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1 Million+ Step-by-step solutionsmath books Q:Which of the following compounds are isomersWhich of the following compounds are isomers of spiropentane?Q:Use the bond-cleavage criterion to verifyUse the bond-cleavage criterion to verify that bicyclobutane and camphene are bicyclic.Q:Write structural formulas for each of the following bicyclic hydrocarbons:Write structural formulas for each of the following bicyclic hydrocarbons:
(a) Bicyclo [2.2.1] heptane (c) Bicyclo [3.1.1] heptane
(b) Bicyclo [5.2.0] nonane (d) Bicyclo [3.3.0] octaneQ:Draw or build a molecular modelDraw or build a molecular model of what you would expect to be the most stable conformation of the piperidine derivative in which the hydrogen bonded to nitrogen has been replaced by methyl.Q:Like hydrogen peroxide, the inorganic substancesLike hydrogen peroxide, the inorganic substances hydrazine (H2NNH2) and hydroxylamine (H2NOH) possess conformational mobility. Write structural representations or build molecular models of two different staggered conformations of (a) hydrazine and (b) hydroxylamine.Q:Of the three conformations of propane shown,Of the three conformations of propane shown, which one is the most stable? Which one is the least stable? Why?Q:Sight down the C-2─C-3 bond, and draw NewmanSight down the C-2─C-3 bond, and draw Newman projection formulas for the
(a) Most stable conformation of 2, 2-dimethylbutane
(b) Two most stable conformations of 2-methylbutane
(c) Two most stable conformations of 2, 3-dimethylbutaneQ:One of the staggered conformations of 2-methylbutaneOne of the staggered conformations of 2-methylbutane in Problem 3.17b is more stable than the other. Which one is more stable? Why?Q:(a) Write Newman projections for the gauche(a) Write Newman projections for the gauche and anti conformations of 1, 2-dichloroethane (ClCH2CH2Cl).
(b) The measured dipole moment of ClCH2CH2Cl is 1.12 D. Which one of the following statements about 1, 2-dichloroethane is false?
(1) It may exist entirely in the anti conformation.
(2) It may exist entirely in the gauche conformation.
(3) It may exist as a mixture of anti and gauche conformations.Q:Sketch an approximate potential energy diagramSketch an approximate potential energy diagram similar to that shown in Figures 3.4 and 3.7 for rotation about the carbon–carbon bond in 2,2-dimethylpropane. Does the form of the potential energy curve of 2, 2-dimethylpropane more closely resemble that of ethane or that of butane?Q:Repeat Problem 3.19 for the case of 2-methylbutane.Repeat Problem 3.19 for the case of 2-methylbutane.Q:One of the C─C─C angles of 2, 2, 4,One of the C─C─C angles of 2, 2, 4, 4-tetramethylpentane is very much larger than the others. Which angle? Why?Q:Even though the methyl group occupies an equatorialEven though the methyl group occupies an equatorial site, the conformation shown is not the most stable one for methylcyclohexane. Explain.Q:Which of the structures shown for the axial conformationWhich of the structures shown for the axial conformation of methylcyclohexane do you think is more stable, A or B? Why?Q:Which do you expect to be the more stable conformationWhich do you expect to be the more stable conformation of cis-1,3-dimethylcyclobutane, A or B? Why?Q:Determine whether the two structuresDetermine whether the two structures in each of the following pairs represent constitutional isomers, different conformations of the same compound, or stereoisomers that cannot be interconverted by rotation about single bonds.Q:Excluding compounds that contain methyl or ethylExcluding compounds that contain methyl or ethyl groups, write structural formulas for all the bicyclic isomers of (a) C5H8 and (b) C6H10.Q:In each of the following groups of compounds, identify the oneIn each of the following groups of compounds, identify the one with the largest heat of combustion and the one with the smallest. In which cases can a comparison of heats of combustion be used to assess relative stability?
(a) Cyclopropane, cyclobutane, Cyclopentane
(b) cis-1,2-Dimethylcyclopentane, methylcyclohexane,
1,1,2,2-tetramethylcyclopropaneQ:Write a structural formula for the most stable conformation ofWrite a structural formula for the most stable conformation of each of the following compounds:
(a) 2, 2, 5, 5-Tetramethylhexane (Newman projection of conformation about C-3—C-4 bond)
(b) 2, 2, 5, 5-Tetramethylhexane (zigzag conformation of entire molecule)
(c) cis-1-Isopropyl-3-methylcyclohexane
(d) trans-1-Isopropyl-3-methylcyclohexane
(e) cis-1-tert-Butyl-4-ethylcyclohexane
(f) cis-1, 1, 3, 4-TetramethylcyclohexaneQ:Identify the more stable stereoisomer in eachIdentify the more stable stereoisomer in each of the following pairs, and give the reason for your choice:
(a) cis- or trans-1-Isopropyl-2-methylcyclohexane
(b) cis- or trans-1-Isopropyl-3-methylcyclohexane
(c) cis- or trans-1-Isopropyl-4-methylcyclohexaneQ:One stereoisomer of 1, 1, 3, 5-tetramethylcyclohexaneOne stereoisomer of 1, 1, 3, 5-tetramethylcyclohexane is 15 kJ/mol (3.7 kcal/mol) less stable than the other. Indicate which isomer is the less stable, and identify the reason for its decreased stability.Q:One of the following two stereoisomers is 20 kJ/mol (4.9One of the following two stereoisomers is 20 kJ/mol (4.9 kcal/mol) less stable than the other. Indicate which isomer is the less stable, and identify the reason for its decreased stability.Q:Cubane (C8H8) is the common name of a polycyclicCubane (C8H8) is the common name of a polycyclic hydrocarbon that was first synthesized in the early 1960s. As its name implies, its structure is that of a cube. How many rings are present in Cubane?Q:The following are representationsThe following are representations of two forms of glucose. The six-membered ring is known to exist in a chair conformation in each form. Draw clear representations of the most stable conformation of each. Are they two different conformations of the same molecule, or are they stereoisomers? Which substituents (if any) occupy axial sites?Q:A typical steroid skeleton is shown along withA typical steroid skeleton is shown along with the numbering scheme used for this class of compounds. Specify in each case whether the designated substituent is axial or equatorial.Q:Repeat Problem 3.34 for the stereoisomeric steroidRepeat Problem 3.34 for the stereoisomeric steroid skeleton having a cis ring fusion between the first two rings.Q:Write structural formulas, and give the functional class and substitutiveWrite structural formulas, and give the functional class and substitutive names of all the isomeric alkyl chlorides that have the molecular formula C4H9Cl.Q:Write structural formulas, and give the functional class and substitutive namesWrite structural formulas, and give the functional class and substitutive names of all the isomeric alcohols that have the molecular formula C4H10O.Q:Classify the isomeric C4H10O alcohols as being primary,Classify the isomeric C4H10O alcohols as being primary, secondary, or tertiary.Q:Bromine is less electronegative than chlorine,Bromine is less electronegative than chlorine, yet methyl bromide and methyl chloride have very similar dipole moments. Why?Q:The constitutional isomer of ethanol, dimethyl etherThe constitutional isomer of ethanol, dimethyl ether (CH3OCH3), is a gas at room temperature. Suggest an explanation for this observation.Q:Write an equation for the reaction of ammoniaWrite an equation for the reaction of ammonia (NH3) with hydrogen chloride (HCl). Use curved arrows to track electron movement, and identify the acid, base, conjugate acid, and conjugate base.Q:Hydrogen cyanide (HCN) has a pKa of 9.1.Hydrogen cyanide (HCN) has a pKa of 9.1. What is its Ka? Is HCN a strong or a weak acid?Q:As noted in Problem 4.7, hydrogen cyanide (HCN)As noted in Problem 4.7, hydrogen cyanide (HCN) has a pKa of 9.1. Is cyanide ion (CN─) a stronger base or a weaker base than hydroxide ion (HO─)?Q:Write an equation for proton transfer from hydrogenWrite an equation for proton transfer from hydrogen chloride to tert-butyl alcohol. Use curved arrows to track electron movement, and identify the acid, base, conjugate acid, and conjugate base.Q:Is the equilibrium constant for proton transferIs the equilibrium constant for proton transfer from hydrogen chloride to tert-butyl alcohol greater than 1 or less than 1?Q:Represent the structure of the transitionRepresent the structure of the transition state for proton transfer from hydrogen chloride to tert-butyl alcohol.Q:Write chemical equations for the reactionWrite chemical equations for the reaction that takes place between each of the following pairs of reactants:
(a) 2-Butanol and hydrogen bromide
(b) 3-Ethyl-3-pentanol and hydrogen chloride
(c) 1-Tetradecanol and hydrogen bromideQ:Of the isomeric C5H11+ carbocations,Of the isomeric C5H11+ carbocations, which one is the most stable?Q:1-Butanol and 2-butanol are converted1-Butanol and 2-butanol are converted to their corresponding bromides on being heated with hydrogen bromide. Write a suitable mechanism for each reaction, and assign each the appropriate symbol (SN1 or SN2).Q:Write a structural formula for the most stable of the freeWrite a structural formula for the most stable of the free radicals that have the formula C5H11.Q:Carbon–carbon bond dissociation energiesCarbon–carbon bond dissociation energies have been measured for alkanes. Without referring to Table 4.3, identify the alkane in each of the following pairs that has the lower carbon–carbon bond dissociation energy, and explain the reason for your choice.
(a) Ethane or propane
(b) Propane or 2-methylpropane
(c) 2-Methylpropane or 2,2-dimethylpropaneQ:Write equations for the initiation and propagationWrite equations for the initiation and propagation steps for the formation of dichloromethane by free-radical chlorination of chloromethaneQ:Chlorination of ethane yields,Chlorination of ethane yields, in addition to ethyl chloride, a mixture of two isomeric dichlorides. What are the structures of these two dichlorides?Q:Assuming the relative rate of secondaryAssuming the relative rate of secondary to primary hydrogen atom abstraction to be the same in the chlorination of propane as it is in that of butane, calculate the relative amounts of propyl chloride and isopropyl chloride obtained in the free-radical chlorination of propane.Q:Give the structure of the principal organic product formed byGive the structure of the principal organic product formed by free-radical bromination of each of the following:
(a) Methylcyclopentane (c) 2, 2, 4-Trimethylpentane
(b) 1-Isopropyl-1-methylcyclopentaneQ:Write structural formulas for each of the following alcohols and alkylWrite structural formulas for each of the following alcohols and alkyl halides:
(a) Cyclobutanol
(e) 2,6-Dichloro-4-methyl-4-octanol
(b) sec-Butyl alcohol
(f) trans-4-tert-Butylcyclohexanol
(c) 3-Heptanol
(g) 1-Cyclopropylethanol
(d) trans-2-Chlorocyclopentanol
(h) 2-CyclopropylethanolQ:Name each of the following compounds accordingName each of the following compounds according to substitutive IUPAC nomenclature:
(a) (CH3)2CHCH2CH2CH2Br
(b) (CH3)2CHCH2CH2CH2OH
(c) Cl3CCH2Br
(d) Cl2CHCHB
(e) CF3CH2OHQ:Write structural formulas, or build molecularWrite structural formulas, or build molecular models for all the constitutionally isomeric alcohols of molecular formula C5H12O. Assign a substitutive and a functional class name to each one, and specify whether it is a primary, secondary, or tertiary alcoholQ:A hydroxyl group is a somewhat “smaller” substituentA hydroxyl group is a somewhat “smaller” substituent on a six-membered ring than is a methyl group. That is, the preference of a hydroxyl group for the equatorial orientation is less pronounced than that of a methyl group. Given this information, write structural formulas or build molecular models for all the isomeric methylcyclohexanols, showing each one in its most stable conformation. Give the substitutive IUPAC name for each isomer.Q:By assuming that the heat of combustionBy assuming that the heat of combustion of the cis isomer was larger than the trans, structural assignments were made many years ago for the stereoisomeric 2-, 3-, and 4-methylcyclohexanols. This assumption is valid for two of the stereoisomeric pairs but is incorrect for the other. For which pair of stereoisomers is the assumption incorrect? Why?Q:(a) Menthol, used to flavor various foods and tobacco,(a) Menthol, used to flavor various foods and tobacco, is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol. Draw or make a molecular model of its most stable conformation. Is the hydroxyl group cis or trans to the isopropyl group? To the methylgroup?
(b) Neomenthol is a stereoisomer of menthol. That is, it has the same constitution but differs in the arrangement of its atoms in space. Neomenthol is the second most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol; it is less stable than menthol but more stable than any other stereoisomer. Write the structure, or make a molecular model of Neomenthol in its most stable conformation.Q:Each of the following pairs of compounds undergoesEach of the following pairs of compounds undergoes a Bronsted acid–base reaction for which the equilibrium lies to the right. Give the products of each reaction, and identify the acid, the base, the conjugate acid, and the conjugate base.Q:Transition-state representations are shownTransition-state representations are shown for two acid–base reactions. For each one, write the equation for the reaction it represents in the direction for which the equilibrium lies to the right. Label the acid, the base, the conjugate acid, and the conjugate base, and use curved arrows to show the flow of electrons.Q:Calculate Ka for each of the following acids,Calculate Ka for each of the following acids, given its pKa. Rank the compounds in order of decreasing acidity.
(a) Aspirin: pKa = 3.48
(b) Vitamin C (ascorbic acid): pKa = 4.17
(c) Formic acid (present in sting of ants): pKa = 3.75
(d) Oxalic acid (poisonous substance found in certain berries): pKa = 1.19Q:The pKa’s of methanol (CH3OH) and methanethiolThe pKa’s of methanol (CH3OH) and methanethiol (CH3SH) are 16 and 11, respectively. Which is more basic, KOCH3 or KSCH3?Q:Write a chemical equation for the reactionWrite a chemical equation for the reaction of 1-butanol with each of the following:
(a) Sodium amide (NaNH2) (d) Phosphorus tribromide
(b) Hydrogen bromide, heat (e) Thionyl chloride
(c) Sodium bromide, sulfuric acid, heatQ:4.32 Each of the following reactions4.32 Each of the following reactions has been described in the chemical literature and involves an organic starting material somewhat more complex than those we have encountered so far. Nevertheless, on the basis of the topics covered in this chapter, you should be able to write the structure of the principal organic product of each reaction.Q:Select the compound in each of the following pairsSelect the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice.
(a) 1-Butanol or 2-butanol
(b) 2-Methyl-1-butanol or 2-butanol
(c) 2-Methyl-2-butanol or 2-butanol
(d) 2-Methylbutane or 2-butanol
(e) 1-Methylcyclopentanol or cyclohexanol
(f) 1-Methylcyclopentanol or trans-2-methylcyclopentanol
(g) 1-Cyclopentylethanol or 1-ethylcyclopentanolQ:Assuming that the rate-determining stepAssuming that the rate-determining step in the reaction of cyclohexanol with hydrogen bromide to give cyclohexyl bromide is unimolecular, write an equation for this step. Use curved arrows to show the flow of electrons.Q:Assuming that the rate-determining step in the reactionAssuming that the rate-determining step in the reaction of 1-hexanol with hydrogen bromide to give 1-bromohexane is an attack by a nucleophile on an alkyloxonium ion; write an equation for this step. Use curved arrows to show the flow of electrons.Q:Two stereoisomers of 1-bromo-4-methylcyclohexaneTwo stereoisomers of 1-bromo-4-methylcyclohexane are formed when trans-4-methylcyclohexanol reacts with hydrogen bromide. Write structural formulas or make molecular models of:
(a) trans-4-Methylcylohexanol
(b) The carbocation intermediate in this reaction
(c) The two stereoisomers of 1-bromo-4-methylcyclohexaneQ:Basing your answers on the bond dissociationBasing your answers on the bond dissociation energies in Table 4.3, calculate which of the following reactions are endothermic and which are exothermic:
(a) (CH3)2CHOH + HF → (CH3)2CHF + H2O
(b) (CH3)2CHOH + HCl → (CH3)2CHCl + H2O
(c) CH3CH2CH3 + HCl → (CH3)2CHCl + H2Q:By carrying out the reaction at -78°CBy carrying out the reaction at -78°C it is possible to fluorinate 2, 2-dimethylpropane to yield (CF3)4C. Write a balanced chemical equation for this reaction.Q:In a search for fluorocarbons having anestheticIn a search for fluorocarbons having anesthetic properties, 1, 2-dichloro-1, 1-difluoropropane was subjected to photochemical chlorination. Two isomeric products were obtained, one of which was identified as 1,2,3-trichloro-1,1-difluoropropane. What is the structure of the second compound?Q:Among the isomeric alkanes of molecular formula C5H12,Among the isomeric alkanes of molecular formula C5H12, identify the one that on photochemical chlorination yields
(a) A single monochloride
(c) Four isomeric monochlorides
(b) Three isomeric monochlorides
(d) Two isomeric dichloridesQ:In both the following exercises, assumeIn both the following exercises, assume that all the methylene groups in the alkane are equally reactive as sites of free-radical chlorination.
(a) Photochemical chlorination of heptane gave a mixture of monochlorides containing 15% 1-chloroheptane. What other monochlorides are present? Estimate the percentage of each of these additional C7H15Cl isomers in the monochloride fraction.
(b) Photochemical chlorination of dodecane gave a monochloride fraction containing 19% 2-chlorododecane. Estimate the percentage of 1-chlorododecane present in that fraction.Q:Photochemical chlorination of 2,2,4-trimethylpentanePhotochemical chlorination of 2,2,4-trimethylpentane gives four isomeric monochlorides.
(a) Write structural formulas for these four isomers.
(b) The two primary chlorides make up 65% of the monochloride fraction. Assuming that all the primary hydrogens in 2,2,4-trimethylpentane are equally reactive, estimate the percentage of each of the two primary chlorides in the product mixture.Q:Photochemical chlorination of pentanePhotochemical chlorination of pentane gave a mixture of three isomeric monochlorides. The principal monochloride constituted 46% of the total, and the remaining 54% was approximately a 1:1 mixture of the other two isomers. Write structural formulas for the three monochloride isomers and specify which one was formed in greatest amount. (Recall that a secondary hydrogen is abstracted three times faster by a chlorine atom than a primary hydrogen.)Q:Cyclopropyl chloride has been preparedCyclopropyl chloride has been prepared by the free-radical chlorination of cyclopropane. Write a stepwise mechanism for this reaction.Q:Name each of the following using IUPACName each of the following using IUPAC nomenclature:
(a) (CH3)2CoeC (CH3)2
(d) CH2 = CHCH2 CHCH3
(b) (CH3)3CCHoeCH2
(e) CH2 = CHCH2CHCH3
(c) (CH3)2CoeCHCH2CH2CH3Q:Write structural formulas or build molecular models and give theWrite structural formulas or build molecular models and give the IUPAC names of all the monochloro-substituted derivatives of cyclopenteneQ:We can use bond-line formulas to represent alkenesWe can use bond-line formulas to represent alkenes in much the same way that we use them to represent alkanes. Consider the following alkene:
(a) What is the molecular formula of this alkene?
(b) What is its IUPAC name?
(c) How many carbon atoms are sp2-hybridized in this alkene? How many are sp3-hybridized?
(d) How many bonds are of the sp2–sp3 type? How many are of the sp3–sp3 type?Q:How many alkenes have the molecular formula C5H10?How many alkenes have the molecular formula C5H10? Write their structures and give their IUPAC names. Specify the configuration of stereoisomers as cis or trans as appropriate.Q:Female houseflies attract males by sending a chemicalFemale houseflies attract males by sending a chemical signal known as a pheromone. The substance emitted by the female housefly that attracts the male has been identified as cis-9-tricosene, C23H46. Write a structural formula, including stereochemistry, for this compound.Q:Determine the configuration of eachDetermine the configuration of each of the following alkenes as Z or E as appropriate:Q:Write structural formulas or build molecular modelsWrite structural formulas or build molecular models and give the IUPAC names for all the alkenes of molecular formula C6H12 that contain a trisubstituted double bond. (Don’t forget to include stereoisomers.)Q:Give the structure or make a molecular modelGive the structure or make a molecular model of the most stable C6H12 alkene.Q:Arrange the following alkenes in orderArrange the following alkenes in order of decreasing stability: 1-pentene; (E)-2-pentene; (Z)-2-pentene; 2-methyl-2-butene.Q:Despite numerous attempts, the alkene 3,4-di-tert-butylDespite numerous attempts, the alkene 3,4-di-tert-butyl-2,2,5,5-tetramethyl-3-hexene has never been synthesized. Can you explain why? Try making a space-filling model of this compound.Q:Place a double bond in the carbon skeleton shownPlace a double bond in the carbon skeleton shown so as to represent
(a) (Z)-1-Methylcyclodecene
(d) (E)-3-Methylcyclodecene
(b) (E)-1-Methylcyclodecene
(e) (Z)-5-Methylcyclodecene
(c) (Z)-3-Methylcyclodecene
(f) (E)-5-MethylcyclodeceneQ:Identify the alkene obtained on dehydrationIdentify the alkene obtained on dehydration of each of the following alcohols: (a) 3-Ethyl-3-pentanol
(c) 2-Propanol
(b) 1-Propanol
(d) 2,3,3-Trimethyl-2-butanolQ:Each of the following alcohols has been subjectedEach of the following alcohols has been subjected to acidcatalyzed dehydration and yields a mixture of two isomeric alkenes. Identify the two alkenes in each case, and predict which one is the major product on the basis of the Zaitsev rule.Q:What three alkenes are formed in the acid-catalyzedWhat three alkenes are formed in the acid-catalyzed dehydration of 2-pentanol?Q:Write a structural formula for the carbocationWrite a structural formula for the carbocation intermediate formed in the dehydration of each of the alcohols in Problem 5.13 (Section 5.10). Using curved arrows, show how each carbocation is deprotonated by water to give a mixture of alkenes.Q:The alkene mixture obtained on dehydration of 2,2The alkene mixture obtained on dehydration of 2,2-dimethylcyclohexanol contains appreciable amounts of 1,2-dimethylcyclohexene. Give a mechanistic explanation for the formation of this product.Q:Write the structures of all the alkenes that can be formedWrite the structures of all the alkenes that can be formed by dehydrohalogenation of each of the following alkyl halides. Apply the Zaitsev rule to predict the alkene formed in greatest amount in each case.
(a) 2-Bromo-2,3-dimethylbutane (d) 2-Bromo-3-methylbutane
(b) tert-Butyl chloride (e) 1-Bromo-3-methylbutane
(c) 3-Bromo-3-ethylpentane (f) 1-Iodo-1-methylcyclohexaneQ:Write structural formulas for all the alkenesWrite structural formulas for all the alkenes that can be formed in the reaction of 2-bromobutane with potassium ethoxide.Q:Use curved arrows to track electron movementUse curved arrows to track electron movement in the dehydrohalogenation of tert-butyl chloride by sodium methoxide by the E2 mechanism.Q:Use curved arrow notation to showUse curved arrow notation to show the bonding changes in the reaction of cis-4-tert-butylcyclohexyl bromide with potassium tert-butoxide. Be sure your drawing correctly represents the spatial relationship between the leaving group and the proton that is lost.Q:Write structural formulas for each of the following: (a) 1-Heptene (g) 1-Bromo-3-methylcyclohexeneWrite structural formulas for each of the following:
(a) 1-Heptene (g) 1-Bromo-3-methylcyclohexene
(b) 3-Ethyl-2-pentene (h) 1-Bromo-6-methylcyclohexene
(c) cis-3-Octene (i) 4-Methyl-4-penten-2-ol
(d) trans-1,4-Dichloro-2-butene ( j) Vinylcycloheptane
(e) (Z)-3-Methyl-2-hexene (k) 1,1-Diallylcyclopropane
(f) (E)-3-Chloro-2-hexene (l) trans-1-Isopropenyl-3-methylcyclohexaneQ:Write a structural formula or build a molecular modelWrite a structural formula or build a molecular model and give a correct IUPAC name for each alkene of molecular formula C7H14 that has a tetrasubstituted double bond.Q:Give the IUPAC names for each of the followingGive the IUPAC names for each of the following compounds:
(a) (CH3CH2)2C = CHCH3
(b) (CH3CH2)2C = C (CH2CH3)2
(c) (CH3)3CCH = CCl2Q:(a) A hydrocarbon isolated from fish oil and from plankton(a) A hydrocarbon isolated from fish oil and from plankton was identified as 2,6,10,14-tetramethyl-2-pentadecene. Write its structure.
(b) Alkyl isothiocyanates are compounds of the type RN = C = S. Write a structural formula for allyl isothiocyanate, a pungent-smelling compound isolated from mustard.Q:(a) The sex attractant of the Mediterranean(a) The sex attractant of the Mediterranean fruit fly is (E)-6-nonen-1-ol. Write a structural formula or build a molecular model for this compound, showing the stereochemistry of the double bond.
(b) Geraniol is a naturally occurring substance present in the fragrant oil of many plants.
It has a pleasing, roselike odor. Geraniol is the E isomer of (CH3)2C = CHCH2CH2C = CHCH2OH
CH3 Write a structural formula or build a molecular model for geraniol, showing its stereochemistry.
(c) Nerol is a naturally occurring substance that is a stereoisomer of geraniol. Write its structure or build a molecular model.
(d) The sex attractant of the codling moth is the 2Z, 6E stereoisomer of (CH3)2CCH2C = CHCH2CH2C = CHCH2OH
CH3
CH2CH3
Write the structure of this substance or build a molecular model in a way that clearly shows its stereochemistry. (e) The sex pheromone of the honeybee is the E stereoisomer of the compound shown. Write a structural formula or build a molecular model for this compound. CH3C (CH2)4CH2CH = CHCO2H
(f) A growth hormone from the cecropia moth has the structure shown. Express the stereochemistry of the double bonds according to the E–Z system.Q:Which one of the following has the largest dipoleWhich one of the following has the largest dipole moment (is the most polar)? Compare your answer with the calculated dipole moments on the Learning By Modeling CD.Q:Match each alkene with the appropriateMatch each alkene with the appropriate heat of combustion:
Heats of combustion (kJ/mol): 5293; 4658; 4650; 4638; 4632
Heats of combustion (kcal/mol): 1264.9; 1113.4; 1111.4; 1108.6; 1107.1
(a) 1-Heptene
((d) (Z)-4, 4-Dimethyl-2-pentene
(b) 2, 4-Dimethyl-1-pentene
(e) 2, 4, 4-Trimethyl-2-pentene
(c) 2, 4-Dimethyl-2-penteneQ:Choose the more stable alkene in each of the followingChoose the more stable alkene in each of the following pairs. Explain your reasoning.
(a) 1-Methylcyclohexene or 3-methylcyclohexene
(b) Isopropenylcyclopentane or allylcyclopentaneQ:(a) Suggest an explanation for the fact that(a) Suggest an explanation for the fact that 1-methylcyclopropene is some 42 kJ/mol (10 kcal/mol) less stable than methylenecyclopropaneQ:How many alkenes would you expect to be formedHow many alkenes would you expect to be formed from each of the following alkyl bromides under conditions of E2 elimination? Identify the alkenes in each case.
(a) 1-Bromohexane
(e) 2-Bromo-3-methylpentane
(b) 2-Bromohexane
(f) 3-Bromo-2-methylpentane
(c) 3-Bromohexane
(g) 3-Bromo-3-methylpentane
(d) 2-Bromo-2-methylpentane (h) 3-Bromo-2,2-dimethylbutane Showing 100 – 200 of 15569 12345 > >> Join SolutionInn Study Help for 1 Million+ Textbook Solutions Learn the step-by-step answers to your textbook problems, just enter our Solution Library containing more than 1 Million+ textbooks solutions and help guides from over 1300 courses. 24/7 Online Tutors Tune up your concepts by asking our tutors any time around the clock and get prompt responses. Start Membership ×NO, THANKSTRY NOW

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