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# Alkene and Alkyne Reactions Cheat Sheet: A Comprehensive Guide
Author: Dr. Anya Sharma, PhD in Organic Chemistry, Professor of Chemistry at the University of California, Berkeley. Dr. Sharma has over 15 years of experience in teaching and researching organic chemistry, with a particular focus on the reactivity of unsaturated hydrocarbons.
Publisher: Oxford University Press, a leading academic publisher known for its high-quality textbooks and reference materials in chemistry and related fields. Their commitment to accuracy and pedagogical excellence makes them an ideal publisher for this comprehensive alkene and alkyne reactions cheat sheet.
Editor: Dr. David Lee, PhD in Chemical Education, experienced editor of numerous chemistry textbooks and educational resources. Dr. Lee’s expertise ensures the clarity and accessibility of this alkene and alkyne reactions cheat sheet.
Introduction: Mastering the Reactivity of Alkenes and Alkynes
This alkene and alkyne reactions cheat sheet serves as a comprehensive guide to understanding and predicting the reactions of alkenes and alkynes, two fundamental classes of hydrocarbons featuring carbon-carbon double and triple bonds, respectively. These unsaturated functional groups lend themselves to a rich array of reactions, making them crucial components in organic synthesis and industrial processes. This resource will provide a concise yet thorough overview, enabling students and researchers alike to quickly access key information on reaction mechanisms, reagents, and product predictions. We will cover a broad spectrum of reactions, including addition, oxidation, reduction, and polymerization, focusing on both the similarities and differences in alkene and alkyne reactivity.
Addition Reactions: The Hallmark of Unsaturated Hydrocarbons
This section of our alkene and alkyne reactions cheat sheet will detail the crucial addition reactions. The presence of π bonds in alkenes and alkynes makes them susceptible to electrophilic addition.
Electrophilic Addition to Alkenes:
Halogenation: Reaction with halogens (Cl₂, Br₂) to form vicinal dihalides. Mechanism involves a halonium ion intermediate.
Hydrohalogenation: Reaction with hydrogen halides (HCl, HBr, HI) to form haloalkanes. Markovnikov's rule governs regioselectivity.
Hydration: Addition of water (H₂O) in the presence of an acid catalyst (H₂SO₄) to form alcohols. Again, Markovnikov's rule applies.
Oxymercuration-Demercuration: A regioselective method for hydration, avoiding carbocation rearrangements.
Hydroboration-Oxidation: An anti-Markovnikov regioselective hydration method, yielding anti-Markovnikov alcohols.
Electrophilic Addition to Alkynes:
Alkynes, with their two π bonds, undergo similar addition reactions, often requiring two equivalents of the reagent.
Halogenation: Forms tetrahalides.
Hydrohalogenation: Forms geminal dihalides (Markovnikov addition). Further addition can lead to tetrahalides.
Hydration: Forms ketones (via enol tautomerization).
Hydroboration-Oxidation: Forms aldehydes (or ketones depending on the alkyne structure).
Oxidation Reactions: Transforming Unsaturated Hydrocarbons
This section of our alkene and alkyne reactions cheat sheet covers the oxidation reactions.
Oxidation of Alkenes:
Epoxidation: Reaction with peroxyacids (e.g., mCPBA) to form epoxides.
Ozonolysis: Cleavage of the double bond with ozone (O₃) followed by a reducing agent (e.g., Zn) to yield aldehydes or ketones.
Syn-dihydroxylation: Addition of two hydroxyl groups to the same face of the alkene using osmium tetroxide (OsO₄).
Anti-dihydroxylation: Formation of vicinal diols with anti stereochemistry using potassium permanganate (KMnO₄).
Oxidation of Alkynes:
Ozonolysis: Similar to alkenes, but yields carboxylic acids or ketones.
Potassium Permanganate Oxidation: Leads to carboxylic acids.
Reduction Reactions: Adding Hydrogen
Our alkene and alkyne reactions cheat sheet also covers reduction.
Reduction of Alkenes:
Catalytic Hydrogenation: Addition of hydrogen (H₂) in the presence of a metal catalyst (e.g., Pt, Pd, Ni) to form alkanes. Syn addition occurs.
Reduction of Alkynes:
Catalytic Hydrogenation: Can be controlled to yield either cis-alkenes (Lindlar catalyst) or trans-alkenes (sodium in liquid ammonia). Complete reduction to alkanes is also possible.
Polymerization: Creating Long Chains
This section of our alkene and alkyne reactions cheat sheet focuses on the crucial process of polymerization.
Alkenes, particularly those with simple substituents, readily undergo addition polymerization to form long-chain polymers like polyethylene (from ethene) and polypropylene (from propene).
Other Important Reactions: A Glimpse into Further Reactivity
This alkene and alkyne reactions cheat sheet also includes other noteworthy reactions. These include:
Allylic halogenation: Substitution of a hydrogen atom on the carbon atom adjacent to the double bond.
Free radical addition: Addition of radicals to alkenes (e.g., radical polymerization).
Alkylation of alkynes: Addition of alkyl groups to alkynes using strong bases.
Conclusion: Utilizing the Alkene and Alkyne Reactions Cheat Sheet
This comprehensive alkene and alkyne reactions cheat sheet provides a solid foundation for understanding the diverse reactivity of alkenes and alkynes. Mastering these reactions is paramount for success in organic chemistry, and this resource aims to streamline the learning process and provide a readily accessible reference for both students and professionals. By understanding the mechanisms and reaction conditions, one can accurately predict the products of reactions and design efficient synthetic routes. Remember to always consider steric hindrance and electronic effects when predicting the outcome of reactions.
FAQs
1. What is Markovnikov's rule? Markovnikov's rule states that in the addition of a protic acid to an alkene, the hydrogen atom adds to the carbon atom that already has the greater number of hydrogen atoms.
2. What is the difference between syn and anti addition? Syn addition involves the addition of two substituents to the same face of a double or triple bond, while anti addition involves addition to opposite faces.
3. What is the role of a catalyst in alkene hydrogenation? The catalyst (e.g., Pt, Pd, Ni) provides a surface for the adsorption of hydrogen, facilitating its heterolytic cleavage and subsequent addition to the alkene.
4. How can I distinguish between an alkene and an alkyne? Alkynes have a higher degree of unsaturation than alkenes and often show different reactivity patterns, particularly in their oxidation reactions. Spectroscopic techniques (IR, NMR) can also be used for definitive identification.
5. What are some common reagents used in alkene and alkyne reactions? Common reagents include halogens (Cl₂, Br₂), hydrogen halides (HCl, HBr, HI), water (H₂O), peroxyacids (mCPBA), ozone (O₃), potassium permanganate (KMnO₄), and hydrogen (H₂).
6. What are some industrial applications of alkene and alkyne reactions? These reactions are crucial in the production of plastics (polymerization), pharmaceuticals, and various other chemicals.
7. What are the limitations of this alkene and alkyne reactions cheat sheet? This cheat sheet serves as a concise overview; more detailed explanations of mechanisms and nuances can be found in advanced organic chemistry textbooks.
8. How can I improve my understanding of alkene and alkyne reaction mechanisms? Practice drawing reaction mechanisms and working through example problems. Consult textbooks and online resources for detailed explanations.
9. Are there any safety precautions to consider when working with alkenes and alkynes and their reagents? Many reagents used in alkene and alkyne reactions are hazardous. Always wear appropriate personal protective equipment (PPE) and follow safe laboratory procedures.
Related Articles
1. Alkene Electrophilic Addition Mechanisms: A detailed explanation of the mechanisms involved in electrophilic addition reactions to alkenes.
2. Alkene Oxidation Reactions: A Deep Dive: A thorough exploration of different alkene oxidation reactions, including mechanisms and stereochemistry.
3. Alkynes: Synthesis and Reactivity: A comprehensive review of alkyne synthesis methods and their unique reactivity patterns.
4. Regioselectivity and Stereoselectivity in Alkene Reactions: An in-depth look at the factors influencing regio- and stereoselectivity in alkene reactions.
5. Practical Applications of Alkene and Alkyne Chemistry: Case studies highlighting the industrial and commercial applications of alkene and alkyne chemistry.
6. Spectroscopic Analysis of Alkenes and Alkynes: Techniques such as IR and NMR spectroscopy for identifying and characterizing alkenes and alkynes.
7. Advanced Alkene and Alkyne Transformations: Exploration of more complex and specialized reactions involving alkenes and alkynes.
8. Stereochemistry in Alkene and Alkyne Reactions: A comprehensive overview of the stereochemical aspects of alkene and alkyne reactions, including syn and anti addition.
9. Polymerization Reactions: From Monomers to Polymers: An explanation of polymerization reactions, including chain-growth and step-growth mechanisms, relevant to alkenes.
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| alkene and alkyne reactions cheat sheet: Mcat , 2010 Includes 2 full-length practice test online--Cover. |
| alkene and alkyne reactions cheat sheet: The Chemistry of Alkenes Saul Patai, Jacob Zabicky, 1964 |
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| alkene and alkyne reactions cheat sheet: Student's Guide to Brown and LeMay, Chemistry, the Central Science, 2nd Edition James C. Hill, 1981 |
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| alkene and alkyne reactions cheat sheet: Principles of Chemical Nomenclature G. J. Leigh, 2011 Aimed at pre-university and undergraduate students, this volume surveys the current IUPAC nomenclature recommendations in organic, inorganic and macromolecular chemistry. |
| alkene and alkyne reactions cheat sheet: Hypervalent Iodine in Organic Synthesis A. Varvoglis, 1996-11-14 This book describes the fascinating chemistry of the many kinds of organic compounds of hypervalent iodine. Each chapter deals with a particular iodine compound or families of compounds which have been used as reagents in a plethora of useful transformations. These include assorted oxidation, such as with the precious Dess-Martin reagent as well as with a wide range of further reactions. Prominent features of hypervalent iodine reagents derived from iodobenzene are: ready availability, operational simplicity, mild reaction conditions, and high efficiency. They are environmentally safe and can be recycled. New species may be easily prepared by introducing substituents in the benzene ring or changing the ligand attached to iodine. Their combination with other reagents broadens considerably their synthetic potential. Today, no synthetic chemist can afford to ignore the valuable hypervalentiodine reagents. - Features up-to-date coverage of a wide range of topics - Includes many tables featuring a diversity of reactivity, and a comprehensive index - Acts as a comprehensive, up-to-date reference on all aspects of hypervalent iodine chemistry - Contains a section on unusual efficiency of hypervalent iodine reactions |
| alkene and alkyne reactions cheat sheet: Flow Chemistry – Fundamentals Ferenc Darvas, György Dormán, Volker Hessel, Steven V. Ley, 2021-10-25 The fully up-dated edition of the two-volume work covers both the theoretical foundation as well as the practical aspects. Presenting the complete insight into driving a chemical reaction provides a deep understanding for new potential technologies. Updated overview on devices and new key concepts of experimental procedures. Vol. 2: Applications. |
| alkene and alkyne reactions cheat sheet: Dynamic Combinatorial Chemistry Benjamin L. Miller, 2009-12-30 Effective techniques for applying Dynamic Combinatorial Chemistry In a relatively short period, Dynamic Combinatorial Chemistry (DCC) has grown from proof-of-concept experiments in a few isolated labs to a broad conceptual framework with applications to an exceptional range of problems in molecular recognition, lead compound identification, catalyst design, nanotechnology, polymer science, and others. Bringing together a group of respected experts, this overview explains how chemists can apply DCC and fragment-based library methods to lead generation for drug discovery and molecular recognition in bioorganic chemistry and materials science. Chapters cover: Basic theory Approaches to binding in proteins and nucleic acids Molecular recognition Self-sorting Catalyst discovery Materials discovery Analytical chemistry challenges A comprehensive, single-source reference about DCC methods and applications including aspects of fragment-based drug discovery, this is a core reference that will spark the development of new solutions and strategies for chemists building structure libraries and designing compounds and materials. |
DAT Organic Chemistry Reaction Summary Sheet Alkene …
will also convert an alkyne to an alkene in 1 equivalent and to an alkane in another equivalent. Note the effect of the nucleophilic H, it will attack the partially positive carbonyl carbon, …
Reaction Summary Sheet - Amazon Web Services, Inc.
DAT Organic Chemistry Reaction Details Sheet Rearrangements Details When carbocations form, H’s and CH 3’s can do a 1,2-shift to generate a more stable carbocation intermediate 1,2 …
but may not be edited in any way - Study Hall with Leah4sci
These cheat sheets may be shared with friends/classmates but may not be edited in any way I create 1-3 cheat sheets per semester, here is a copy of all orgo cheat sheets to date. You can …
Alkene And Alkyne Reactions Cheat Sheet (2024)
Alkene And Alkyne Reactions Cheat Sheet Barry M. Trost,Chao-Jun Li Organic Chemistry John M. McIntosh,2022-07-18 This book is intended for beginning students both chemistry majors
Alkenes: Summary of All Alkene Reactions (With …
Alkenes: Summary of All Alkene Reactions (With Example/Important Notes) 1.) Catalytic Hydrogenation • Syn Addition (added to same side) • Can occur with D 2 or T 2 (deuterium or …
Organic Chemistry Exam 1 Cheat Sheet by teganski
Feb 24, 2025 · C=C (Alkene) → ~1650 cm C≡C, C≡N → ~2100-2200 cm Terms to Know Markov nikov's Rule → addition reactions proton added to the carbon with the most hydrogen atoms …
Alkene Reactions Cheat Sheet [PDF] - cleanplates.com
The Alkene Reactions Cheat Sheet (The Practical Tool) Visual Table: A well-organized table summarizing the key reactions: reagents, conditions, products, and stereochemistry.
Summary of Alkene Reactions, Ch. 8. Memorize Reaction, …
Summary of Mechanisms, Ch. 7 + 8. Alkene Synthesis and Reactions. Hg(OAc)2, H2O. NaBH4. BH3•THF. H2O2, NaOH. Hg(OAc)2, ROH. NaBH4. concerted addition of B-H across C=C …
Alkene And Alkyne Reactions Cheat Sheet (Download Only)
Alkene And Alkyne Reactions Cheat Sheet: Organic Chemistry John M. McIntosh,2022-07-18 This book is intended for beginning students both chemistry majors and other students who …
Organic Chemistry Cheat Sheet - Cheatography.com
Page 1 of 1. Halogenation... Hydrogenation... Hydroh‐alogenation... Hydration. Learn to solve cryptic crosswords!
Chapter 8 - Alkenes, Alkynes and Aromatic Compounds
1. Briefly identify the important differences between an alkene and an alkyne. How are they similar? 2. The alkene (CH 3) 2 CHCH 2 CH=CH 2 is named 4-methyl-1-pentene. What is the …
but may not be edited in any way - Study Hall with Leah4sci
Feb 20, 2020 · These cheat sheets may be shared with friends/classmates but may not be edited in any way I create 1-3 cheat sheets per semester, here is a copy of all orgo cheat sheets to …
AdditionstoAlkenes Click here for more study guides
2)NaBH4,NaOH H2SO4 dilute 1)BH3,THF 2)H2O2,NaOH KMnO4-OH,cold1)O3 2)Me2S 1)RCO 3H OsO4 Br2 H2O Additionof Hydrogenhalide(HX) Hydroboration-Oxidation Oxymercuration …
Reactions of Alkenes: Summary - MIT OpenCourseWare
Reactions of Alkenes: Summary Intermediate: Carbocation Radical 3-Membered Ring None or Cyclic (concerted) Regiochemisty: Markovnikov* Anti-Markovnikov* Markovnikov-like N/A …
Alkene And Alkyne Reactions Cheat Sheet (2024) - x-plane.com
This alkene and alkyne reactions cheat sheet serves as a comprehensive guide to understanding and predicting the reactions of alkenes and alkynes, two fundamental classes of hydrocarbons …
alkane, alkene, alkyne Cheat Sheet - Cheatography
Last updated 6th February, 2019. Page 1 of 1. Learn to solve cryptic crosswords!
© Leah4sci.com These cheat sheets may be shared with …
Alkene Reactions Alkyne Reactions Reaction Map SN1 SN2 E1 E2 Electrophilic Aromatic Substitution Oxidation and Reduction Carboxylic Acid Derivatives. Visit ... ALKYNE …
Alkene Reactions Cheat Sheet (Download Only)
Feb 6, 2019 · The Alkene Reactions Cheat Sheet (The Practical Tool) Visual Table: A well-organized table summarizing the key reactions: reagents, conditions, products, and …
Alkenes Cheat Sheet by bubblysoul - Cheatography
%PDF-1.4 1 0 obj /Title (þÿAlkenes Cheat Sheet by bubblysoul - Cheatography.com) /Creator (þÿwkhtmltopdf 0.12.5) /Producer (þÿQt 4.8.7) /CreationDate (D:20240815154528Z) >> endobj …
DAT Organic Chemistry Reaction Summary Sheet Alkene …
will also convert an alkyne to an alkene in 1 equivalent and to an alkane in another equivalent. Note the effect of the nucleophilic H, it will attack the partially positive carbonyl carbon, …
Reaction Summary Sheet - Amazon Web Services, Inc.
DAT Organic Chemistry Reaction Details Sheet Rearrangements Details When carbocations form, H’s and CH 3’s can do a 1,2-shift to generate a more stable carbocation intermediate 1,2 …
but may not be edited in any way - Study Hall with Leah4sci
These cheat sheets may be shared with friends/classmates but may not be edited in any way I create 1-3 cheat sheets per semester, here is a copy of all orgo cheat sheets to date. You can …
Alkene And Alkyne Reactions Cheat Sheet (2024)
Alkene And Alkyne Reactions Cheat Sheet Barry M. Trost,Chao-Jun Li Organic Chemistry John M. McIntosh,2022-07-18 This book is intended for beginning students both chemistry majors
Alkenes: Summary of All Alkene Reactions (With …
Alkenes: Summary of All Alkene Reactions (With Example/Important Notes) 1.) Catalytic Hydrogenation • Syn Addition (added to same side) • Can occur with D 2 or T 2 (deuterium or …
Organic Chemistry Exam 1 Cheat Sheet by teganski
Feb 24, 2025 · C=C (Alkene) → ~1650 cm C≡C, C≡N → ~2100-2200 cm Terms to Know Markov nikov's Rule → addition reactions proton added to the carbon with the most hydrogen atoms …
Alkene Reactions Cheat Sheet [PDF] - cleanplates.com
The Alkene Reactions Cheat Sheet (The Practical Tool) Visual Table: A well-organized table summarizing the key reactions: reagents, conditions, products, and stereochemistry.
Summary of Alkene Reactions, Ch. 8. Memorize Reaction, …
Summary of Mechanisms, Ch. 7 + 8. Alkene Synthesis and Reactions. Hg(OAc)2, H2O. NaBH4. BH3•THF. H2O2, NaOH. Hg(OAc)2, ROH. NaBH4. concerted addition of B-H across C=C …
Alkene And Alkyne Reactions Cheat Sheet (Download Only)
Alkene And Alkyne Reactions Cheat Sheet: Organic Chemistry John M. McIntosh,2022-07-18 This book is intended for beginning students both chemistry majors and other students who …
Organic Chemistry Cheat Sheet - Cheatography.com
Page 1 of 1. Halogenation... Hydrogenation... Hydroh‐alogenation... Hydration. Learn to solve cryptic crosswords!
Chapter 8 - Alkenes, Alkynes and Aromatic Compounds
1. Briefly identify the important differences between an alkene and an alkyne. How are they similar? 2. The alkene (CH 3) 2 CHCH 2 CH=CH 2 is named 4-methyl-1-pentene. What is the …
but may not be edited in any way - Study Hall with Leah4sci
Feb 20, 2020 · These cheat sheets may be shared with friends/classmates but may not be edited in any way I create 1-3 cheat sheets per semester, here is a copy of all orgo cheat sheets to …
AdditionstoAlkenes Click here for more study guides
2)NaBH4,NaOH H2SO4 dilute 1)BH3,THF 2)H2O2,NaOH KMnO4-OH,cold1)O3 2)Me2S 1)RCO 3H OsO4 Br2 H2O Additionof Hydrogenhalide(HX) Hydroboration-Oxidation Oxymercuration …
Reactions of Alkenes: Summary - MIT OpenCourseWare
Reactions of Alkenes: Summary Intermediate: Carbocation Radical 3-Membered Ring None or Cyclic (concerted) Regiochemisty: Markovnikov* Anti-Markovnikov* Markovnikov-like N/A …
Alkene And Alkyne Reactions Cheat Sheet (2024) - x …
This alkene and alkyne reactions cheat sheet serves as a comprehensive guide to understanding and predicting the reactions of alkenes and alkynes, two fundamental classes of hydrocarbons …
alkane, alkene, alkyne Cheat Sheet - Cheatography
Last updated 6th February, 2019. Page 1 of 1. Learn to solve cryptic crosswords!
© Leah4sci.com These cheat sheets may be shared with …
Alkene Reactions Alkyne Reactions Reaction Map SN1 SN2 E1 E2 Electrophilic Aromatic Substitution Oxidation and Reduction Carboxylic Acid Derivatives. Visit ... ALKYNE …
Alkene Reactions Cheat Sheet (Download Only)
Feb 6, 2019 · The Alkene Reactions Cheat Sheet (The Practical Tool) Visual Table: A well-organized table summarizing the key reactions: reagents, conditions, products, and …
Alkenes Cheat Sheet by bubblysoul - Cheatography
%PDF-1.4 1 0 obj /Title (þÿAlkenes Cheat Sheet by bubblysoul - Cheatography.com) /Creator (þÿwkhtmltopdf 0.12.5) /Producer (þÿQt 4.8.7) /CreationDate (D:20240815154528Z) >> endobj …
