(Ebook) Solutions Manual For Accompany Organic Chemistry 2nd edition by Stuart Warren, Johnathan Clayden, Nick Greeves, Warren, Peter Wothers 0198700385 9780198700388

(Ebook) Solutions Manual For Accompany Organic Chemistry 2nd edition by Stuart Warren, Johnathan Clayden, Nick Greeves, Warren, Peter Wothers 0198700385 9780198700388

Solutions Manual For Accompany Organic Chemistry 2nd edition by Stuart Warren, Johnathan Clayden, Nick Greeves, Warren, Peter Wothers - Ebook PDF Instant Download/DeliveryISBN:  0198700385, 9780198700388 

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ISBN-10 :  0198700385 

ISBN-13 : 9780198700388

Author:  Stuart Warren, Johnathan Clayden, Nick Greeves, Warren, Peter Wothers 

Inspiring and motivating students from the moment it published, Organic Chemistry has established itself in just one edition as the student's choice of an organic chemistry text.

The second edition refines and refocuses Organic Chemistry to produce a text that is even more student-friendly, coherent, and logical in its presentation than before.

Solutions Manual For Accompany Organic Chemistry 2nd Table of contents:

1 What is organic chemistry?
Organic chemistry and you
Organic compounds
Organic chemistry and industry
Organic chemistry and the periodic table
Organic chemistry and this book
Further reading
2 Organic structures
Hydrocarbon frameworks and functional groups
Drawing molecules
Hydrocarbon frameworks
Functional groups
Carbon atoms carrying functional groups can be classified by oxidation level
Naming compounds
What do chemists really call compounds?
How should you name compounds?
Further reading
3 Determining organic structures
Introduction
Mass spectrometry
Mass spectrometry detects isotopes
Atomic composition can be determined by high-resolution mass spectrometry
Nuclear magnetic resonance
Regions of the 13C NMR spectrum
Different ways of describing chemical shift
A guided tour of the 13C NMR spectra of some simple molecules
The 1H NMR spectrum
Infrared spectra
Mass spectra, NMR, and IR combined make quick identification possible
Double bond equivalents help in the search for a structure
Looking forward to Chapters 13 and 18
Further reading
4 Structure of molecules
Introduction
Electrons occupy atomic orbitals
Molecular orbitals—diatomic molecules
Bonds between different atoms
Hybridization of atomic orbitals
Rotation and rigidity
Conclusion
Looking forward
Further reading
5 Organic reactions
Chemical reactions
Nucleophiles and electrophiles
Curly arrows represent reaction mechanisms
Drawing your own mechanisms with curly arrows
Further reading
6 Nucleophilic addition to the carbonyl group
Molecular orbitals explain the reactivity of the carbonyl group
Attack of cyanide on aldehydes and ketones
The angle of nucleophilic attack on aldehydes and ketones
Nucleophilic attack by ‘hydride’ on aldehydes and ketones
Addition of organometallic reagents to aldehydes and ketones
Addition of water to aldehydes and ketones
Hemiacetals from reaction of alcohols with aldehydes and ketones
Ketones also form hemiacetals
Acid and base catalysis of hemiacetal and hydrate formation
Bisulfite addition compounds
Further reading
7 Delocalization and conjugation
Introduction
The structure of ethene (ethylene, CH2=CH2)
Molecules with more than one C=C double bond
The conjugation of two π bonds
UV and visible spectra
The allyl system
Delocalization over three atoms is a common structural feature
Aromaticity
Further reading
8 Acidity, basicity, and pKa
Organic compounds are more soluble in water as ions
Acids, bases, and pKa
Acidity
The definition of pKa
Constructing a pKa scale
Nitrogen compounds as acids and bases
Substituents affect the pKa
Carbon acids
pKa in action—the development of the drug cimetidine
Lewis acids and bases
Further reading
9 Using organometallic reagents to make C–C bonds
Introduction
Organometallic compounds contain a carbon–metal bond
Making organometallics
Using organometallics to make organic molecules
Oxidation of alcohols
Looking forward
Further reading
10 Nucleophilic substitution at the carbonyl group
The product of nucleophilic addition to a carbonyl group is not always a stable compound
Carboxylic acid derivatives
Why are the tetrahedral intermediates unstable?
Not all carboxylic acid derivatives are equally reactive
Acid catalysts increase the reactivity of a carbonyl group
Acid chlorides can be made from carboxylic acids using SOCl2 or PCl5
Making other compounds by substitution reactions of acid derivatives
Making ketones from esters: the problem
Making ketones from esters: the solution
To summarize…
And to conclude…
Further reading
11 Nucleophilic substitution at C=O with loss of carbonyl oxygen
Introduction
Aldehydes can react with alcohols to form hemiacetals
Acetals are formed from aldehydes or ketones plus alcohols in the presence of acid
Amines react with carbonyl compounds
Imines are the nitrogen analogues of carbonyl compounds
Summary
Further reading
12 Equilibria, rates, and mechanisms
How far and how fast?
How to make the equilibrium favour the product you want
Entropy is important in determining equilibrium constants
Equilibrium constants vary with temperature
Introducing kinetics: how to make reactions go faster and cleaner
Rate equations
Catalysis in carbonyl substitution reactions
Kinetic versus thermodynamic products
Summary of mechanisms from Chapters 6–12
Further reading
13 1H NMR: Proton nuclear magnetic resonance
The differences between carbon and proton NMR
Integration tells us the number of hydrogen atoms in each peak
Regions of the proton NMR spectrum
Protons on saturated carbon atoms
The alkene region and the benzene region
The aldehyde region: unsaturated carbon bonded to oxygen
Protons on heteroatoms have more variable shifts than protons on carbon
Coupling in the proton NMR spectrum
To conclude
Further reading
14 Stereochemistry
Some compounds can exist as a pair of mirror-image forms
Diastereoisomers are stereoisomers that are not enantiomers
Chiral compounds with no stereogenic centres
Axes and centres of symmetry
Separating enantiomers is called resolution
Further reading
15 Nucleophilic substitution at saturated carbon
Mechanisms for nucleophilic substitution
How can we decide which mechanism (SN1 or SN2) will apply to a given organic compound?
A closer look at the SN1 reaction
A closer look at the SN2 reaction
Contrasts between SN1 and SN2
The leaving group in SN1 and SN2 reactions
The nucleophile in SN1 reactions
The nucleophile in the SN2 reaction
Nucleophiles and leaving groups compared
Looking forward: elimination and rearrangement reactions
Further reading
16 Conformational analysis
Bond rotation allows chains of atoms to adopt a number of conformations
Conformation and configuration
Barriers to rotation
Conformations of ethane
Conformations of propane
Conformations of butane
Ring strain
A closer look at cyclohexane
Substituted cyclohexanes
To conclude…
Further reading
17 Elimination reactions
Substitution and elimination
How the nucleophile affects elimination versus substitution
E1 and E2 mechanisms
Substrate structure may allow E1
The role of the leaving group
E1 reactions can be stereoselective
E2 eliminations have anti-periplanar transition states
The regioselectivity of E2 eliminations
Anion-stabilizing groups allow another mechanism—E1cB
To conclude
Further reading
18 Review of spectroscopic methods
There are three reasons for this chapter
Spectroscopy and carbonyl chemistry
Acid derivatives are best distinguished by infrared
Small rings introduce strain inside the ring and higher s character outside it
Simple calculations of C=O stretching frequencies in IR spectra
NMR spectra of alkynes and small rings
Proton NMR distinguishes axial and equatorial protons in cyclohexanes
Interactions between different nuclei can give enormous coupling constants
Identifying products spectroscopically
Tables
Shifts in proton NMR are easier to calculate and more informative than those in carbon NMR
Further reading
19 Electrophilic addition to alkenes
Alkenes react with bromine
Oxidation of alkenes to form epoxides
Electrophilic addition to unsymmetrical alkenes is regioselective
Electrophilic addition to dienes
Unsymmetrical bromonium ions open regioselectively
Electrophilic additions to alkenes can be stereospecific
Adding two hydroxyl groups: dihydroxylation
Breaking a double bond completely: periodate cleavage and ozonolysis
Adding one hydroxyl group: how to add water across a double bond
To conclude…a synopsis of electrophilic addition reactions
Further reading
20 Formation and reactions of enols and enolates
Would you accept a mixture of compounds as a pure substance?
Tautomerism: formation of enols by proton transfer
Why don’t simple aldehydes and ketones exist as enols?
Evidence for the equilibration of carbonyl compounds with enols
Enolization is catalysed by acids and bases
The intermediate in the base-catalysed reaction is an enolate ion
Summary of types of enol and enolate
Stable enols
Consequences of enolization
Reaction with enols or enolates as intermediates
Stable equivalents of enolate ions
Enol and enolate reactions at oxygen: preparation of enol ethers
Reactions of enol ethers
To conclude
Further reading
21 Electrophilic aromatic substitution
Introduction: enols and phenols
Benzene and its reactions with electrophiles
Electrophilic substitution on phenols
A nitrogen lone pair activates even more strongly
Alkyl benzenes also react at the ortho and para positions
Electron-withdrawing substituents give meta products
Halogens show evidence of both electron withdrawal and donation
Two or more substituents may cooperate or compete
Some problems and some opportunities
A closer look at Friedel–Crafts chemistry
Exploiting the chemistry of the nitro group
Summary
Further reading
22 Conjugate addition and nucleophilic aromatic substitution
Alkenes conjugated with carbonyl groups
Conjugated alkenes can be electrophilic
Summary: factors controlling conjugate addition
Extending the reaction to other electron-deficient alkenes
Conjugate substitution reactions
Nucleophilic epoxidation
Nucleophilic aromatic substitution
The addition–elimination mechanism
The SN1 mechanism for nucleophilic aromatic substitution: diazonium compounds
The benzyne mechanism
To conclude…
Further reading
23 Chemoselectivity and protecting groups
Selectivity
Reducing agents
Reduction of carbonyl groups
Hydrogen as a reducing agent: catalytic hydrogenation
Getting rid of functional groups
Dissolving metal reductions
Selectivity in oxidation reactions
Competing reactivity: choosing which group reacts
A survey of protecting groups
Further reading
24 Regioselectivity
Introduction
Regioselectivity in electrophilic aromatic substitution
Electrophilic attack on alkenes
Regioselectivity in radical reactions
Nucleophilic attack on allylic compounds
Electrophilic attack on conjugated dienes
Conjugate addition
Regioselectivity in action
Further reading
25 Alkylation of enolates
Carbonyl groups show diverse reactivity
Some important considerations that affect all alkylations
Nitriles and nitroalkanes can be alkylated
Choice of electrophile for alkylation
Lithium enolates of carbonyl compounds
Alkylations of lithium enolates
Using specific enol equivalents to alkylate aldehydes and ketones
Alkylation of β-dicarbonyl compounds
Ketone alkylation poses a problem in regioselectivity
Enones provide a solution to regioselectivity problems
Using Michael acceptors as electrophiles
To conclude…
Further reading
26 Reactions of enolates with carbonyl compounds: the aldol and Claisen reactions
Introduction
The aldol reaction
Cross-condensations
Specific enol equivalents can be used to control aldol reactions
How to control aldol reactions of esters
How to control aldol reactions of aldehydes
How to control aldol reactions of ketones
Intramolecular aldol reactions
Acylation at carbon
Crossed ester condensations
Summary of the preparation of keto-esters by the Claisen reaction
Controlling acylation with specific enol equivalents
Intramolecular crossed Claisen ester condensations
Carbonyl chemistry—where next?
Further reading
27 Sulfur, silicon, and phosphorus in organic chemistry
Useful main group elements
Sulfur: an element of contradictions
Sulfur-stabilized anions
Sulfonium salts
Sulfonium ylids
Silicon and carbon compared
Allyl silanes as nucleophiles
The selective synthesis of alkenes
The properties of alkenes depend on their geometry
Exploiting cyclic compounds
Equilibration of alkenes
E and Z alkenes can be made by stereoselective addition to alkynes
Predominantly E alkenes can be formed by stereoselective elimination reactions
The Julia olefination is regiospecific and connective
Stereospecific eliminations can give pure single isomers of alkenes
Perhaps the most important way of making alkenes—the Wittig reaction
To conclude
Further reading
28 Retrosynthetic analysis
Creative chemistry
Retrosynthetic analysis: synthesis backwards
Disconnections must correspond to known, reliable reactions
Synthons are idealized reagents
Multiple step syntheses: avoid chemoselectivity problems
Functional group interconversion
Two-group disconnections are better than one-group disconnections
C–C disconnections
Available starting materials
Donor and acceptor synthons
Two-group C–C disconnections
1,5-Related functional groups
‘Natural reactivity’ and ‘umpolung’
To conclude…
Further reading
29 Aromatic heterocycles 1: reactions
Introduction
Aromaticity survives when parts of benzene’s ring are replaced by nitrogen atoms
Pyridine is a very unreactive aromatic imine
Six-membered aromatic heterocycles can have oxygen in the ring
Five-membered aromatic heterocycles are good at electrophilic substitution
Furan and thiophene are oxygen and sulfur analogues of pyrrole
More reactions of five-membered heterocycles
Five-membered rings with two or more nitrogen atoms
Benzo-fused heterocycles
Putting more nitrogen atoms in a six-membered ring
Fusing rings to pyridines: quinolines and isoquinolines
Aromatic heterocycles can have many nitrogens but only one sulfur or oxygen in any ring
There are thousands more heterocycles out there
Which heterocyclic structures should you learn?
Further reading
30 Aromatic heterocycles 2: synthesis
Thermodynamics is on our side
Disconnect the carbon–heteroatom bonds first
Pyrroles, thiophenes, and furans from 1,4-dicarbonyl compounds
How to make pyridines: the Hantzsch pyridine synthesis
Pyrazoles and pyridazines from hydrazine and dicarbonyl compounds
Pyrimidines can be made from 1,3-dicarbonyl compounds and amidines
Unsymmetrical nucleophiles lead to selectivity questions
Isoxazoles are made from hydroxylamine or by cycloaddition
Tetrazoles and triazoles are also made by cycloadditions
The Fischer indole synthesis
Quinolines and isoquinolines
More heteroatoms in fused rings mean more choice in synthesis
Summary: the three major approaches to the synthesis of aromatic heterocycles
Further reading
31 Saturated heterocycles and stereoelectronics
Introduction
Reactions of saturated heterocycles
Conformation of saturated heterocycles
Making heterocycles: ring-closing reactions
Ring size and NMR
Geminal (2J ) coupling
Diastereotopic groups
To summarize…
Further reading
32 Stereoselectivity in cyclic molecules
Introduction
Stereochemical control in six-membered rings
Reactions on small rings
Regiochemical control in cyclohexene epoxides
Stereoselectivity in bicyclic compounds
Fused bicyclic compounds
Spirocyclic compounds
Reactions with cyclic intermediates or cyclic transition states
To summarize…
Further reading
33 Diastereoselectivity
Looking back
Prochirality
Additions to carbonyl groups can be diastereoselective even without rings
Stereoselective reactions of acyclic alkenes
Aldol reactions can be stereoselective
Single enantiomers from diastereoselective reactions
Looking forward
Further reading
34 Pericyclic reactions 1: cycloadditions
A new sort of reaction
General description of the Diels–Alder reaction
The frontier orbital description of cycloadditions
Regioselectivity in Diels–Alder reactions
The Woodward–Hoffmann description of the Diels–Alder reaction
Trapping reactive intermediates by cycloadditions
Other thermal cycloadditions
Photochemical [2 + 2] cycloadditions
Thermal [2 + 2] cycloadditions
Making five-membered rings: 1,3-dipolar cycloadditions
Two very important synthetic reactions: cycloaddition of alkenes with osmium tetroxide and with ozone
Summary of cycloaddition reactions
Further reading
35 Pericyclic reactions 2: sigmatropic and electrocyclic reactions
Sigmatropic rearrangements
Orbital descriptions of [3,3]-sigmatropic rearrangements
The direction of [3,3]-sigmatropic rearrangements
[2,3]-Sigmatropic rearrangements
[1,5]-Sigmatropic hydrogen shifts
Electrocyclic reactions
Further reading
36 Participation, rearrangement, and fragmentation
Neighbouring groups can accelerate substitution reactions
Rearrangements occur when a participating group ends up bonded to a different atom
Carbocations readily rearrange
The pinacol rearrangement
The dienone-phenol rearrangement
The benzilic acid rearrangement
The Favorskii rearrangement
Migration to oxygen: the Baeyer–Villiger reaction
The Beckmann rearrangement
Polarization of C–C bonds helps fragmentation
Fragmentations are controlled by stereochemistry
Ring expansion by fragmentation
Controlling double bonds using fragmentation
The synthesis of nootkatone: fragmentation showcase
Looking forward
Further reading
37 Radical reactions
Radicals contain unpaired electrons
Radicals form by homolysis of weak bonds
Most radicals are extremely reactive…
How to analyse the structure of radicals: electron spin resonance
Radical stability
How do radicals react?
Radical–radical reactions
Radical chain reactions
Chlorination of alkanes
Allylic bromination
Reversing the selectivity: radical substitution of Br by H
Carbon–carbon bond formation with radicals
The reactivity pattern of radicals is quite different from that of polar reagents
Alkyl radicals from boranes and oxygen
Intramolecular radical reactions are more efficient than intermolecular ones
Looking forward
Further reading
38 Synthesis and reactions of carbenes
Diazomethane makes methyl esters from carboxylic acids
Photolysis of diazomethane produces a carbene
How do we know that carbenes exist?
Ways to make carbenes
Carbenes can be divided into two types
How do carbenes react?
Carbenes react with alkenes to give cyclopropanes
Insertion into C–H bonds
Rearrangement reactions
Nitrenes are the nitrogen analogues of carbenes
Alkene metathesis
Summary
Further reading
39 Determining reaction mechanisms
There are mechanisms and there are mechanisms
Determining reaction mechanisms: the Cannizzaro reaction
Be sure of the structure of the product
Systematic structural variation
The Hammett relationship
Other kinetic evidence for reaction mechanisms
Acid and base catalysis
The detection of intermediates
Stereochemistry and mechanism
Summary of methods for the investigation of mechanism
Further reading
40 Organometallic chemistry
Transition metals extend the range of organic reactions
The 18 electron rule
Bonding and reactions in transition metal complexes
Palladium is the most widely used metal in homogeneous catalysis
The Heck reaction couples together an organic halide or triflate and an alkene
Cross-coupling of organometallics and halides
Allylic electrophiles are activated by palladium(0)
Palladium-catalysed amination of aromatic rings
Alkenes coordinated to palladium(II) are attacked by nucleophiles
Palladium catalysis in the total synthesis of a natural alkaloid
An overview of some other transition metals
Further reading
41 Asymmetric synthesis
Nature is asymmetric
The chiral pool: Nature’s chiral centres ‘off the shelf’
Resolution can be used to separate enantiomers
Chiral auxiliaries
Chiral reagents
Asymmetric catalysis
Asymmetric formation of carbon–carbon bonds
Asymmetric aldol reactions
Enzymes as catalysts
Further reading
42 Organic chemistry of life
Primary metabolism
Life begins with nucleic acids
Proteins are made of amino acids
Sugars—just energy sources?
Lipids
Mechanisms in biological chemistry
Natural products
Fatty acids and other polyketides are made from acetyl CoA
Terpenes are volatile constituents of plants
Further reading
43 Organic chemistry today
Science advances through interaction between disciplines
Chemistry vs viruses
The future of organic chemistry
Further reading
Figure acknowledgements
Periodic table of the elements

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