There is overlap between the two when dehydration leads to formation of a double bond. If the epoxide is asymmetric, the structure of the product will vary according to which mechanism dominates. H_2SO_4, H_2O, What is the major product of this reaction? Reaction of Ether with Sulphuric Acid. Provide the synthesis of the following reaction. write an equation to describe the opening of an epoxide ring under mildly acidic conditions. So to edge too gives me two moles off Georgian, plus one more off water. Provide a mechanism of the following reaction: Provide a mechanism for the following reaction. Since there isnt a good nucleophile around, elimination occurs in such a way that the most substituted alkene is formed. Provide a mechanism for the following reaction shown below. Balance the equation C7H6O3 + CH3OH + H2SO4 = C9H8O4 + H2S using the algebraic method. William Reusch, Professor Emeritus (Michigan State U. just want to thankyou for this clear explanation. Attack takes place preferentially from the backside (like in an SN2 reaction) because the carbon-oxygen bond is still to some degree in place, and the oxygen blocks attack from the front side. Download scientific diagram | (a1) Cyclic voltammograms of catalysts in 1 M H2SO4 at a scan rate of 50 mV s and (a2) calculated ECSA values; (b1-b2) Mass activities of MOR in a mixture of 0.5 . Depict a stepwise mechanism for the following reaction. In this section, we introduce Lewis acids and bases and the use of curved arrows to show the mechanism of a Lewis acid-base reaction. Draw the major product for the following reaction. Propose a mechanism for the following reaction: Write the mechanism for the following reactions . Give the likely products of these reactions, and indicate whether methanol is acting in each as an acid or base. NO2 and Cl. Provide the mechanisms for the following reaction: Write a complete mechanism for the following reaction, Complete the following reaction: CHO H2SO4, Write a mechanism for the following reaction. When an asymmetric epoxide undergoes solvolysis in basic methanol, ring-opening occurs by an S . (Because sulfur is larger than oxygen, the ethyl sulde ion . [Protonation of alcohol, then loss of H2O to form a carbocation, then attack of nucleophile on carbocation]. It is OK to show the mechanism with H^+ instead of H_2SO_4. Note: Please keep in mind that for the reaction that involves carbocation intermediate, the rearrangement of carbocation is always an option. Hi James. ), Virtual Textbook ofOrganicChemistry. write an equation to illustrate the cleavage of an epoxide ring by a base. All other trademarks and copyrights are the property of their respective owners. Since there is an equal number of each element in the reactants and products of 2CH3OH + H2SO4 = (CH3)2SO4 + 2H2O, the equation is balanced. The answer is that theHSO4 anion is a very poor nucleophile, being quite stabilized by resonance. This reaction follows the same SN2 mechanism as the opening of epoxide rings under basic conditions since Grignard reagents are both strong nucleophiles and strong bases. The LibreTexts libraries arePowered by NICE CXone Expertand are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. First, the oxygen is protonated, creating a good leaving group (step 1 below) . Methanol - CH 3 OH. Count the number of atoms of each element on each side of the equation and verify that all elements and electrons (if there are charges/ions) are balanced. The Fischer esterification proceeds via a carbocation mechanism. During the ring-opening of an asymmetrical epoxide, the regiochemical control of the reaction usually allows for one stereoisomer to be produced. Write a mechanism for the following reaction. The reaction exists in an equilibrium condition and does not go to completion unless a product is removed as fast as it forms. Acid makes the OH a better leaving group, since the new leaving group will be the weaker base H2O, not HO(-). Create an equation for each element (C, H, O, S) where each term represents the number of atoms of the element in each reactant or product. Both substitution and elimination reactions of alcohols can be catalyzed by acid. What type of reaction is this? 58 reaction i.e. Indeed, larger cyclic ethers would not be susceptible to either acidcatalyzed or basecatalyzed cleavage under the same conditions because the ring strain is not as great as in the threemembered epoxide ring. Why Do H2SO4, H3PO4 and TsOH Give Elimination Products? 11 Bonding, 144 Lewis Electron-Dot Structures, 145 Ionic and Covalent Bonding, 145 Molecular GeometryVSEPR, 149 Valence Bond Theory, 151 Molecular Orbital Theory, 153 Resonance, 154 Bond Length, Strength, and Magnetic Properties, 155 Experimental, 155 Common Mistakes to Avoid, 155 Review Questions, 156 Rapid Review, 159 12 Solids, Liquids . Provide the mechanism for the following reaction: H2SO4, CH3OH, Heat. Your email address will not be published. This video describes the mechanism for the reaction between hydrochloric acid and methanol, using standard arrows to explain the "electron pushing". In the last example, E2 reaction with a primary alcohol, why does 2-butene (the more stable alkene) not formed from 1-butanol? ethanol and a small amount of sodium hydroxide, ethanol and a small amount of sulfuric acid, Layne Morsch (University of Illinois Springfield). Draw the mechanism of the reaction shown. The carboxyl carbon of the carboxylic acid is protonated. Hydrohalic Acids (HX) Plus Alcohols Give Substitution Products, Elimination of Tertiary Alcohols Proceeds Through an E1 Mechanism. Next Post: Elimination Of Alcohols To Alkenes With POCl3. Now lets ask: How could this have formed? The final class of alcohols to be concerned about is primary alcohols. The reaction is given below: CH 3CH 2OH conc.H 2SO 4170 oC C 2H 4. Provide the organic product of the following reaction or sequence of reactions: Deduce a stepwise mechanism for the following reaction. The H+ ions react with the water molecules to form the hydronium ions. [That carbon adjacent to the carbocation is often referred to as the (beta) carbon. Learn how your comment data is processed. Download Citation | Investigation of Cr-MIL-100 and Cr-MIL-101 activity and stability in amidation reaction of fatty acid methyl esters | Chromium containing metal-organic frameworks (MOFs) Cr . why elimination? We formed C-C () and broke C-OH and C-H. (We also formed H-O , in that molecule of water that formsas a byproduct). Legal. 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. Ring-opening reactions can proceed by either S N 2 or S N 1 mechanisms, depending on the nature of the epoxide and on the reaction conditions. These topics will be used again in Chapter 13, Organic Chemistry. When a nucleophilic substitution reaction involves a poor leaving group and a powerful nucleophile, it is very likely to proceed by an SN2 mechanism. evolution and absorption of heat respectively. NBS hv. Draw a mechanism for the following chemical reaction. There is! What is the electrophile? I would assume that secondary alcohols can undergo both E1 and E2 reactions. Predict the product and provide the mechanism for the following reaction. The balanced equation will appear above. Concerning the 4th picture (Elimination of alcohols with H2SO4 mechanism [E1]), why does water deprotonate the carbocation in step 3? HSO,methyl hydrogen sulphate is obtained in first step.This on further treatment with another mole of methanol gives methoxy methane along with HSO. The best way to depict the acid-catalyzed epoxide ring-opening reaction is as a hybrid, or cross, between an SN2 and SN1 mechanism. Recall that alkyl substituents can donate electron density through hyper conjugation and stabilize a positive charge on a carbon. For example, treatment of the alcohol below with H2SO4 leads to formation of a secondary carbocation, followed by a hydride shift to give a tertiary carbocation, followed by deprotonation at whichever carbon leads to the most substituted alkene. ; With tertiary alcohols, H 2 O can then leave, resulting in a carbocation. 6.11 (a) Being primary halides, the reactions are most likely to be S . This is an E1 process[elimination (E) , unimolecular (1) rate determining step]. The loss of water from 3 may be stepwise but, to save space, I have presented the loss of water in a single operation. All rights reserved. sorry I put my e mail wrong, posting my question again. 3. Get more out of your subscription* Access to over 100 million course-specific study resources; 24/7 help from Expert Tutors on 140+ subjects; Full access to over 1 million Textbook Solutions In the diagram below, note how that negative charge is delocalized over three different oxygens [the same is true for the TsO and H2PO4 anions]. Required fields are marked *. For example, C6H5C2H5 + O2 = C6H5OH + CO2 + H2O will not be balanced, but XC2H5 + O2 = XOH + CO2 + H2O will. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. Predict the product and provide the complete mechanism for the following below reaction. Very reasonable to propose. Save my name, email, and website in this browser for the next time I comment. Here is the reaction off. Monochlorination Products Of Propane, Pentane, And Other Alkanes, Selectivity in Free Radical Reactions: Bromination vs. Chlorination, Types of Isomers: Constitutional Isomers, Stereoisomers, Enantiomers, and Diastereomers, Introduction to Assigning (R) and (S): The Cahn-Ingold-Prelog Rules, Assigning Cahn-Ingold-Prelog (CIP) Priorities (2) - The Method of Dots, Enantiomers vs Diastereomers vs The Same? When both the epoxide carbons are either primary or secondary the halogen anion will attack the less substituted carbon through an SN2 like reaction. Reactants. 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. why. Draw the mechanism of the following reaction: Draw a mechanism for the following reaction. please help me draw the structure. Balance CH3OH + H2SO4 = (CH3)2SO4 + H2O by inspection or trial and error with steps. What happens if you use two cis or trans OH in the educt? (Remember stereochemistry). Epoxides can undergo ring-opening with nucleophiles under acidic conditions. Thank you for your keen eye, as always! and the ion of an acid. N2O and CN. Markovnikov's Rule is a useful guide for you to work out which way round to add something across a double bond, but it . Epoxides may be cleaved by aqueous acid to give glycols that are often diastereomeric with those prepared by the syn-hydroxylation reaction described above. To balance a chemical equation, enter an equation of a chemical reaction and press the Balance button. identify the product formed from the reaction of a given epoxide with given base. Not conventional E2 reactions. The acid such as sulfuric acid makes the hydroxyl group a better leaving group by protonating it. CH3OH + H2SO4 = (CH3)2SO4 + H2O might be a redox reaction. Label Each Compound With a Variable. 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 reaction between the keto form of acetone 1a and its enol 1b forms aldol 2. Then the carbon-oxygen bond begins to break (step 2) and positive charge begins to build up on the more substituted carbon. The ions from the acids H2SO4 and HNO3 are SO42, NO3. If we add a strong base here (to perform an E2) it will just end up neutralizing this species. So far weve learned two ways to convert alcohols to alkenes: Ideally, wed like to just use one step. Step 2: Methanol reacts with the carbocation. If an acid name has the suffix ic, the ion of this acid has a name with the suffix ate. Your email address will not be published. HEAT CAPACITY Heat capacity is the quantity of heat required to raise the temperature by one degree Celsius . Cyclohexane Chair Conformation Stability: Which One Is Lower Energy? For that reason we usually just stick to H2SO4 or H3PO4! S N 1 Reaction Mechanism. Label each compound (reactant or product) in the equation with a variable to represent the unknown coefficients. After deprotonation to reform the acid catalyst a 1,2-diol product is formed. Under the reaction conditions, I readily decomps. Free Radical Initiation: Why Is "Light" Or "Heat" Required? Not in one step. identify the product formed from the reaction of a given epoxide with given base. The Hg(II) ion reacts with CH4 by an electrophilic displacement mechanism to produce an observable species, MeHgOSO3H (I). 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. 2 CH_3CH_2CH_2OH and H_2SO_4 at 140 degrees C. What is the major product of the following reaction? In this reaction, the electrophile is SO3 formed as shown in the following equation. Explain the reaction mechanism for the following reaction: What products would you obtain from reaction of 1-methylcyclohexanol with the following reagents? If the alcohol is a primary or secondary alcohol, this can then be oxidized to an aldehyde or ketone, or onwards. In what cases does rearrangement take place ? Concentrated HNO3 contains some NO2+ which is an excellent electrophile, which the alcohol can add to, leading to R-ONO2 . Provide a reasonable mechanism for the following reaction: Write a mechanism for the following reaction. Two Methods For Solving Problems, Assigning R/S To Newman Projections (And Converting Newman To Line Diagrams), How To Determine R and S Configurations On A Fischer Projection, Optical Rotation, Optical Activity, and Specific Rotation, Stereochemistry Practice Problems and Quizzes, Introduction to Nucleophilic Substitution Reactions, Walkthrough of Substitution Reactions (1) - Introduction, Two Types of Nucleophilic Substitution Reactions, The Conjugate Acid Is A Better Leaving Group, Polar Protic? In a regioselective reaction, two (or more) different constitutional isomers are possible as products, but one is formed preferentially (or sometimes exclusively). What would be the elimination product of 2-methyl-2-phenylpropan-1-ol? it explains how to determine the major product or the most stable zaitsev product. Write a complete mechanism for the following reaction. Please provide the products and mechanism of the following reaction. Be sure to include proper stereochemistry. c. 57. Use H^+ to illustrate the mechanism. Hi James, If I got any doubt in organic chemistry, I look upto your work. Can alcohols undergo an E2 reaction? 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? Write the plausible reaction mechanism of the following reaction: 1-methyl-1-cyclohexanol + H_2SO_4 with heat to, Give the product of the following reaction: MaCO_3 (s) + H_2SO_4 (aq) to. The third unit of acetone is incorporated via the vinylogous enol 4b to . If the epoxide is asymmetric, the structure of the product will vary according to which mechanism dominates. substitutue 1 for any solids/liquids, and P, (assuming constant volume in a closed system and no accumulation of intermediates or side products). Write the stepwise mechanism for sulfonation of benzene by hot, concentrated sulfuric acid. Read our article on how to balance chemical equations or ask for help in our chat. Since it requires deprotonation to create a better leaving group, I would think not but Im not sure. Answer (1 of 7): Agree with Dr. Luong, however I'd note two points: (1) that the reaction is preferably called an elimination, rather than a dehydration, although I personally like the term dehydration because it emphasizes the strong dehydrating power of H2SO4 that is unfotunately forgotten t. Alkenes react with concentrated sulphuric acid in the cold to produce alkyl hydrogensulphates. In a regioselective reaction, two (or more) different constitutional isomers are possible as products, but one is formed preferentially (or sometimes exclusively). Evidence for the formation of methyl hydrogen sulfate (MHS) was obtained by the presence of a new peak in the 800 cm-1 region, not present in either the neat methanol or concentrated sulfuric acid spectra. identify the product formed from the hydrolysis of an epoxide. Provide a detailed mechanism of the following reaction sequence. Epoxides may be cleaved by hydrolysis to give trans-1,2-diols (1,2 diols are also called vicinal diols or vicinal glycols). (15 points) Write a complete mechanism for the reactions shown below. 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). The sulfonation of an aromatic ring with SO_3 and H_2SO_4 is reversible. Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. Note: No effect on tertiary alcohols: Na2Cr2O7 . 100% (5 ratings) Transcribed image text: Reaction of propene with CH3OH in the presence of H2SO4 catalyst yields 2-methoxypropane by a mechanism analogous to that of acid catalyzed alkene hydration Draw curved arrows to show the movement of electrons in this step of the reaction mechanism. Balance the equation CH3OH + H2SO4 = (CH3)2SO4 + H2O using the algebraic method. Is there a way to convert a diol to alkene from ways mentioned above? Reactants: 1. CH3OH + H2SO4 + (NH4)2SO4 = C8H6N2OS2 + H2O + O2, CH3OH + H2SO4 + BO2 = B(OCH3) + H2O + SO4, CH3OH + H2SO4 + C2H6O = (CH3)2(C2H5)2SO3 + H2O, CH3OH + H2SO4 + CH4N2O + H3PO4 + C2H5OH = C5H12NO3PS2 + H2O, CH3OH + H2SO4 + CH4N2O + H3PO4 = C5H12NO3PS2 + CO2 + H2O, CH3OH + H2SO4 + CON2H4 = C12H17N4OS + CO2 + H2O, H8N2O4S + Ba(C2H3O2)2 = BaO4S + NH4C2H3O2, KMnO4 + H2O2 + H2SO4 = MnSO2 + K2SO4 + H2OO2. Mixed ethers under similar conditions give a mixture of alcohols. Provide the synthesis of the following reaction. An acid catalyzed hydro-alkoxy addition is the addition of an alcohol to a C=C double bond to form an ether.. An example is the addition of methanol to 2-methylpropene to form t-butyl methyl ether.. Step 3: Deprotonation to get neutral product. The leaving group is an alkoxide anion, because there is no acid available to protonate the oxygen prior to ring opening. predict the major product from the acidic cleavage of a given unsymmetrical epoxide. Question: 3. The electrons, from the. Scroll down to see reaction info, how-to steps or balance another equation. H2O is a good leaving group and primary carbon is not hindered, a perfect recipe for SN2. Acid-catalyzed dehydration of 2 via the enol 3 leads to mesityl oxide 4. As with all elimination reactions, there are two things to watch out for: first, the most substituted alkene (Zaitsev) will be the dominant product, and also, dont forget that trans alkenes will be favoured (more stable) than cis alkenes due to less steric strain. Provide the mechanism for the reaction below. 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? Predict the reaction. Dont know why that comment didnt post. HO Na2Cr207 H2SO4 /H20. why not a SN2 reaction after protonation of primary alcohols??? The air-water counterflowing heat exchanger given in earlier problem has an air exit temperature of 360 K 360 \mathrm{~K} 360 K.Suppose the air exit temperature is listed as 300 K 300 \mathrm{~K} 300 K; then a ratio of the mass flow rates is found from the energy equation to be 5 5 5.Show that this is an impossible process by looking at air and water temperatures at several locations inside . The last column of the resulting matrix will contain solutions for each of the coefficients. Reactants are H2SO4 and heat. Given the following, predict the product assuming only the epoxide is affected. The catalytic cycle is completed by the reoxidn. A wide variety of basic nucleophiles can be used for the ring opening of an epoxide including, amines, hydrides, Grignard reagents, acetylide anions, and hydride. It is OK to show the mechanism with H^+ instead of H_2SO_4. ch3oh h2so4 reaction mechanism. The Third Most Important Question to Ask When Learning A New Reaction, 7 Factors that stabilize negative charge in organic chemistry, 7 Factors That Stabilize Positive Charge in Organic Chemistry, Common Mistakes: Formal Charges Can Mislead, Curved Arrows (2): Initial Tails and Final Heads, Three Factors that Destabilize Carbocations, Learning Organic Chemistry Reactions: A Checklist (PDF), Introduction to Free Radical Substitution Reactions, Introduction to Oxidative Cleavage Reactions, Bond Dissociation Energies = Homolytic Cleavage. The best way to depict the acid-catalyzed epoxide ring-opening reaction is as a hybrid, or cross, between an S N 2 and S N 1 mechanism. Dilute HNO3 by itself is probably fine. Label each compound (reactant or product) in the equation with a variable . Provide the reagents that are required to complete the following reaction mechanism for the following product. thank you so much for these information but i have a small question is there a difference between Elimination and dehydration ?? It covers the E1 reaction where an alcohol is convert. By no means is H2SO4 the only acid that does this. Redox (Oxidation-Reduction) Reaction. What is the best mechanism for the following reaction? Predict the product of the reaction: C_6H_6NH_2 reacts with H_2SO_4. CH3CH2OH + H2SO4 -> C2H5OC2H5 Here product is ether an happens at 413 K temperature. Ethene reacts to give ethyl hydrogensulphate. Predict the products from the reaction of 5-decyne with H_2O, H_2SO_4, HgSO_4. Draw the major organic product formed by the reaction of 2-hexyne with the following reagent: H_2O in H_2SO_4/HgSO_4. Greenwood & Earnshaw note the following species present in pure sulfuric acid (in order of decreasing abundance, with $\ce{H2SO4}$ itself being the solvent): $\ce{HSO4 . Alcohols can be transformed into ethers through acid catalyzed solvolysis reaction. Thats made by adding HNO3 (as well as a bit of H2SO4) to the tri-ol glycerin, which leads to potentially explosive results. Draw the mechanism of the reaction shown. It *can* be true that rearrangements of tertiary carbocations occur, but generally only in situations where they would be more stabilized (e.g. I need to know, Does primary alcohols on acid catalysed elimination produces any rearranged products. After completing this section, you should be able to. Predict the product for the following reaction. Notice, however, how the regiochemical outcome is different from the base-catalyzed reaction: in the acid-catalyzed process, the nucleophile attacks the more substituted carbon because it is this carbon that holds a greater degree of positive charge. Its somewhat possible that you might get some epoxide formation, or even formation of a ketone/aldehyde. The nucleophile itself is potent: a deprotonated, negatively charged methoxide ion. Heat generally tends to favour elimination reactions. Reaction (2) because the ethyl sulde ion is a stronger nucleophile than the ethoxide ion in a protic solvent. Ring-opening reactions can proceed by either SN2 or SN1 mechanisms, depending on the nature of the epoxide and on the reaction conditions. Step 1: Electrophilic attack of H 3 O + to the alkene, carbocation intermediate formed. Previously (See post: Making Alkyl Halides from Alcohols) we saw that treating an alcohol with a strong hydrohalic acid think HCl, HBr, or HI resulted in the formation of alkyl halides. CH3OH: Note: NaBH4 is not strong enough to reduce . A: The addition of Cl2 to an alkyne is analogous to adding Cl2 to an alkene. A: The Grignard reaction is an organometallic chemical reaction in which alkyl, allyl, vinyl, or question_answer Q: Propose a mechanism for the following reaction: If . This lesson introduces the organic functional group ethers, and ethers' preparation from an alkoxide ion. Is that true only if a secondary carbocation can rearrange to give a tertiary? The nonenzymatic ring-opening reactions of epoxides provide a nice overview of many of the concepts we have seen already in this chapter. What's The Alpha Carbon In Carbonyl Compounds? As a result, product A predominates. Provide the mechanism for the following esterification reaction. 18: Ethers and Epoxides; Thiols and Sulfides, { "18.00:_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:_Preparing_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:_Interchapter-_A_Preview_of_Carbonyl_Chemistry" : "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]()", "01:_Structure_and_Bonding" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "02:_Polar_Covalent_Bonds_Acids_and_Bases" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "03:_Organic_Compounds-_Alkanes_and_Their_Stereochemistry" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "04:_Organic_Compounds-_Cycloalkanes_and_their_Stereochemistry" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "05:_Stereochemistry_at_Tetrahedral_Centers" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "06:_An_Overview_of_Organic_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "07:_Alkenes-_Structure_and_Reactivity" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "08:_Alkenes-_Reactions_and_Synthesis" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "09:_Alkynes_-_An_Introduction_to_Organic_Synthesis" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "10:_Organohalides" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "11:_Reactions_of_Alkyl_Halides-_Nucleophilic_Substitutions_and_Eliminations" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "12:_Structure_Determination_-_Mass_Spectrometry_and_Infrared_Spectroscopy" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13:_Structure_Determination_-_Nuclear_Magnetic_Resonance_Spectroscopy" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "14:_Conjugated_Compounds_and_Ultraviolet_Spectroscopy" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "15:_Benzene_and_Aromaticity" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "16:_Chemistry_of_Benzene_-_Electrophilic_Aromatic_Substitution" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "17:_Alcohols_and_Phenols" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "18:_Ethers_and_Epoxides_Thiols_and_Sulfides" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "19:_Aldehydes_and_Ketones-_Nucleophilic_Addition_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "20:_Carboxylic_Acids_and_Nitriles" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "21:_Carboxylic_Acid_Derivatives-_Nucleophilic_Acyl_Substitution_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22:_Carbonyl_Alpha-Substitution_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "23:_Carbonyl_Condensation_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "24:_Amines_and_Heterocycles" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "25:_Biomolecules-_Carbohydrates" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "26:_Biomolecules-_Amino_Acids_Peptides_and_Proteins" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "27:_Biomolecules_-_Lipids" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "28:_Biomolecules_-_Nucleic_Acids" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Chapter_30:_Orbitals_and_Organic_Chemistry_-_Pericyclic_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Chapter_31:_Synthetic_Polymers" : "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]()" }, 18.6: Reactions of Epoxides- Ring-opening, [ "article:topic", "showtoc:no", "license:ccbysa", "source[1]-chem-61701", "licenseversion:40", "author@Steven Farmer", "author@Dietmar Kennepohl" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FOrganic_Chemistry_(Morsch_et_al.