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Chemical Principles The Quest For Insight 7th Edition Peter Atkins, Loretta Jones, Leroy Laverman - Solutions

Write the formulas of the following compounds and state whether each one is a primary, secondary, or tertiary alcohol or a phenol:(a) 1-hexanol;(b) 1-phenyl-1-ethanol;(c) 2,4- dimethylphenol;(d) 3-ethyl-2,2-dimethyl-3-pentanol.
Give the systematic name of(a) CH3CH2CH(CH3)CH2CH3;(b) CH3CH(CH2CH3)CH(CH3)2;(c) (CH3)3C(CH2)3CH(CH3)2;(d) (CH3)3CC(CH3)3.
Draw line structures of the possible products for the reaction of sodium ethoxide with(a) 1-bromobutane;(b) 2-bromobutane.
How many different compounds can be produced when naphthalene, C10H8 (2), undergoes electrophilic aromatic substitution by a single electrophile (denoted E)? Draw line structures to represent them.
The structure of decalin is shown below.(a) From an examination of this structure, determine its chemical formula.(b) From what aromatic hydrocarbon may decalin be produced by complete hydrogenation?(c) Are isomers possible for decalin? If so, draw the appropriate line structures.
Identify the type of copolymer formed by monomers A and B: —BBBBAA—.
Use bond enthalpies (Tables 4E.2 and 4E.3) to estimate the reaction enthalpies for the halogenation of ethene by chlorine, bromine, and iodine. What trend, if any, exists in these values? TABLE 4E.2 Bond Enthalpies of Diatomic Molecules Molecule H N 0 CO F Cl Br 1 HF HCI HBr HI AHB/(kJ.mol-) 436
Write the formula of(a) Methyl propyl ether;(b) Ethyl butyl ether;(c) Dipropyl ether.
Give the systematic name of(a) CH3CH=CHCH(CH3)2;(b) CH3CH2CH(CH3)C(CH3)3.
The structure of benzaldehyde, the main flavoring agent in bitter almond oil, isDo you expect the aldehyde functional group (CHO) to act as a meta-directing or as an ortho, para-directing group? Explain your conclusion. H
Nonsystematic names for organic compounds may still be found in the chemical literature and chemical supply catalogs, so it is important to be familiar with them as well as with the IUPAC names.(a) Give the systematic name of (i) isobutane and (ii) isopentane.(b) Formulate a rule for using the
Identify the type of copolymer formed by monomers A and B: —AABABBAA —.
Use bond enthalpies (Tables 4E.2 and 4E.3) to estimate the reaction enthalpies for the hydrohalogenation of ethene by HX, where X = Cl, Br, I. What trend, if any, exists in these values? TABLE 4E.2 Bond Enthalpies of Diatomic Molecules Molecule H N 0 CO F Cl Br 1 HF HCI HBr HI AHB/(kJ.mol-) 436
Write the formula of(a) Methyl cyclopropyl ether;(b) Dibutyl ether;(c) Ethyl pentyl ether.
Give the systematic name of(a) CH2=CHCH2CH(C6H5)(CH2)4CH3;(b) (CH3)2CHCH(CH3)CHClC≡CCH3
Give the molecular formulas corresponding to the following line structures and identify each as an alkane, an alkene, an alkyne, or an aromatic hydrocarbon. (a) (b)
Why do polymers not have definite molar masses? How does the fact that polymers have average molar masses affect their melting points?
A carbocation is a positively charged organic ion. The first stable carbocation, the pentamethylcyclopentadienyl cation, was reported in 2002. This cation has a charge of 11.(a) Draw the molecular structure of this ion and identify which carbon atom bears most of the positive charge.(b) How many
Name each compound:(a) CH3CH2CH2OCH2CH2CH2CH3;(b) C6H5OCH3;(c) CH2CH2CH2OCH2CH2CH2CH2CH3.
Give the molecular formulas corresponding to the following line structures and identify each as an alkane, an alkene, an alkyne, or an aromatic hydrocarbon: (a) (b) (c) (d)
Write the shortened (condensed) structural formula of(a) 3-methyl-1-pentene;(b) 4-ethyl-3,3-dimethylheptane;(c) 5,5-dimethyl-1-hexyne;(d) 3-ethyl-2,4-dimethylpentane.
Rank the following polymers according to increasing value as fibers: polyesters, polyamides, polyalkenes. Explain your reasoning.
The chemists who synthesized the pentamethylcyclopentadienyl cation (see Exercise 11.11) found that its p-electrons are found in one double bond and a p-orbital that is delocalized across the three other carbon atoms.(a) Draw a structure for the ion that illustrates this bonding.(b) On which
Name each compound:(a) CH3(CH2)3CH2OCH3;(b) CH3CH2OCH2CH2CH2CH3;(c) CH3CH2CH2OCH2CH2CH3.
Give the molecular formulas corresponding to the following line structures and identify each as an alkane, an alkene, an alkyne, or an aromatic hydrocarbon: (a) (c) (b) (d)
Write the shortened (condensed) structural formula of(a) 4-ethyl-2, 2-dimethylhexane;(b) 3-ethyl-4-methyl-1-pentene;(c) cis-4-ethyl-3-heptene;(d) trans-4-methyl-2-hexene.
The polymer polylactic acid (see structure (2)) was used for a while to replace polyethylene terephthalate (PETE) in the bags containing certain kinds of snack foods. However, polylactic acid is stiffer than PETE and so the bags made loud crackling sounds when they were handled. The problem was
The following names of organic molecules are incorrect. Draw line structures and identify the correct systematic name for(a) 4-methyl-3-propylheptane;(b) 4,6-dimethyloctane;(c) 2,2-dimethyl-4-propylhexane;(d) 2,2-dimethyl-3-ethylhexane.
Identify each compound as an aldehyde or a ketone and give its systematic name:(a) CH3CHO;(b) CH3COCH3;(c) (CH3CH2)2CO.
Give the molecular formulas corresponding to the following line structures and identify each as an alkane, an alkene, an alkyne, or an aromatic hydrocarbon: (a) (b) (c) (d)
Write the structural formula of(a) 4,4-dimethylnonane;(b) 4-propyl-5,5-diethyl-1-decyne;(c) 2,2,4-trimethylpentane;(d) trans-3-hexene.
Polyacrylamide is used in coatings for wooden floors. It is made by addition polymerization of the monomer H2C=CHCONH2.(a) Draw three repeating units of polyacrylamide.(b) How do the side chains in polyacrylamide contribute to its hardness and strength?
Identify each compound as an aldehyde or a ketone and give its systematic name:(a) CH3CH2CH(CH3)CHO;(b)(c) (CH3CH2)2CHCH2COCH2CH3 HC- -CHO
Alkanes undergo substitution of hydrogen atoms when treated with halogens. Bromination of which of the following compounds could give rise to chiral monosubstituted products:(a) Ethane;(b) Propane;(c) Butane;(d) Pentane? Include in your answer the names of the chiral compounds that would be
Write the structural formula of(a) 4-ethyl-2,3,6-trimethyloctane;(b) cis-4-ethyl-2-hexene;(c) 1-ethyl-2,3-dimethylcyclopentane;(d) 5-ethyl-1-heptene.
How does average molar mass (which is proportional to the chain length) affect each of the following polymer characteristics:(a) Softening point;(b) Viscosity;(c) Strength?
A hydrocarbon with the formula C3H6 reacts with bromine only in the presence of light, producing C3H5Br. What is the name of this hydrocarbon?
Write the structural formula of(a) Butanal;(b) 3- hexanone;(c) 2-heptanone.
Draw line structures to represent each of the following molecules:(a) Nonane, CH3(CH2)7CH3;(b) Cyclopropane, C3H6;(c) Cyclohexene, C6H10.
How does the polarity of the side chains in a polymer affect each of the following characteristics of the polymer:(a) Softening point;(b) Viscosity;(c) Strength?
A hydrocarbon is 90% carbon by mass and 10% hydrogen by mass and has a molar mass of 40 g · mol–1. It decolorizes bromine water, and 1.46 g of the hydrocarbon reacts with 1.60 L of hydrogen (measured at STP) in the presence of a nickel catalyst. Write the molecular formula of the hydrocarbon and
Write the structural formula of(a) 2-ethyl-2- methylpentanal;(b) 3,5-dihydroxy-4-octanone;(c) 4,5- dimethyl-3-hexanone.
Draw line structures to represent each of the following species:(a) 2,2,3,3-tetramethylhexane, CH3C(CH3)2C(CH3)2CH2CH2CH3;(b) The trityl cation, (C6H5)3C+;(c) Butadiene, CH2CHCHCH2.
The compound 1-bromo-4-nitrobenzene (p-bromonitrobenzene) can be brominated. What do you expect to be the major product and why? Draw appropriate structures to support your answer.
Describe how the linearity of the polymer chain affects polymer strength.
Give the systematic name of(a) CH3COOH;(b) CH3CH2CH2COOH;(c) CH2(NH2)COOH.
Consider the nitration of the compoundIf the reaction can be controlled so that one NO2 group replaces one H atom of the molecule, where do you expect the nitro group to end up in the product? H 0 HO-
Identify the type and number of bonds on carbon atom 2 in(a) Pentane;(b) 2-pentene;(c) 2-pentyne.
Describe how cross-linking affects the elasticity and rigidity of a polymer.
Give the systematic name of(a) CH3CH(CH3)CH2COOH;(b) CH2ClCH2COOH;(c) CH3(CH2)7COOH.
Predict the geometry and hybridization of the orbitals used in bonding on carbon atom 2 in(a) Pentane;(b) 2-pentene;(c) 2-pentyne.
(a) Draw the structure of 3,4,6-trimethyl-1-heptene. (b) Identify the chiral carbon atoms in the structure with stars.(c) Are cis and trans isomers possible for this molecule?
(a) Draw the structure of the peptide bond that links the amino acids in proteins.(b) Identify the functional group formed.(c) Identify the type of polymer formed (addition or condensation).
Draw the structure of(a) Benzoic acid, C6H5COOH;(b) 2-chloro-3-methylpentanoic acid;(c) Hexanoic acid;(d) Propenoic acid.
Draw the structures of cis-1,2-dichloropropene and trans-1,2-dichloropropene. Which of these molecules is polar?
Trinitrotoluene, TNT, is a well-known explosive.(a) Use the following structure to identify the systematic name of TNT.(b) TNT is made by nitrating toluene (methylbenzene) with a mixture of concentrated nitric and sulfuric acids. Explain why this particular trisubstituted isomer is the one that
(a) Draw the structure of the link between glucose units that creates amylose.(b) Identify the functional group formed.(c) Identify the type of polymer formed (addition or condensation).
Name the amino acids in Table 11E.3 that contain side groups capable of forming hydrogen bonds. This interaction contributes to the tertiary structure of a protein. TABLE 11E.3 The Naturally Occurring Amino Acids, R-CH(NH)COOH R -H -CH3 CH -CH(CH3)2 -CHCH(CH3)2 -CH(CH3)CHCH3 -CHOH -CH(OH)CH CH,
Draw the structure of(a) 2-methylpropanoic acid;(b) 2,2-dichlorobutanoic acid;(c) 2,2,2-trifluoroethanoic acid;(d) 4,4-dimethylpentanoic acid.
Draw the structure of 1,3-pentadiene. Use valence-bond and molecular orbital pictures to describe the bonding for the s-framework and π-orbitals, respectively.
Conjugated polyenes are hydrocarbons with alternating single and double bonds. They are commonly used as dyes because they absorb in the visible range. Two such molecules have the formulas C6H8 and C8H10. Of the two, which has its maximum absorption at the longer wavelength? Justify your answer.
(a) How many liters of hydrogen at 1.00 atm and 298 K are needed to hydrogenate(i) 1.00 mol C6H10, cyclohexene; (ii) 1.00 mol C6H6, benzene, completely?(b) Estimate the reaction enthalpy of each hydrogenation from the average bond enthalpies in Tables 4E.2 and 4E.3.(c) A Kekulé structure of
Name the amino acids in Table 11E.3 that contain nonpolar side groups. These groups contribute to the tertiary structure of a protein by preventing contact with water. TABLE 11E.3 The Naturally Occurring Amino Acids, R-CH(NH)COOH R -H -CH3 CH -CH(CH3)2 -CHCH(CH3)2 -CH(CH3)CHCH3 -CHOH -CH(OH)CH CH,
Give the systematic name of each of the following amines:(a) CH3NH2;(b) (CH3CH2)2NH;(c) o-CH3C6H4NH2.
Write the structural formulas for and name(a) At least 10 alkene isomers having the formula C6H12;(b) At least 10 cycloalkane isomers having the formula C6H12.
Give the systematic name of each of the following amines:(a) CH3CH2CH2NH2;(b) (CH3CH2)4N+;(c) p-ClC6H4NH2.
Write the chemical formula of the compound represented by each of the following line structures: HN HN (a) Guanine Z ZH N H HO TRA H H CHO OH H OH OH CHOH (b) D-Glucose HN (c) Alanine
Write the structural formulas for and name all the isomers (including geometrical isomers) of the alkenes(a) C4H8;(b) C5H10.
Identify each of the following pairs as structural isomers, geometrical isomers, or not isomers:(a) Butane and cyclobutane;(b) Cyclopentane and pentene;(c)(d) and
Draw the structure of the peptide formed from the reaction of the acid group of tyrosine with the amine group of glycine.
Write the structural formula of each of the following amines:(a) o-methylphenylamine;(b) Triethylamine;(c) Tetramethylammonium ion.
Write the chemical formula of the compound represented by each of the following line structures: HN OH SH (a) Cysteine NH N (b) Adenine ZH N H OH (c) Eugenol
Draw the line structure of the peptide formed from the reaction of the acid group of aspartic acid with the amine group of phenylalanine. The acid side chain of aspartic acid is not involved in this reaction. The resulting peptide is related to the artificial sweetener aspartame.
Identify each of the following pairs as structural isomers, geometrical isomers, or not isomers:(a) 1-chlorohexane and chloro cyclohexane;(b)(c) and
Write the structural formula of each of the following amines:(a) Methylpropylamine;(b) Dimethylamine;(c) M- methylphenylamine.
Identify all the functional groups in each of the following compounds:(a) Vanillin, the compound responsible for vanilla flavor,(b) Carvone, the compound responsible for spearmint flavor,(c) Caffeine, the stimulant in coffee, tea, and cola drinks, HO- -CHO
Identify(a) The functional groups and(b) The chiral carbon atoms in the mannose molecule shown here. H T ----- HO HO
Identify all the functional groups in each of the following compounds:(a) Zingerone, the pungent, hot component of ginger,(b) Tylenol (acetaminophen), an analgesic,(c) Procaine, a local anesthetic, HO 0
Which of the following molecules or ions may function as a nucleophile in a nucleophilic substitution reaction:(a) NH3;(b) CO2;(c) Br–;(d) SiH4?
A branched hydrocarbon C4H10 reacts with chlorine in the presence of light to give two branched structural isomers with the formula C4H9Cl. Write the structural formulas of(a) The hydrocarbon;(b) The isomeric products.
Identify(a) The functional groups and(b) The chiral carbon atoms in the histidine molecule shown here. HN N H,N HO
Which of the following molecules or ions may function as a nucleophile in a nucleophilic substitution reaction:(a) OH–;(b) NH4+;(c) NH2 2;(d) H2O?
Identify the chiral carbon atoms in each of the following compounds:(a) Camphor, used in cooling salves,(b) Testosterone, a male sex hormone,
A branched hydrocarbon C6H14 reacts with chlorine in the presence of light to give only two structural isomers with the formula C6H13Cl. Write the structural formulas of(a) The hydrocarbon;(b) The two isomeric products.
Write the complementary nucleic acid sequence that would pair with each of the following DNA sequences:(a) CATGAGTTA;(b) TGAATTGCA.
Identify the chiral carbon atoms in each of the following compounds:(a) Menthol, the flavor of peppermint,(b) Estradiol, a female sex hormone, HO
Suggest an alcohol that could be used for the preparation of each of the following compounds and indicate how the reaction would be carried out:(a) Ethanal;(b) 2-octanone;(c) 5- methyloctanal.
Indicate which of the following molecules are optical isomers and identify the chiral carbon atoms in those that are:(a) CH3CHBrCH2CH3;(b) CH3CH2CHCl2;(c) 1-bromo-2- chloropropane;(d) 1,2-dichloropentane.
Write the complementary nucleic acid sequence that would pair with each of the following DNA sequences:(a) ATTAGATCAT;(b) GACTAGGATCT.
Identify the hybridization of each carbon and nitrogen atom in guanine (see Exercise 11.23a).Exercise 11.23aWrite the chemical formula of the compound represented by each of the following line structures: HN HN N (a) Guanine N ZH N H
Suggest an alcohol that could be used for the preparation of each of the following compounds and indicate how the reaction would be carried out:(a) Propanal;(b) 2-pentanone;(c) 5- ethyl-3-nonanone.
Indicate which of the following molecules are optical isomers and identify the chiral carbon atoms in those that are:(a) CH3CHBrCH2Br;(b) CH3CH2CHClCH2CH3;(c) 2-bromo- 2-methylpropane;(d) 2,3-dimethylpentane.
Identify the hybridization of each carbon and nitrogen atom in caffeine (see Exercise 11.25c).Exercise 11.25cIdentify all the functional groups in each of the following compounds:(c) caffeine, the stimulant in coffee, tea, and cola drinks, Z Z - Z Z
Draw the structure of the principal product formed from each pair of reagents in condensation reactions:(a) Butanoic acid with 2-propanol;(b) Ethanoic acid with 1-pentanol;(c) Hexanoic acid with methylethyl amine;(d) Ethanoic acid with propylamine.
Draw the structure of the principal product formed from each pair of reagents in condensation reactions:(a) Propanoic acid with 2-methylpropanol;(b) Ethanoic acid with cyclohexanol;(c) Butanoic acid with dimethylamine;(d) 2-methyl-pentanoic acid with ethylamine.
The structures of the following molecules can be found on the website for this book. Draw the structure of each and identify its chiral carbon atoms:(a) Cocaine;(b) Aflatoxin B2, a toxin and carcinogen that occurs naturally in peanuts as a byproduct of the growth of fungi.
Classify each of the following reactions as an addition reaction, a nucleophilic substitution reaction, an electrophilic substitution reaction, or a condensation reaction:(a) The reaction of 1-butene with chlorine in the absence of light;(b) The polymerization of the amino acid glycine;(c) The
The structures of the following molecules can be found on the website for this book. Draw the line structure of each and identify its chiral carbon atoms:(a) Cephalosporin C, toxic to penicillin-resistant staphylococci;(b) Thromboxane A2 (C20H32O5), a substance that promotes the clotting of blood.
Classify each of the following reactions as an addition reaction, a nucleophilic substitution reaction, an electrophilic substitution reaction, or a condensation reaction:(a) The reaction of terephthalic acid with 1,2-ethanediol;(b) The reaction of 3-chlorohexane with concentrated sodium
(a) Write the structural formulas of diethyl ether and 1-butanol (note that they are isomers).(b) The boiling point of 1-butanol is 117°C, higher than that of diethyl ether (35°C), yet the solubility of both compounds in water is about 8 g per 100 mL. Account for these observations.

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