Strategies and Solutions to Advanced Organic Reaction Mechanisms

Front-Matter_2019_Strategies-and-Solutions-to-Advanced-Organic-Reaction-Mech
	Front Matter
Copyright_2019_Strategies-and-Solutions-to-Advanced-Organic-Reaction-Mechani
	Copyright
Dedication_2019_Strategies-and-Solutions-to-Advanced-Organic-Reaction-Mechan
	Dedication
Preface_2019_Strategies-and-Solutions-to-Advanced-Organic-Reaction-Mechanism
	Preface
		The Purpose of Writing This Book
		What This Book Offers
		Organization of Book and Layout of Solutions
		Acknowledgments
		References
Chapter-1---The-Logic-of-Organic_2019_Strategies-and-Solutions-to-Advanced-O
	The Logic of Organic Reaction Mechanisms
		What is an Organic Chemical Reaction?
		The Balanced Chemical Equation
		What Is Contained in a Reaction Scheme?
		Principle of Conservation of Structural Aspect
		Curly Arrow Notation
		Baeyer-Villiger Oxidation Mechanism
		Table of Recommended Textbooks on Physical Organic Chemistry
		Base Strength and pKA
		Autoxidation
		References
Chapter-2---Evidence-for-Organic_2019_Strategies-and-Solutions-to-Advanced-O
	Evidence for Organic Reaction Mechanisms
		What Is Physical Organic Chemistry?
		Experimental Physical Organic Chemistry
		Applying Experimental Techniques-Baeyer-Villiger Oxidation Revisited
		References
Chapter-3---Problem-Solving-Organ_2019_Strategies-and-Solutions-to-Advanced-
	Problem Solving Organic Reaction Mechanisms
		Theoretical Problem-Solving Strategy
		Experimental Problem-Solving Strategy
		Case Study: Rearrangement of Cinenic Acid to Geronic Acid
		Current State of Pedagogy and Academic and Future Directions
		References
Chapter-4---Solutions-_2019_Strategies-and-Solutions-to-Advanced-Organic-Rea
	Solutions 1 - 50
		A Tandem Route to 1,2,3,4-Tetrasubstituted Naphthalenes
			Solution: 1 to 2
			Solution: 2 to 3
			Solution: D to 4
			Balanced chemical equations
			Key Steps Explained
			Additional Resources
			References
		Hydroazulenes by Radical Cyclization
			Solution
			Balanced chemical equation
			Key Steps Explained
			Additional Resources
			References
		Cinnolines to Indoles
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Rearrangement During NMR Studies
			Solution
			Key Steps Explained
			Additional Resources
			References
		Synthesis of Trifluoromethyl Heterocycles
			Solution: 1 to 2
			Solution: 2 to 3
			Solution: 3 to 4
			Balanced chemical equations
			Key Steps Explained
			Additional Resources
			References
		3-Substituted Chromones From Pyranobenzopyrans
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Acid-Catalyzed Rearrangements of 1-Arylindoles
			Solution: 1 to 2
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		An Unusual Deprotection of an Aryl Ester
			Solution: 2 to 3
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		3,1-Benzoxathiin Formation
			Solution: Mechanism 1
			Solution: Mechanism 2
			Key Steps Explained
			Additional Resources
			References
		Arylacetone Synthesis by Carroll-Type Rearrangement
			Solution: 1 and 2 to 3
			Solution: 3 to 4
			Key Steps Explained
			Additional Resources
			References
		Attempted Knoevenagel Reaction Gives Mannich-Type Products
			Solution: 1 to 2
			Balanced Chemical Equation: 1 to 2
			Solution: 3 to 2
			Balanced Chemical Equation: 3 to 2
			Key Steps Explained
			Additional Resources
			References
		Pyridinium Salt Rearrangements
			Solution: 1 to 2
			Solution: 3 to 4
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		A Pyridazine From a Thiophene Dioxide
			Solution: 1 and 2 to 3
			Solution: 3 to 4
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Biomimetic Synthesis of Litebamine
			Solution: 1 to 2
			Balanced Chemical Equation: 1 to 2
			Solution: 4 to 5
			Solution: 5 to 6
			Balanced Chemical Equation: 5 to 6
			Key Steps Explained
			Additional Resources
			References
		Acid-Catalyzed Degradation of N-Nitroso-2,3-didehydromorpholine
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A New Route to 4-Amino-3-arylcinnolines
			Solution: 2 to 3 (Path a)
			Solution: 2 to 3 (Path b)
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Base-Induced Cyclizations of o-Ethynylaryl-Substituted Benzyl Alcohols
			Solution: 1 to 2
			Solution: 3 to 5
			Key Steps Explained
			Additional Resources
			References
		Trifluoromethylpyrroles From Trifluoromethyloxazolones
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		The Hooker Oxidation
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Synthesis of 1,3-Disubstituted Pyrroles
			Solution: 3 to 4
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Grob Fragmentation of a 1-Azaadamantane
			Solution: 1 to 2
			Balanced Chemical Equation
			Solution: 2 to 3
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Selective Substitution of 3-Methoxypyrazine N-Oxide
			Solution: 1, 2, and 3 to 4 (When ZnBr2 Present)
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Reactions of Ethacrylate Esters With NO2BF4
			Solution: 1 to 2
			Solution: A to 3
			Solution: 4 to 5
			Balanced Chemical Equation: 4 to 5
			Solution: C to 6
			Balanced Chemical Equation: 4 to 6
			Key Steps Explained
			Additional Resources
			References
		A Furan Synthesis
			Solution: 1 to 2
			Solution: 2 to 3 (Authors Mechanism)
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Dimerization of Vinca Alkaloids
			Solution
			Key Steps Explained
			Additional Resources
			References
		Nitration of a Quinoline Derivative
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Synthesis of Binaphthyldiquinones
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Heterocyclic Fun With DMAD
			Solution: Mechanism 1
			Solution: Mechanism 2
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Unexpected Formation of a 1,5-Benzodiazonine
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Thiopyran to Thiophene Transformation
			Solution: 1 to 2
			Solution: 3 to 4 (Path a: F to 4)
			Solution: 3 to 4 (Path b: F to 4)
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Skeletal Rearrangements of a Diterpene
			Solution: 1 to 2
			Solution: B to 4
			Solution: 4 to 3
			Solution: 3 to 5
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Reissert Reactions of Quinoxaline N-Oxides
			Solution: 1 to 2
			Solution: 1 to 3
			Solution: 4 to 5
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Unexpected Results in Directed Metalation
			Solution: 3 to 4/5
			Key Steps Explained
			Additional Resources
			References
		1,4-Dioxene in Synthesis
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Collins Oxidation of Phenylethanols
			Solution: 1 to 2
			Solution: 4 to 5
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Allene Sulfoxide Rearrangement
			Solution: 2 to 3
			Solution: 3 to 4
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		A Failed ``Pinacol-Type´´ Rearrangement
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Allylation of 1,4-Benzoquinones
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Benzopyrene Synthesis-By Accident
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Rearrangement of Ketene Acetals
			Solution: 2E to 3
			Solution: 2Z to 3
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Nucleophilic Additions to a Heterocyclic o-Quinone
			Solution: 1 to 2
			Solution: 1 to 3
			Key Steps Explained
			Additional Resources
			References
		How Mitomycin C Can Crosslink DNA
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Two Carbon Ring Expansions of Cycloalkanones
			Solution: 1 to 2
			Balanced Chemical Equation: 1 to 2
			Solution: 3 to 4
			Balanced Chemical Equation: 3 to 4
			Solution: 3 to 5
			Balanced Chemical Equation: 3 to 5
			Key Steps Explained
			Additional Resources
			References
		Fulgides: Synthesis and Photochromism
			Solution: 1 and 2 to 3 (Stobbe Condensation)
			Balanced Chemical Equation: 1 and 2 to 3
			Solution: 3 to 4 (Lactone Opening Esterification)
			Balanced Chemical Equation: 3 to 4
			Solution: 4 to 5 (Stobbe Condensation)
			Balanced Chemical Equation: 4 to 5
			Solution: 5 to 6 (Saponification of Diester to Diacid)
			Balanced Chemical Equation: 5 to 6
			Solution: 6 to 7
			Balanced Chemical Equation: 6 to 7
			Solution: 7 to 8 (Base-Assisted Ring Opening Alkylation)
			Balanced Chemical Equation: 7 to 8
			Solution: 8 to 9 (Acetyl Chloride-Assisted Cyclization)
			Balanced Chemical Equation: 8 to 9
			Solution: 9 to 10 (Photochromism Mechanism)
			Key Steps Explained
			Additional Resources
			References
		Benzodiazepines From (R)-(+)-Pulegone
			Solution
			Key Steps Explained
			Additional Resources
			References
		A Furan to Pyran Ring Expansion
			Solution: 1 to 2 (Mechanism 1: Consistent With Deuterium Labeling Study)
			Solution: 1 to 2 (Mechanism 2: Inconsistent With Deuterium Labeling Study)
			Key Steps Explained
			References
		A Structure and Mechanism Correction
			Solution: 1 and 2 to 3 (Claimed Reaction)
			Solution: 3 to 4 (Claimed Reaction)
			Solution: 1 and 2 to 5 (Actual Reaction)
			Solution: 5 to 4 (Actual Reaction)
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Propargylbenzotriazoles to Five-membered Heterocycles
			Solution: 1 and 2 to 3
			Balanced Chemical Equation: 1 and 2 to 3
			Solution: 3 to 4
			Balanced Chemical Equation: 3 to 4
			Key Steps Explained
			Additional Resources
			References
		From Carvone to an Isoxazoloazepine
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Isoxazoles From Cyclopropanes
			Solution: 1 to 2
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
Chapter-5---Solutions-5_2019_Strategies-and-Solutions-to-Advanced-Organic-Re
	Solutions 51 - 100
		A Radical Cascade From a Ketene Dithioacetal
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Synthesis of 3-Alkyl-1-naphthols
			Solution: 2 to 3
			Solution: 4 to 5
			Solution: 6 to 7
			Key Steps Explained
			Additional Resources
			References
		An Entry to Indole Alkaloids of Unusual Structural Type
			Solution: 1 to 2
			Solution: 2 to 3
			Solution: 3 to 5 and 4
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Cyclization as a Key Step to Hirsutene
			Solution
			Key Steps Explained
			Additional Resources
			References
		A 1,3-Cyclopentanedione to 1,4-Cyclohexanedione Transformation
			Solution: Originally Proposed Mechanism for 1 to 2
			Solution: Revised Mechanism for 1 to 2 Part 1: 1 to 3
			Solution: Revised Mechanism for 1 to 2 Part 2: 3 to 2
			Key Steps Explained
			Additional Resources
			References
		Conversion of o-Hydroxyaryl Ketones Into 1,2-Diacylbenzenes
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Mechanisms of Bimane Formation
			Solution: 1 to syn-2
			Solution: A and B to anti-2
			Balanced Chemical Equation: 1 to syn-2/anti-2
			Solution: 3 to syn-4
			Balanced Chemical Equation: 3 to syn-4
			Key Steps Explained
			Additional Resources
			References
		A Carbohydrate to Cyclopentanol Conversion
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Balanced Chemical Equation: Scheme 2
			Balanced Chemical Equation: Scheme 3
			Balanced Chemical Equation: Scheme 4
			Additional Resources
			References
		Pyridazines From 1,2,4-Triazines
			Solution: 1 to 2 Using 15N Label on Phenylacetonitrile
			Solution: 2 to 3 Using 15N Label on Phenylacetonitrile
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Natural Product Degradation During Extraction and/or Chromatography
			Solution: Authors Proposal (Ionic Mechanism)
			Solution: Alternative Proposal (Radical Mechanism)
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Simple Access to Oxaadamantanes
			Solution: 1 to 2
			Balanced Chemical Equation: 1 to 2
			Solution: I to 3
			Balanced Chemical Equation: 1 to 3
			Solution: D to 4
			Balanced Chemical Equation: 1 to 4
			Key Steps Explained
			Additional Resources
			References
		A Pyrimidine Rearrangement
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		1,4-Thiazin-3-ones From 1,4-Oxathiins
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		An Unusual Route to 3-Acylfurans
			Solution: 1 to 2
			Solution: 2 to 3
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Reaction of PQQ With l-Tryptophan
			Solution
			Additional Resources
			References
		An Unexpected Result From an Attempted Double Bischler-Napieralski Reaction
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Bis-Indole Alkaloid Formation
			Solution: 1 to 2
			Solution: 3 to 4 and 5
			Solution: 6 to 7 and 8
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Azaphenalene Alkaloid Synthesis: A Key Step
			Solution: Path A
			Solution: Path B (C to 2 Alternative)
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Primary Nitroalkane to Carboxylic Acid Transformation
			Solution: 1 to 2
			Solution: 3 to 2
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		α-Diazoketones With Rhodium(II) Acetate
			Solution: 1 to 2
			Solution: E to 3
			Solution: C to J and 4
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Pyrrolo[1,2-a]benzimidazole Synthesis by Ortho Nitro Interaction
			Solution: 1 to 2
			Solution: H to 3
			Solution: H to 4
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Horner-Wittig Reaction on a Bifuranylidenedione
			Solution: 1 and 2 to 3
			Solution: 3 to 4
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Lactone Ammonolysis
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Intramolecular Schmidt Reaction
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Indolizidones by Intermolecular Photochemical Reaction
			Solution: 1 to E
			Solution: E to G
			Solution: G to 3 (Author Mechanism)
			Solution: G to 3 (Alternative Proposal)
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		An Unexpected Product From Amine Oxidation
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Degradation of Pyripyropene A
			Solution: 1 to 2
			Balanced Chemical Equation: 1 to 2
			Solution: 2 to 3 and 4
			Balanced Chemical Equation: 2 to 3 and 4
			Key Steps Explained
			Additional Resources
			References
		Benzofurans From Cyclobutenediones
			Solution: 1 and 2 to 3
			Solution: 3 to 4
			Solution: 4 to 5
			Solution: 5 to 6
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Acid-Catalyzed Condensation of Indole With Acetone
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Synthesis of 2-Formylpyrrolidines
			Solution: 1 to 2
			Solution: 2 to 3
			Balanced Chemical Equation: 2 to 3
			Solution: 3 to 4
			Key Steps Explained
			Additional Resources
			References
		An Abnormal Claisen Rearrangement
			Solution
			Key Steps Explained
			Additional Resources
			References
		Benzoxepinones From Phthalides
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		m-Terphenyls From Pyrones
			Solution: 1 to 2
			Solution: B to 3
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		A Cascade Reaction
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Photochemical Ortho Rearrangements
			Solution: 1 to 3
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		From Bicycle to Pentacycle to Tricycle
			Solution: 1 and 2 to 3
			Solution: 3 to 4
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Lewis Acid-Catalyzed Cyclopropyl Ketone Rearrangement
			Solution
			Key Steps Explained
			Additional Resources
			References
		An Intramolecular Ring Closure
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Photochemical Rearrangement of Pyran-2-ones
			Solution: 1 to 2
			Solution: F to H (Alternative Path)
			Key Steps Explained
			Additional Resources
			References
		A Paclitaxel Rearrangement
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		An Ionic Diels-Alder Reaction
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		The Eschenmoser Fragmentation Reaction Extended
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Modified Batcho-Leimgruber Synthesis
			Solution: 1 to 4 p-TsOH Acid Catalysis
			Key Steps Explained
			Additional Resources
			References
		A Pyrone to Pyran Conversion
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Conformationally Rigid 4-Oxoquinolines
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		An Efficient Chromene Synthesis
			Solution: 1 and 2 to 3
			Solution: 3 to 4
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Flash Vacuum Pyrolysis of o-Xylylene Dimers
			Solution: 1 to 2
			Solution: 3 to 4
			Key Steps Explained
			Additional Resources
			References
		Synthesis of a Neocarzinostatin Building Block
			Solution
			Key Steps Explained
			Additional Resources
			References
		Oxazole Esters From α-Amino Acids
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Unexpected Formation of a Phenazine
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
Chapter-6---Solutions-1_2019_Strategies-and-Solutions-to-Advanced-Organic-Re
	Solutions 101 - 150
		Conversion of Primary Amides Into Nitriles
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		An Efficient Benzo[b]fluorene Synthesis
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Facile Synthesis of Tetracyclic Pyrroloquinazolines
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Ethyl 2-Chloronicotinate From Acyclic Precursors
			Solution: 1, 2, and 3 to 4
			Solution: 4 to 5
			Balanced Chemical Equation: 1, 2, and 3 to 4
			Balanced Chemical Equation: 4 to 5
			Key Steps Explained
			Additional Resources
			References
		A 2-Arylpropanoic Acid Synthesis
			Solution: 1 to 2
			Solution: 2 to 3
			Solution: 3 to 4
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Synthesis of Isoquinolin-4-ones
			Solution: 1 to 2
			Solution: 1 to 3
			Key Steps Explained
			Additional Resources
			References
		Naphthopyrandione From 1,4-Naphthoquinone
			Solution: 1a to 3
			Solution: 1b to 4
			Balanced Chemical Equations
			Key Steps Explained
			Reference
		A Photochromic Product for Sunglasses
			Solution: 1 to 2
			Solution: 2 to 3
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		A Quick Entry to the Aklavinone Ring System
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A ``Stable Enol´´ That Doesnt Exist
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Conversion of an Indole-Based Bicyclo[5.3.1]undecane Into a Bicyclo[5.4.0]undecane
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Classical Mannich Approach to Isoquinoline Alkaloids Leads to an Unexpected Product
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Reaction of Benzothiazole With DMAD
			Solution
			Key Steps Explained
			Additional Resources
			References
		Inhibition of the l-DOPA to l-Dopaquinone Oxidation
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A One-Pot Synthesis of 1,3,6,8-Tetramethyl-2,7-naphthyridine
			Solution: Formation of 1 Part 1 (A to H)
			Solution: Formation of 1 Part 2 (H to 1 Path A)
			Solution: Formation of 1 Part 3 (H to 1 Path B)
			Solution: Formation of 1 Part 4 (ALTERNATE ROUTE: B to O1)
			Solution: Formation of 1 Part 5 (ALTERNATE ROUTE: S to H)
			Solution: Formation of 2
			Balanced Chemical Equations
			Key Steps Explained
			References
		Unexpected Course of a Mannich Reaction in Alkaloid Synthesis
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Synthesis of Thioindigo
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		An Unexpected Reaction During Studies of Amine Oxide Rearrangements
			Solution: 1 to 3 (Expected Product)
			Solution: 1 to 2 (Observed Product)
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		An Unusual Phosphite-Induced Deoxygenation of a Nitronaphthalene
			Solution: 1 to 2 Authors Mechanism
			Solution: 1 to 2 Alternative Mechanism
			Solution: 3 to 2 Authors Mechanism
			Solution: 3 to 2 Alternative Mechanism
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Benzimidazole to Pyrroloquinoxaline Transformation
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Acid-Catalyzed Benzophenone Isomerization
			Solution: Hayashi Mechanism1
			Solution: Sandin Mechanism2
			Solution: Wang Mechanism3
			Key Steps Explained
			Additional Resources
			References
		2-Oxabicyclo[1.1.0]butanone Is Not Easily Accessible
			Solution: Authors Mechanism
			Solution: Alternative Mechanism
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Simple Synthesis of the Indole Alkaloid Yuehchukene
			Solution
			Key Steps Explained
			Additional Resources
			References
		Isoquinoline Rearrangement
			Solution
			Key Steps Explained
			Additional Resources
			References
		Multiple Sigmatropic Rearrangements
			Solution: 1 to 2 in PhCl
			Solution: 1 to 2 and 3 in PhCl and AIBN
			Solution: 1 to 3 in pTsOH
			Key Steps Explained
			Additional Resources
			References
		A Vilsmeier-Induced Annulation to Benzene
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Isopropylidene to 2-Alkyne Conversion
			Solution: Corey2 Mechanism
			Solution: Zard4 Mechanism
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		A Tryptamine to Pentacyclic Indoline Transformation
			Solution: 1 to 2
			Catalyst Regeneration
			Balanced Chemical Equation: 1 to 2
			Solution: 1 to 3
			Balanced Chemical Equation: 1 to 3
			Key Steps Explained
			Additional Resources
			References
		Ring Contractions of a Dibenzothiepinone
			Solution: 1 to 2
			Solution: 1 to 3
			Solution: 1 to 4
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Steroid Fragmentation With DDQ
			Solution: 1 to 2
			Solution: 1 to 3
			Solution: 1 to 4
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		A Base-Induced Vinylcyclopropane Rearrangement
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		4-Demethoxydaunomycin: The Desired Result, but Not According to Plan
			Solution: 1 to 3
			Solution: 3 to 4
			Solution: 4 to 5
			Solution: 5 to 2
			Key Steps Explained
			Additional Resources
			References
		Three Isomeric Hexadienols Give the Same Bicyclic Lactone
			Solution: 1 to 4
			Solution: 2 to 4
			Solution: 3 to 4
			Key Steps Explained
			Additional Resources
			References
		Degradation of Antibiotic X-537A
			Solution: 2 to 3 and A
			Solution: A to 5
			Balanced Chemical Equation: 2 to 3 and 5
			Solution: 2 to 4
			Solution: D to 6
			Balanced Chemical Equation: 2 to 3 and 6
			Key Steps Explained
			Additional Resources
			References
		Steroid Rearrangements: Appearances Can Be Deceptive
			Solution
			Additional Resources
			References
		Synthesis of Eburna and Aspidosperma Alkaloids
			Solution: 2 to 3a and 3b
			Balanced Chemical Equation: 2 to 3a and 3b
			Solution: 2 to 4 and 5
			Balanced Chemical Equations: 2 to 4 and 5
			Key Steps Explained
			Additional Resources
			References
		Synthesis of Highly Hindered Cyclic Amines
			Solution: 1 to 2
			Solution: 1 to 3
			Balanced Chemical Equations: 1 to 2 and 3
			Solution: 4 to 5 and 6
			Balanced Chemical Equations: 4 to 5 and 6
			Key Steps Explained
			Additional Resources
			References
		A 1,2-Dihydrobenzocyclobutane to Isochroman-3-one Conversion
			Solution
			Key Steps Explained
			Additional Resources
			References
		An Unexpectedly Facile Decarboxylation
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Regiospecific Synthesis of a 1,2-Dihydronaphthalene
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Degradation of Terramycin
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Synthesis of Bi-indane-l,3-dione
			Solution: 1 and 2 to 3
			Solution: 3 to 4
			Solution: 4 to 5
			Solution: 5 to 6
			Key Steps Explained
			Additional Resources
			References
		A Coumarin to Cyclopentenone Transformation
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		``Synthetic Heroin´´ and Parkinsonism
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Rearrangement of 6-Hydroxyprotopine to Dihydrosanguinarine
			Solution
			Key Steps Explained
			Additional Resources
			References
		Biotin Synthesis: Sulfur Preempts a Beckmann Rearrangement
			Solution
			Key Steps Explained
			Additional Resources
			References
		A 1,4-Dithiin to Thiophene Rearrangement
			Solution: 1 to 2
			Solution: 1 to 3
			Balanced Chemical Equation: 1 to 3
			Key Steps Explained
			Additional Resources
			References
		An Intramolecular Wittig Reaction
			Solution: 1 to 2
			Solution: 1 to 3
			Key Steps Explained
			Additional Resources
			References
		Amination of a Cephalosporin
			Solution: 1 to 2
			Solution: 2 to 3
			Key Steps Explained
			Additional Resources
			References
		A Uracil to 1,2,3-Triazole Conversion
			Solution: Authors Mechanism
			Solution: Alternative Mechanism
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
Chapter-7---Solutions-1_2019_Strategies-and-Solutions-to-Advanced-Organic-Re
	Solutions 151 - 200
		Schumm Devinylation of Vinyl Porphyrins
			Solution: Mechanism 1A
			Solution: Mechanism 1B
			Solution: Mechanism 2A
			Solution: Mechanism 2B
			Solution: Mechanism 3
			Solution: Mechanism 4
			Key Steps Explained
			Additional Resources
			References
		A Uracil to Substituted Benzene Transformation
			Solution: 1 to 2
			Solution: 1 to 3
			Key Steps Explained
			Additional Resources
			References
		γ-Lactones From Vinyl Sulfoxides
			Solution
			Key Steps Explained
			Additional Resources
			References
		Tetrahydrothieno[2,3-c]- and -[3,2-c]pyridine Synthesis
			Solution: 1 to 2 (Weakly Acidic Medium)
			Solution: 1 to 2 and 3 (Strongly Acidic Medium)
			Key Steps Explained
			Additional Resources
			References
		Oxothiolan  Oxathian  Oxothiolan  Oxathian
			Solution: 1 to 2
			Balanced Chemical Equation: 1 to 2
			Solution: 2 to 3
			Balanced Chemical Equation: 2 to 3
			Solution: 3 to 4
			Balanced Chemical Equation: 3 to 4
			Key Steps Explained
			Additional Resources
			References
		A Thiazolopyrimidine to Pyrrolopyrimidine Transformation
			Solution: 1 and 2 to 3
			Balanced Chemical Equation: 1 and 2 to 3
			Solution: 3 to 6 to 5
			Balanced Chemical Equation: 3 to 6 to 5
			Solution: 5 to 4
			Key Steps Explained
			Additional Resources
			References
		Oxidation of 1,5-Diacetoxynaphthalene With NBS
			Solution: 1 to 3 to 2
			Balanced Chemical Equation: 1 to 3
			Balanced Chemical Equation: 3 to 2
			Balanced Chemical Equation: 4 to 2
			Key Steps Explained
			Additional Resources
			References
		Badly Chosen Reaction Conditions?
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		One Step Synthesis of a Highly Symmetrical Hexacyclic System From a Simple Naphthol
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Method for Aryloxylation of p-Cresol
			Solution: 1 to 2
			Balanced Chemical Equation: 1 to 2
			Solution: 2 to 3
			Solution: 2 to 3 Alternative
			Balanced Chemical Equation: 2 to 3
			Solution: 3 to 4
			Balanced Chemical Equation: 3 to 4
			Solution: 3 to 5
			Balanced Chemical Equation: 3 to 5
			Key Steps Explained
			Additional Resources
			References
		Nitriles From N-Chlorosulfonylamides
			Solution: Nitrile Formation Via Triethylamine
			Solution: Nitrile Formation Via Dimethylformamide (DMF)
			Key Steps Explained
			Additional Resources
			References
		Synthesis of Perylenequinone
			Solution
			Balanced Chemical Equation
			Balanced Chemical Redox Equation
			Key Steps Explained
			Additional Resources
			References
		A Route to 2-Vinylindoles
			Solution
			Key Steps Explained
			Additional Resources
			References
		Brain Cancer: The Mechanism of Action of Temozolomide
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Attempted Nef-Type Reaction Leads to 3-Arylpyridine Synthesis
			Solution: Part 1-Reduction
			Solution: Part 2-Rearrangement
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		The ArCOMe  ArCCH Transformation
			Solution: 1 to 2
			Balanced Chemical Equation: 1 to 2
			Solution: 2 to 3
			Balanced Chemical Equation: 2 to 3
			Key Steps Explained
			Additional Resources
			References
		β-Amino Nitriles From Azetidones
			Solution
			Key Steps Explained
			Additional Resources
			References
		A New Route to 1,3-Disubstituted Naphthalenes
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		An Efficient Annulation Route to 6-Substituted Indoles
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Failure of a Rearrangement: From a Useful Compound to a Useless Product
			Solution
			Key Steps Explained
			Additional Resources
			References
		Synthesis of Trisubstituted Isoxazoles
			Solution: 1 to 2 and 2 to 3
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		2,3-Dihydrobenzofurans From 1,4-Benzoquinones
			Solution: 1 and 2 to 3 and 3 to 4
			Solution: 5 and 6 to 7
			Solution: 7 to 8
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Easy Construction of a Tricyclic Indole Related to the Mitomycins
			Solution: 1 to 2
			Solution: 2 to 3
			Key Steps Explained
			Additional Resources
			References
		Cycloaddition to a Benzothiopyrylium Salt
			Solution: 3 to 4
			Solution: 3 to 5
			Key Steps Explained
			Additional Resources
			References
		Benzotriazole From 1,2,4-Benzotriazine N-Oxides
			Solution: 1 to 3
			Solution: 2 to 3
			Key Steps Explained
			Additional Resources
			References
		A Furan  Furan Transformation
			Solution
			Key Steps Explained
			Additional Resources
			References
		Ring Expansion of Both Rings of Penicillin Sulfoxides
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Retro-Pictet-Spengler Reaction
			Solution: Epimerization Mechanism 1 (C1N2 Bond Scission)
			Solution: Epimerization Mechanism 2 (Olefin Protonation)
			Solution: Epimerization Mechanism 3 (Iminium Ion Formation)
			Solution: Degradation Mechanism 1 (Retro-Pictet-Spengler) Path A
			Solution: Degradation Mechanism 1 (Retro-Pictet-Spengler) Path B
			Key Steps Explained
			Additional Resources
			References
		An Olefin to α-Hydroxy Ketone Transformation
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Benzofuran From a Cyclopropachromone
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Pyridocarbazole to Pyridazinocarbazole Rearrangement
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Substituent Group Effect During Sulfide  Sulfoxide Oxidation
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Ring Contraction of a Benzodiazepine
			Solution: Mechanism 1A (Authors Mechanism)
			Solution: Mechanism 1B (Authors Mechanism)
			Solution: Mechanism 2 (Alternative Mechanism)
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		An Indane-1,3-dione Synthesis
			Solution: Mechanism 1 (Mosher and Meier)
			Solution: Mechanism 2 (Alternative)
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		An Azepine to Cyclohexadienone Ring Contraction
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Xanthopterin From Pterin 8-Oxide
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Fused Dihydro-l,4-dithiins From Chromanones
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		The ``Additive Pummerer Reaction´´
			Solution: 1 to 3
			Solution: 1 to 4
			Key Steps Explained
			Additional Resources
			References
		An Illustration of the Problem of Artifacts in Natural Product Chemistry
			Solution
			Key Steps Explained
			Additional Resources
			References
		Vinylogy, and a Stereochemical Puzzle
			Solution: Mechanism 1 (Kiehlmann et al.)
			Balanced Chemical Equation: Mechanism 1
			Solution: Mechanism 2 (Acevado et al.)
			Balanced Chemical Equation: Mechanism 2
			Key Steps Explained
			Additional Resources
			References
		A Simple, High Yielding Route to a Cage Compound
			Solution: 1 to 2
			Solution: 1 to 3
			Key Steps Explained
			Additional Resources
			References
		Not All Ketals Hydrolyze Easily in the Expected Manner
			Solution: 1 to 2
			Solution: 1 to 2 and 3
			Key Steps Explained
			Additional Resources
			References
		From a Tricycle to a Ring Expanded Bicycle
			Solution
			Key Steps Explained
			Additional Resources
			References
		A Flavone From a Chromanone
			Solution: 1 to 2
			Solution: 2 to 3 (at Elevated Temperature)
			Solution: 2 to 4 (at Elevated Temperature NO Added Base)
			Solution: 1 to 4 (With Added Base)
			Key Steps Explained
			Additional Resources
			References
		Thiophene Ylide Rearrangement
			Solution
			Key Steps Explained
			Additional Resources
			References
		A Stepwise 2π+2π Intermolecular Cycloaddition
			Solution
			Key Steps Explained
			Additional Resources
			References
		Rearrangement of an Aryl Propargyl Ether
			Solution
			Key Steps Explained
			Additional Resources
			References
		The Best Laid Plans
			Solution: 1 to 2 (Expected Result) Step 1
			Solution: 1 to 2 (Expected Result) Step 2
			Solution: 1 to 3 (Observed Result)
			Alternative Pathway From Intermediate D
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		A New Synthesis of Substituted Ninhydrins
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Thermal Elimination Reactions Often Fail
			Solution
			Key Steps Explained
			Additional Resources
			References
Chapter-8---Solutions-2_2019_Strategies-and-Solutions-to-Advanced-Organic-Re
	Solutions 201 - 250
		The Wrong Choice of Reaction Conditions? How Not to Prepare an Acid Chloride
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Quantitative Yield Isomerization of a Xylenol Derivative
			Solution
			Key Steps Explained
			Additional Resources
			References
		and an Alternative Route to the Starting Material for Problem 202
			Solution: 1 to 2
			Solution: 1 to A
			Solution: A to 2
			Key Steps Explained
			Additional Resources
			References
		Hydride-Induced Rearrangements With Indole Alkaloid Intermediates
			Solution
			Balanced Chemical Equation
			Work-Up Reaction
			Key Steps Explained
			Additional Resources
			References
		An Unusual ``Hydrolysis´´ Product of 2-Nitrosopyridine
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Quinolizine to Indolizine Transformation
			Solution: 1 to A
			Solution: A to 2
			Key Steps Explained
			Additional Resources
			References
		SNHetAr Reactions Often Proceed With Complications
			Solution: 1 to 2 (ipso Substitution)
			Solution: 1 to 3 (tele Substitution)
			Solution: 1 to 4 (ANRORC Mechanism)
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Rearrangement During Recrystallization
			Solution: 1 and 2 to 3
			Solution: 3 to 4
			Solution: 4 to 5
			Balanced Chemical Equation (4 to 5)
			Key Steps Explained
			Additional Resources
			References
		Another Attempt to Reduce a Ketone Goes Wrong
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A More Complex Benzocyclobutane to Isochroman-3-one Rearrangement (c.f. Problem 138)
			Solution
			Key Steps Explained
			Additional Resources
			References
		Indoles by Solvometalation Ring Closure
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		An Unusual-But Inefficient-Synthesis of Methyl 1-Hydroxynaphthalene-2-carboxylate
			Solution: Mechanism A
			Solution: Mechanism B
			Solution: Mechanism C
			Key Steps Explained
			Additional Resources
			References
		Synthesis of α-Arylalkanoic Acids From Acetophenones
			Solution: B to C
			Solution: C to D
			Solution: D to 2
			Key Steps Explained
			Additional Resources
			References
		Triazene-Triazole-Triazole Interconversions
			Solution: 1 to 2 to 3
			Key Steps Explained
			Additional Resources
			References
		Reissert Compounds as Precursors to Novel Phthalides
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Di-t-butylacetylene Does Not Cycloadd to 2-Pyrone
			Solution
			Key Steps Explained
			Additional Resources
			References
		A Failed Thorpe-Dieckmann Cyclization: ``Obvious´´ Reactions Are Not Always Well Behaved
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		and Can Lead to Remarkable Rearrangements: A Failed Thorpe-Ziegler Cyclization
			Solution
			Key Steps Explained
			Additional Resources
			References
		A Remarkably Stable Tertiary Alcohol by Solvolysis of a Primary Tosylate
			Solution: Mechanism A-Bornyl Path (Helicopter View)
			Solution: Mechanism B-Fenchyl Path (Helicopter View)
			Key Steps Explained
			Additional Resources
			References
		``Anionic Activation´´ for the Preparation of Fluoroheterocycles
			Solution: 1 to 2 Via Phenylacetylene
			Balanced Chemical Equation: 1 to 2 Via Phenylacetylene
			Solution: 1 to 2 Via Acetophenone
			Balanced Chemical Equation: 1 to 2 Via Acetophenone
			Solution: 3 to 4
			Balanced Chemical Equation: 3 to 4
			Key Steps Explained
			Additional Resources
			References
		Synthesis of a 5-(2-Quinolyl)pyrimidine
			Solution: B to C
			Balanced Chemical Equation: B to C
			Key Steps Explained
			Additional Resources
			References
		``Obvious´´ and ``Nonobvious´´ Pathways to a Highly Substituted Pyridine and Aniline
			Solution: Formation of 3
			Balanced Chemical Equation for Formation of 3
			Solution: Formation of 4 Obvious Pathway
			Balanced Chemical Equation for Formation of 4 Obvious Pathway
			Solution: Formation of 4 Nonobvious Pathway
			Balanced Chemical Equation for Formation of 4 Nonobvious Pathway
			Key Steps Explained
			Additional Resources
			References
		A 1-Isoquinolone Synthesis
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Selective Cleavage of the Mycinose Sugar From the Macrolide Antibiotic Tylosin
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Unexpected Formation of an Enamide
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Highly Functionalized Furans From 3-Bromochromone
			Solution
			Key Steps Explained
			Additional Resources
			References
		A One-Pot Benzene  Naphthalene Transformation
			Solution
			Key Steps Explained
			Additional Resources
			References
		Vicarious Nucleophilic Substitution Routes From Simple to Complex Phenols
			Solution: Formation of 1
			Solution: Formation of 2 (Mechanism Version 1)
			Solution: Formation of 3 (Mechanism Version 2)
			Solution: Formation of 4 (Mechanism Version 3)
			Key Steps Explained
			Additional Resources
			References
		Lewis Acid-Catalyzed Rearrangement of Humulene 8,9-Epoxide
			Solution
			Key Steps Explained
			Additional Resources
			References
		From a Dihydrofuran to an Indole-3-acetate
			Solution: Formation of 1
			Solution: Formation of 2
			Key Steps Explained
			Additional Resources
			References
		Reaction of Fervenulin 4-Oxide With DMAD: The Role of Solvent
			Solution: 1  2
			Solution: 1  3
			Solution: 1  4
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Rearrangement of 4-Quinazolinylhydrazines
			Solution: Rearrangement Under Neutral pH
			Solution: Hydrolysis Under Acidic pH
			Solution: Hydrolysis Under Basic pH
			Key Steps Explained
			Additional Resources
			References
		A Failed Approach to the Oxetan-3-one System
			Balanced Chemical Equations
			Additional Resources
			References
		Tricyclics From Furfural
			Solution: Furfural to 2
			Solution: 2 to 3
			Solution: 3 to 4
			Solution: 4 to 5
			Solution: 5 to 6
			Key Steps Explained
			Additional Resources
			References
			Further Reading
		An Ylide-Based Synthesis of 4-Phenylisocoumarin
			Solution: 1  2
			Solution: 2  3
			Balanced Chemical Equations
			Key Steps Explained
			Additional Resources
			References
		Model Studies for Mitomycin A Synthesis Lead to a New Preparation of Pyrroloindoles
			Solution: 1  2
			Solution: 1  3
			Solution: 1  4
			Key Steps Explained
			Additional Resources
			References
		Formation of N-Cyanofluoren-9-imine From 9-Dinitromethylenefluorene
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Methylphenylacetic Acids From Butenolides
			Solution: 1  2
			Solution: 3  4
			Key Steps Explained
			Additional Resources
			References
		Base-Induced Quinoline Rearrangements
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		The Angucyclines: Rearrangement of Angular to Linear Tetracycles
			Solution
			Key Steps Explained
			Additional Resources
			References
		1,2-Dihydropyridines From 2,3-Dihydro-4-pyridones
			Solution
			Key Steps Explained
			Additional Resources
			References
		The Vitamin K to Vitamin K Oxide Transformation
			Solution: Mechanism 1
			Solution: Mechanism 2
			Key Steps Explained
			Additional Resources
			References
		Rearrangement During Intramolecular Cyclization to the Indole 4-Position
			Solution
			Key Steps Explained
			Additional Resources
			References
		4-Quinolone Antibacterials: A New Synthesis
			Solution: 1 to 2
			Solution: 2 to 3
			Solution: 3 to 4
			Key Steps Explained
			Additional Resources
			References
		An Efficient Synthesis of Fused 1,3-Dithiol-2-ones
			Solution
			Key Steps Explained
			Additional Resources
			References
		The ``Double Functional Group Transformation´´: Terminally Unsaturated Nitriles From 1-Nitrocycl ...
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Lewis Acid-Catalyzed Condensation of Indole With 1,3-Cydohexanedione
			Solution: Formation of 1
			Solution: Formation of 2
			Key Steps Explained
			Additional Resources
			References
		Serendipitous Preparation of a Pyrrole Precursor to Porphyrins
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Chromone Ring Contraction
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Simple Conversion of Hydroquinone to a Benzofuran, but Which Mechanism?
			Solution: Mechanism 1 (C-Alkylation-Lactonization)
			Solution: Mechanism 2 (O-Alkylation-Michael-Lactonization)
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
Chapter-9---Solutions-2_2019_Strategies-and-Solutions-to-Advanced-Organic-Re
	Solutions 251 - 300
		A Remarkable Loss of One Carbon Atom in the Indole Alkaloid Field
			Solution
			Solution-Possibility 1 (With Intervention of Retro-Mannich Process)
			Solution-Possibility 2 (Without Intervention of Retro-Mannich Process)
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A ``Nonobvious´´ Cycloaddition Reaction
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		More Radical Cascades and a Formal [2+2+2] Cycloaddition of a Dienyne
			Solution
			Key Steps Explained
			Additional Resources
			References
		LTA-Induced Acetoxylation and Rearrangement of a Phenol
			Key Steps Explained
			Solution
			Balanced Chemical Equation
			Mechanism for 3
			Additional Resources
			References
		How Cocaine Decomposes at 550C
			Solution
			Key Steps Explained
			Additional Resources
			References
		A Highly Efficient Anilide to Benzimidazole Transformation
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		The Baeyer-Drewson Synthesis of Indigo
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		The Marschalk Reaction
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A 1,3-Cyclohexanedione to 2-Cyclohexenone Conversion
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Reaction of a Steroidal Olefin With Br2/AgOAc
			Key Steps Explained
			Solution
			Balanced Chemical Equation
			Additional Resources
			References
		A Most Unusual Synthesis of Tropones From Phenols
			Solution: 1 to 2
			Solution: 3 to G
			Solution: G to 4
			Balanced Chemical Equation: G to 4
			Key Steps Explained
			Additional Resources
			References
		Side-Chain Manipulation With a Purine Derivative: Unexpected Formation of a Thietane
			Solution
			Key Steps Explained
			Additional Resources
			References
		An Isoxazoline to Pyridine N-Oxide Transformation
			Solution
			Key Steps Explained
			Additional Resources
			References
		A Simple Synthesis of the Lignan Carpanone
			Solution
			Key Steps Explained
			Additional Resources
			References
		Cyclopentaquinolines by Tandem Reactions
			Solution
			Experimental Results and Verification
			Additional Resources
			References
		Epimerization of Herqueinone
			Solution: Brooks Mechanism
			Solution: Proposed Mechanism
			Key Steps Explained
			Additional Resources
			References
		A New Method for Amide Bond Formation
			Solution
			Key Steps Explained
			Additional Resources
			References
		A Benzothiazole From Oxidation of Mammalian Red Hair With Hydrogen Peroxide
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Cyclopentenones From 1,3-Cyclopentanediones
			Solution: 12
			Solution: C3
			Key Steps Explained
			Additional Resources
			References
		A New Synthesis of 1- and 2-Chloronaphthalenes by an Annulation Process
			Solution: 1  2
			Solution: 3  4
			Key Steps Explained
			Additional Resources
			References
		From the Diterpene Carnosol to the Benzodiazepine Agonist Miltirone
			Solution: 1A
			Solution: A2a
			Solution: A2b
			Balanced Chemical Equation: 12a
			Solution: 2b3
			Solution: 34
			Balanced Chemical Equation: 12b
			Balanced Chemical Equation: 2b3
			Balanced Chemical Equation: 34
			Key Steps Explained
			Additional Resources
			References
		Synthesis of Chiral Phthalimidine Derivatives
			Solution: Synthesis of 1
			Solution: Synthesis of 1: Pathway A
			Solution: Synthesis of 1: Pathway B
			Solution: Synthesis of 2
			Balanced Chemical Equation for the Synthesis of 1
			Key Steps Explained
			Additional Resources
			References
		Remarkable Rearrangement of a Camphor Derivative
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		A Failed Attempt to Prepare Benzylidenethiophthalide by the ``Obvious´´ Method
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Base-Catalyzed Reactions of Highly Hindered Phenols Used as Antioxidants
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Oxidative Rearrangement of an Aconitine Derivative
			Solution: 1 to 2
			Balanced Redox Chemical Equation for 1 to 2
			Solution: 2 to 3
			Balanced Chemical Equation for 2 to 3
			Key Steps Explained
			Balanced Chemical Equation for Hydroxydiphenylacetaldehyde to Benzophenone Transformation
			Additional Resources
			References
		Decomposition of Akuammicine
			Solution: Decomposition at 100C
			Solution: Decomposition at 140C
			Balanced Chemical Equation: Decomposition at 100C
			Balanced Chemical Equation: Decomposition at 140C
			Key Steps Explained
			Additional Resources
			References
		Extending the Favorskii Reaction
			Solution: 12
			Solution: 13
			Solution: 14
			Balanced Chemical Equation: 12
			Balanced Chemical Equation: 13
			Balanced Chemical Equation: 14
			Key Steps Explained
			Additional Resources
			References
		Dihydroxylation/Base Treatment of the Westphalen Ketone
			Solution: 1A
			Balanced Chemical Equation: 1A
			Solution: A2
			Solution: B3
			Balanced Chemical Equation: A2
			Balanced Chemical Equation: 23
			Key Steps Explained
			Additional Resources
			References
		Quantitative Conversion of a Vinylogous Thioamide Into a Thiophene
			Solution: Possibility 1: Sulfonium Ion Intermediate
			Solution: Possibility 2: Iminium Ion Intermediate
			Solution: Possibility 3
			Key Steps Explained
			Additional Resources
			References
		Rearrangements During Synthetic Studies on Carba-Sugars
			Solution: (i) 23 With Triflic Anhydride
			Solution: (ii) Dihydroxylation Mechanism
			Balanced Chemical Equation: Dihydroxylation of 4
			Solution: (ii) Formation of 6
			Solution: (ii) Formation of 5
			Key Steps Explained
			Additional Resources
			References
		A Pyrimidine to Pyrazole Transformation
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Attempted Diastereocontrol in Synthesis of a Homoallylic Alcohol
			Solution
			Key Steps Explained
			Additional Resources
			References
		Arsonium Ylides for Cyclopropane Synthesis
			Solution
			Alternate Possible Pathway
			Key Steps Explained
			Additional Resources
			References
		Pyridoacridines From 4-Quinolones
			Solution: 1 to 2
			Balanced Chemical Equation: 12
			Solution: F to 3
			Balanced Chemical Equation: 13
			Solution: CAN Oxidation of 24
			Balanced Chemical Equation: 24
			Solution: CAN Oxidation of 34
			Balanced Chemical Equation: 34
			Additional Resources
			References
			Further Reading
		Imidoyl Radicals in a New Quinoline Synthesis
			Solution-1 to B
			Solution-B to 2
			Solution-B to 3
			Key Steps Explained
			Additional Resources
			References
		Electrolytic Fluorinative Ring Expansion Reactions
			Solution
			Key Steps Explained
			Additional Resources
			References
		An Isoxazole to 1,3-Oxazine Transformation
			Key Steps Explained
			Solution: 3-Phenyl-5-isoxazolone  1
			Solution: 1  2
			Additional Resources
			References
		Synthesis of Folate Antimetabolites: A Furan to Pyrrole Transformation
			Solution: Mechanism A
			Solution: Mechanism B
			Balanced Chemical Equation (Applies to Both Mechanism A and B)
			Key Steps Explained
			Additional Resources
			References
		Rearrangement of a Silylacetylenic Ketone
			Solution
			Key Steps Explained
			Additional Resources
			References
		And More Silyl Rearrangements: A Brook-Retro-Brook Sequence
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Two Syntheses of Dehydrorotenone
			Solution: (i) From 21
			Balanced Chemical Equation for (i)
			Solution: (ii) From 3 and 42 Mechanism A
			Balanced Chemical Equation for Mechanism A
			Solution: (ii) From 3 and 42 Mechanism B
			Balanced Chemical Equation for Mechanism B
			Key Steps Explained
			Additional Resources
			References
		Radical-Induced Decarboxylation of a Lactone
			Solution: Pathway A
			Pathway B
			Key Steps Explained
			Additional Resources
			References
		Aryl Azide Thermolysis: ``A Series of Rather Involved Rearrangement Reactions´´
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Balanced Chemical Equation
			Balanced Chemical Equation
			Additional Resources
			References
		An Efficient Route to Hexakis(trifluoromethyl)cyclopentadiene
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Exploitation of the Boulton-Katritzky Rearrangement: Synthesis of 4,4-Diamino-3,3-bifurazan
			Solution
			Additional Resources
			References
		Rearrangement During Hydrolysis of a Cyclohexadienone
			Solution: 12
			Balanced Chemical Equation: 12
			Solution: 23, 4
			Balanced Chemical Equation: 13, 4
			Key Steps Explained
			Additional Resources
			References
		Less Common Sigmatropic Rearrangements: [3,4], [3,5], or Even [2,3]?
			Solution: Thionation Mechanism
			Solution: A2
			Balanced Chemical Equation: 12
			Solution: B3
			Balanced Chemical Equation: 13
			Key Steps Explained
			Additional Resources
			References
		Failure to Construct an Oxetane by SN Rearrangement
			Solution
			Balanced Chemical Equation
			Key Steps Explained
			Additional Resources
			References
		Acid-Catalyzed Isomerization of a Tetraspiroketone
			Solution: 12
			Solution: 13
			Key Steps Explained
			Additional Resources
			References
Index_2019_Strategies-and-Solutions-to-Advanced-Organic-Reaction-Mechanisms
	Index
		A
		B
		C
		D
		E
		F
		G
		H
		I
		J
		K
		L
		M
		N
		O
		P
		Q
		R
		S
		T
		U
		V
		W
		X
		Y
		Z