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. As far as rearrangement is concerned, it will generally only be favoured in a situation where a more stable carbocation will form. Examples: Fe, Au, Co, Br, C, O, N, F. Ionic charges are not yet supported and will be ignored. First, the oxygen is protonated, creating a good leaving group (step 1 below). The electrons, from the. Which is the product of the reaction of 1-methylcyclohexene with H2O/H2SO4? (Base) CH 3OH + HCl ! B. a nucleophilic attack followed by a proton transfer. As an amazon associate, I earn from qualifying purchases that you may make through such affiliate links. Is it safe to say that otherwise, secondary alcohols can undergo both E1 and E2? Acid makes the OH a better leaving group, since the new leaving group will be the weaker base H2O, not HO(-). This reaction is known as continuous etherification reaction. Write the complete mechanism and the product for the following reaction: Provide a stepwise mechanism for the given reaction. a =CH_2. And if you see that a more stable carbocation could be formed through migration of an adjacent H or alkyl group, expect that to happen. When this occurs the product typically contains a mixture of enantiomers. Epoxides can undergo ring-opening with nucleophiles under acidic conditions. The epoxide ring is opened by an SN2 like mechanism so the two -OH groups will be trans to each other in the product. All About Elimination Reactions of Alcohols (With Acid) The hydroxyl group of alcohols is normally a poor leaving group. Thats what well cover in the next post. Label each compound (reactant or product) in the equation with a variable to represent the . For example, C 2 H 5 OC 2 H 5 + H 2 O ---- ( dil.H2so4,high pressure )-----> 2C 2 H 5 OH. 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. Phosphoric acid (H3PO4) as well as tosic acid (p-toluenesulfonic acid) also tend to form elimination products. 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? Its necessary to do a reduction of some kind. Propose a suitable mechanism for the following reaction. Draw the mechanism of the following reaction: Draw a mechanism for the following reaction. Nonpolar? 58 reaction i.e. The upshot is that delocalization of charge results in a slower reaction of HSO4 as a nucleophile compared to deprotonation of C-H by a base, and the alkene product dominates. Explain the reaction mechanism for the following reaction: What products would you obtain from reaction of 1-methylcyclohexanol with the following reagents? However, if the epoxide is symmetrical, each epoxide carbon has roughly the same ability to accept the incoming nucleophile. 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. 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). (Because sulfur is larger than oxygen, the ethyl sulde ion . To balance a chemical equation, enter an equation of a chemical reaction and press the Balance button. The sulfonation of an aromatic ring with SO_3 and H_2SO_4 is reversible. The loss of water from 3 may be stepwise but, to save space, I have presented the loss of water in a single operation. 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 . 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. Chemistry questions and answers. Label Each Compound With a Variable. Draw a mechanism for the following chemical reaction. Elimination in the sense of this post refers to formation of a double bond. CH-OH + HSO-> CH-OSOH +. The ring-opening reactions of epoxides provide a nice overview of many of the concepts discussed in earlier chapters of this book. Expert Answer. William Reusch, Professor Emeritus (Michigan State U. ), Virtual Textbook ofOrganicChemistry. Give the structure of the major organic product for the following reaction: SO3 H2SO4 conc. identify the product formed from the reaction of a given epoxide with given base. Then the carbon-oxygen bond begins to break (step 2) and positive charge begins to build up on the more substituted carbon. There is! Next Post: Elimination Of Alcohols To Alkenes With POCl3. This hydration of an epoxide does not change the oxidation state of any atoms or groups. Createyouraccount. While oxygen is a poor leaving group, the ring strain of the epoxide really helps to drive this reaction to completion. The epoxide oxygen forms an alkoxide which is subsequently protonated by water forming the 1,2-diol product. The str. A variety of conditions are possible for this transformation (alcohol -> alkene), all of which involve converting the -OH into a better leaving group. Free Radical Initiation: Why Is "Light" Or "Heat" Required? Epoxides can also be opened by other anhydrous acids (HX) to form a trans halohydrin. i was really confused why H2SO4 was only explained as forming E1 E2 products but not SN1 SN2. For that reason we usually just stick to H2SO4 or H3PO4! Propose the mechanism of the following chemical reaction. Since it requires deprotonation to create a better leaving group, I would think not but Im not sure. Cant find a solution anywhere. ethanol and a small amount of sodium hydroxide, ethanol and a small amount of sulfuric acid, Layne Morsch (University of Illinois Springfield). To balance a chemical equation, enter an equation of a chemical reaction and press the Balance button. 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 . Here is the reaction off. 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 Deprotonation of the hydroxyl group would make the resulting species (O-) an even worse leaving group! 3. Propose a mechanism for the following transformation reaction. Provide a detailed mechanism of the following reaction sequence. This video describes the mechanism for the reaction between hydrochloric acid and methanol, using standard arrows to explain the "electron pushing". why not a SN2 reaction after protonation of primary alcohols??? The ions from the acids H2SO4 and HNO3 are SO42, NO3. H2O is a good leaving group and primary carbon is not hindered, a perfect recipe for SN2. The proton becomes attached to one of the lone pairs on the oxygen which is double-bonded to the carbon. how long can a dog live with parathyroid disease. If a more stable carbocation can be formed through migration of an adjacent hydride (H- ) or an alkyl group, then that migration will occur. 2-cyclopentylethanol reacts with H2SO4 at 140degrees C yields? What is the best mechanism for the following reaction? Your email address will not be published. octubre 2nd, 2021 | when did bruce jenner come out to kris. 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. Then the carbon-oxygen bond begins to break (step 2) and positive charge begins to build up on the more substituted carbon. Dont know why that comment didnt post. Since there is an equal number of each element in the reactants and products of 2CH3OH + H2SO4 = (CH3)2SO4 + 2H2O, the equation is balanced. This is an E1 process[elimination (E) , unimolecular (1) rate determining step]. Because the reaction takes place by an SN2 mechanism the two -OH groups in the product will be trans to each other. . Suggest the mechanism for the following reaction. it explains how to determine the major product or the most stable zaitsev product. What about the electrophile? (10 pts) H2SO4 CH3OH. Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. 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. Provide the mechanism of the following reaction. That is, heating benzenesulfonic acid with H_2SO_4 yields benzene. Provide the mechanism for the following reaction: H2SO4, CH3OH, Heat. Step 1: Protonation of the hydroxy group. Arrow-pushing Instructions no XT . [That carbon adjacent to the carbocation is often referred to as the (beta) carbon. Famous What Is The Product Of The Following Reaction Ch3Oh H+ References . Step 1. The Hg(II) ion reacts with CH4 by an electrophilic displacement mechanism to produce an observable species, MeHgOSO3H (I). Hydrohalic Acids (HX) Plus Alcohols Give Substitution Products, Elimination of Tertiary Alcohols Proceeds Through an E1 Mechanism. 2) Predict the product for the following reaction. The reaction with ethene. That is true for the conversion of secondary carbocations to tertiary carbocations. Step 3: Deprotonation to get neutral product. 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. Same deal as with tertiary alcohols: expect an alkene to form. ; The best analogy is that it is a lot like the Markovnikov opening of . 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. copyright 2003-2023 Homework.Study.com. 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 There is one last thing to watch out for with secondary alcohols, though like a bad nightmare, they keep coming back. Explain why 1-bromohex-2-ene reacts rapidly with a weak nucleophile (CH3OH) under SN1 reaction conditions, even though it is a 1 degree alkyl h; Draw the structure of the major organic product formed in the reaction. The identity of the acid is important. In Step 1, a hydronium or oxonium ion is attacked by the bond.. Your email address will not be published. CH3OH: Note: NaBH4 is not strong enough to reduce . Read our article on how to balance chemical equations or ask for help in our chat. The reaction between methanol and sulfuric acid (SA) was investigated using Raman and vibrational broad bandwidth sum frequency generation spectroscopies. 2. 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. Let us examine the basic, SN2 case first. identify the product formed when an epoxide ring is opened by a hydrogen halide under anhydrous conditions. Is there a way to convert a diol to alkene from ways mentioned above? Was just wondering if HNO3 would cause the same reaction to occur as H2SO4 or H3PO4 (an E1 rxn)? Step 1. 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. 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). Yes, alkenes can be formed this way (along with some formation of symmetrical ethers[see this previous post]). Step 2: Loss of water as the leaving group to create a Our experts can answer your tough homework and study questions. 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; 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. Elimination of Alcohols To Alkenes With POCl3, All About Elimination Reactions of Alcohols (With Acid). Provide the mechanism for the following reaction. When a nucleophilic substitution reaction involves a poor leaving group and a powerful nucleophile, it is very likely to proceed by an SN2 mechanism. So the bottom line here is that heating tertiary alcohols with these acids will result in loss of water [dehydration] and formation of an alkene [elimination]. Heat generally tends to favour elimination reactions. During the ring-opening of an asymmetrical epoxide, the regiochemical control of the reaction usually allows for one stereoisomer to be produced. Concerning the 4th picture (Elimination of alcohols with H2SO4 mechanism [E1]), why does water deprotonate the carbocation in step 3? Propose a full mechanism for the following reaction. Predict the product for the following reaction. Provide the reagents for the following reaction. If an acid name has the suffix ic, the ion of this acid has a name with the suffix ate. Provide the synthesis of the following reaction. Q: Draw the major monobromination product of this reaction. 6.11 (a) Being primary halides, the reactions are most likely to be S . Like in other SN2 reactions, nucleophilic attack takes place from the backside, resulting in inversion at the electrophilic carbon. document.getElementById( "ak_js_1" ).setAttribute( "value", ( new Date() ).getTime() ); This site uses Akismet to reduce spam. If the epoxide is asymmetric the incoming hydroxide nucleophile will preferable attack the less substituted epoxide carbon. These are both good examples of regioselective reactions. Not conventional E2 reactions. As we saw with the reactions of HCl, HBr, and HI with secondary alcohols, we have to watch out for carbocation rearrangement reactions. It covers the E1 reaction where an alcohol is convert. Methanol - CH 3 OH. A. a proton transfer followed by a nucleophilic attack. First, NaBH4 is not so reactive and the reaction is usually carried out in protic solvents such as ethanol or methanol. 6.!Methanol (CH 3OH) is "amphoteric", meaning it can act as both a Brnsted acid and a Brnsted base. 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. All rights reserved. provide the mechanism of the organic reaction bellow. ch3oh h2so4 reaction mechanismbone graft acl tunnel cpt. CH3OH + H2SO4 = (CH3)2SO4 + H2O might be a redox reaction. Epoxides may be cleaved by aqueous acid to give glycols that are often diastereomeric with those prepared by the syn-hydroxylation reaction described above. Write the stepwise mechanism for sulfonation of benzene by hot, concentrated sulfuric acid. Show all steps and all resonance forms for intermediates. just want to thankyou for this clear explanation. Show a detailed reaction mechanism for the following reaction. The Fischer esterification proceeds via a carbocation mechanism. CuO + H2SO4 arrow. Its somewhat possible that you might get some epoxide formation, or even formation of a ketone/aldehyde. 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). Propose the mechanism for the following reaction. Therefore the addition . 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. tertiary carbocation to a resonance-stabilized tertiary carbocation ). It also discusses the SN1 / SN2 dehydration of a diol into a cyclic ether.My Website: https://www.video-tutor.netPatreon: https://www.patreon.com/MathScienceTutorAmazon Store: https://www.amazon.com/shop/theorganicchemistrytutorDisclaimer: Some of the links associated with this video may generate affiliate commissions on my behalf. Compare that to halide anions, where the negative charge cannot be spread over more than one atom. 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. Provide the synthesis of the following reaction. NO2 and Br. Heat generally tends to favour elimination reactions.]. Like in other SN2 reactions, nucleophilic attack takes place from the backside, resulting in inversion at the electrophilic carbon. Draw the mechanism for the following reaction. The transfer of the proton to the oxygen gives it a positive charge, but it is actually misleading to draw the structure in . Reaction (2) because the ethyl sulde ion is a stronger nucleophile than the ethoxide ion in a protic solvent. 2. Learn how your comment data is processed. thank you so much for these information but i have a small question is there a difference between Elimination and dehydration ?? The balanced equation will appear above. This would be an example of anchimeric assistance (neighboring group participation). write an equation to describe the opening of an epoxide ring under mildly acidic conditions. 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. Compound states [like (s) (aq) or (g)] are not required. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. Decomposition off water. Label Each Compound With a Variable. Draw the mechanism of the reaction shown. Reactants: 1. If the epoxide is asymmetric, the structure of the product will . Use substitution, Gaussian elimination, or a calculator to solve for each variable. Mixed ethers under similar conditions give a mixture of alcohols. write an equation to describe the opening of an epoxide ring under mildly acidic conditions. Dehydration specifically refers to loss of water. explain why epoxides are susceptible to cleavage by bases, whereas other cyclic ethers are not. Draw the mechanism of the following reaction shown below: Draw a stepwise mechanism for the following reaction. Use the calculator below to balance chemical equations and determine the type of reaction (instructions). 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. Predict the product and provide the mechanism for the following reaction below. [By the way, you might ask why heat ? write an equation to illustrate the cleavage of an epoxide ring by a base. 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 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! N2O and CN. Both substitution and elimination reactions of alcohols can be catalyzed by acid. 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. Base makes the OH a better nucleophile, since RO(-) is a better nucleophile than the neutral alcohol ROH. Label each compound (reactant or product) in the equation with a variable . 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. 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. Elimination Reactions With Carbocation Rearrangements, Primary Alcohols and H2SO4 Can Form Alkenes (via E2), Summary: Elimination Reactions of Alcohols, (Advanced) References and Further Reading. Write a mechanism for the following reaction. You can also ask for help in our chat or forums. H_2O + H_2SO_4 \rightarrow H_3O^+ + HSO_{4}^-. Predict the product of the following reaction. Use uppercase for the first character in the element and lowercase for the second character. 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 exists in an equilibrium condition and does not go to completion unless a product is removed as fast as it forms. When a more stable carbocation is formed or are there any other criteria as well ? 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. Why we use H2SO4 in case of alcohols reacting with HBr and that of we use H3PO4 in case of alcohols reacting with HI . 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