Experimental Organic Chemistry - 1st Edition - ISBN: 9780128038932, 9780128039359

Experimental Organic Chemistry

1st Edition

Laboratory Manual

Authors: Joaquín Isac-García José A. Dobado Francisco G. Calvo-Flores Henar Martínez-García
eBook ISBN: 9780128039359
Paperback ISBN: 9780128038932
Imprint: Academic Press
Published Date: 20th October 2015
Page Count: 500
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Description

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

Readership

Upper level undergraduate students in organic chemistry lab courses

Table of Contents

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  • 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 (SEAr): 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 (SEAr): 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 (SEAr): 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

Details

No. of pages:
500
Language:
English
Copyright:
© Academic Press 2016
Published:
Imprint:
Academic Press
eBook ISBN:
9780128039359
Paperback ISBN:
9780128038932

About the Author

Joaquín Isac-García

Joaquín Isac-García

Joaquín García Isac is an Associate Professor in the Department of Organic Chemistry at the University of Granada.

Affiliations and Expertise

Universidad de Granada, Spain

José A. Dobado

José A. Dobado

José Antonio Jimenez Dobado received his PhD in Chemistry at the University of Granada in 1994. From 1995 to 1997, he was a postdoctoral fellow at Zurich University and Helsinki University. He joined the Department of Organic Chemistry at the University of Granada as a postdoctoral researcher from 1997 to 1998, Associate Professor from 1998 to 2002, and Profesor since 2003. In that period, he spent also several months at McMaster University and Helsinki University. His area of research is in computational Chemistry, and he directs the Molecular Modelling and Design research group financed (FQM-174) by the Andalusian Government.

Affiliations and Expertise

Universidad de Granada, Spain

Francisco G. Calvo-Flores

Francisco G. Calvo-Flores

Francisco García Calvo-Flores is a Professor of Organic Chemistry at the University of Granada.

Affiliations and Expertise

Universidad de Granada, Spain

Henar Martínez-García

Henar Martínez-García

Henar Martínez García is in the Department of Organic Chemistry in the School of Industrial Engineering at the University of Valladolid.

Affiliations and Expertise

Universidad de Valladolid, Spain