Youd be forgiven forthinking that if we treated an alcohol with H2SO4 (sulfuric acid) the same type of thing would occur, and the carbocation would be attacked by the (-)OSO3H anion to make the product below. Proton transfer from the acid catalyst generates the conjugate acid of the epoxide, which is attacked by nucleophiles such as water in the same way that the cyclic bromonium ion described above undergoes reaction. Compare that to halide anions, where the negative charge cannot be spread over more than one atom. 8. Predict the major product(s) of the ring opening reaction that occurs when the epoxide shown below is treated with: Hint: be sure to consider both regiochemistry and stereochemistry! Depends on the structure of the substrate. Provide the organic product of the following reaction or sequence of reactions: Deduce a stepwise mechanism for the following reaction. What would be the elimination product of 2-methyl-2-phenylpropan-1-ol? ; With tertiary alcohols, H 2 O can then leave, resulting in a carbocation. Provide a mechanism of the following reaction: Provide a mechanism for the following reaction. Redox (Oxidation-Reduction) Reaction. how often are general elections held in jamaica; allison transmission service intervals; hays county housing authority; golden dipt breading recipe; measuring communication effectiveness ppt; kim coles child; door county cherry vodka recipes; S N 1 Reaction Mechanism. write an equation to describe the opening of an epoxide ring under mildly acidic conditions. The last column of the resulting matrix will contain solutions for each of the coefficients. (Because sulfur is larger than oxygen, the ethyl sulde ion . If the epoxide is asymmetric, the structure of the product will vary according to which mechanism dominates. WOULD YOU MIND TELLING ME THE MECHANISM OF ALCOHOL and Me2C(OMe)2 and p-TsOH(CATALYST)?Thanks in advance, Its a way of forming a cyclic acetonide from a diol. Base makes the OH a better nucleophile, since RO(-) is a better nucleophile than the neutral alcohol ROH. Ring-opening reactions can proceed by either SN2 or SN1 mechanisms, depending on the nature of the epoxide and on the reaction conditions. Draw an E1 mechanism for the following reaction. Same deal as with tertiary alcohols: expect an alkene to form. document.getElementById( "ak_js_1" ).setAttribute( "value", ( new Date() ).getTime() ); This site uses Akismet to reduce spam. Which is the product of the reaction of 1-methylcyclohexene with H2O/H2SO4? There is a catch however: the E1 pathway (formation of a primary carbocation) is not the most likely pathway here. Predict the product of the following reaction. The nucleophile itself is potent: a deprotonated, negatively charged methoxide ion. Label each compound (reactant or product) in the equation with a variable to represent the . CuO + H2SO4 arrow. Save my name, email, and website in this browser for the next time I comment. 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. This is an electrophilic addition reaction. This would be an example of anchimeric assistance (neighboring group participation). (15 points) Write a complete . Alcohols can be transformed into ethers through acid catalyzed solvolysis reaction. 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. Famous What Is The Product Of The Following Reaction Ch3Oh H+ References . HO Na2Cr207 H2SO4 /H20. This is an E1 process[elimination (E) , unimolecular (1) rate determining step]. Select Draw Ring H CI CH;CH,C=CCH, CH, + 2Cl, . However, there is a reaction called the Corey-Winter reaction that will reduce diols to alkenes. Free Radical Initiation: Why Is "Light" Or "Heat" Required? Not in one step. If the epoxide is asymmetric, the structure of the product will . First, NaBH4 is not so reactive and the reaction is usually carried out in protic solvents such as ethanol or methanol. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. But strong acid can lead to complications (carbocation rearrangements, cough cough) and we might ask: isnt there an easier way? Ethene reacts to give ethyl hydrogensulphate. Recall that alkyl substituents can donate electron density through hyper conjugation and stabilize a positive charge on a carbon. Reactants are H2SO4 and heat. With a tertiary alcohol like the one drawn below, this proceeds through an SN1 mechanism. Then the carbon-oxygen bond begins to break (step 2) and positive charge begins to build up on the more substituted carbon. Is it safe to say that otherwise, secondary alcohols can undergo both E1 and E2? These are both good examples of regioselective reactions. The reaction between the keto form of acetone 1a and its enol 1b forms aldol 2. Loss of H2O to form a carbocation followed by elimination will be the favoured pathway. HSO,methyl hydrogen sulphate is obtained in first step.This on further treatment with another mole of methanol gives methoxy methane along with HSO. As we saw with the reactions of HCl, HBr, and HI with secondary alcohols, Elimination Of Alcohols To Alkenes With POCl, Valence Electrons of the First Row Elements, How Concepts Build Up In Org 1 ("The Pyramid"). This video describes the mechanism for the reaction between hydrochloric acid and methanol, using standard arrows to explain the "electron pushing". tertiary carbocation to a resonance-stabilized tertiary carbocation ). Why Do H2SO4, H3PO4 and TsOH Give Elimination Products? Reactions. It covers the E1 reaction where an alcohol is converted into an alkene. Maybe they should call them, "Formal Wins" ? 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. Probably the best way to depict the acid-catalyzed epoxide ring-opening reaction is as a hybrid, or cross, between an SN2 and SN1 mechanism. . According to the following reaction, which molecule is acting as an acid? Be sure to include proper stereochemistry. The reaction exists in an equilibrium condition and does not go to completion unless a product is removed as fast as it forms. Note: No effect on tertiary alcohols: Na2Cr2O7 . Balance the equation CH3OH + H2SO4 = (CH3)2SO4 + H2O using the algebraic method. Show the final product for the reaction using H2SO4 and Heat. The carbocation itself is the (alpha) carbon]. So far weve learned two ways to convert alcohols to alkenes: Ideally, wed like to just use one step. If a more stable carbocation can be formed through migration of an adjacent hydride (H- ) or an alkyl group, then that migration will occur. 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. For that reason we usually just stick to H2SO4 or H3PO4! 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. In this mechanism, an alcohol is added to a carboxylic acid by the following steps: 1. Like in other SN2 reactions, nucleophilic attack takes place from the backside, resulting in inversion at the electrophilic carbon. Required fields are marked *. couldnt find the answer anywhere until i stumbled on this page. When an asymmetric epoxide undergoes solvolysis in basic methanol, ring-opening occurs by an S . write the mechanism for the opening of an epoxide ring by an aqueous acid, paying particular attention to the stereochemistry of the product. Video transcript. N1 mechanism because it is a tertiary alkyl halide, whereas (a) is primary and (b) is secondary. Complete and write a mechanism for the following reaction. CH3OH + H2SO4 = (CH3)2SO4 + H2O might be a redox reaction. why. Cyclohexane Chair Conformation Stability: Which One Is Lower Energy? Unlike in an SN1 reaction, the nucleophile attacks the electrophilic carbon (step 3) before a complete carbocation intermediate has a chance to form. The reaction can be preformed under acidic or basic conditions which will provide the same regioselectivity previously discussed. Hi James, If I got any doubt in organic chemistry, I look upto your work. Heat generally tends to favour elimination reactions. 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: Yes, alkenes can be formed this way (along with some formation of symmetrical ethers[see this previous post]). 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. For example, C6H5C2H5 + O2 = C6H5OH + CO2 + H2O will not be balanced, but XC2H5 + O2 = XOH + CO2 + H2O will. Reactants: 1. When both the epoxide carbons are either primary or secondary the halogen anion will attack the less substituted carbon and an SN2 like reaction. 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). and the ion of an acid. The str. A. a proton transfer followed by a nucleophilic attack. The second step of the mechanism involves the protonation of the alkoxide to form an alcohol. 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. Thats what well cover in the next post. HEAT CAPACITY Heat capacity is the quantity of heat required to raise the temperature by one degree Celsius . Provide the mechanism of the following reaction. Please show the mechanism of the following reactions. Write a mechanism for the following reaction. Is this a beta elimination reaction?? Draw the major organic product formed by the reaction of 2-hexyne with the following reagent: H_2O in H_2SO_4/HgSO_4. 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? Provide the mechanism for the reaction below. Then the carbon-oxygen bond begins to break (step 2) and positive charge begins to build up on the more substituted carbon (recall the discussion from section 8.4B about carbocation stability). Another problem with alcohols: youve heard of nitroglycerin? By this de nition, a large number of reactions can be classi ed as acid-base reactions. Since there isnt a good nucleophile around, elimination occurs in such a way that the most substituted alkene is formed. Write the stepwise mechanism for sulfonation of benzene by hot, concentrated sulfuric acid. CH3CH2OH + H2SO4 -> CH2CH2 Here product is having a double bond (ethene) and this reaction happens at 443 K temperature. Not conventional E2 reactions. Next Post: Elimination Of Alcohols To Alkenes With POCl3. Migration of Ph- is faster than R- but will lead to a less stable intermediate and vice versa. 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. Some Practice Problems, Antiaromatic Compounds and Antiaromaticity, The Pi Molecular Orbitals of Cyclobutadiene, Electrophilic Aromatic Substitution: Introduction, Activating and Deactivating Groups In Electrophilic Aromatic Substitution, Electrophilic Aromatic Substitution - The Mechanism, Ortho-, Para- and Meta- Directors in Electrophilic Aromatic Substitution, Understanding Ortho, Para, and Meta Directors, Disubstituted Benzenes: The Strongest Electron-Donor "Wins", Electrophilic Aromatic Substitutions (1) - Halogenation of Benzene, Electrophilic Aromatic Substitutions (2) - Nitration and Sulfonation, EAS Reactions (3) - Friedel-Crafts Acylation and Friedel-Crafts Alkylation, Nucleophilic Aromatic Substitution (2) - The Benzyne Mechanism, Reactions on the "Benzylic" Carbon: Bromination And Oxidation, The Wolff-Kishner, Clemmensen, And Other Carbonyl Reductions, More Reactions on the Aromatic Sidechain: Reduction of Nitro Groups and the Baeyer Villiger, Aromatic Synthesis (1) - "Order Of Operations", Synthesis of Benzene Derivatives (2) - Polarity Reversal, Aromatic Synthesis (3) - Sulfonyl Blocking Groups, Synthesis (7): Reaction Map of Benzene and Related Aromatic Compounds, Aromatic Reactions and Synthesis Practice, Electrophilic Aromatic Substitution Practice Problems. When a nucleophilic substitution reaction involves a poor leaving group and a powerful nucleophile, it is very likely to proceed by an SN2 mechanism. Predict the products from the reaction of 1-hexyne with H_2O, H_2SO_4, HgSO_4. Was just wondering if HNO3 would cause the same reaction to occur as H2SO4 or H3PO4 (an E1 rxn)? Chemical properties such as reactions with chlorine, HI, and oxidation reactions are also discussed. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. As a result, product A predominates. Learn how your comment data is processed. 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? How Do We Know Methane (CH4) Is Tetrahedral? predict the major product from the acidic cleavage of a given unsymmetrical epoxide. ; The best analogy is that it is a lot like the Markovnikov opening of . This lesson introduces the organic functional group ethers, and ethers' preparation from an alkoxide ion. Give the mechanism of the following reaction: Give a mechanism for the following reaction. 2) The sodium ion is a weaker Lewis acid than the lithium ion and, in this case, the hydrogen bonding between the . However, if the epoxide is symmetrical, each epoxide carbon has roughly the same ability to accept the incoming nucleophile. Show the mechanism of the desulfonation reaction. The carbon-bromine bond is a polar covalent bond. First, the oxygen is protonated, creating a good leaving group (step 1 below). You might ask: if we treat a primary alcohol (say, 1-butanol) with a strong acid like H2SO4, will also get elimination to an alkene? Write detailed mechanisms for the following reaction. The volume off oxygen can be obtained from the reaction is 1.4 . Further information about equation CH 3 OH + H 2 O + H 2 SO 4 + C 2 H 3 CN NH 4 HSO 4 + C 2 H 3 COOCH 3 What is reaction condition of CH3OH (methanol) reacts with H2O (water) reacts with H2SO4 (sulfuric acid) reacts with C2H3CN (Ventox; Acritet; Acrylon; Carbacryl; Fumigrain; Acrylonitrile; Cyanoethylene; Vinyl cyanide; 2-Propenenitrile; TL-314; RCRA waste number U-009; ENT-54; VCN; 2-1513 . Polar Aprotic? Both substitution and elimination reactions of alcohols can be catalyzed by acid. 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. As a result, product A predominates. Unlike in an SN1 reaction, the nucleophile attacks the electrophilic carbon (step 3) before a complete carbocation intermediate has a chance to form. 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. )%2F18%253A_Ethers_and_Epoxides_Thiols_and_Sulfides%2F18.06%253A_Reactions_of_Epoxides-_Ring-opening, \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\), Basic Epoxide Ring-Opening by Alcoholysis, Acid-Catalyzed Epoxide Ring-Opening by Alcoholysis, Epoxide Ring-Opening by Other Basic Nucleophiles, Additional Stereochemical Considerations of Ring-Opening, status page at https://status.libretexts.org. It *can* be true that rearrangements of tertiary carbocations occur, but generally only in situations where they would be more stabilized (e.g. Predict the product of the reaction: C_6H_6NH_2 reacts with H_2SO_4. 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. Balance CH3OH + H2SO4 = (CH3)2SO4 + H2O by inspection or trial and error with steps. There is overlap between the two when dehydration leads to formation of a double bond. If you see a primary alcohol with H2SO4, TsOH, or H3PO4, expect symmetrical ether formation accompanied by elimination to form the alkene. The transfer of the proton to the oxygen gives it a positive charge, but it is actually misleading to draw the structure in . In a regioselective reaction, two (or more) different constitutional isomers are possible as products, but one is formed preferentially (or sometimes exclusively). 2 CH_3CH_2CH_2OH and H_2SO_4 at 140 degrees C. What is the major product of the following reaction? Please help. 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]. You can also ask for help in our chat or forums. For example, C 2 H 5 OC 2 H 5 + H 2 O ---- ( dil.H2so4,high pressure )-----> 2C 2 H 5 OH. During the ring-opening of an asymmetrical epoxide, the regiochemical control of the reaction usually allows for one stereoisomer to be produced. 18.6: Reactions of Epoxides- Ring-opening is shared under a CC BY-SA 4.0 license and was authored, remixed, and/or curated by Steven Farmer & Dietmar Kennepohl. This Organic Chemistry video tutorial discusses the alcohol dehydration reaction mechanism with H2SO4. Information about the equation, such as the type of reaction may also be calculated. https://en.wikipedia.org/wiki/Acetonide. What about the electrophile? 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. The first step of the mechanism of this reaction involves the SN2 attack of the Grignard reaction to open the epoxide to form an alkoxide. Answer (1 of 4): when methanol is heated with conc. Please provide the products and mechanism of the following reaction. A compound with two OH groups attached to the same carbon is known as ______. identify the product formed when an epoxide ring is opened by a hydrogen halide under anhydrous conditions. 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. Is that true only if a secondary carbocation can rearrange to give a tertiary? Click hereto get an answer to your question (a) Write the mechanism of the following reaction: 2CH3CH2OH H^+CH3CH2 - O - CH2CH3 (b) Write the equation involved in the acetylation of salicyclic acid While oxygen is a poor leaving group, the ring strain of the epoxide really helps to drive this reaction to completion. If Kw = 1.0 x 10^-14 then shouldnt the formation of H3O+ be very unfavorable? Explain the reaction mechanism for the following reaction: What products would you obtain from reaction of 1-methylcyclohexanol with the following reagents?