In the mass spectrum of 2, 6-dimethyl-4-heptanol there are prominent peaks at m/z 87, 111, and 126. Propose reasonable structures for these fragment ions.
In the mass spectrum of 4-methyl-2-pentanone a McLafferty rearrangement and two other major fragmentation pathways occur. Propose reasonable structures for these fragment ions and specify the m/z

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