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Experimental Organic Chemistry,

Edition 1 Laboratory Manual

Editors: By Joaquín Isac-García, José A. Dobado, Francisco G. Calvo-Flores and Henar Martínez-García

Publication Date: 20 Oct 2015

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Experimental Organic Chemistry: Laboratory Manual is designed as a primer to initiate students in Organic Chemistry laboratory work. Organic Chemistry is an eminently experimental science that is based on a well-established theoretical framework where the basic aspects are well established but at the same time are under constant development. Therefore, it is essential for future professionals to develop a strong background in the laboratory as soon as possible, forming good habits from the outset and developing the necessary skills to address the challenges of the experimental work.

This book is divided into three parts. In the first, safety issues in laboratories are addressed, offering tips for keeping laboratory notebooks. In the second, the material, the main basic laboratory procedures, preparation of samples for different spectroscopic techniques, Microscale, Green Chemistry, and qualitative organic analysis are described. The third part consists of a collection of 84 experiments, divided into 5 modules and arranged according to complexity. The last two chapters are devoted to the practices at Microscale Synthesis and Green Chemistry, seeking alternatives to traditional Organic Chemistry.

Key Features

Organizes lab course coverage in a logical and useful way
Features a valuable chapter on Green Chemistry Experiments
Includes 84 experiments arranged according to increasing complexity

About the author

By Joaquín Isac-García, Universidad de Granada, Spain; José A. Dobado, Universidad de Granada, Spain; Francisco G. Calvo-Flores, Universidad de Granada, Spain and Henar Martínez-García, Universidad de Valladolid, Spain

Preface
Chapter 1: Laboratory Safety
- 1.1 The lab as a safe place
- 1.2 Personal protective equipment
- 1.3 Emergency equipment for general purpose
- 1.4 GHS for classification and labeling of chemicals
- 1.5 Chemical incompatibility and storage
- 1.6 Substances with risk of fire and explosion
- 1.7 Waste treatment and disposal
Chapter 2: Lab Notebook
- 2.1 Notebook structure
- 2.2 Experiment report for a practice course
- 2.3 Some guidelines for keeping a notebook
- 2.4 Example of an experiment description
- 2.5 Basic calculations
Chapter 3: Laboratory Equipment
- 3.1 Introduction
- 3.2 Manufacture of lab equipment
- 3.3 Cleaning of glassware
- 3.4 General-purpose glassware
- 3.5 Fastening and anchoring
- 3.6 Pressure and vacuum equipment
- 3.7 Pressure reactors and hydrogenators
- 3.8 Other materials
Chapter 4: Basic Laboratory Operations
- 4.1 Introduction
- 4.2 Weighing of solids and liquids
- 4.3 Measurement of liquid volumes or solutions
- 4.4 Transfer of solids and liquids
- 4.5 Techniques used in chemical reactions
- 4.6 Reflux
- 4.7 Isolation and purification of solids
- 4.8 Liquid-liquid extraction
- 4.9 Solid-liquid extraction (Soxhlet)
- 4.10 Removal of solvents under reduced pressure (rotary evaporator)
- 4.11 Distillation
- 4.12 Reactions in an inert atmosphere
- 4.13 Reaction and removing of gaseous products
- 4.14 Chromatographic techniques
Chapter 5: Determining Physical and Spectroscopic Properties
- 5.1 Introduction
- 5.2 Determining physical properties
- 5.3 Determining spectroscopic properties
- 5.4 Preparation of samples for spectroscopy
Chapter 6: Functional-Group Analysis
- 6.1 Introduction
- 6.2 Qualitative elemental analysis
- 6.3 Organoleptic and physical properties
- 6.4 Classification by solubility (solubility tests)
- 6.5 Functional-group analysis
- 6.6 Identification of an unknown substance
Chapter 7: Basic Operation Experiments
- 7.1 Recrystallization and solubility tests: from water and from organic solvents
- 7.2 Stirring and decanting: preparing biodiesel from cooking oil
- 7.3 Simple distillation: isolation of alcohol from wine
- 7.4 Extraction and “rotary evaporator”: obtaining cloves and cinnamon oils
- 7.5 Liquid-liquid extraction (with centrifuge): isolation of caffeine from soluble coffee
- 7.6 Liquid-liquid extraction (with separatory funnel): separating components of a mixture
- 7.7 Reflux, simple, and fractional distillation: ethyl acetate preparation
- 7.8 Steam distillation and vacuum distillation: isolation of limonene from citrus peel
- 7.9 Solid-liquid extraction (Soxhlet): sunflower oil from seeds
- 7.10 TLC and CC chromatography: separation of the pigments from spinach leaf
Chapter 8: Organic Synthesis Experiments
- 8.1 Alkene oxidation: preparation of adipic acid from cyclohexene
- 8.2 Dehydration of alcohols: synthesis of cyclohexene from cyclohexanol
- 8.3 Oxidation of alcohols: 4-chlorobenzoic acid from 4-chlorobenzyl alcohol
- 8.4 Nucleophilic substitution reactions: synthesis of 1-bromobutane
- 8.5 Synthesis of an ether: preparation of β-naphthyl methyl ether
- 8.6 Aromatic electrophilic substitution of an ester: methyl benzoate nitration
- 8.7 Electrophilic aromatic substitution (S_EAr): preparation of a synthetic detergent
- 8.8 Synthesis of azo dyes: methyl orange
- 8.9 Auto-oxidation−reduction of aromatic aldehydes: cannizzaro reaction
- 8.10 Synthesis of α, β-unsaturated ketones: Claisen-Schmidt reaction
- 8.11 Saponification reaction: preparation of soap from vegetable oil
- 8.12 Esterification: synthesis of aspirin
- 8.13 Difunctional compound chemoselectivity: reduction of 4-nitroacetophenone
- 8.14 Perkin reaction: cinnamic acid synthesis
- 8.15 Synthesis of imide: preparation of N-(p-chlorophenyl)-maleimide
- 8.16 Condensation polymerization reaction: synthesis of nylon 6,6
- 8.17 Radical polymerization: producing polystyrene
- 8.18 Multistep synthesis of a drug: paracetamol
- 8.19 Multistep synthesis of an anesthetic: preparation of benzocaine
- 8.20 Using protecting groups: multistep synthesis of p-nitroaniline
Chapter 9: Advanced Organic Synthesis Experiments
- 9.1 Reductive amination: producing (±)-α-methylbenzylamme
- 9.2 Chiral resolution: (±)-α-methylbenzylamme
- 9.3 Stereospecific synthesis of glycols: preparation of trans-cyclohexane-1,2-diol
- 9.4 Reactivity of carbenes: preparation of 7,7-dichlorobicyclo [4.1.0] heptane
- 9.5 Regioselective halogenations: bromation of α-methylstyrene
- 9.6 Oxidative coupling of alkynes: the Glaser-Eglinton-Hay coupling
- 9.7 Diels-Alder reactions: butadiene and maleic anhydride
- 9.8 Wittig reaction: 4-vinylbenzoic acid synthesis
- 9.9 Grignard reagents: synthesis of triphenylmethanol (triphenylcarbinol)
- 9.10 Organometallic compounds: synthesis of acetylferrocene
- 9.11 Chemoselectivity: cinnamaldehyde reduction with LiAlH₄
- 9.12 Electrophilic aromatic substitution (S_EAr): 1,4-di-tert-butylbenzene
- 9.13 Hofmann rearrangement: synthesis of 2-aminobenzoic acid (anthranilic acid)
- 9.14 Radical coupling: synthesis of pinacol and pinacolone
- 9.15 Synthesis of a heterocyclic drug: n-butylbarbituric acid
- 9.16 Transformations of hydroxy ketone: synthesis and reactions of benzoin
- 9.17 Enamines as reaction intermediates: producing 2-acetylcyclohexanone
- 9.18 N-Heterocycle synthesis: producing benzotriazol
- 9.19 Synthesis of macrocycles: preparation of calix[4]pyrrole
- 9.20 Preparation of a sports dietary supplement: creatine synthesis
- 9.21 Claisen condensation: synthesis of ethyl acetoacetate
- 9.22 Terpene transformation: citral conversion in α- and β-ionone
- 9.23 Carbohydrates: diisopropylidene derivative of glucose
- 9.24 Preparation of a nucleoside: multistep synthesis of uridine derivative
Chapter 10: Microscale
- 10.1 Introduction
- 10.2 The scales in the Organic Chemistry laboratory
- 10.3 Pros of working at the microscale
- 10.4 Specific microscale lab equipment
- 10.5 Microscale laboratory techniques
Chapter 11: Microscale Experiments
- 11.1 Addition of HX to alkenes: synthesis of 2-bromohexane
- 11.2 Production of margarine: partial hydrogenation of a vegetable oil with cyclohexene and Pd(C)
- 11.3 Isomerization of alkenes: derivatives of fumarie acid from maleic acid
- 11.4 Nucleophilic substitution reaction: ethyl iodide from ethanol
- 11.5 Methylketone reactivity: acetophenone oxidation with sodium hypochlorite
- 11.6 Electrophilic aromatic substitution (S_EAr): preparation of 4-methyl-3- and 4-methyl-2-nitroacetanilide from 4-methylaniline
- 11.7 Sandmeyer reaction: 2-iodobenzoic acid synthesis
- 11.8 Synthesis of a carbohydrate derivative:preparation of 2,3:5,6-di-O-isopropylidene-α-d-mannofuranose
- 11.9 Free-radical halogenation: 9-bromoanthracene preparation
- 11.10 Alkylbenzene oxidation: reactivity of alkyl groups in aromatic compounds with KMnO₄
- 11.11 Reduction of anthraquinone: anthrone synthesis
- 11.12 Compounds for the fragrance industry: ester synthesis
- 11.13 Tandem transesterification-esterification: wintergreen oil from aspirin tablets
- 11.14 Polyfunctional molecule reactivity: vanillin transformations
- 11.15 Multistep synthesis of N-heterocycles: triphenylpyridine preparation
- 11.16 Synthesis of five-membered heterocycles: 2,5-dimethyl-1-phenylpyrrole by Paal-Knorr reaction
Chapter 12: Green Chemistry
- 12.1 Introduction
- 12.2 The 12 principles of Green Chemistry
- 12.3 Goals of Green Chemistry
- 12.4 Parameters to evaluate chemical processes
- 12.5 Green Chemistry for undergraduate laboratories
Chapter 13: Green Chemistry Experiments
- 13.1 Oxidative cleavage of alkenes: producing adipic acid with H₂O₂/Na₂WO₄
- 13.2 Halogen addition to alkenes: addition of bromine to cyclohexene
- 13.3 Green epoxidation: cyclohexene reaction with Oxone^®
- 13.4 Acylation of aromatic amines: obtention of acetanilide with acetic acid and Zn
- 13.5 Solvent-free reductive amination: preparation of dibenzylamine hydrochloride
- 13.6 Friedel-Crafts alkylation: xylene reaction with 2-bromopropane catalyzed with graphite
- 13.7 Regiospecific nitration of phenols: obtention of ortho-nitrophenol
- 13.8 Oxidation of aromatic aldehydes: reaction of benzaldehyde with Oxone^®
- 13.9 Green synthesis of ethers: preparation of benzyl butyl ether
- 13.10 Synthesis of an acetal in water: preparation of 5,5-bis(hydroxymethyl)-2-phenyl-1,3-dioxane
- 13.11 Reduction of a ketone alkaline solution: cyclohexanone reaction with NaBH₄
- 13.12 Solvent-free Baeyer–Villiger reaction: oxidation of 4-tert-butylcyclohexanone
- 13.13 Enzymatic reduction of β-ketoesters: synthesis of chiral ethyl 3-hydroxybutanoate
- 13.14 C–C Bond forming: suzuki reaction
- 13.15 C=C Bond formation in the absence of solvent: the Wittig reaction
- 13.16 Diels-Alder in water: reaction of 9-anthracenemethanol with N-methylmaleimide
- 13.17 Green synthesis of a p-cymene: preparation of p-cymene from limonene
- 13.18 Oxidative coupling reaction in water: synthesis of racemic 1,1^′-bi-2-naphthol
- 13.19 Organic compounds from recycled polymer: phthalate derived from PET
- 13.20 Crosslinked biodegradable polymers: producing slime
- 13.21 Polymers from renewable raw materials: starch
- 13.22 Organocatalysis: reaction of 4-nitrobenzaldehyde and dimedone
- 13.23 Knoevenagel-Pinner reactions in water: synthesis of 7-hydroxy-3-carboxycoumarin
- 13.24 Biginelli reaction: synthesis of tetrahydropyrimidinone
- 13.25 Multi-component synthesis in water: Passerini reaction
- 13.26 Preparation of a dipyrrol derivative in water: meso-diethyl-2,2^′-dipyrromethane
- 13.27 Ionic liquid in water: one-pot 1-butyl-3-methylimidazolium derivative preparation
- 13.28 Beckmann rearrangement: synthesis of laurolactam from cyclododecanone
- 13.29 Fluorescent natural product: preparation of 7-hydroxy-4-methyl-2H-chromen-2-one
- 13.30 Photochemical solid phase: [2+2] cycloaddition of cinnamic acid
Index

ISBN: 9780128038932

Page Count: 500

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