2-cyclopentylethanol reacts with H2SO4 at 140degrees C yields? Answered: CH3OH H2SO4 | bartleby Use the calculator below to balance chemical equations and determine the type of reaction (instructions). Fused Rings - Cis-Decalin and Trans-Decalin, Naming Bicyclic Compounds - Fused, Bridged, and Spiro, Bredt's Rule (And Summary of Cycloalkanes), The Most Important Question To Ask When Learning a New Reaction, The 4 Major Classes of Reactions in Org 1. ch3oh h2so4 reaction mechanism - juliocarmona.com Acid catalysed mechanism of the addition of alcohols to alkenes Ethene reacts to give ethyl hydrogensulphate. Reactants: Sulfuric acid and heat, Write another part of the reaction and write what will happen to the reaction: AgNO_3 (aq) + H_2SO_4 (aq). Diels-Alder Reaction: Kinetic and Thermodynamic Control, Regiochemistry In The Diels-Alder Reaction, Electrocyclic Ring Opening And Closure (2) - Six (or Eight) Pi Electrons, Aromatic, Non-Aromatic, or Antiaromatic? The reaction can be preformed under acidic or basic conditions which will provide the same regioselectivity previously discussed. Question : 3. Draw the mechanism of the reaction shown. (10 pts) H2SO4 Propose an organic mechanism for the following reaction: Provide the reagents for the following reactions: Draw a plausible mechanism for the following reaction: 1) Show the mechanism for the following reaction: 2) What is the major product for the following reaction? Compound states [like (s) (aq) or (g)] are not required. Use H^+ to illustrate the mechanism. Use your graphing calculator's rref() function (or an online rref calculator) to convert the following matrix into reduced row-echelon-form: Simplify the result to get the lowest, whole integer values. The volume off oxygen can be obtained from the reaction is 1.4 . First, the oxygen is protonated, creating a good leaving group (step 1 below) . There are two electrophilic carbons in the epoxide, but the best target for the nucleophile in an SN2 reaction is the carbon that is least hindered. When an asymmetric epoxide undergoes alcoholysis in basic methanol, ring-opening occurs by an SN2 mechanism, and the less substituted carbon is the site of nucleophilic attack, leading to what we will refer to as product B: Conversely, when solvolysis occurs in acidic methanol, the reaction occurs by a mechanism with substantial SN1 character, and the more substituted carbon is the site of attack. Concerning the 4th picture (Elimination of alcohols with H2SO4 mechanism [E1]), why does water deprotonate the carbocation in step 3? If the epoxide is asymmetric, the structure of the product will vary according to which mechanism dominates. How To Determine Hybridization: A Shortcut, Sigma bonds come in six varieties: Pi bonds come in one, A Key Skill: How to Calculate Formal Charge, Partial Charges Give Clues About Electron Flow, The Four Intermolecular Forces and How They Affect Boiling Points, How To Use Electronegativity To Determine Electron Density (and why NOT to trust formal charge), How To Use Curved Arrows To Interchange Resonance Forms, Evaluating Resonance Forms (1) - The Rule of Least Charges, How To Find The Best Resonance Structure By Applying Electronegativity, Evaluating Resonance Structures With Negative Charges, Evaluating Resonance Structures With Positive Charge, In Summary: Evaluating Resonance Structures, Drawing Resonance Structures: 3 Common Mistakes To Avoid, How to apply electronegativity and resonance to understand reactivity, The Stronger The Acid, The Weaker The Conjugate Base, Walkthrough of Acid-Base Reactions (3) - Acidity Trends, Acid-Base Reactions: Introducing Ka and pKa, A Handy Rule of Thumb for Acid-Base Reactions, How Protonation and Deprotonation Affect Reactivity, Meet the (Most Important) Functional Groups, Condensed Formulas: Deciphering What the Brackets Mean, Hidden Hydrogens, Hidden Lone Pairs, Hidden Counterions, Primary, Secondary, Tertiary, Quaternary In Organic Chemistry, Branching, and Its Affect On Melting and Boiling Points, Wedge And Dash Convention For Tetrahedral Carbon, Common Mistakes in Organic Chemistry: Pentavalent Carbon, Table of Functional Group Priorities for Nomenclature, Organic Chemistry IUPAC Nomenclature Demystified With A Simple Puzzle Piece Approach, Staggered vs Eclipsed Conformations of Ethane, Newman Projection of Butane (and Gauche Conformation), Geometric Isomers In Small Rings: Cis And Trans Cycloalkanes, Calculation of Ring Strain In Cycloalkanes, Cycloalkanes - Ring Strain In Cyclopropane And Cyclobutane, Cyclohexane Chair Conformation: An Aerial Tour, How To Draw The Cyclohexane Chair Conformation, The Cyclohexane Chair Flip - Energy Diagram, Substituted Cyclohexanes - Axial vs Equatorial, Ranking The Bulkiness Of Substituents On Cyclohexanes: "A-Values". ; The best analogy is that it is a lot like the Markovnikov opening of . given that HSO4- is a week base too. Weve seen this type of process before actually! Reactants: 1. Since there is an equal number of each element in the reactants and products of 2CH3OH + H2SO4 = (CH3)2SO4 + 2H2O, the equation is balanced. Provide the synthesis of the following reaction. 18.6 Reactions of Epoxides: Ring-opening - Chemistry LibreTexts The nucleophile itself is potent: a deprotonated, negatively charged methoxide ion. Heres an example. Provide the synthesis of the following reaction. ethanol and a small amount of sodium hydroxide, ethanol and a small amount of sulfuric acid, Layne Morsch (University of Illinois Springfield). Master Organic Chemistry LLC, 1831 12th Avenue South, #171, Nashville TN, USA 37203, Copyright 2023, Master Organic Chemistry, Elimination Reactions Are Favored By Heat, Elimination Reactions (2): The Zaitsev Rule, Elimination (E1) Reactions With Rearrangements, Elimination (E1) Practice Problems And Solutions (MOC Membership). You can also ask for help in our chat or forums. If the epoxide is asymmetric the incoming hydroxide nucleophile will preferable attack the less substituted epoxide carbon. HSO,methyl hydrogen sulphate is obtained in first step.This on further treatment with another mole of methanol gives methoxy methane along with HSO. It *can* be true that rearrangements of tertiary carbocations occur, but generally only in situations where they would be more stabilized (e.g. Therefore the addition . (Remember stereochemistry). (15 points) Complete each of the following reactions by writing the missing part: either the necessary reagents and conditions or the structure of the expected major product: . I knew two chemical reactions of alcohol with sulfuric acid 1. Under the reaction conditions, I readily decomps. This reaction is known as continuous etherification reaction. For example in the case below the key step is where the C3-C4 bond breaks to form the C2-C4 bond, resulting in a new (tertiary) carbocation on C-3 as well as a less strained ring. The reaction is given below: CH 3CH 2OH conc.H 2SO 4170 oC C 2H 4. LiAlH4 and NaBH4 Carbonyl Reduction Mechanism - Chemistry Steps Draw the mechanism for the following reaction as seen below. The last column of the resulting matrix will contain solutions for each of the coefficients. Its also possible foralkyl shifts to occur to give a more stable carbocation. Predict the reaction. Draw an E1 mechanism for the following reaction. While oxygen is a poor leaving group, the ring strain of the epoxide really helps to drive this reaction to completion. Propose the mechanism for the following reaction. The solvent has two functions here: 1) It serves as the source of a proton (H +) once the reduction is complete. This is an electrophilic addition reaction. Alcohols can be transformed into ethers through acid catalyzed solvolysis reaction. Heat generally tends to favour elimination reactions.]. Show all steps. why elimination? Aldehydes and Ketones: 14 Reactions With The Same Mechanism, Sodium Borohydride (NaBH4) Reduction of Aldehydes and Ketones, Grignard Reagents For Addition To Aldehydes and Ketones, Imines - Properties, Formation, Reactions, and Mechanisms, Breaking Down Carbonyl Reaction Mechanisms: Reactions of Anionic Nucleophiles (Part2), Nucleophilic Acyl Substitution (With Negatively Charged Nucleophiles), Addition-Elimination Mechanisms With Neutral Nucleophiles (Including Acid Catalysis), Basic Hydrolysis of Esters - Saponification, Fischer Esterification - Carboxylic Acid to Ester Under Acidic Conditions, Lithium Aluminum Hydride (LiAlH4) For Reduction of Carboxylic Acid Derivatives, LiAlH[Ot-Bu]3 For The Reduction of Acid Halides To Aldehydes, Di-isobutyl Aluminum Hydride (DIBAL) For The Partial Reduction of Esters and Nitriles, Carbonyl Chemistry: Learn Six Mechanisms For the Price Of One, Carboxylic Acid Derivatives Practice Questions, Enolates - Formation, Stability, and Simple Reactions, Aldol Addition and Condensation Reactions, Reactions of Enols - Acid-Catalyzed Aldol, Halogenation, and Mannich Reactions, Claisen Condensation and Dieckmann Condensation, The Malonic Ester and Acetoacetic Ester Synthesis, The Amide Functional Group: Properties, Synthesis, and Nomenclature, Protecting Groups for Amines - Carbamates, Reactions of Diazonium Salts: Sandmeyer and Related Reactions, Pyranoses and Furanoses: Ring-Chain Tautomerism In Sugars, The Big Damn Post Of Carbohydrate-Related Chemistry Definitions, Converting a Fischer Projection To A Haworth (And Vice Versa), Reactions of Sugars: Glycosylation and Protection, The Ruff Degradation and Kiliani-Fischer Synthesis, Isoelectric Points of Amino Acids (and How To Calculate Them), A Gallery of Some Interesting Molecules From Nature. identify the product formed when an epoxide ring is opened by a hydrogen halide under anhydrous conditions. This accounts for the observed regiochemical outcome. A carbon-carbon triple bond may be located at any unbranched site within a carbon chain or at the end of a chain, in which case it is called terminal.Because of its linear configuration ( the bond angle of a sp-hybridized carbon is 180 ), a ten-membered carbon ring is the smallest that can accommodate this function without excessive strain. write an equation to illustrate the cleavage of an epoxide ring by a base. identify the product formed from the hydrolysis of an epoxide. All About Solvents, Common Blind Spot: Intramolecular Reactions, The Conjugate Base is Always a Stronger Nucleophile, Elimination Reactions (1): Introduction And The Key Pattern, E1 vs E2: Comparing the E1 and E2 Reactions, Antiperiplanar Relationships: The E2 Reaction and Cyclohexane Rings, E1cB - Elimination (Unimolecular) Conjugate Base, Elimination (E1) Practice Problems And Solutions, Elimination (E2) Practice Problems and Solutions, Rearrangement Reactions (1) - Hydride Shifts, Carbocation Rearrangement Reactions (2) - Alkyl Shifts, The SN1, E1, and Alkene Addition Reactions All Pass Through A Carbocation Intermediate, Identifying Where Substitution and Elimination Reactions Happen, Deciding SN1/SN2/E1/E2 (1) - The Substrate, Deciding SN1/SN2/E1/E2 (2) - The Nucleophile/Base, Deciding SN1/SN2/E1/E2 (4) - The Temperature, Wrapup: The Quick N' Dirty Guide To SN1/SN2/E1/E2, E and Z Notation For Alkenes (+ Cis/Trans), Addition Reactions: Elimination's Opposite, Regioselectivity In Alkene Addition Reactions, Stereoselectivity In Alkene Addition Reactions: Syn vs Anti Addition, Alkene Hydrohalogenation Mechanism And How It Explains Markovnikov's Rule, Arrow Pushing and Alkene Addition Reactions, Addition Pattern #1: The "Carbocation Pathway", Rearrangements in Alkene Addition Reactions, Alkene Addition Pattern #2: The "Three-Membered Ring" Pathway, Hydroboration Oxidation of Alkenes Mechanism, Alkene Addition Pattern #3: The "Concerted" Pathway, Bromonium Ion Formation: A (Minor) Arrow-Pushing Dilemma, A Fourth Alkene Addition Pattern - Free Radical Addition, Summary: Three Key Families Of Alkene Reaction Mechanisms, Palladium on Carbon (Pd/C) for Catalytic Hydrogenation, OsO4 (Osmium Tetroxide) for Dihydroxylation of Alkenes, Synthesis (4) - Alkene Reaction Map, Including Alkyl Halide Reactions, Acetylides from Alkynes, And Substitution Reactions of Acetylides, Partial Reduction of Alkynes With Lindlar's Catalyst or Na/NH3 To Obtain Cis or Trans Alkenes, Hydroboration and Oxymercuration of Alkynes, Alkyne Reaction Patterns - Hydrohalogenation - Carbocation Pathway, Alkyne Halogenation: Bromination, Chlorination, and Iodination of Alkynes, Alkyne Reactions - The "Concerted" Pathway, Alkenes To Alkynes Via Halogenation And Elimination Reactions, Alkyne Reactions Practice Problems With Answers, Alcohols Can Act As Acids Or Bases (And Why It Matters), Ethers From Alkenes, Tertiary Alkyl Halides and Alkoxymercuration, Epoxides - The Outlier Of The Ether Family, Alcohol Oxidation: "Strong" and "Weak" Oxidants, Demystifying The Mechanisms of Alcohol Oxidations, Intramolecular Reactions of Alcohols and Ethers, Calculating the oxidation state of a carbon, Oxidation and Reduction in Organic Chemistry, SOCl2 Mechanism For Alcohols To Alkyl Halides: SN2 versus SNi, Formation of Grignard and Organolithium Reagents, Grignard Practice Problems: Synthesis (1), Organocuprates (Gilman Reagents): How They're Made, Gilman Reagents (Organocuprates): What They're Used For, The Heck, Suzuki, and Olefin Metathesis Reactions (And Why They Don't Belong In Most Introductory Organic Chemistry Courses), Reaction Map: Reactions of Organometallics, Degrees of Unsaturation (or IHD, Index of Hydrogen Deficiency), Conjugation And Color (+ How Bleach Works), UV-Vis Spectroscopy: Absorbance of Carbonyls, Bond Vibrations, Infrared Spectroscopy, and the "Ball and Spring" Model, Infrared Spectroscopy: A Quick Primer On Interpreting Spectra, Diastereotopic Protons in 1H NMR Spectroscopy: Examples, Natural Product Isolation (1) - Extraction, Natural Product Isolation (2) - Purification Techniques, An Overview, Structure Determination Case Study: Deer Tarsal Gland Pheromone, Conjugation And Resonance In Organic Chemistry, Molecular Orbitals of The Allyl Cation, Allyl Radical, and Allyl Anion, Reactions of Dienes: 1,2 and 1,4 Addition, Cyclic Dienes and Dienophiles in the Diels-Alder Reaction, Stereochemistry of the Diels-Alder Reaction, Exo vs Endo Products In The Diels Alder: How To Tell Them Apart, HOMO and LUMO In the Diels Alder Reaction. Attack of water on the bridged intermediate gives 2-methyl-1-phenyl-2-ol, which then undergoes a normal dehydration to give 2-methyl-1-phenyl-1-propene. Chemical properties such as reactions with chlorine, HI, and oxidation reactions are also discussed. Why we use H2SO4 in case of alcohols reacting with HBr and that of we use H3PO4 in case of alcohols reacting with HI . Opening Epoxides With Aqueous Acid. (10 pts) H2SO4 CH3OH. Arrow-pushing Instructions no XT . Give the likely products of these reactions, and indicate whether methanol is acting in each as an acid or base. NaCN, 2. Balance the equation CH3OH + H2SO4 = (CH3)2SO4 + H2O using the algebraic method. Ap Chemistry, 2014-2015 Edition [PDF] [it0c02af2to0] In this reaction, the epoxide oxygen is protonated first, making it a better leaving group; In the second step, the nucleophile tends to attack the more substituted carbon, which breaks the weakest C-O bond. Show a detailed reaction mechanism for the following reaction. These solvents also act as nucleophiles. 2. Give the mechanism of the following reaction: Give a mechanism for the following reaction. Is it safe to say that otherwise, secondary alcohols can undergo both E1 and E2? In this reaction, the electrophile is SO3 formed as shown in the following equation. Phosphoric acid (H3PO4) as well as tosic acid (p-toluenesulfonic acid) also tend to form elimination products. What happens if you use two cis or trans OH in the educt? (a) Write the mechanism of the following reaction: - Toppr Ask Become a Study.com member to unlock this answer! If the alcohol is a primary or secondary alcohol, this can then be oxidized to an aldehyde or ketone, or onwards. Reacting Grignard reagents with ethylene oxide is a particuarly useful reaction because it produces a primary alcohol containing two more carbon atoms than the original Grignard reagent. This video describes the mechanism for the reaction between hydrochloric acid and methanol, using standard arrows to explain the "electron pushing". Alkyne Reactivity - Michigan State University An alkoxide is a poor leaving group (Section 11-3), and thus the ring is unlikely to open without a 'push' from the nucleophile. Correct option is A) When conc. Label Each Compound With a Variable. In the first step, the ethanoic acid takes a proton (a hydrogen ion) from the concentrated sulphuric acid. 2) The sodium ion is a weaker Lewis acid than the lithium ion and, in this case, the hydrogen bonding between the . it explains how to determine the major product or the most stable zaitsev product. Please draw it out and explain. (10 pts) H2SO4 CH3OH. Propose the mechanism of the following chemical reaction. The mass off water can be concluded from its number off molds off border, which can be obtained from the number of moves off oxygen by a psychometric reaction. This is the pattern of an elimination reaction. ; If a strong acid such as H 2 SO 4 or p-TsOH is used, the most likely result is . Please help. The reaction exists in an equilibrium condition and does not go to completion unless a product is removed as fast as it forms. So why do we get elimination reactions with H2SO4 as acid (or H3PO4, or TsOH) whereas we get substitution reactions with HCl, HBr, and HI? In the discussion on base-catalyzed epoxide opening, the mechanism is essentially SN2. The best way to depict the acid-catalyzed epoxide ring-opening reaction is as a hybrid, or cross, between an SN2 and SN1 mechanism. By this de nition, a large number of reactions can be classi ed as acid-base reactions. Elimination in the sense of this post refers to formation of a double bond. Thats made by adding HNO3 (as well as a bit of H2SO4) to the tri-ol glycerin, which leads to potentially explosive results. . identify the product formed from the reaction of a given epoxide with given base. Write a mechanism for the following reaction. Reactions of alcohol with sulfuric acid? | Wyzant Ask An Expert Acid Catalyzed Hydro-alkoxy Addition - Organic Chemistry | Socratic Both substitution and elimination reactions of alcohols can be catalyzed by acid. CrO3 H2SO4. Chapter 18: Ethers and Epoxides; Thiols and Sulfides, { "18.001_Introduction" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "18.01_Names_and_Properties_of_Ethers" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "18.02_Synthesis_of_Ethers" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "18.03_Reactions_of_Ethers:_Acidic_Cleavage" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "18.04_Reactions_of_Ethers_-_Claisen_Rearrangement" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "18.05_Cyclic_Ethers:_Epoxides" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "18.06_Reactions_of_Epoxides:_Ring-opening" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "18.07_Crown_Ethers" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "18.08_Thiols_and_Sulfides" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "18.09_Spectroscopy_of_Ethers" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "18.10_A_Preview_of_Carbonyl_Compounds" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "18.S:_Ethers_and_Epoxides;_Thiols_and_Sulfides_(Summary)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, { "00:_Front_Matter" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Chapter_17:_Alcohols_and_Phenols" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Chapter_18:_Ethers_and_Epoxides_Thiols_and_Sulfides" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Chapter_19:_Aldehydes_and_Ketones:_Nucleophilic_Addition_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Chapter_20:_Carboxylic_Acids_and_Nitriles" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Chapter_21:_Carboxylic_Acid_Derivatives:_Nucleophilic_Acyl_Substitution_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Chapter_22:_Carbonyl_Alpha-Substitution_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Chapter_23:_Carbonyl_Condensation_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Chapter_24:_Amines_and_Heterocycles" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Chapter_25:_Biomolecules:_Carbohydrates" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Chapter_26:_Biomolecules:_Amino_Acids_Peptides_and_Proteins" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Chapter_27:_Biomolecules_-_Lipids" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Chapter_28:_Biomolecules_-_Nucleic_Acids" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "zz:_Back_Matter" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, [ "article:topic", "showtoc:no", "license:ccbyncsa", "cssprint:dense", "licenseversion:40" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FCourses%2FAthabasca_University%2FChemistry_360%253A_Organic_Chemistry_II%2FChapter_18%253A_Ethers_and_Epoxides_Thiols_and_Sulfides%2F18.06_Reactions_of_Epoxides%253A_Ring-opening, \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\), Epoxide ring-opening reactions - SN1 vs. SN2, regioselectivity, and stereoselectivity, status page at https://status.libretexts.org.