ch3oh h2so4 reaction mechanism

The broadest de nition of acids and bases is that of Lewis. For example, C 2 H 5 OC 2 H 5 + H 2 O ---- ( dil.H2so4,high pressure )-----> 2C 2 H 5 OH. It is OK to show the mechanism with H^+ instead of H_2SO_4. 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. Compare that to halide anions, where the negative charge cannot be spread over more than one atom. Your email address will not be published. The epoxide oxygen forms an alkoxide which is subsequently protonated by water forming the 1,2-diol product. If you see a primary alcohol with H2SO4, TsOH, or H3PO4, expect symmetrical ether formation accompanied by elimination to form the alkene. Predict the product and provide the mechanism for the following reaction. CH 3OH 2 Provide the mechanism for the given reaction. Give the likely products of these reactions, and indicate whether methanol is acting in each as an acid or base. Both substitution and elimination reactions of alcohols can be catalyzed by acid. Free Radical Initiation: Why Is "Light" Or "Heat" Required? Dilute HNO3 by itself is probably fine. 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 . Write the mechanism of the following reaction. If the epoxide is asymmetric, the structure of the product will vary according to which mechanism dominates. In the discussion on base-catalyzed epoxide opening, the mechanism is essentially SN2. Cant find a solution anywhere. In this webpage (http://www.columbia.edu/itc/chemistry/c3045/client_edit/ppt/PDF/05_08_13.pdf), Butan-1-ol gave 2-butene as a major product. Markovnikov's Rule is a useful guide for you to work out which way round to add something across a double bond, but it . As a result, product A predominates. Write the complete mechanism and the product for the following reaction: Provide a stepwise mechanism for the given reaction. Step 3: Deprotonation to get neutral product. How Do We Know Methane (CH4) Is Tetrahedral? write the mechanism for the opening of an epoxide ring by an aqueous acid, paying particular attention to the stereochemistry of the product. While oxygen is a poor leaving group, the ring strain of the epoxide really helps to drive this reaction to completion. )%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. Suggest the mechanism for the following reaction. If Kw = 1.0 x 10^-14 then shouldnt the formation of H3O+ be very unfavorable? After completing this section, you should be able to. Note: Please keep in mind that for the reaction that involves carbocation intermediate, the rearrangement of carbocation is always an option. The catalytic cycle is completed by the reoxidn. 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. Provide the synthesis of the following reaction. 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. A variety of conditions are possible for this transformation (alcohol -> alkene), all of which involve converting the -OH into a better leaving group. Note: No effect on tertiary alcohols: Na2Cr2O7 . As we saw with the reactions of HCl, HBr, and HI with secondary alcohols, we have to watch out for carbocation rearrangement reactions. Complete and write a mechanism for the following reaction. Label Each Compound With a Variable. Q: Draw the organic product of the following reaction. H 2SO 4 is added to an alcohol at such a high temperature, it undergoes elimination and thus, gives an alkene. All other trademarks and copyrights are the property of their respective owners. Propose a full mechanism for the following reaction. Provide the synthesis of the following reaction. Provide the synthesis of the following reaction. Loss of H2O to form a carbocation followed by elimination will be the favoured pathway. Step 1. copyright 2003-2023 Homework.Study.com. CH3OH + H2SO4 = (CH3)2SO4 + H2O might be a redox reaction. If the epoxide is asymmetric, the structure of the product will vary according to which mechanism dominates. It covers the E1 reaction where an alcohol is convert. What is the mechanism for the following reaction? You can also ask for help in our chat or forums. predict the major product from the acidic cleavage of a given unsymmetrical epoxide. Reactants. Provide a mechanism for the next reaction, Predict the principle organic product of the following reaction. In Step 1, a hydronium or oxonium ion is attacked by the bond.. Answer (1 of 4): when methanol is heated with conc. identify the product formed when an epoxide ring is opened by a hydrogen halide under anhydrous conditions. 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. But today I came across another reaction. Like in other SN2 reactions, nucleophilic attack takes place from the backside, resulting in inversion at the electrophilic carbon. When both the epoxide carbons are either primary or secondary the halogen anion will attack the less substituted carbon through an SN2 like reaction. Use the calculator below to balance chemical equations and determine the type of reaction (instructions). We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. 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. 6.!Methanol (CH 3OH) is "amphoteric", meaning it can act as both a Brnsted acid and a Brnsted base. 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. Provide a mechanism for the following reaction shown below. Show the mechanism of the following reaction: Show a mechanism for the following reaction. Provide the mechanism for the reaction below. 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; CuO + H2SO4 arrow. CH3OH + H2SO4 = (CH3)2SO4 + H2O might be a redox reaction. Cyclohexane Chair Conformation Stability: Which One Is Lower Energy? In practice, however, it doesnt work that way! 58 reaction i.e. When a nucleophilic substitution reaction involves a poor leaving group and a powerful nucleophile, it is very likely to proceed by an SN2 mechanism. Since it requires deprotonation to create a better leaving group, I would think not but Im not sure. Your email address will not be published. A. an acetal. Hydrohalic Acids (HX) Plus Alcohols Give Substitution Products, Elimination of Tertiary Alcohols Proceeds Through an E1 Mechanism. NaCN, 2. Plus there is heat involved in the reaction..which is favourable for elimination reactionsthank u n feel free to correct if wrong. ; However, when treated with strong acid, R-OH is converted into R-OH 2 (+) and H 2 O is a much better leaving group. Q: Draw the major monobromination product of this reaction. What is the major product of the following reaction? First, NaBH4 is not so reactive and the reaction is usually carried out in protic solvents such as ethanol or methanol. 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. 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. 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 Use uppercase for the first character in the element and lowercase for the second character. 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Not in one step. Reactants: Na_2Cr_2O_7 and H_2SO_4. Complete the following reaction: CHO H2SO4. CH3CH2OH + H2SO4 -> C2H5OC2H5 Here product is ether an happens at 413 K temperature. The proton becomes attached to one of the lone pairs on the oxygen which is double-bonded to the carbon. Because the reaction takes place by an SN2 mechanism the two -OH groups in the product will be trans to each other. 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]. Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. Recall that alkyl substituents can donate electron density through hyper conjugation and stabilize a positive charge on a carbon. write an equation to illustrate the cleavage of an epoxide ring by a base. In the last example, E2 reaction with a primary alcohol, why does 2-butene (the more stable alkene) not formed from 1-butanol? of Hg22+ with H2SO4 to regenerate Hg(II) and byproducts SO2 and H2O. Same deal as with tertiary alcohols: expect an alkene to form. Save my name, email, and website in this browser for the next time I comment. CH4 H2SO4 CH4(-CH, + HO H2304 CH3C=CH2 + H2O, Give the major product for the following reaction. If an acid name has the suffix ic, the ion of this acid has a name with the suffix ate. When a more stable carbocation is formed or are there any other criteria as well ? sorry I put my e mail wrong, posting my question again. The issue with alcohols here is that we are using strong acid to turn the OH into a good leaving group. 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. Reactants Reagents Products Help; Na2Cr2O7 H2SO4, H2O: Note: Oxidation of primary alcohols to carboxylic acids: Na2Cr2O7 H2SO4, H2O: Note: Oxidation of secondary alcohols to ketones: Na2Cr2O7 H2SO4, H2O: No Products Predicted. This accounts for the observed regiochemical outcome. The ring-opening reactions of epoxides provide a nice overview of many of the concepts discussed in earlier chapters of this book. What would be the elimination product of 2-methyl-2-phenylpropan-1-ol? Epoxides can also be opened by other anhydrous acids (HX) to form a trans halohydrin. Is there a way to convert a diol to alkene from ways mentioned above? (10 pts) H2SO4 CH3OH. Then the carbon-oxygen bond begins to break (step 2) and positive charge begins to build up on the more substituted carbon. 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. Note that secondary alkyl halides can undergo E2 reactions just fine. Chemical properties such as reactions with chlorine, HI, and oxidation reactions are also discussed. HSO4- can attack through SN2, why not? 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! The reaction exists in an equilibrium condition and does not go to completion unless a product is removed as fast as it forms. If the alcohol is a primary or secondary alcohol, this can then be oxidized to an aldehyde or ketone, or onwards. In a regioselective reaction, two (or more) different constitutional isomers are possible as products, but one is formed preferentially (or sometimes exclusively). It *can* be true that rearrangements of tertiary carbocations occur, but generally only in situations where they would be more stabilized (e.g. Maybe they should call them, "Formal Wins" ? Please provide the products and mechanism of the following reaction. It is OK to show the mechanism with H^+ instead of H_2SO_4. This peak is attributed to the . You can use parenthesis () or brackets []. Write a complete mechanism for the following reaction. Primary carbocations tend to be extremely unstable, and its more likely that the reaction passes through an E2 mechanism where the transition state will be lower in energy. Complete the following reaction. CH3CH2OH + H2SO4 -> CH2CH2 Here product is having a double bond (ethene) and this reaction happens at 443 K temperature. Therefore the addition . 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: In Step 2, the alcohol attacks the carbocation and forms an oxonium ion. The mechanism of the reaction is given below. The result is anti-hydroxylation of the double bond, in contrast to the syn-stereoselectivity of the earlier method. Polar Aprotic? Provide the reagents that are required to complete the following reaction mechanism for the following product. N1 mechanism because it is a tertiary alkyl halide, whereas (a) is primary and (b) is secondary. Another problem with alcohols: youve heard of nitroglycerin? Because in order for elimination to occur, the C-H bond has to break on the carbon next to the carbon bearing the leaving group. The sulfonation of an aromatic ring with SO_3 and H_2SO_4 is reversible. The Fischer esterification proceeds via a carbocation mechanism. When an asymmetric epoxide undergoes solvolysis in basic methanol, ring-opening occurs by an S . By no means is H2SO4 the only acid that does this. a =CH_2. 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. Step 1: Electrophilic attack of H 3 O + to the alkene, carbocation intermediate formed. This reaction is known as continuous etherification reaction. Propose a mechanism for the following reaction: Write the mechanism for the following reactions . Draw a stepwise mechanism for the following reaction that illustrates how two substitution products are formed. evolution and absorption of heat respectively. 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. Propose the mechanism of the following chemical reaction. Since there are an equal number of atoms of each element on both sides, the equation is balanced. 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. Replace immutable groups in compounds to avoid ambiguity. Arrow-pushing Instructions no XT . thank you so much for these information but i have a small question is there a difference between Elimination and dehydration ?? First, the oxygen is protonated, creating a good leaving group (step 1 below) . Migration of Ph- is faster than R- but will lead to a less stable intermediate and vice versa. Draw an E1 mechanism for the following reaction. predict the major product from the acidic cleavage of a given unsymmetrical epoxide. 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 . Provide reaction mechanism for the following. 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. In this reaction, the electrophile is SO3 formed as shown in the following equation. Predict the reaction. Secondary, tertiary, allylic, and benzylic alcohols appear to react by a mechanism that involves the formation of a carbocation in an \(S_N1\) reaction with the protonated alcohol acting as the substrate.. Createyouraccount. However, if the epoxide is symmetrical, each epoxide carbon has roughly the same ability to accept the incoming nucleophile. Read our article on how to balance chemical equations or ask for help in our chat. Learning New Reactions: How Do The Electrons Move? Indeed, larger cyclic ethers would not be susceptible to either acid-catalyzed or base-catalyzed cleavage under the same conditions because the ring strain is not as great as in the three-membered epoxide ring. In this mechanism, an alcohol is added to a carboxylic acid by the following steps: 1. [That carbon adjacent to the carbocation is often referred to as the (beta) carbon. This accounts for the observed regiochemical outcome. Provide the structure of the product of the following reaction. The reaction is given below: CH 3CH 2OH conc.H 2SO 4170 oC C 2H 4. In wade Jr text book 1-pentanol produced 2-pentene as major product. Why Do H2SO4, H3PO4 and TsOH Give Elimination Products? If you see a tertiary or secondary alcohol with H2SO4, TsOH, or H3PO4 (and especially if you see heat)think: carbocation formation followed by elimination reaction (E1). Write a mechanism for the following reaction. Epoxides may be cleaved by hydrolysis to give trans-1,2-diols (1,2 diols are also called vicinal diols or vicinal glycols). curved arrow mechanism for both the forward and backward reactions of this acid-base reaction. Write detailed mechanisms for the following reaction. When ethanol is heated at 140*C in the presence of conc. . Heres an example. 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. Examples: Fe, Au, Co, Br, C, O, N, F. Ionic charges are not yet supported and will be ignored. HSO,methyl hydrogen sulphate is obtained in first step.This on further treatment with another mole of methanol gives methoxy methane along with HSO. An alkoxide is a poor leaving group (Section 11-3), and thus the ring is unlikely to open without a 'push' from the nucleophile. The reaction with ethene. Hi James. [By the way, you might ask why heat ? Please draw it out and explain. So far weve learned two ways to convert alcohols to alkenes: Ideally, wed like to just use one step. The transfer of the proton to the oxygen gives it a positive charge, but it is actually misleading to draw the structure in . After completing this section, you should be able to. The str. Unlike in an SN1 reaction, the nucleophile attacks the electrophilic carbon (step 3) before a complete carbocation intermediate has a chance to form. Be sure to include proper stereochemistry. Alkenes react with concentrated sulphuric acid in the cold to produce alkyl hydrogensulphates. 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. 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. Use substitution, Gaussian elimination, or a calculator to solve for each variable. This would be an example of anchimeric assistance (neighboring group participation). Acid-catalyzed dehydration of 2 via the enol 3 leads to mesityl oxide 4.

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