Organic Chemistry 9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: John E. McMurry
1 Structure And Bonding 2 Polar Covalent Bonds; Acids And Bases 3 Organic Compounds: Alkanes And Their Stereochemistry 4 Organic Compounds: Cycloalkanes And Their Stereochemistry 5 Stereochemistry At Tetrahedral Centers 6 An Overview Of Organic Reactions 7 Alkenes: Structure And Reactivity 8 Alkenes: Reactions And Synthesis 9 Alkynes: An Introduction To Organic Synthesis 10 Organohalides 11 Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations 12 Structure Determination: Mass Spectrometry And Infrared Spectroscopy 13 Structure Determination: Nuclear Magnetic Resonance Spectroscopy 14 Conjugated Compounds And Ultraviolet Spectroscopy 15 Benzene And Aromaticity 16 Chemistry Of Benzene: Electrophilic Aromatic Substitution 17 Alcohols And Phenols 18 Ethers And Epoxides; Thiols And Sulfides 19 Aldehydes And Ketones: Nucleophilic Addition Reactions 20 Carboxylic Acids And Nitriles 21 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 22 Carbonyl Alpha-substitution Reactions 23 Carbonyl Condensation Reactions 24 Amines And Heterocycles 25 Biomolecules: Carbohydrates 26 Biomolecules: Amino Acids, Peptides, And Proteins 27 Biomolecules: Lipids 28 Biomolecules: Nucleic Acids 29 The Organic Chemistry Of Metabolic Pathways 30 Orbitals And Organic Chemistry: Pericyclic Reactions 31 Synthetic Polymers Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
16.1 Electrophilic Aromatic Substitution Reactions: Bromination 16.2 Other Aromatic Substitutions 16.3 Alkylation And Acylation Of Aromatic Rings: The Friedel–crafts Reaction 16.4 Substituent Effects In Electrophilic Substitutions 16.5 Trisubstituted Benzenes: Additivity Of Effects 16.6 Nucleophilic Aromatic Substitution 16.7 Benzyne 16.8 Oxidation Of Aromatic Compounds 16.9 Reduction Of Aromatic Compounds 16.10 Synthesis Of Polysubstituted Benzenes 16.SE Something Extra Section16.SE: Something Extra
Problem 24VC Problem 25VC: The following molecular model of a dimethyl-substituted biphenyl represents the lowest-energy... Problem 26VC Problem 27VC Problem 28MP: Aromatic iodination can be carried out with a number of reagents, including iodine monochloride,... Problem 29MP Problem 30MP: The carbocation electrophile in a Friede1-Crafts reaction can be generated by an alternate means... Problem 31MP Problem 32MP: The nitroso group, —N=O, is one of the few nonhalogens that is an ortho- and para-directing... Problem 33MP: Triphenylmethane can be prepared by reaction of benzene and chloroform in the presence of AlCl3.... Problem 34MP: Using resonance structures of the intermediates, explain why bromination of biphenyl occurs at ortho... Problem 35MP: Benzene and alkyl -substituted benzenes can be hydroxylated by reaction with H2O2 in the presence of... Problem 36MP Problem 37MP: Hexachlorophene, a substance used in the manufacture of germicidal soaps, is prepared by reaction of... Problem 38MP: Benzenediazonium carboxylate decomposes when heated to yield N2, CO2, and a reactive substance that... Problem 39MP: 4-Chloropyridine undergoes reaction with dimethylamine to yield 4-dimethylaminopyridine. Propose a... Problem 40MP: Propose a mechanism to account for the following reaction: Problem 41MP: In the Gatterman-Kochreaction, a formyl group (—CHO) is introduced directly onto a benzene ring.... Problem 42MP: Treatment of p-tert-butylphenol with a strong acid such as H2SO4 yields phenol and 2-methylpropene.... Problem 43MP: Benzyl bromide is converted into benzaldehyde by heating in dimethyl sulfoxide. Propose a structure... Problem 44MP Problem 45MP Problem 46AP Problem 47AP Problem 48AP Problem 49AP: Predict the major monoalkylation products you would expect to obtain from reaction of the following... Problem 50AP: Name and draw the major product(s) of electrophilic chlorination of the following compounds: (a)... Problem 51AP Problem 52AP Problem 53AP: What product(s) would you expect to obtain from the following reactions? Problem 54AP Problem 55AP: How would you synthesize the following substances starting from benzene or phenol? Assume that ortho... Problem 56AP Problem 57AP Problem 58AP Problem 59AP Problem 60AP Problem 61AP Problem 62AP Problem 63AP Problem 64AP: How would you synthesize the following substances starting from benzene? Problem 65AP Problem 66AP Problem 67AP: Draw resonance structures of the intermediate carbocations in tire bromination of naphthalene, and... Problem 68AP Problem 69AP: p-Bromotoluene reacts with potassium amide to give a mixture of m-and p-methylaniline. Explain. Problem 70AP Problem 71AP Problem 72AP Problem 73AP: Use your knowledge of directing effects, along with the following data, to deduce the directions of... Problem 74AP: Identify the reagents represented by the letters a-e in the following scheme: Problem 75AP: Phenols (ArOH) are relatively acidic, and the presence of a substituent group on the aromatic ring... Problem 76AP Problem 77AP Problem 78AP: Melamine, used as a fire retardant and a component of the writing surface of white boards, can be... Problem 25VC: The following molecular model of a dimethyl-substituted biphenyl represents the lowest-energy...
Draw the possible products of this epoxide ring-opening reaction. Use a dash or wedge to indicate the stereochemistry of substituents on asymmetric centers, where applicable. Ignore any inorganic byproducts.
Transcribed Image Text: Draw the possible products of this epoxide ring-opening reaction.
Use a dash or wedge bond to indicate the stereochemistry of substituents on asymmetric centers, where applicableIgnore any inorganic byproducts.
1) NaOH/HO
2) dilute HCI
Drawing
Definition Definition Special class of cyclic ethers (R-O-R') with a three-atom ring. Epoxides are an important functional group in organic chemistry as they generate reactive centers due to their unusual high reactivity. This high reactivity make epoxides toxic and mutagenic.
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