research paper in organic chemistry pdf

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Organic chemistry articles from across Nature Portfolio

Organic chemistry is the study of the synthesis, structure, reactivity and properties of the diverse group of chemical compounds primarily constructed of carbon. All life on earth is carbon-based, thus organic chemistry is also the basis of biochemistry. The ability to form compounds containing long chains of carbon atoms is the basis of polymer chemistry.

Characterization of a secondary carbon-centred radical

A diazapentadienyl radical featuring a disubstituted carbon centre is discovered allowing the isolation and structural characterization of a stable secondary carbon radical.

• Koushik Saha
• Holger Braunschweig

Related Subjects

• Carbohydrate chemistry
• Combinatorial libraries
• Synthetic chemistry methodology
• Microwave chemistry
• Natural product synthesis
• Reaction mechanisms
• Stereochemistry
• Structure elucidation

Latest Research and Reviews

Para -selective nitrobenzene amination lead by C(sp 2 )-H/N-H oxidative cross-coupling through aminyl radical

Direct radical C–H amination strategies have exhibited innovation, but challenges remain with C–H amination of electron-poor nitroarenes due to the essence of the electron-deficient nitrogen radical. Herein, the authors report a transition metal-free dehydrogenative C(sp 2 )-H/N-H cross-coupling between electron-poor nitroarenes and amines.

• Shusheng Yue

Geometry-controlled reactivity and dynamics in organic molecules

Geometry control in organic reactions can be used to promote dynamic processes or stabilize reactive transition states. This Review discusses the concept of geometry control, its impact on transition states and bonding, as well as the reactivity and properties that emerge as a consequence of constraining molecules.

• Promeet K. Saha
• Trung Tran Ngoc
• Johannes F. Teichert

One-pot synthesis of quinazolinone heterocyclic compounds using functionalized SBA-15 with natural material ellagic acid as a novel nanocatalyst

• Nazanin Mohassel Yazdi
• Mohammad Reza Naimi-Jamal

Late-stage benzenoid-to-troponoid skeletal modification of the cephalotanes exemplified by the total synthesis of harringtonolide

Many natural products exist as families of structurally similar molecules, and therefore developing skeletal modifications of common intermediates offers flexible and powerful approaches for target synthesis. Here, the authors report a single-atom insertion into the framework of the benzenoid subfamily, providing access to the troponoid congeners.

• Stefan Wiesler
• Goh Sennari
• Richmond Sarpong

Introduction of the difluoromethyl group at the meta- or para-position of pyridines through regioselectivity switch

The direct C−H-difluoromethylation of pyridines represents a highly efficient economic way to access azines. However, the direct meta-difluoromethylation of pyridines remains elusive. Here, the authors demonstrate switchable meta- as well as para-C−H difluoromethylation of pyridines through radical processes by using oxazino pyridine intermediates.

• Armido Studer

Asymmetric C–H Dehydrogenative Alkenylation via a Photo-induced Chiral α ‑Imino Radical Intermediate

The direct alkenylation with simple alkenes stands out as the most ideal yet challenging strategy for obtaining high-valued desaturated alkanes. Herein, the authors present a direct asymmetric dehydrogenative α -C(sp3)-H alkenylation of carbonyls based on synergistic photoredox-cobalt-chiral primary amine catalysis under visible light.

• Zongbin Jia
• Liang Cheng
• Sanzhong Luo

News and Comment

Cobalt catalysis for double dehydrogenation

• Thomas West

Enzymatic radical fluorine transfer

• Jan-Stefan Völler

Tailor-made glycans

A highly chemoselective method for the insertion of carbohydrates into existing oligosaccharides has been developed. The reaction sequence involves a selective Lewis-acid catalysed cleavage of one glycosidic bond followed by sequential construction of two new glycosidic bonds.

• Sugyeom Kim
• George A. O’Doherty

Triple catalysis for quaternary stereocentre synthesis

Trio of radicals choreographed for versatile chemical reaction

The idea that three different free radicals could be used together to carry out specific steps in a chemical reaction has long been implausible. A ‘radical sorting’ strategy now achieves this feat to make organic molecules.

• Kenneth F. Clark
• John A. Murphy

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Themed collection Top 50 Articles of 2016: Organic Chemistry

Glycosylation, an effective synthetic strategy to improve the bioavailability of therapeutic peptides

Glycosylation of peptides is a promising strategy for modulating the physicochemical properties of peptide drugs and for improving their absorption through biological membranes.

Pot economy and one-pot synthesis

This review describes the importance and usefulness of pot-economy and one-pot reactions in current synthetic organic chemistry.

Peptide-based synthetic vaccines

This review summarise the current stand and future perspective on synthetic peptide-based vaccines.

Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions

A metal-free C–B bond forming reaction of aryl halides under batch and continuous-flow conditions is described.

The total synthesis of K-252c (staurosporinone) via a sequential C–H functionalisation strategy

A synthesis of the bioactive indolocarbazole alkaloid K-252c (staurosporinone) via a sequential C–H functionalisation strategy is reported.

A visible-light-promoted radical reaction system for azidation and halogenation of tertiary aliphatic C–H bonds

A highly tunable visible-light-promoted reaction system for the radical-mediated functionalization of tertiary aliphatic C–H bonds of complex substrates has been developed.

Aminofluorination: transition-metal-free N–F bond insertion into diazocarbonyl compounds

Gem-aminofluorination of diazocarbonyl compounds has been achieved for the first time.

Rh( III )-catalyzed diastereoselective C–H bond addition/cyclization cascade of enone tethered aldehydes

Rh( III )-catalyzed cascade addition of C–H bonds across alkene and carbonyl π-bonds to form two new σ C–C bonds is accomplished.

Visible light-mediated gold-catalysed carbon(sp 2 )–carbon(sp) cross-coupling

A new method for the alkynylation of aryldiazonium salts with TMS-alkynes via dual gold and photoredox catalysis is described.

Dual gold/photoredox-catalyzed C(sp)–H arylation of terminal alkynes with diazonium salts

The arylation of alkyl and aromatic terminal alkynes by a dual gold/photoredox catalytic system is described.

Access to a new class of synthetic building blocks via trifluoromethoxylation of pyridines and pyrimidines

One-pot trifluoromethoxylation of functionalized pyridines and pyrimidines via OCF 3 -migraion.

Profiling the reactivity of cyclic C-nucleophiles towards electrophilic sulfur in cysteine sulfenic acid

Oxidation of a protein cysteine thiol to sulfenic acid, termed S -sulfenylation, is a reversible post-translational modification that plays a crucial role in regulating protein function and is correlated with disease states.

About this collection

We are delighted to present a collection showcasing the 50 most downloaded Chemical Science articles of 2016. This is only available for a limited time and provides an easy way to quickly access the most important papers published in Chemical Science in the past year. These articles highlight exciting and impactful research across a broad range of subject areas, analytical chemistry, chemical biology, catalysis, energy, inorganic chemistry, materials science, nanoscience, organic chemistry and physical chemistry. We hope you enjoy reading this collection!

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Home > Chemistry > Dissertations, Theses, and Student Research

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Department of chemistry: dissertations, theses, and student research.

Halide Exchange and Transport in Halide Perovskite Lattices , Temban Acha Billy

Synthesis and Study of High-Spin Stable Organic Radicals for Electrical Conductors and Mannosamine Nitroxide for MRI Contrast Agents , Shuyang Zhang

Designing Experiments: The Impact of Peer Review Structure on Organic Chemistry Students' Experimental Designs , Katie Patterson

Study of halide gradient formation via solution-solid halide exchange in crystalline CH 3 NH 3 PbBr 3 thin films , Behnaz Akbari

Oxygen Binding Thermodynamics of Human Hemoglobin in the Red Blood Cell , Kyle K. Hill

Developing Techniques for the Identification of Non-Canonical RNA Pairing and Analysis of LC-MS Datasets , Christopher Jurich

Surface Functionalization of Elastomers for Tunable Crystal Growth and Smart Adhesives , John Kapitan

Issue of False Amphetamine Field Test Positives Caused By Sugar. Use of Baeyer Test as a Secondary Test Solution. , Reed A. Knutson, Jennah Duncan, Kara Peightal, and Samuel Thomas

Harnessing Surface Chemistry and Instabilities in Silicone Elastomers to Synthesize Adaptive Systems with Mechanically Tunable Surface Properties and Functionality , Ali Jamal Mazaltarim

How Oxygen-Binding Affects Structural Evolution of Even-Sized Gold Anion Clusters. (Size Range 20 to 34) , David Brunken-Deibert

Analysis of Hydroxychloroquine Interaction with Serum Proteins by High Performance Affinity Chromatography , Kyungah Suh, Sadia Sharmeen, and David S. Hage

The Application and Development of Metabolomics Methodologies for the Profiling of Food and Cellular Toxicity , Jade Woods

Evaluation of the Overall Binding of Acetohexamide and Tolbutamide with Methyl Glyoxal-Modified HSA by High-Performance Affinity Chromatography , Ashley G. Woolfork and David S. Hage

C(sp2)-C(sp3) Cross-Coupling of Aryl Halides and Active C(sp3)-H Bonds via Dual Catalysis: Organic Photocatalysis/Nickel Redox Catalysis , Nicholas Armada

Phosphonate-Directed Catalytic Asymmetric Hydroboration: Synthesis of Functionalized Chiral Secondary and Tertiary Boronic Esters and Mechanistic Insights , Suman Chakrabarty

COMPUTATIONAL STUDIES OF THERMAL PROPERTIES AND DESALINATION PERFORMANCE OF LOW-DIMENSIONAL MATERIALS , Yang Hong

QUANTUM CHEMICAL CALCULATIONS APPLIED TO SOMO-HOMO CONVERSION AND VIBRATIONALLY AVERAGED NMR SHIELDING PARAMETERS , Erik Johnson

Design and Synthesis of Stable Aminyl and Nitroxide Radical Precursors , Joshua Bryan Lovell

Development of Nanomaterial Supports for the Study of Affinity-Based Analytes Using Ultra-Thin Layer Chromatography , Allegra Pekarek

ANALYSIS OF DRUG-PROTEIN INTERACTIONS DURING DIABETES BY HIGH-PERFORMANCE AFFINITY CHROMATOGRAPHY , Pingyang Tao

Electropolymerization and Characterization of Thin Film Dielectrics , Christopher White II

Synthesis, Characterization, and Catalytic Activity of Copper Palladium Oxide Solid Solutions. , Gregory L. Christensen

GLOBAL MINIMUM SEARCH AND CARBON MONOXIDE BINDING STUDIES OF NOVEL GOLD NANOCLUSTERS , Navneet S. Khetrapal

Mass Spectrometry and Nuclear Magnetic Resonance in the Chemometric Analysis of Cellular Metabolism , Eli Riekeberg

Ultrafast Affinity Extraction and High-Performance Affinity Chromatography Applications for Measuring Free Drug Fractions: Interactions of Sulfonylurea Drugs with Normal and Glycated Human Serum Albumin , Bao Yang

DEVELOPMENT OF ENTRAPMENT COLUMNS FOR THE STUDY OF AFFINITY BASED ANALYSIS OF DRUG-PROTEIN INTERACTIONS , Shiden T. Azaria

Chemical Vapor Deposition of Two-Dimensional Materials and Heterostructures , Alex J. Boson

Bioinformatic and Biophysical Analyses of Proteins , Jonathan Catazaro

Developing Functionalized Peroxide Precursors for the Synthesis of Cyclic and Spirocyclic Ethers , Anna J. Diepenbrock

Decarboxylative Elimination for the Systhesis of Olefins Via Photoredox/Cobalt Dual Catalysis , Renjie Gui

Enantioselective γ- and δ -Borylation of Unsaturated Carbonyl Derivatives: Synthesis, Mechanistic Insights, and Applications. , Gia L. Hoang

Entrapment of proteins in high-performance affinity columns for chromatographic studies of drug-protein interactions , Saumen Poddar, Elliott Rodriguez, Shiden Azaria, and David S. Hage

Genetic Code Expansion in Biochemical Investigations and Biomedical Applications , Nanxi Wang

Applying the Diffusion of Innovation Theory to Characterize STEM Faculty Attending Professional Development Programs , Dihua Xue

Who is attending pedagogical workshops? Applying the Innovation Diffusion to Characterize Faculty Attendees , Victoria Dihua Xue, Trisha Vickrey, and Marilyne Stains

Genetically Encoded Fluorescent Protein Biosensor for Nitric Oxide , Wenjia Zhai

STUDIES IN DIRECTED CATALYTIC ASYMMETRIC HYDROBORATION OF 1,2-DISUBSTITUTED UNSATURATED AMIDE , Shuyang Zhang

Synthesis and Applications of Cyclobutenes , Benjamin Enns

Binding of Oxygen to Human Hemoglobin Within the Erythrocyte Using ICAM Spectrophotometry , Kyle K. Hill

Design and Synthesis of Novel Octacarboxy Porphyrinic Metal-Organic Frameworks , Jacob A. Johnson

Development of a Direct Activity Probe for Rho-Associated Protein Kinase , Maia Kelly

Thermolysis of Hypervalent Iodine Complexes: Synthesis of Fluorinated Radiotracers for Positron Emission Tomography and Synthesis of Quaternary α-Alkyl α-Aryl Amino Acids , Jayson J. Kempinger

Synthesis and Applications of Lanthanide Sulfides and Oxides , Christopher Marin

SELECTIVE IODINATION USING DIARYLIODONIUM SALTS , William H. Miller IV

MOLECULAR MECHANISM FOR THE BIOSYNTHESIS AND REGULATION OF SECONDARY METABOLITES IN LYSOBACTER , Simon Tesfamichael Tombosa

STUDIES IN ASYMMETRIC CATALYSIS: SUPRAMOLECULAR CATALYSIS AND BORANE-ASSISTED HYDROGENATION , Kazuya Toyama

Molecular Mechanism for the Biosynthesis of Antifungal HSAF and Antibacterial WAP-8294A2 , Haotong Chen

Toward the Probing of DHQS Activity by Protein Engineering through the Introduction of Unnatural Amino Acids and the Selection of tRNA/tRNA Synthetase Pairs , Shaina E. Ives

Toward an Expanded Role for Collision-Induced Dissociation in Glycoproteomic Analysis , Venkata Kolli

New Methods for Synthesis of Organic Peroxides and Application of Peroxide Electrophiles to Synthesis of Functionalized Ethers , Shiva Kumar Kyasa

Chromatographic Analysis of Drug-Protein Interactions During Diabetes and Characterization of Human Serum Albumin Through Multidimensional Mass Spectrometry , Ryan E. Matsuda

THREE-DIMENSIONAL SCAFFOLDS OF GRAPHENE, CARBON NANOTUBES AND TRANSITION-METAL OXIDES FOR APPLICATIONS IN ELECTRONICS, SENSORS AND ENERGY STORAGE , Gilbert N. Mbah

TOWARD THE MEASUREMENT OF BIODISTRIBUTION OF 18 F-LABELED INDUSTRIAL CHEMICALS WITH POSITRON EMISSION TOMOGRAPHY (PET) , Katelyenn S. McCauley

Investigations into the Molecular Mechanisms of Bacterial Pathogen-Host Interactions: Construction of a Dual Plasmid System for Incorporation of Unnatural Amino Acids into Pseudomonas syringae pv. tomato DC3000 , Scotty D. Raber

Applications of High Performance Affinity Chromatography with High Capacity Stationary Phases Made by Entrapment , John A. Vargas Badilla

Uses of Diaryliodonium Salts and Methods for their Synthesis , Jordan M. Veness

The intersection of nuclear magnetic resonance and quantum chemistry , Yali Wang

Chemometric and Bioinformatic Analyses of Cellular Biochemistry , Bradley Worley

Analysis of Free Solute Fractions and Solute-Protein Interactions Using Ultrafast Affinity Extraction and Affinity Microcolumns , Xiwei Zheng

The 8-Silyloxyquinoline Scaffold as a Versatile Platform for the Sensitive Detection of Aqueous Fluoride , Xinqi Zhou

Nanostructured Cerium Oxide Based Catalysts: Synthesis, Physical Properties, and Catalytic Performance , Yunyun Zhou

Hydrolytically Stable Analogues of Sugar Phosphates and a Miniaturized in Situ Enzymatic Screen , Xiang Fei

Development and Application of Combined Quantum Mechanical and Molecular Mechanical Methods , Rui Lai

Syntheses of Aminyl Diradicals and Nitroxide Tetra- and Octaradicals , Arnon Olankitwanit

Analysis of Drug Interactions with Lipoproteins by High Performance Affinity Chromatography , Matthew R. Sobansky

Studies in Asymmetric Synthesis: Supramolecular Catalysis, C-H Activation, and D-Cycloserine Synthesis , Nathan C. Thacker

Application of Nuclear Magnetic Resonance Based Metabolomics to Study the Central Metabolism of Staphylococci , Bo Zhang

IMPLEMENTATION AND APPLICATION OF THE MMFF94 FORCE FIELD , Hongbo Zhu

The Electrochemical Analysis of Bovine Bone Derived Supercapacitors, Organic Peroxide Explosives, and Conducting Polymer Nanojunctions , Paul Goodman

The Development and Applications of NMR Metabolomics Analysis of Bacterial Metabolomes , Steven M. Halouska

Utilizing NMR Spectroscopy and Molecular Docking as Tools for the Structural Determination and Functional Annotation of Proteins , Jaime Stark

A. Catalysis of CO-PROX by Water-Soluble Rhodium Fluorinated Porphyrins B. Studies toward Fluorination of Electron Rich Aromatics by Nucleophilic Fluoride , Shri Harsha Uppaluri

Regulation of Secondary Metabolism in Lysobacter enzymogenes : Studies of Intercellular and Intracellular Signaling , Stephen J. Wright

DIRECTED CATALYTIC ASYMMETRIC HYDROBORATION OF 1,1-DISUBSTITUTED ALKENES , Mohammad Odeh Bani Khaled

I. Synthesis of β-Sitosterol and Phytosterol Esters; II. New Methodology for Singlet Oxygen Generation from 1,1-Dihydroperoxides , Jiliang Hang

Experimental and Theoretical Studies in Solid-state Nuclear Magnetic Resonance , Monica N. Kinde

Experimental and Theoretical Studies in Nuclear Magnetic Resonance , John D. Persons

RHODIUM-CATALYZED HYDROBORATION OF 1,1-DISUBSTITUTED ALKENES , Scott A. Pettibone

INVESTIGATIONS OF INTER- AND INTRAMOLECULAR C-O BOND FORMING REACTIONS OF PEROXIDE ELECTROPHILES , Benjamin W. Puffer

The Use of Rhenium (VII) Oxide as a Catalyst for the Substution of Hemiacetals , Michael W. Richardson

Characterization of Novel Macrocyclic Polyether Modified Pseudostationary Phases for use in Micellar Electrokinetic Chromatography and Development of a Chemiluminescence Presumptive Assay for Peroxide-based Explosives , Raychelle Burks

Preparation and Characterization of Biomimetic Hydroxyapatite-Resorbable Polymer Composites for Hard Tissue Repair , Kristopher R. Hiebner

High Yield Synthesis of Positron Emission Tomography Ligands for Metabotropic Glutamate Receptor Imaging , Saraanne E. Hitchcock

Optimization and Implementation of Entrapment: A Novel Immobilization Technique for High-performance Affinity Chromatography , Abby J. Jackson

Fabrication and Catalytic Property of Cerium Oxide Nanomaterials , Keren Jiang

Affinity Chromatography in Environmental Analysis and Drug-Protein Interaction Studies , Efthimia Papastavros

Development and Optimization of Organic Based Monoliths for Use in Affinity Chromatography , Erika L. Pfaunmiller

I. An Improved Procedure for Alkene Ozonolysis. II. Exploring a New Structural Paradigm for Peroxide Antimalarials. , Charles Edward Schiaffo

QUANTUM MECHANICAL AND MOLECULAR MECHANICAL STUDY OF SOLVENT EFFECTS , Dejun Si

Resorbable Polymer-Hydroxyapatite Composites for Bone Trauma Treatment: Synthesis and Properties , Troy E. Wiegand

PURIFICATION OF LYSINE DECARBOXYLASE: A MODEL SYSTEM FOR PLP ENZYME INHIBITOR DEVELOPMENT AND STUDY , Leah C. Zohner

Characterization of Glycation Sites on Human Serum Albumin using Mass Spectrometry , Omar S. Barnaby

HIGH TEMPERATURE RARE EARTH COMPOUNDS: SYNTHESIS, CHARACTERIZATION AND APPLICATIONS IN DEVICE FABRICATION , Joseph R. Brewer

Classification, Synthesis and Characterization of Pyridyl Porphyrin Frameworks , Lucas D. DeVries

Ultrasonic Activation of Triacetone Triperoxide , LaTravia R. Dobson

Characteristics and Stability of Oxide Films on Plutonium Surfaces , Harry Guillermo García Flores

Controlling Reductive Elimination From Novel I(III) Salts Using a SECURE Method , Joseph W. Graskemper

I. A NEW SYNTHETIC APPROACH TO THE SYNTHESIS OF N-(PHOSPHONOACETYL)-L-ORNITHINE, II. THE INFLUENCE OF PYRIDINE ON THE OZONOLYSIS OF ALKENES , Bradley M. Johnson

Chromatographic Studies of Drug-Protein Binding in Diabetes , Kathryn (Krina) S. Joseph

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Organic Chemistry - A Tenth Edition

(2 reviews)

John E. McMurry, Cornell University

Copyright Year: 2023

ISBN 13: 9781951693985

Publisher: OpenStax

Language: English

Formats Available

Conditions of use.

Learn more about reviews.

Reviewed by Vanessa Garcia, Lecturer, University of Texas Rio Grande Valley on 5/3/24

McMurry does a great job at breaking down terms in the glossary. read more

Comprehensiveness rating: 5 see less

McMurry does a great job at breaking down terms in the glossary.

Content Accuracy rating: 5

To the best of my knowledge, McMurry applies accurate content that is error-free and unbiased.

Relevance/Longevity rating: 5

McMurry's examples of real world applications is relevant not only today, but from years past that can be applied today.

Clarity rating: 5

I enjoy that the textbook is full of color as this helps those visualize how certain processes take place.

Consistency rating: 5

I appreciate the summary at the end of chapters as this will help students get the big scope of the content being discussed.

Modularity rating: 5

McMurry does well at incorporating applications/word-problems after a few sections as this lets students begin to apply what was just discussed.

Organization/Structure/Flow rating: 5

The books organization is very well done, full of color, and easy break down of the concepts.

Interface rating: 5

To the best of my knowledge, I did not encounter problems with navigation or distorted images.

Grammatical Errors rating: 5

To the best of my knowledge, I did not encounter grammatical errors.

Cultural Relevance rating: 5

To the best of my knowledge, I did not encounter text that was insensitive or offensive.

The first organic chemistry textbook I bought as an undergraduate was McMurry's 6th edition. I have been a fan of his books ever since. Now that the latest edition is available via OpenStax, I cannot be more excited. Students will learn to apply for the fundamentals of Organic Chemistry as McMurry does a great job of breaking down the subject matter and incorporating real world applications.

Reviewed by Mary Robert Garrett, Professor of Chemistry and Division I (BIO, CHM, MAT, NUR, PHY) Chair, Berea College on 11/29/23

Yes. This textbook covers a wealth of organic chemistry content and could be used for three organic chemistry courses--Organic Chemistry I, Organic Chemistry II, and Advanced Organic Chemistry. Key terms can be found bolded in the text, and in a... read more

Yes. This textbook covers a wealth of organic chemistry content and could be used for three organic chemistry courses--Organic Chemistry I, Organic Chemistry II, and Advanced Organic Chemistry. Key terms can be found bolded in the text, and in a list at the end of each chapter with links to where they are used in the text. The Study Guide and Student Solutions manual are also openly licensed and free for students in digital formats.

The content appears to be essentially error-free. There may be a missing chemical subscript missing in a place, or two, but nothing that will confuse a student or hinder their learning.

The content is current with applications to everyday life at the end of each chapter in a section titled, “Chemistry Matters.” Examples range from the importance of Vitamin D, to how epoxy resins and adhesives are used in commercial products, to cocaine and anesthetics.

The text is very easy to follow with figures and tables well-placed. New terms are highlighted and strengthen content knowledge.

Yes, each chapter is displayed in the same format beginning with a "Why is this important" and ending with "Chemistry Matters." The subsections are consistent as well.

The textbook has excellent modularity. I see chapters that can be pulled for three different courses—Organic Chemistry I (Chapters 1-13); Organic Chemistry II (Chapters 14-24); and Advanced Organic Chemistry (Sections 5.9-5.12, Chapter 30, and 31), where students can read a later chapter and understand it at a particular level without rereading a previous chapter.

The order of the content is different than the text I normally teach from, but the author does an excellent job of defending this specific order, so I think I’ll give it a try. I like the chapter on “An Overview of Organic Reactions” before diving into reaction classes. I think it will help students recognize the similarities and patterns between reactions. I normally teach the mass spec, NMR and IR chapters out of order, sooner than listed. The analysis of those instruments is so different, that students normally struggle with such a “different” concept at the end of a semester.

Interface rating: 4

One inconsistency that I found distracting was the size of the structures throughout the text. In one table, the chemical structures changed size from molecule to molecule which distracted from the flow. The interface was okay moving between the end-of-section practice problems and the solutions, but it gave away all of the answers with one click. I was also hoping for a bit of interaction with the 3D molecules. I was expecting to be able to manipulate them. While that certainly goes beyond what a typical textbook can do, that would certainly make the online textbook far more engaging.

I did not notice any.

Cultural Relevance rating: 2

I was pleased to see a linked resource by Dr. Rhett Smith (Clemson University) to provide a “more complete, diverse, and inclusive picture of the development and current state of organic chemistry research.” This component acknowledges the need for diversity. While there was a Japanese track team, a black music conductor (leading a white orchestra), and one sunbather of color, the majority of images were of white people (scientist on the computer (though female), pole vaulter, Kansas City pitcher, officer with a "drunkometer" test, kayaker, rock climber, officers with tear gas masks, etc.). I would have appreciated more diversity in the images.

I do really like the content, the level of explanation, the images, and clarity of this textbook. I plan to use it for my Organic Chemistry II course next spring, as well as my Advanced Organic Chemistry course.

Table of Contents

• Dedication and Preface
• Chapter 1: Structure and Bonding
• Chapter  2: Polar Covalent Bonds; Acids and Bases
• Chapter  3: Organic Compounds: Alkanes and Their Stereochemistry
• Chapter  4: Organic Compounds: Cycloalkanes and Their Stereochemistry
• Chapter  5: Stereochemistry at Tetrahedral Centers
• Chapter  6: An Overview of Organic Reactions
• Chapter  7: Alkenes: Structure and Reactivity
• Chapter  8: Alkenes: Reactions and Synthesis
• Chapter  9: Alkynes: An Introduction to Organic Synthesis
• Chapter  10: Organohalides
• Chapter  11: Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
• Chapter  12: Structure Determination: Mass Spectrometry and Infrared Spectroscopy
• Chapter  13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
• Chapter  14: Conjugated Compounds and Ultraviolet Spectroscopy
• Chapter  15: Benzene and Aromaticity
• Chapter  16: Chemistry of Benzene: Electrophilic Aromatic Substitution
• Chapter  17: Alcohols and Phenols
• Chapter  18: Ethers and Epoxides; Thiols and Sulfides
• Chapter  19: Aldehydes and Ketones: Nucleophilic Addition Reactions
• Chapter  20: Carboxylic Acids and Nitriles
• Chapter  21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
• Chapter  22: Carbonyl Alpha-Substitution Reactions
• Chapter  23: Carbonyl Condensation Reactions
• Chapter  24: Amines and Heterocycles
• Chapter  25: Biomolecules: Carbohydrates
• Chapter  26: Biomolecules: Amino Acids, Peptides, and Proteins
• Chapter  27: Biomolecules: Lipids
• Chapter  28: Biomolecules: Nucleic Acids
• Chapter  29: The Organic Chemistry of Metabolic Pathways
• Chapter  30: Orbitals and Organic Chemistry: Pericyclic Reactions
• Chapter  31: Synthetic Polymers
• Appendix A. Nomenclature of Polyfunctional Organic Compounds
• Appendix B. Acidity Constants for Some Organic Compounds
• Appendix C. Glossary
• Appendix D. Periodic Table

Ancillary Material

About the book.

John McMurry's  Organic Chemistry  is renowned as the most clearly written book available for organic chemistry. In John McMurry's words, "I wrote this book because I love writing. I get great pleasure and satisfaction from taking a complicated subject, turning it around until I see it clearly from a new angle, and then explaining it in simple words." In  Organic Chemistry: A Tenth Edition  from OpenStax, McMurry continues this tradition while updating scientific discoveries, highlighting new applications, scrutinizing every piece of art, and providing example problems to assist students.  Organic Chemistry: A Tenth Edition  continues to meet the scope and sequence of a two-semester organic chemistry course that follows a functional group approach. A highlighted list of changes along with a detailed table of contents and ancillary descriptions can be found on the Instructor and Student resources sections of this page. John McMurry decided to publish  Organic Chemistry: A Tenth Edition  under an open license as a tribute to his son, Peter McMurry, who passed away from cystic fibrosis in December 2019. Please  click here  to learn more about Peter's legacy and to  support the fight against cystic fibrosis.

About the Contributors

John E. McMurry is a Professor Emeritus in the Department of Chemistry and Chemical Biology at Cornell University. He holds an A.B. degree from Harvard University and a Ph.D. from Columbia University. McMurry has authored over 100 research papers and is well-known for his contributions to the field of chemistry, particularly the development of the McMurry reaction. This reaction involves the coupling of two molecules of ketone or aldehyde to produce an alkene when treated with titanium(III) chloride and a reducing agent like Zn(Cu). The McMurry reaction has found extensive use in the laboratory synthesis of complex organic molecules and in the commercial synthesis of various drugs by the pharmaceutical industry.

McMurry was elected a Fellow of the American Association for the Advancement of Science in 1985 and received a Max Planck Society Research Award in 1991. Apart from his scientific contributions, McMurry is also a prolific author in the field of chemistry education. He has written 45 undergraduate chemistry textbooks, which have been translated into 12 languages and used worldwide. Among his notable works,  Organic Chemistry , first published in 1984, stands as his most popular textbook.

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