Organic Chemistry - 9th Edition - by John E. McMurry - ISBN 9781305080485

Organic Chemistry
9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485

Solutions for Organic Chemistry

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Chapter 2.3 - Formal ChargesChapter 2.6 - Drawing Resonance FormsChapter 2.7 - Acids And Bases: The Brønsted–lowry DefinitionChapter 2.8 - Acid And Base StrengthChapter 2.9 - Predicting Acid–base Reactions From Pka ValuesChapter 2.11 - Acids And Bases: The Lewis DefinitionChapter 2.12 - Noncovalent Interactions Between MoleculesChapter 2.SE - Something ExtraChapter 3.1 - Functional GroupsChapter 3.2 - Alkanes And Alkane IsomersChapter 3.3 - Alkyl GroupsChapter 3.4 - Naming AlkanesChapter 3.7 - Conformations Of Other AlkanesChapter 3.SE - Something ExtraChapter 4.1 - Naming CycloalkanesChapter 4.2 - Cis–trans Isomerism In CycloalkanesChapter 4.3 - Stability Of Cycloalkanes: Ring StrainChapter 4.4 - Conformations Of CycloalkanesChapter 4.6 - Axial And Equatorial Bonds In CyclohexaneChapter 4.7 - Conformations Of Monosubstituted CyclohexanesChapter 4.8 - Conformations Of Disubstituted CyclohexanesChapter 4.9 - Conformations Of Polycyclic MoleculesChapter 4.SE - Something ExtraChapter 5.2 - The Reason For Handedness In Molecules: ChiralityChapter 5.3 - Optical ActivityChapter 5.5 - Sequence Rules For Specifying ConfigurationChapter 5.6 - DiastereomersChapter 5.7 - Meso CompoundsChapter 5.8 - Racemic Mixtures And The Resolution Of EnantiomersChapter 5.9 - A Review Of IsomerismChapter 5.11 - ProchiralityChapter 5.SE - Something ExtraChapter 6.1 - Kinds Of Organic ReactionsChapter 6.3 - Radical ReactionsChapter 6.4 - Polar ReactionsChapter 6.5 - An Example Of A Polar Reaction: Addition Of Hbr To EthyleneChapter 6.6 - Using Curved Arrows In Polar Reaction MechanismsChapter 6.7 - Describing A Reaction: Equilibria, Rates, And Energy ChangesChapter 6.9 - Describing A Reaction: Energy Diagrams And Transition StatesChapter 6.10 - Describing A Reaction: IntermediatesChapter 6.SE - Something ExtraChapter 7.2 - Calculating Degree Of UnsaturationChapter 7.3 - Naming AlkenesChapter 7.4 - Cis–trans Isomerism In AlkenesChapter 7.5 - Alkene Stereochemistry And The E,z DesignationChapter 7.6 - Stability Of AlkenesChapter 7.8 - Orientation Of Electrophilic Additions: Markovnikov’s RuleChapter 7.9 - Carbocation Structure And StabilityChapter 7.10 - The Hammond PostulateChapter 7.11 - Evidence For The Mechanism Of Electrophilic Additions: Carbocation RearrangementsChapter 7.SE - Something ExtraChapter 8.1 - Preparing Alkenes: A Preview Of Elimination ReactionsChapter 8.2 - Halogenation Of Alkenes: Addition Of X2Chapter 8.3 - Halohydrins From Alkenes: Addition Of HoxChapter 8.4 - Hydration Of Alkenes: Addition Of H2o By OxymercurationChapter 8.5 - Hydration Of Alkenes: Addition Of H2o By HydroborationChapter 8.6 - Reduction Of Alkenes: HydrogenationChapter 8.7 - Oxidation Of Alkenes: Epoxidation And HydroxylationChapter 8.8 - Oxidation Of Alkenes: Cleavage To Carbonyl CompoundsChapter 8.9 - Addition Of Carbenes To Alkenes: Cyclopropane SynthesisChapter 8.10 - Radical Additions To Alkenes: Chain-growth PolymersChapter 8.13 - Reaction Stereochemistry: Addition Of H2o To A Chiral AlkeneChapter 8.SE - Something ExtraChapter 9.1 - Naming AlkynesChapter 9.3 - Reactions Of Alkynes: Addition Of Hx And X2Chapter 9.4 - Hydration Of AlkynesChapter 9.5 - Reduction Of AlkynesChapter 9.7 - Alkyne Acidity: Formation Of Acetylide AnionsChapter 9.8 - Alkylation Of Acetylide AnionsChapter 9.9 - An Introduction To Organic SynthesisChapter 9.SE - Something ExtraChapter 10.1 - Names And Structures Of Alkyl HalidesChapter 10.2 - Preparing Alkyl Halides From Alkanes: Radical HalogenationChapter 10.4 - Stability Of The Allyl Radical: Resonance RevisitedChapter 10.5 - Preparing Alkyl Halides From AlcoholsChapter 10.6 - Reactions Of Alkyl Halides: Grignard ReagentsChapter 10.7 - Organometallic Coupling ReactionsChapter 10.8 - Oxidation And Reduction In Organic ChemistryChapter 10.SE - Something ExtraChapter 11.1 - The Discovery Of Nucleophilic Substitution ReactionsChapter 11.2 - The Sn2 ReactionChapter 11.3 - Characteristics Of The Sn2 ReactionChapter 11.4 - The Sn1 ReactionChapter 11.5 - Characteristics Of The Sn1 ReactionChapter 11.6 - Biological Substitution ReactionsChapter 11.7 - Elimination Reactions: Zaitsev’s RuleChapter 11.8 - The E2 Reaction And The Deuterium Isotope EffectChapter 11.9 - The E2 Reaction And Cyclohexane ConformationChapter 11.12 - A Summary Of Reactivity: Sn1, Sn2, E1, E1cb, And E2Chapter 11.SE - Something ExtraChapter 12.2 - Interpreting Mass SpectraChapter 12.3 - Mass Spectrometry Of Some Common Functional GroupsChapter 12.5 - Spectroscopy And The Electromagnetic SpectrumChapter 12.7 - Interpreting Infrared SpectraChapter 12.8 - Infrared Spectra Of Some Common Functional GroupsChapter 12.SE - Something ExtraChapter 13.1 - Nuclear Magnetic Resonance SpectroscopyChapter 13.2 - The Nature Of Nmr AbsorptionsChapter 13.3 - The Chemical ShiftChapter 13.4 - Chemical Shifts In 1h Nmr SpectroscopyChapter 13.5 - Integration Of 1h Nmr Absorptions: Proton CountingChapter 13.6 - Spin–spin Splitting In 1h Nmr SpectraChapter 13.7 - 1h Nmr Spectroscopy And Proton EquivalenceChapter 13.8 - More Complex Spin–spin Splitting PatternsChapter 13.9 - Uses Of 1h Nmr SpectroscopyChapter 13.11 - Characteristics Of 13c Nmr SpectroscopyChapter 13.12 - Dept 13c Nmr SpectroscopyChapter 13.13 - Uses Of 13c Nmr SpectroscopyChapter 13.SE - Something ExtraChapter 14.1 - Stability Of Conjugated Dienes: Molecular Orbital TheoryChapter 14.2 - Electrophilic Additions To Conjugated Dienes: Allylic CarbocationsChapter 14.3 - Kinetic Versus Thermodynamic Control Of ReactionsChapter 14.5 - Characteristics Of The Diels–alder ReactionChapter 14.6 - Diene Polymers: Natural And Synthetic RubbersChapter 14.7 - Ultraviolet SpectroscopyChapter 14.8 - Interpreting Ultraviolet Spectra: The Effect Of ConjugationChapter 14.SE - Something ExtraChapter 15.1 - Naming Aromatic CompoundsChapter 15.2 - Structure And Stability Of BenzeneChapter 15.3 - Aromaticity And The Hückel 4n 1 2 RuleChapter 15.4 - Aromatic IonsChapter 15.5 - Aromatic Heterocycles: Pyridine And PyrroleChapter 15.6 - Polycyclic Aromatic CompoundsChapter 15.SE - Something ExtraChapter 16.1 - Electrophilic Aromatic Substitution Reactions: BrominationChapter 16.2 - Other Aromatic SubstitutionsChapter 16.3 - Alkylation And Acylation Of Aromatic Rings: The Friedel–crafts ReactionChapter 16.4 - Substituent Effects In Electrophilic SubstitutionsChapter 16.5 - Trisubstituted Benzenes: Additivity Of EffectsChapter 16.6 - Nucleophilic Aromatic SubstitutionChapter 16.7 - BenzyneChapter 16.8 - Oxidation Of Aromatic CompoundsChapter 16.9 - Reduction Of Aromatic CompoundsChapter 16.10 - Synthesis Of Polysubstituted BenzenesChapter 16.SE - Something ExtraChapter 17.1 - Naming Alcohols And PhenolsChapter 17.2 - Properties Of Alcohols And PhenolsChapter 17.3 - Preparation Of Alcohols: A ReviewChapter 17.4 - Alcohols From Carbonyl Compounds: ReductionChapter 17.5 - Alcohols From Carbonyl Compounds: Grignard ReactionChapter 17.6 - Reactions Of AlcoholsChapter 17.7 - Oxidation Of AlcoholsChapter 17.8 - Protection Of AlcoholsChapter 17.9 - Phenols And Their UsesChapter 17.11 - Spectroscopy Of Alcohols And PhenolsChapter 17.SE - Something ExtraChapter 18.1 - Names And Properties Of EthersChapter 18.2 - Preparing EthersChapter 18.3 - Reactions Of Ethers: Acidic CleavageChapter 18.4 - Reactions Of Ethers: Claisen RearrangementChapter 18.5 - Cyclic Ethers: EpoxidesChapter 18.6 - Reactions Of Epoxides: Ring-openingChapter 18.7 - Crown EthersChapter 18.8 - Thiols And SulfidesChapter 18.9 - Spectroscopy Of EthersChapter 18.SE - Something ExtraChapter 19.1 - Naming Aldehydes And KetonesChapter 19.2 - Preparing Aldehydes And KetonesChapter 19.4 - Nucleophilic Addition Reactions Of Aldehydes And KetonesChapter 19.5 - Nucleophilic Addition Of H2o: HydrationChapter 19.6 - Nucleophilic Addition Of Hcn: Cyanohydrin FormationChapter 19.8 - Nucleophilic Addition Of Amines: Imine And Enamine FormationChapter 19.9 - Nucleophilic Addition Of Hydrazine: The Wolff–kishner ReactionChapter 19.10 - Nucleophilic Addition Of Alcohols: Acetal FormationChapter 19.11 - Nucleophilic Addition Of Phosphorus Ylides: The Wittig ReactionChapter 19.12 - Biological ReductionsChapter 19.13 - Conjugate Nucleophilic Addition To A,b-unsaturated Aldehydes And KetonesChapter 19.14 - Spectroscopy Of Aldehydes And KetonesChapter 19.SE - Something ExtraChapter 20.1 - Naming Carboxylic Acids And NitrilesChapter 20.2 - Structure And Properties Of Carboxylic AcidsChapter 20.3 - Biological Acids And The Henderson–hasselbalch EquationChapter 20.4 - Substituent Effects On AcidityChapter 20.5 - Preparing Carboxylic AcidsChapter 20.6 - Reactions Of Carboxylic Acids: An OverviewChapter 20.7 - Chemistry Of NitrilesChapter 20.8 - Spectroscopy Of Carboxylic Acids And NitrilesChapter 20.SE - Something ExtraChapter 21.1 - Naming Carboxylic Acid DerivativesChapter 21.2 - Nucleophilic Acyl Substitution ReactionsChapter 21.3 - Reactions Of Carboxylic AcidsChapter 21.4 - Chemistry Of Acid HalidesChapter 21.5 - Chemistry Of Acid AnhydridesChapter 21.6 - Chemistry Of EstersChapter 21.7 - Chemistry Of AmidesChapter 21.8 - Chemistry Of Thioesters And Acyl Phosphates: Biological Carboxylic Acid DerivativesChapter 21.9 - Polyamides And Polyesters: Step-growth PolymersChapter 21.10 - Spectroscopy Of Carboxylic Acid DerivativesChapter 21.SE - Something ExtraChapter 22.1 - Keto–enol TautomerismChapter 22.3 - Alpha Halogenation Of Aldehydes And KetonesChapter 22.4 - Alpha Bromination Of Carboxylic AcidsChapter 22.5 - Acidity Of Alpha Hydrogen Atoms: Enolate Ion FormationChapter 22.6 - Reactivity Of Enolate IonsChapter 22.7 - Alkylation Of Enolate IonsChapter 22.SE - Something ExtraChapter 23.1 - Carbonyl Condensations: The Aldol ReactionChapter 23.3 - Dehydration Of Aldol Products: Synthesis Of EnonesChapter 23.4 - Using Aldol Reactions In SynthesisChapter 23.5 - Mixed Aldol ReactionsChapter 23.6 - Intramolecular Aldol ReactionsChapter 23.7 - The Claisen Condensation ReactionChapter 23.8 - Mixed Claisen CondensationsChapter 23.9 - Intramolecular Claisen Condensations: The Dieckmann CyclizationChapter 23.10 - Conjugate Carbonyl Additions: The Michael ReactionChapter 23.11 - Carbonyl Condensations With Enamines: The Stork ReactionChapter 23.12 - The Robinson Annulation ReactionChapter 23.SE - Something ExtraChapter 24.1 - Naming AminesChapter 24.3 - Basicity Of AminesChapter 24.4 - Basicity Of ArylaminesChapter 24.5 - Biological Amines And The Henderson–hasselbalch EquationChapter 24.6 - Synthesis Of AminesChapter 24.7 - Reactions Of AminesChapter 24.8 - Reactions Of ArylaminesChapter 24.9 - Heterocyclic AminesChapter 24.10 - Spectroscopy Of AminesChapter 24.SE - Something ExtraChapter 25.1 - Classification Of CarbohydratesChapter 25.2 - Representing Carbohydrate Stereochemistry: Fischer ProjectionsChapter 25.3 - D,l SugarsChapter 25.4 - Configurations Of The AldosesChapter 25.5 - Cyclic Structures Of Monosaccharides: AnomersChapter 25.6 - Reactions Of MonosaccharidesChapter 25.7 - The Eight Essential MonosaccharidesChapter 25.8 - DisaccharidesChapter 25.SE - Something ExtraChapter 26.1 - Structures Of Amino AcidsChapter 26.2 - Amino Acids And The Henderson–hasselbalch Equation: Isoelectric PointsChapter 26.3 - Synthesis Of Amino AcidsChapter 26.4 - Peptides And ProteinsChapter 26.5 - Amino Acid Analysis Of PeptidesChapter 26.6 - Peptide Sequencing: The Edman DegradationChapter 26.7 - Peptide SynthesisChapter 26.10 - Enzymes And CoenzymesChapter 26.SE - Something ExtraChapter 27.1 - Waxes, Fats, And OilsChapter 27.2 - SoapChapter 27.4 - Prostaglandins And Other EicosanoidsChapter 27.5 - TerpenoidsChapter 27.6 - SteroidsChapter 27.7 - Biosynthesis Of SteroidsChapter 27.SE - Something ExtraChapter 28.1 - Nucleotides And Nucleic AcidsChapter 28.2 - Base Pairing In Dna: The Watson–crick ModelChapter 28.4 - Transcription Of DnaChapter 28.5 - Translation Of Rna: Protein BiosynthesisChapter 28.7 - Dna SynthesisChapter 28.SE - Something ExtraChapter 29.1 - An Overview Of Metabolism And Biochemical EnergyChapter 29.3 - Catabolism Of Triacylglycerols: B-oxidationChapter 29.4 - Biosynthesis Of Fatty AcidsChapter 29.5 - Catabolism Of Carbohydrates: GlycolysisChapter 29.6 - Conversion Of Pyruvate To Acetyl CoaChapter 29.7 - The Citric Acid CycleChapter 29.8 - Carbohydrate Biosynthesis: GluconeogenesisChapter 29.9 - Catabolism Of Proteins: DeaminationChapter 29.SE - Something ExtraChapter 30.1 - Molecular Orbitals Of Conjugated Pi SystemsChapter 30.3 - Stereochemistry Of Thermal Electrocyclic ReactionsChapter 30.4 - Photochemical Electrocyclic ReactionsChapter 30.6 - Stereochemistry Of CycloadditionsChapter 30.7 - Sigmatropic RearrangementsChapter 30.8 - Some Examples Of Sigmatropic RearrangementsChapter 30.9 - A Summary Of Rules For Pericyclic ReactionsChapter 30.SE - Something ExtraChapter 31.1 - Chain-growth PolymersChapter 31.2 - Stereochemistry Of Polymerization: Ziegler–natta CatalystsChapter 31.3 - CopolymersChapter 31.4 - Step-growth PolymersChapter 31.5 - Olefin Metathesis PolymerizationChapter 31.6 - Polymer Structure And Physical PropertiesChapter 31.SE - Something Extra

Book Details

Master organic chemistry with the help of this proven best-seller! John McMurry's ORGANIC CHEMISTRY is consistently praised as the most clearly written book available for the course. In John McMurry's words: "I wrote this book because I love writing. I get great pleasure and satisfaction from taking a complicated subject, turning it around until I see it clearly from a new angle, and then explaining it in simple words." Through his lucid writing and ability to show the beauty and logic of organic chemistry, McMurry makes learning enjoyable. The highest compliment that can be given to a chemistry book applies to McMurry: It works!

Sample Solutions for this Textbook

We offer sample solutions for Organic Chemistry homework problems. See examples below:

From the structure of phenylalanine, it is quite evident that the terminal hydrogen of alanine is...Chapter 3.SE, Problem 24APBy following IUPAC rules for naming these molecules, a. Parent chain-cyclopentane ring. Two...Chapter 5.SE, Problem 26VCBy ranking the substituent in the following examples based on Cahn-Ingold Prelog rules, R and S...Both 1-pentene and 2-pentene have double bonds in a position to yield the alkyl bromide when treated...Chapter 6.SE, Problem 30APThe compound given has a continuous chain of six carbons with a double bond between C2 and C3 and...Chapter 7.SE, Problem 34APChapter 7.SE, Problem 38APThe first atoms in the substituents given are I, Br, C and CH. Their atomic numbers are 53, 35, 12,...Chapter 7.SE, Problem 47APMolecular formula of cholesterol is C27H46O. If oxygens are ignored the formula becomes C27H46. A...Chapter 8.SE, Problem 22VCIodine has seven valence electrons (5s25p5) and nitrogen (2s22p3) has five (2s22p3) valence...The addition of hydrogen takes place to the double bond in the side chain with syn stereochemistry....Chapter 8.SE, Problem 43APChapter 8.SE, Problem 48APChapter 8.SE, Problem 50APChapter 9.SE, Problem 14VCChapter 9.SE, Problem 27APChapter 9.SE, Problem 31APWhen 5-decyne reacts with hydrogen in the presence of Lindlar catalyst, the addition of hydrogens to...Alkynes when treated with H2 in the presence of Pd-BaSO4 add two equivalents of hydrogen to yield an...The compound has a cyclohexane ring with a Cl atom on C1 and a methyl on C3 both at equatorial...Chapter 10.SE, Problem 25APWhen 1-methylcyclohexanol is treated with HBr, the OH group in it is replaced by the bromine to...Chapter 10.SE, Problem 48APThe ethyl chloride undergoes SN2 reaction with Na+SCH3- and NaOH to yield a product. The product is...Given information: The product of the reaction is given below, The reaction is given below, The...Chapter 11.SE, Problem 49APChapter 11.SE, Problem 50APPhenylacetaldehyde, being an aldehyde is reduced by NaBH4 to a primary alcohol, 2-phenylethanol....The molecular formula of the compound is C6H12O. Ignoring oxygen the molecular formula of the parent...Chapter 11.SE, Problem 81APa) In the molecule C-H stretch shows an absorption at 3100 cm-1 , C=C aromatic stretching around...Chapter 12.SE, Problem 33APChapter 13.SE, Problem 24VCChapter 13.SE, Problem 47APCalculate HDI: The HDI calculation led to confirm about the presence of a double bond or a ring....Chapter 13.SE, Problem 55GPChapter 13.SE, Problem 58GP1-Vinylcyclopentene is an unsymmetrical conjugated diene. Protonation of the CH2 in double bond and...1,3-cyclohexadiene is a conjugated diene. When treated with one mole of bromine in CH2Cl2 it yields...Chapter 15.SE, Problem 13VCChapter 15.SE, Problem 19APChapter 15.SE, Problem 23APThe molecular formula of the compound is C8H9Br. Thus the compound has four unsaturation units like...The methoxy group attached to the benzene ring is an ortho & para directing group. When...Bromine is an o- and p-directing group. It also has considerable electron withdrawing inductive...Chapter 16.SE, Problem 49APFluorine attached to an aromatic ring is an o- and p- directing deactivating group. Hence it directs...Chapter 16.SE, Problem 53APThe electrophile, NO2+, attacks the aromatic ring in the first step to produce a resonance...Chapter 17.SE, Problem 20VCThe reaction of the alcohol with PBr3 is a bimolecular nucleophilic substitution (SN2) reaction. It...Chapter 17.SE, Problem 42APChapter 17.SE, Problem 44AP2-Phenylethanol when treated with POCl3 in pyridine eliminates a molecule of water from the side...Chapter 17.SE, Problem 55APChapter 18.SE, Problem 19VCThe ether given has a secondary carbon and a primary carbon attached to the oxygen. The acid...The reaction occurs following SN1 mechanism. The acid protonates the ether initially and the...The sulfide contains a sulfur atom attached to a cyclohexyl group and an isopropyl group.Chapter 18.SE, Problem 40APWhen cyclohexene is treated with trifluoromercuric acetate, a mercurinium ion is formed. The attack...Chapter 19.SE, Problem 27VCThe hydroxide ion from KOH abstracts a weakly acidic H from –NH2 of the hydrazone of isopropyl...The name indicates that the compound is a ketone with three carbon straight chain with a bromine...Chapter 19.SE, Problem 58APChapter 19.SE, Problem 64APChapter 19.SE, Problem 69APChapter 19.SE, Problem 86APThe compound represented by the model is It is a benzoic acid derivative with a bromine atom on C3...The nucleophilic attack of the hydroxide ion the nitrile carbon in hexanenitrile yields an imine...Chapter 20.SE, Problem 25MPThe name shows that the compound has a cyclohexane ring with two carboxylic acid groups in 1,2...Chapter 20.SE, Problem 55APChapter 21.SE, Problem 27VCChapter 21.SE, Problem 31MPChapter 21.SE, Problem 32MPChapter 21.SE, Problem 33MPChapter 21.SE, Problem 45APTo derive the structure corresponding to the given IUPAC name, we need to take recourse to the IUPAC...The compound represented by the model is 6-methylhept-5-ene-2-one. It is a methyl ketone and hence...The compound shown is a derivative of carboxylic acid. Hence it can be prepared using malonic ester...Chapter 22.SE, Problem 58APThe compound represented by the model is An analysis of the structure indicates it can be produced...In the first step the base picks up an acidic proton from the diketone to produce the enolate anion....Chapter 23.SE, Problem 29MPThe requirement of aldol reaction is the aldehyde or ketone should have α-hydrogen atom....An analysis of the structure of the compound indicates that it is formed by the reaction between the...Chapter 24.SE, Problem 26VCChapter 24.SE, Problem 30MPThe longest carbon chain containing the double bond to be chosen. Based on the name of the parent...Concept strategy: The Fischer projection of the given monosaccharide is drawn vertically, by...Chapter 26.SE, Problem 19VCThe structure of cholic acid represented by the model is Since lithocholic acid has the rings A and...Chapter 27.SE, Problem 20APChapter 27.SE, Problem 21APChapter 28.SE, Problem 13VCThe original DNA sequence on which mRNA is formed is none other than antisense DNA. mRNA is a...As the anticodon sequence on tRNAs are the complement of the mRNAs, therefore, we will just replace...Catabolism of proteins occurs by a discrimination of α – amino acids according to the following...Chapter 30.SE, Problem 11VC

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