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All Textbook Solutions for Introduction to General, Organic and Biochemistry

9.18P 9.19P 9.20P 9.21P 9.22P 9.23P 9.24P 9.25P 9.26P 9.27P 9.28P 9.29P 9.30P 9.31P 9.32P 9.33P 9.34P 9.35P 9.36P 9.37P 9.38P 9-39 If you work in a lab containing radioisotopes emitting all kinds of radiation, from which emission should you seek the most protection?9.40P 9.41P 9.42P 9.43P 9.44P 9.45P 9.46P 9.47P 9.48P 9.49P 9.50P 9.51P 9.52P 9.53P 9.54P 9.55P 9.56P 9.57P 9.58P 9.59P 9.60P 9.61P 9.62P 9.63P 9.64P 9.65P 9.66P 9.67P 9.68P 9.69P 9.70P 9.71P 9.72P 9.73P 9.74P 9.75P 9.76P 9.77P 9.78P 9.79P 9.80P 9.81P 9.82P 9.83P 9.84P 9.85P 9-86 is effective in prostate cancer therapy when administered at kBq levels. If an antibody tagged with has an intensity of 2 million Bq/mg and if a solution contains 5 mg/L tagged antibody, how many milliliters of the solution should you use for an injection to administer 1 kBq intensity?9.87P 9.88P 9.89P 9.90P 9.91P 9.92P 9.93P 10.1P 10.2P 10.3P 10.4P 10.5P 10.6P 10.7P 10.8P 10-9 Is there any difference between vanillin made synthetically and vanillin extracted from vanilla beans?10.10P 10-11 What important experiment did Wohler carry out in 1828?10.12P 10.13P 10.14P 10-15 How many electrons are in the valence shell of each of the following atoms? Write a Lewis structure for an atom of each element. (Hint: Use the Periodic Table.) (a) Carbon(b) Oxygen (c) Nitrogen(d) Fluorine 10-16 What is the relationship between the number of electrons in the valence shell of each of the following atoms and the number of covalent bonds each forms? (a) Carbon(b) Oxygen (c) Nitrogen(d) Hydrogen 10.17P 10.18P 10-19 Write Lewis structures for these ions. (a) HCOf(b) CO32- Bicarbonate ionCarbonate ion (c) ch3coo-(d)Cr Acetate ionChloride ion 10-20 Why are the following molecular formulas impossible? (a) CH5 C2H7 10-21 Explain how to use the valence-shell electron-pair repulsion (VSEPR) model to predict bond angles and geometry about atoms of carbon, oxygen, and nitrogen.10-22 Suppose you forget to take into account the presence of the unshared pair of electrons on nitrogen in the molecule NH3. What would you then predict for the H—N—H bond angles and the geometry (bond angles and shape) of ammonia?Suppose you forget to take into account the presence of the two unshared pairs of electrons on the oxygen atom of ethanol, CH3CH2OH. What would you then predict for the C—O—H bond angle and the geometry of ethanol?10-24 Use the VSEPR model to predict the bond angles and geometry about each highlighted atom. (Hint-. Remember to take into account the presence of unshared pairs of electrons.) H H I I H-C-C-O-H I I H H H-C=C-C1 H H 10.25P 10.26P 10-27 What is meant by the term functional group?10-28 List three reasons why functional groups are important in organic chemistry.10.29P 10.30P 10.31P 10-32 Draw a structural formula for the one tertiary (3°)alcohol with the molecular formula C4Hi0O.10-33 What is the meaning of the term tertiary ( 3° , when it is used to classify amines?10.34P Draw structural formulas for each of the following: The four primary (1°) alcohols with the molecular formula C5H12O. The three secondary (2°) alcohols with the molecular formula C5H12O. The one tertiary (3°) alcohol with the molecular formula C5H12O.10-36 Draw structural formulas for the six ketones with the molecular formula C6H12O.10-37 Draw structural formulas for the eight carboxylicacids with the molecular formula C6H12O2.10.38P 10-39 (Chemical Connections 10A) How was Taxol discovered?10.40P 10.41P Silicon is immediately below carbon in Group 4A of the Periodic Table. Predict the C—Si—C bond angles in tetramethylsilane, (CH3)4Si.10-43 Phosphorus is immediately below nitrogen in Group 5A of the Periodic Table. Predict the C—P—C bond angles in trimethylphosphine, (CHaJaP.Draw the structure for a compound with the molecular formula: C2HeO that is an alcohol C3HcO that is an aldehyde C3HGO that is a ketone C3HeO2 that is a carboxylic acid 10-45 Draw structural formulas for the eight aldehydes with the molecular formula CgHi2O.10.46P 10-47 Which of these covalent bonds are polar, and whichare nonpolar? (Hint: Review Section 3-7B.) (a) C—C (b) C=C(c) C—H (d) C—O (e) O—H (f) C—N(g) N—H (h) N—O Of the bonds in Problem 10-47, which is the most polar? Which is the least polar?10.49P 10.50P Following is a structural formula for naphthalene. It was first obtained by heating coal to a high temperature in the absence of air (oxygen). At one time, it was used in "mothballs.” Predict the shape of naphthalene. Is a naphthalene molecule polar or nonpolar?10.52P 10.53P Urea, (NH.,)2CO, is used in plastics and in fertil izers. It is also the primary nitrogen-containing substance excreted by humans. O I I H H Urea Complete the Lewis structure of urea, showing all valence electrons. Predict the bond angle about each C and N. Which is the most polar bond in the molecule? (d, Is urea polar or nonpolar?10.55P 10.56P Aspirin is prepared by the reaction of salicylic- acid with acetic anhydride as shown in the following equation. The stoichiometry of the reaction is given in the equation. Acetic acid is a by-product of the reaction and must be separated and removed so that aspirin can then be sold as a pure product. How many grams of aspirin can be prepared from 120 grams of salicylic acid? Assume that there is an excess of acetic anhydride. (Chapter 4) Acetylsalieylic acid (Aspirin)Following is the structural formula of acetamide. H O H — C—C— N— H I I H H Acetamide (an amide > Complete the Lewis structure for acetamide, showing all valence electrons. Use the valence-shell electron-pair repulsion (VSEPR) model (Section 3-10) to predict all bond angles in acetamide. Which is the most polar bond in acetamide?10.59P 11.1P 11.2P 11.3P Problem 11-4 Write the molecular formula and IUPAC name for each alkane.Problem 11-5 Write the molecular formula and IUPAC name for each cycloalkane. (a,11.6P 11.7P 11.8P 11.9P Answer true or false. A hydrocarbon is composed only of the elements carbon and hydrogen. Alkanes are saturated hydrocarbons. The general formula of an alkane is C„H2„.2, where n is the number of carbons in the alkane, Alkenes and alkynes are unsaturated hydrocarbons.11-11 Define: Hydrocarbon Alkane Saturated hydrocarbon 11-12 Why is it not accurate to describe an unbranchedalkane as a “straight-chain” hydrocarbon?11-13 What is meant by the term line-angle formula as applied to alkanes and cycloalkanes?11.14P Write the molecular formula for each alkane.Answer true or false. Constitutional isomers have the same molecular formulas and the same connectivity of their atoms. There are two constitutional isomers with the molecular formula C3H8. There are four constitutional isomers with the molecular formula C4H10. There are five constitutional isomers with the molecular formula C5H12.Which statements are true about constitutional isomers? They have the same molecular formula. They have the same molecular weight. They have the same connectivity of their atoms. They have the same physical properties.11.18P Each member of the following set of compounds is an amine; that is, each contains a nitrogen atom bonded to one, two, or three carbon groups (Section 10-4B). Which structural formulas represent the same compound, and which represent constitutional isomers? NH.,11.20P 11-21 In the six following sets, which pairs of structural formulas represent constitutional isomers?Draw line-angle formulas for the nine constitutional isomers with the molecular formula C7Hi6.Answer true or false. The parent name of an alkane is the name of the longest chain of carbon atoms in the alkane. Propyl and isopropyl groups are constitutional isomers. There are four alkyl groups with the molecular formula C4H9.11.24P Among the ingredients listed in one commercial foam shaving gel are isobutane and isopentane. Write the 1UPAC name of each hydrocarbon. Why are these two hydrocarbons added to the formulation of the shaving gel?11.26P Answer true or false. Cycloalkanes are saturated hydrocarbons. Hexane and cyclohexane are constitutional isomers. The parent name of a cycloalkane is the name of the unbranched alkane with the same number of carbon atoms as are in the cycloalkane ring.11.28P 11.29P 11.30P 11.31P 11-32 Calculate the actual C-C-C bond angles in planar (a) cyclopropane and (b) cyclopentane and com pare them with optimal bond angles.11.33P 11-34 What structural feature of cycloalkanes makes cis- trans isomerism in them possible?11.35P 11-36 Name and draw structural formulas for the cis andtrans isomers of 1,2-dimethylcyclopropane.Name and draw structural formulas for the six cycloalkanes with the molecular formula C5H10. Include cis-trans isomers as well as constitutional isomers.11-38 Why is equatorial methylcyclohexane more stable than axial methylcyclohexane?11.39P Consider a cyclohexane ring substituted with one methyl group and one hydroxyl group. Draw the structural formula for a compound with this composition that: Does not show cis/trans isomerism. Does show cis/trans isomerism.11.41P In Problem 11-22, you drew structural formulas for the nine constitutional isomers with molecular formula C7Hie. Predict which isomer has the lowest boiling point and which has the highest boiling point.Which unbranched alkane (Table 11-4) has about the same boiling point as water? Calculate the molecular weight of this alkane and compare it with the molecular weight of water.11.44P 11.45P 11.46P 11.47P 11-48 How are the boiling points of hydrocarbons during petroleum refining related to their molecular weight?Answer true or false. Combustion of alkanes is an endothermic reaction. The products of complete combustion of an alkane are carbon dioxide and water. Halogenation of an alkane converts it to a haloalkane.11-50 Write balanced equations for the combustion of each of the following hydrocarbons. Assume that each is converted completely to carbon dioxide and water. Hexane Cyclohexane 2-Methylpentane The heat of combustion of methane, a component of natural gas, is 212 kcal/mol. That of propane, a component of LP gas, is 530 kcal/mol. On a gram- for-gram basis, which hydrocarbon is the better source of heat energy?11-52 Draw structural formulas for these haloalkanes Bromomethane Chlorocyclohexane 1,2-Dibromoethane 2-Chloro-2-methylpropane Dichlorodilluoromethane (Freon-12)11.53P 11-54 Complete and balance the equation for the complete combustion of each hydrocarbon. (a) Hexane(b) Cyclohexane (c) 2-Methylpentane Name and draw structural formulas for all pos sible monochlorination products that might be formed in each reaction.11.56P 11.57P 11-58 (Chemical Connections 11A) How many rings in te trodotoxin contain only carbon atoms? How many contain nitrogen atoms? How many contain two oxygen atoms?11.59P 11.60P 11.61P 11-62(Chemical Connections 11C) What are Freons? Why were they considered ideal compounds to use as heat-transfer agents in refrigeration systems? Give structural formulas of two Freons used for this purpose.11-63 (Chemical Connections 11C) In what way do Fre- ons negatively affect the environment?(Chemical Connections 11C) What are HFCs and HCFCs? How does their use in refrigeration systems prevent the environmental problems associated with the use of Freons?11.65P 11.66P Which of the following compounds can exist as cis-trans isomers? For each that can, draw both isomers using solid and dashed wedges to show 11.68P Dodecane, C12H26, is an unbranched alkane Predict the following: Will it dissolve in water? Will it dissolve in hexane? Will it burn when ignited? Is it a liquid, solid, or gas at room temperature and atmospheric pressure? Is it more or less dense than water?11.70P 11.71P 11.72P As stated in Section 11-9, the wax found in apple skins is an unbranched alkane with the molecular formula C^H^. Explain how the presence of this alkane in apple skins prevents the loss of moisture from within the apple.11.74P 12.1P 12.2P Problem 12-3 Write the IUPAC name for each cycloalkene.Problem 12-4 Draw structural formulas for the other two stereoisomers of 2,4-heptadiene Problem 12-5 How many stereoisomers are possible for the following unsaturated alcohol? ch3 ch3 ch3 ch3c=chch2ch2c=chch2ch2c=chch2oh 12.6P Problem 12-7 Propose a two-step mechanism for the addition of HBr to 1-methylcyclohexene to give 1-bromo-l-methylcyclohexane.12.8P Problem 12-9 Propose a three-step reaction mechanism for the acid-catalyzed hydration of 1-methylcyclohexene to give 1-methylcyclohexanol.12.10P 12.11P Answer true or false. Both ethylene and acetylene are planar molecules. An alkene in which each carbon of the double bond has two different groups bonded to it will show cis-trans isomerism. Cis-trans isomers have the same molecular formula but a different connectivity of their atoms. Cis-2-butene and trans-2-butene can be inter- converted by rotation about the carbon-carbon double bond. Cis-trans isomerism is possible only among appropriately substituted alkenes. Both 2-hexene and 3-hexene can exist as pairs of cis-trans isomers. ( g) Cyclohexene can exist as a pair of cis-trans isomers. (h) 1-Chloropropene can exist as a pair of cis-trans isomers.12-13 What is the difference in structure between a saturated hydrocarbon and an unsaturated hydrocarbon?There are three compounds with the molecular formula C.,H,,Br2. Two of these are polar and have a dipole, and one has no dipole (it is not polar). Draw structural formulas for these three compounds and explain why two are polar and the third is not.12-15 Name and draw structural formulas for all alkenes with the molecular formula C5H1U. As you draw these alkenes, remember that cis and trans isomers are different compounds and must be counted separately.12.16P Draw a structural formula for at least one bromoalkene with the molecular formula C5H9Br that (a) shows cis/trans isomerism and (b) does not show cis /trans isomerism.Each carbon atom in ethane and in ethylene is surrounded by eight valence electrons and has four bonds to it. Explain how the VSEPR model (Section 3-10) predicts a bond angle of 109.5° about each carbon in ethane but an angle of 120° about each carbon in ethylene.12.19P 12.20P 12.21P 12*22 Draw a structural formula for each compound. /ra7is-2-Methyl-3-hexene 2-Methyl-3-hexyne 2-Methyl-l-butene 3-Ethyl-3-methyl-l-pentyne 2,3-Dimethyl-2-pentene 12-23 Draw a structural formula for each compound. 3-Chloropropene 3-Methylcyclohexene 1,2-Dimethylcyclohexene /runs-3,4-Dimethyl-3-heptene Cydopropene 3-Hexyne 12.24P 12-25 Write the IUPAC name for each unsaturated hydrocarbon. (d)c=ch2 ch3ch,ch2 Explain why each name is incorrect and then write a correct name. Strategy: First draw the structural formula suggested by the incorrect name. Then identify the error, for example, failure to locate the longest chain that contains the alkene functional group etc., and then write the correct name. (a) 1-Methylpropene (b) 3-Pentene (c) 2-Methylcyclohexene (d) 3,3-Dimethylpentene (e) 4-Hexyne (f) 2-lsopropyl-2-butene 12-27 Explain why each name is incorrect and then write a correct name. 2-Ethyl-l-propene 5-lsopropylcyclohexene 4-Methyl-4-hexene 2-sec-Butyl-l-butene 6,6-Dimethylcyclohexene 2-Ethyl-2-hexene 12.28P 12-29 Which of these alkenes show cis-trans isomerism? For each that does, draw structural formulas for both isomers. (a) 1-Hexene(b)2-Hexene (c) 3-Hexene(d)2-Methyl-2-hexene (e) 3-Methyl-2-hexene(f)2,3-Dimethyl-2-hexene 12-30 Which of these alkenes shows cis-trans isomerism? For each that does, draw structural formulas for both isomers. 1-Pentene 2-Pentene 3-Ethyl-2-pentene 2,3-Dimethyl-2-pentene 2-Methyl-2-pentene 2,4-Dimethy 1-2-pentene 12-31 Cyclodecene exists as both cis and trans isomers. Draw line-angle formulas for each isomer, showing the configuration of the double bond in each.Arachidonic acid is a naturally occurring C„o polyunsaturated fatty acid. Draw a line-angle formula for arachidonic acid showing the cis configuration about each double bond. CH2(CH2)4(CH=CHCH2)4CH2CH2COOH Arachidonic acid 12.33P If you examine the structural formulas for the following cycloalkenes, you will see that the configuration of the double bond is cis in each. Cyclopentene Cyclohexene Cycloheptene All attempts to synthesize these cycloalkenes in which the double bond has a trans configuration have failed. Apparently, it is impossible to have a trans configuration in these cycloalkenes. Offer an explanation for why this is so.12*35 For each molecule that shows eis-trans isomerism, draw the cis isomer.Name and draw structural formulas for all compounds with the molecular formula C.H10 that are: Alkenes that do not show cis-trans isomerism Alkenes that show cis-trans isomerism Cycloalkanes that do not show cis-trans isomerism Cycloalkanes that show cis-trans isomerism /3-Ocimene, a triene found in the fragrance of cotton blossoms and several essential oils, has the 1UPAC name czs-3,7-dimethyl-l,3,6-octatriene. (Cis refers to the configuration of the double bond between carbons 3 and 4, the only double bond in this molecule about which cis-trans isomerism is possible.) Draw a structural formula for /3-ocimene.Answer true or false. Alkenes and alkynes are nonpolar molecules. The physical properties of alkenes are similar to those of alkanes of the same carbon skeletons. Alkenes that are liquid at room temperature are insoluble in water and when added to water, will float on water.12.39P 12-40 Define alkene addition reaction. Write an equation for an addition reaction of propene.12.41P 12-42 Complete these equations.Draw structural formulas for all possible carbocations formed by the reaction of each alkene with HC1. Label each carbocation as primary, secondary, or tertiary. ch3 I ch3ch,c=chch3 ch3ch2ch=chch3 12.44P 12-45 Draw a structural formula for the product of each reaction. 1-Methylcyclohexene + Br2 1,2-Dimethylcyclopentene + Cl2 Draw a structural formula for an alkene with the indicated molecular formula that gives the compound shown as the major product. Note that more than one alkene may give the same compound as the major product. CHa | C5Hw + H,O CH3CCH2CH3 OH CHa I C5H10 + Br2 » CH3CHCHCH, Br Br 7H12 + HC1 oe 12-47 Draw a structural formula for an alkene with the molecular formula C5H10that reacts with Br2to give each product. ch3 I (a) ch3c—chch3Br Br (c) CH2CHCH2CH2CH3Br Br Draw a structural formula for an alkene with the molecular formula C5H10 that reacts with HC1 to give the indicated chloroalkane as the major product. More than one alkene may give the same compound as the major product. ch3 ch3 (a) CH3CCH9CH3 ch3chchch3I I Cl Cl (C) ch3chch2ch2ch3Cl 12.49P 12-50 Draw the structural formula of an alkene that undergoes acid-catalyzed hydration to give the indicated alcohol as the major product. More than one alkene may give each alcohol as the major product. 3-Hexanol 1-Methylcyclobutanol 2-Methyl-2-butanol 2-Propanol 12.51P 12.52P Following is the structural formula of hexabromocyclododecane. This compound was at one time used as a flame retardant in polystyrene foam insulation in buildings, but has now been banned because it had been shown to be toxic to aquatic organisms, and can disrupt thyroid hormone levels in laboratory test animals. In addition, it persists in the environment. Show how this flame retardant could be synthesized from a cycloalkatriene and write the structural formula and IUPAC name of this starting material. Br Hexabromocyclododecane Propose an explanation for the following experimental observations: Acid-catalyzed hydration of 1-hexene gives a single alcohol in high yield. Acid-catalyzed hydration of cis- or f rans-2-hexene gives a mixture of two alcohols in approximately equal amounts. Acid-catalyzed hydration of cis- or irnns-3-hexene gives a single alcohol in high yield.There are nine alkenes with the molecular formula C6H12. Five of these were given in Problem 12-54. Draw structural formulas for the other four, and predict the product(s) of the acid-catalyzed hydration of each.12.56P 12-57 Hydrocarbon A, Cf,Hs, reacts with 2 moles of Br2to give l,2,3,4-tetrabromo-2-methylbutane. What is the structure of hydrocarbon A?12-58 Show how to convert ethylene to these compounds (a) Ethane(b) Ethanol (c) Bromoethane(d) 1,2-Dibromoethane (e) Chloroethane 12-59 Show how to convert 1-butene to these compounds, (a) Butane(b) 2-Butanol (c) 2-Bromobutane(d) 1,2-Dibromobutane 12.60P 12-61 (Chemical Connections 12A) What is one function of ethylene as a plant growth regulator?12.62P 12.63P 12-64 (Chemical Connections 120 What is the molecular formula of 11-tetradecenyl acetate? What is its molecular weight?(Chemical Connections 120 Assume that 1 X IO-12 g of 11-tetradecenyl acetate is secreted by a single corn borer. How many molecules is this?12.66P 12-67 (Chemical Connections 12D ) In which isomer of retinal is the end-to-end distance longer, the all-frans isomer or the 11-crs isomer?12.68P 12.69P 12.70P 12.71P 12.72P 12.73P Propose a structural formula for the product!s) when each of the following alkenes is treated with H2O/HaSO4. Why are two products formed in part (b), but only one in parts (a, and (c)? 1-Hexene gives one alcohol with a molecular formula of C6H14O. 2-Hexene gives two alcohols, each with a molecular formula of CeHuO. 3-Hexene gives one alcohol with a molecular formula of CgH14O.12.75P Draw the structural formula of an alkene that undergoes acid-catalyzed hydration to give each of the following alcohols as the major product. More than one alkene may give each compound as the major product 12-77 Show how to convert cyclopentene into these compounds. 1,2-Dibromocyclopentane Cyclopentanol Iodocyclopentane Cyclopentane 12.78P 12.79P In omega-3 fatty adds, the last carbon of the last double bond of the hydrocarbon chain ends three carbons from the methyl terminal end of the chain. The last carbon of the chain is called the omega carbon, hence, the designation omega-3. Eicosapentae- noic acid is a common omega-3 fatty acid found in cold water fatty fish and health food supplements. CH3(CH2CH=CH )5CH2CH2CH2CO2H Eicosapentaenoic acid a C20 polyunsaturated fatty acid How many cis-trans isomers are possible for this fatty acid? Draw a line-angle formula for eicosapentaenoic acid, showing the cis configuration of all carbon- carbon double bonds in the hydrocarbon chain.12.81P 13.1P Answer true or false. Alkenes, alkynes, and arenes are unsaturated hydrocarbons. Aromatic compounds were so named because many of them have pleasant odors. According to the resonance model of bonding, benzene is best described as a hybrid of two equivalent contributing structures. Benzene is a planar molecule.13-3 What is the difference in structure between a saturated and an unsaturated hydrocarbon?13-4 Define aromatic compound.13-5 Why are alkenes, alkynes, and aromatic compounds said to be unsaturated?13-B Do aromatic rings have double bonds? Are they unsaturated? Explain.13-7 Can an aromatic compound be a saturated compound?Draw at least two structural formulas for each of the following. (Several constitutional isomers are possible for each part.) An alkene with six carbons A cycloalkene with six carbons An alkyne with six carbons An aromatic hydrocarbon with eight carbons 13-9 Write a structural formula and the name for the simplest (a) alkane, (b) alkene, (c) alkyne, and (d) aromatic hydrocarbon.13-10 Account for the fact that the six-membered ring in benzene is planar but the six-membered ring in cyclohexane is not.

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