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organic chemistry

Questions and Answers of Organic Chemistry

Convert the following perspective formulas to Fischer projections.(a)(b)(c)(d) H OH .C. CH; CH,OH
A chiral sample gives a rotation that is close to 180°. How can one tell whether this rotation is +180° or -180°?
When it is strongly heated, ethyl diazoacetate decomposes to give nitrogen gas and a carbene. Draw a Lewis structure of the carbene. :N=N-CH-C-O-CH,CH, ethyl diazoacetate
Write an equation for the reaction of vitamin E with an oxidizing radical (RO∙) to give ROH and a less reactive free radical.
In the presence of a small amount of bromine, cyclohexene undergoes the following lightpromoted reaction:(a) Propose a mechanism for this reaction.(b) Draw the structure of the rate-limiting
In the presence of a small amount of bromine, cyclohexene undergoes the following lightpromoted reaction:(a) Propose a mechanism for this reaction.(b) Draw the structure of the rate-limiting
2,3-Dimethylbutane reacts with bromine in the presence of light to give a monobrominated product. Further reaction gives a good yield of a dibrominated product. Predict the structures of these
(a) Compute the heats of reaction for abstraction of a primary hydrogen and a secondary hydrogen from propane by a fluorine radical.(b) How selective do you expect free-radical fluorination to be?(c)
(a) When n-heptane burns in a gasoline engine, the combustion process takes place too quickly. The explosive detonation makes a noise called knocking. When 2,2,4-trimethylpentane (isooctane) is
Predict the ratios of products that result from chlorination of isopentane (2-methylbutane).
Use the bond-dissociation enthalpies in Table 4-2 to calculate the heats of reaction for the two possible first propagation steps in the chlorination of isobutane. Use this information to draw a
Write structures for a homologous series of alcohols (R-OH) having from one to six carbons.
Draw a graph, similar to Figure 3-9, of the torsional strain of 2-methylpropane as it rotates about the bond between C1 and C2. Show the dihedral angle and draw a Newman projection for each staggered
Give the structures of 4-isopropyloctane and 5-tert-butyldecane.
If the carbon atom in CH2Cl2 were flat, there would be two stereoisomers. The carbon atom in CH2Cl2 is actually tetrahedral. Make a model of this compound, and determine whether there are any
Draw a Lewis structure, and classify each of the following compounds:(a) CH3CH2CONHCH3(b) (CH3CH2)2NH(c) (CH3)2CHCOOCH3(d) CH3CHCHCOCl(e) (CH3CH2)2O(f) CH3CH2CH2CN(g)
Draw a Lewis structure, and classify each of the following compounds. The possible classifications are as follows:(a) CH2CHCHO(b) CH3CH2CH(OH)CH3(c) CH3COCH2CH3(d) CH3CH2OCHCH2(e)(f)(g)(h)(i)
Classify the following hydrocarbons, and draw a Lewis structure for each one. A compound may fit into more than one of the following classifications:(a) (CH3CH2)2CHCH(CH3)2(b) CH3CHCHCH2CH3(c)
For each of the following compounds:1. Draw the Lewis structure.2. Show how the bond dipole moments (and those of any nonbonding pairs of electrons) contribute to the molecular dipole moment.3.
The N-F bond is more polar than the N-H bond, but NF3 has a smaller dipole moment than NH3. Explain this curious result.NH3 ………..….. NF3µ = 1.5D …… µ = 0.2D
The C=O double bond has a dipole moment of about 2.4 D and a bond length of about 1.23 Å.(a) Calculate the amount of charge separation in this bond.(b) Use this information to evaluate the relative
Give the relationship between the following pairs of structures. The possible relationships are:same compound cis-trans isomersconstitutional isomers (structural isomers) not isomers (different
Which of the following compounds show cis-trans isomerism? Draw the cis and trans isomers of those that do.a. CHF=CHFb. F2C=CH2c. CH2=CH-CH2-CH3d.e.f. CHCH,
Two compounds with the formula CH3-CH=N-CH3 are known.(a) Draw a Lewis structure for this molecule, and label the hybridization of each carbon and nitrogen atom.(b) What two compounds have this
For each pair of structures, determine whether they represent different compounds or a single compound.a.b.c.d. H;C CH,CH; H3C CH3 and H CH3 H CH,CH3
Name the element that corresponds to each electronic configuration.a. 1s22s22p2b. 1s22s22p4c. 1s22s22p63s23p3d. 1s22s22p63s23p5
The terminal carboxyl groups of glutamic acid and aspartic acid are often protected through their conversion to benzyl esters. What mild method could be used for removal of this protecting group?
The estrogens (estrone and estradiol) are easily separated from the androgens (androsterone and testosterone) on the basis of one of their chemical properties. What is that property, and how could
What simple chemical test could you use to distinguish between geraniol and menthol?
One reference book lists d-mannose as being dextrorotatory; another lists it as being levorotatory. Both references are correct. Explain.
How might you distinguish between α-D-glucopyranose (i.e., D-glucose) and methyl α-D-glucopyranoside?
Describe with equations how you might separate a mixture of aniline, p-cresol, benzoic acid, and toluene using ordinary laboratory reagents.
(a) What products would you expect to be formed when each of the amines in the preceding problem reacts with benzenesulfonyl chloride and excess aqueous potassium hydroxide?(b) What would you observe
Explain the variation in enol content that is observed for solutions of acetylacetone (pentane-2,4-dione) in the several solvents indicated:Solvent ............. % EnolH2O .........................
In the synthesis of the keto acid just given, the dicarboxylic acid decarboxylates in a specific way; it givesExplain. HO rather than HO
Why do we say that the halogenation of ketones in a base is “base promoted” rather than “base catalyzed”?
Ketene, H2C=C=O, is an important industrial chemical. Predict the products that would be formed when ketene reacts with(a) Ethanol,(b) Acetic acid,(c) Ethylamine.Markovnikov addition occurs.
Write detailed mechanisms for the acidic and basic hydrolysis of propanamide.
Where would you expect to find the labeled oxygen if you carried out an acid-catalyzed hydrolysis of methyl benzoate in 18O-labeled water? Write a detailed mechanism to support your answer.
What would be the major product formed in the Baeyer-Villiger oxidation of 3-methyl-2-butanone?
The reactions of aldehydes and ketones with LiAlH4 and NaBH4 (Section 12.3) are nucleophilic additions to the carbonyl group. What is the nucleophile in these reactions?
Birch reduction of toluene leads to a product with the molecular formula C7H10. On ozonolysis followed by reduction with dimethyl sulfide, the product is transformed intoWhat is the structure of the
Compound E has the spectral features given below. What is its structure?MS (m/z): M⨥ 202IR (cm-1): 3030–3080, 2150 (very weak), 1600, 1490, 760, and 6901H NMR (δ): narrow multiplet centered at
The 1H NMR spectrum of cyclooctatetraene consists of a single line located at δ 5.78. What does the location of this signal suggest about electron delocalization in cyclooctatetraene?
In addition to a signal downfield, the 1H NMR spectrum of trans-15,16-dimethyldihydro- tice pyrene has a signal far upfield at δ -4.2. Account for the presence of this upfield signal.
Listed below are four compounds that have the molecular formula C6H6. Which of these compounds would yield only one monosubstitution product, if, for example, one hydrogen were replaced by
How many 13C NMR signals would you predict for(a) Naphthalene,(b) Anthracene,(c) Phenanthrene, (d) Pyrene?
Listed below are four compounds that have the molecular formula C6H6. Which of these Practice Problem 14.2 compounds would yield only one monosubstitution product, if, for example, one hydrogen were
When furan and maleimide undergo a Diels–Alder reaction at 25 °C, the major product is the endo adduct G. When the reaction is carried out at 90 °C, however, the major product is the exo isomer
When furan and maleimide undergo a Diels–Alder reaction at 25 °C, the major product is the endo adduct G. When the reaction is carried out at 90 °C, however, the major product is the exo isomer
Why does the molecule shown below, although a conjugated diene, fail to undergo a Diels–Alder reaction?
What product would you expect from the following reaction? 2 NaOEt ELOH, heat CI
Although oxirane (oxacyclopropane) and oxetane (oxacyclobutane) react with Grignard and organolithium reagents to form alcohols, tetrahydrofuran (oxacyclopentane) is so unreactive that it can be used
When the bicyclic alkene I, a trans-decalin derivative, reacts with a peroxy acid, II is the major product. What factor favors the formation of II in preference to III? (You may find it helpful to
If the goal is to synthesize CCl4 in maximum yield, this can be accomplished by using a large excess of chlorine. Explain.
The mass spectra of many benzene derivatives show a peak at m/z 51. What could account for this fragment?
How many signals would you expect to obtain in the 1H NMR spectrum of undecadeuteriocyclohexane at room temperature?
How many signals would you expect to obtain in the 1H NMR spectrum of undecadeuteriocyclohexane at room temperature?
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.
Shown below is the final step in a synthesis of an important perfume constituent, cis-jasmone. Which reagents would you choose to carry out this last step? cis-Jasmone
The double bond of tetrachloroethene is undetectable in the bromine test for unsaturation. Give a plausible explanation for this behavior.
When ethene gas is passed into an aqueous solution containing bromine and sodium chloride, the products of the reaction are the following:Write mechanisms showing how each product is formed. Br Br-
Give the structure and name of the product that would be obtained from the ionic addition of IBr to propene.
What is the index of hydrogen deficiency for(a) C7H10O2(b) C5H4N4?
What is the index of hydrogen deficiency (IHD) (degree of unsaturation) for each of the following compounds?a.b. C6H8Br4
Without consulting tables, arrange the following compounds in order of decreasing acidity:Pentane 1-Pentene 1-Pentyne
Examine Solved Problem 7.3. Your task is to prepare A in the highest possible yield by dehydrobromination. Which base would you use?Solved Problem 7.3Using Zaitsev’s rule, predict which would be
Which would you expect to be the stronger nucleophile in a polar aprotic solvent?a. CH3CO2- or CH3O-b. H2O or H2Sc. (CH3)3P or (CH3)3N
Which of the following alkyl halides is most likely to undergo substitution by an SN1 mechanism?a.b.c. Br
Rank the following in terms of decreasing nucleophilicity in a protic solvent.CH3CO2- CH3O- CH3S- CH3SH
Rank the following in terms of decreasing nucleophilicity:CH3CO2- CH3OH CH3O- CH3CO2H N≡C-
Rank the following carbocations in order of increasing stability:a.b.c.
asasas
Classify each of the following organic halides as primary, secondary, tertiary, alkenyl, or aryl.a.b.c.d.e. Br
Give IUPAC names for each of the following.a.b.c. Br
If a sample of a pure substance that has two or more chirality centers has an observed rotation of zero, it could be a racemate. Could it possibly be a pure stereoisomer? Could it possibly be a pure
Tell whether the compounds of each pair are enantiomers, diastereomers, constitutional isomers, or not isomeric.a.b.c.d. CHO СНО H- -OH HO- HO and H- H- HO- HO- ČH,OH ČH2OH
Discuss the anticipated stereochemistry of each of the following compounds.(a) ClCH=C=C= CHCl(b) CH2=C=C=CHCl(c) ClCH=C=C= CCl2
Shown below are Newman projection formulas for (R,R)-, (S,S )-, and (R,S )-2,3-dichlorobutane.(a) Which is which?(b) Which formula is a meso compound?
(a) How many carbon atoms does an alkane (not a cycloalkane) need before it is capable of existing in enantiomeric forms?(b) Give correct names for two sets of enantiomers with this minimum number of
Which of the following are chiral and, therefore, capable of existing as enantiomers?(a) 1,3-Dichlorobutane(b) 1,2-Dibromopropane(c) 1,5-Dichloropentane(d) 3-Ethylpentane(e)
Give the (R,S ) designation for each compound given as an answer to Practice Problem 5.29.Practice Problem 5.29(a) 1-Bromo-2-chlorocyclohexane(c) 1-Bromo-4-chlorocyclohexane(b)
Give names that include (R) and (S ) designations for compounds B and C in Section 5.12B.Section 5.12 H Br Br. レH Br H H Br A
The following are formulas for three compounds, written in noneclipsed conformations. In each instance tell which compound (A, B, or C above) each formula represents.a.b.c. Br Br
(a) If 3 and 4 are enantiomers, what are 1 and 4?(b) What are 2 and 3, and 2 and 4?(c) Would you expect 1 and 3 to have the same melting point?(d) The same boiling point?(e) The same vapor pressure?
Tell whether the two structures in each pair represent enantiomers or two molecules of the same compound in different orientations.a.b.c. Br. CI Br Cl I F and H F H
Assign (R ) or (S ) designations to each of the following compounds:a.b.c.d. H,C, CI
Which of the objects listed in Practice Problem 5.1 possess a plane of symmetry and are, therefore, achiral?Problem 5.1(a) A screwdriver(b) A baseball bat(c) A golf club(d) A tennis shoe(e) An ear(f)
Demonstrate the validity of what we have represented in Fig. 5.5 by constructing models. Demonstrate for yourself that III and IV are related as an object and its mirror image and that they are not
Construct handheld models of the 2-butanols represented in Fig. 5.3 and demonstrate for yourself that they are not mutually superposable.(a) Make similar models of 2-bromopropane. Are they
Use the S - A + 1 = N method, to determine the number of rings in cubane Section 4.14.
The name sec-butyl alcohol defines a specific structure but the name sec-pentyl alcohol is ambiguous. Explain.
(a) Write structural formulas for the two chair conformations of cis-1-isopropyl-4-methylcyclohexane.(b) Are these two conformations equivalent?(c) If not, which would be more stable?(d) Which would
Write the structure and give the IUPAC name for an alkane with formula C6H14 that has only primary and secondary carbon atoms.
Which structure does not represent 2-methylpentane?a.b.c.d.
The free-energy change, ΔG°, for the ionization of acid HA is 21 kJ mol-1; for acid HB it is -21 kJ mol-1. Which is the stronger acid?
(a) The Ka of formic acid (HCO2H) is 1.77 × 10-4. What is the pKa?(b) What is the Ka of an acid whose pKa = 13?
When methyl alcohol is treated with NaH, the product is CH3O-Na+ (and H2) and not Na+ -CH2OH (and H2). Explain why this is so.
List the acids you gave as answers to Exercise 3.20 in order of decreasing acidity.(a) HSO4-(b) H2O(c) CH3NH2(d) -NH2(e) CH3CH2(f) CH3CO2-
List the bases you gave as answers to Exercise 3.18 in order of decreasing basicity.

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