Important derivatives of acetanilide include: To unlock this lesson you must be a Study.com Member. It is combustible and generates toxic gas or fumes when heated. To log in and use all the features of Khan Academy, please enable JavaScript in your browser. This results View the full answer Transcribed image text: Draw the other resonance structure of acetamide, and answer the questions. 2) Draw four additional resonance contributors for the molecule below. Sulfanilamide can be prepared from acetanilide very easily, even by students in introductory organic chemistry laboratory courses, and is known for its antibacterial properties. 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. Did you know that there's a pain medication that used to be quite common but is no longer in use? Five minus six, we have one the resonance structures where individual atoms have formal charges as close to zero as possible. Charge separation being formal charges on atoms where they would normally like to be neutral. You wouldn't be able to write or throw, correct? And so four minus four, you How do we know that structure C is the minor contributor? So the way that we do that is 1) There is ONLY ONE REAL STRUCTURE for each molecule or ion. The contributor on the right is least stable: there are formal charges, and a carbon has an incomplete octet. For instance, the C6 H5 portion of the chemical formula represents the aromatic ring, and the NHCOCH3 piece represents the amide functional group. Penicillin: Allergy & Difference, What is Naphthalene? Deliquescent. 1) Structure I would be the most stable because all the non-hydrogen atoms have a full octet and the negative charge is on the more electronegative nitrogen. So it's in the second resonance structure, you have the negative Here, we have one, two, three, four, five, six outer electrons So individual atoms have [13] This finding is potentially significant because acetamide has an amide bond, similar to the essential bond between amino acids in proteins. The structures with the least separation of formal charges is more stable. 6. Food Chem., 36(1), 1988, 123-129. ass: Standard non-polar; Column diameter: 0.32 mm; Column length: 30 m; Column type: Capillary; Heat rate: 4 K/min; Start T: 40 C; End T: 200 C; Start time: 12.5 min; CAS no: 60355; Active phase: SPB-Sulfur; Phase thickness: 4 um; Data type: Linear RI; Authors: de Lacy Costello, B.P.J. What is the Difference Between Cis and Trans Fats? Posted 2 years ago. Today, we're going to be talking about acetanilide in terms of its chemical formula, resonance structures, and some of its important derivatives. Plus, get practice tests, quizzes, and personalized coaching to help you Legal. two resonance structures as contributing more Hi can we say structure3 is our dominant lewis structure because it contrubute most to resonance hybrid ? ; Comellas, L.; Broto-Puig, F., Pyrolysis-gas chromatography applied to the study of organic matter evolution in sewage sludge-amended soils using nitrogen-phosphorus, flame ionization and mass spectrometric detection, J. Chromatogr. Organic Compound; Pollutant; Food Toxin; Plant Toxin; Metabolite; Cigarette Toxin; Natural Compound, ORL-RAT LD50 7000 mg kg-1, SCU-MUS LD50 8300 mg kg-1, IPR-MUS LD50 10000 mg kg-1, SCU-RAT LD50 10 mg kg-1, IPR-RAT LD50 10300 mg kg-1, WARNING: Irritates skin and eyes, harmful if swallowed. Direct link to Anuja's post If there is one resonance, Posted 2 years ago. Direct link to BootesVoidPointer's post Do we always check for th. It is a weak base because of the resonance structures it shows. Include all three resonance structures by alternating the double bond among the three oxygen atoms. (rule #4). She has a teaching certification, Bachelor of Education, from University of Delhi. Except where otherwise noted, data are given for materials in their, Ullmann's Encyclopedia of Industrial Chemistry, 10.1002/0471238961.0103052023010714.a02.pub2, "Philae probe finds evidence that comets can be cosmic labs", "Philae's First Days on the Comet - Introduction to Special Issue", https://en.wikipedia.org/w/index.php?title=Acetamide&oldid=1141031755, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License 3.0, 79 to 81C (174 to 178F; 352 to 354K), 221.2C (430.2F; 494.3K) (decomposes), This page was last edited on 23 February 2023, at 00:44. How many electrons are shared in a single bond? On an industrial scale, it can be produced by dehydrating ammonium acetate or by hydrolyzing acetonitrile. It has an application as an accelerator in the rubber industry. You can look it up on a Acetamide is an acetic acid-derived chemical that has been identified as smelling like vinegar or ammonia. Herein, we report the high-yield isolation of phenolic natural products, N-formyl-4-hydroxyphenyl-acetamide 1 (~117 mg/L) and atraric acid 2 (~18 mg/L), from the ethyl acetate extract of the soil-derived fungus, Aspergillus fumigatus. Nitration Reaction, Products & Uses | What Is Nitration? Researchers discovered that acetanilide changed into acetaminophen in the body and that compound has the analgesic effect. Other names: Acetanilide; Acetamidobenzene; Acetanil; Acetoanilide; Acetylaniline; . And they have given us Step 2: The resonance structures of acetamide Resonance structures of acetamide The nitrogen is sp 2 hybridized because it is involved in resonance with the carbonyl group. Using the curved arrow convention, a lone pair on the oxygen can be moved to the adjacent bond to the left, and the electrons in the double bond shifted over to the left (see the rules for drawing resonance contributors to convince yourself that these are 'legal' moves). See Answer The IUPAC name of acetanilide is N-phenylacetamide. This finding lends support to the theory that organic molecules that can lead to life (as we know it on Earth) can form in space. Draw the major resonance contributor for the enamine, and explain why your contributor is the major one. The depiction of benzene using the two resonance contributors A and B in the figure above does not imply that the molecule at one moment looks like structure A, then at the next moment shifts to look like structure B. six valence electrons in a typically neutral sulfur free atom, and so it's one less electron. about it is typically, six valence electrons and, but we are only seeing five hanging out in this Lewis structure, so that's where we get our plus one from. Resonance in amides. Also, the two structures have different net charges (neutral Vs. positive). conjugated to) pi bonds. . Direct link to Richard's post If a molecule does have r, Posted a year ago. Understand the properties of acetanilide such as density, melting point, molar mass, and its applications. Jayashree has taught high school chemistry for over thirty years. resonance structures, we only have one atom whose The resulting structure contains a carbon with ten electrons, which violates the octet rule, making it invalid. CHEBI:7331, CHEBI:22164. So in this far structure, it's neutral. In addition, acetamide is found infrequently on burning coal dumps, as a mineral of the same name.[17][18]. + 2 V = 6 * 4 + 2 24 = 2. Resonance structures for an amide. We've looked at the formal - Foods & Plants, What is Absolute Alcohol? Acetanilide is an organic compound. - Definition, Properties & Examples, What is Furfural? The functional group is highlighted in blue in the image below. [11] It is a precursor to thioacetamide.[12]. So any formal charge, so once again, we're not In the DEPA with polymeric nanomicelles the hydrodynamic mean exhibited typical core shell structure of micelle with an eight fold lower lethal concentration (48h) for C. tritaeniorhynchus 3rd instar larvae in relation with that of bulk DEPA. {eq}R_{1} {/eq} in this case, is the phenyl group. How A: Given diagram is : a). Acetanilide Structure, Uses & Hazards | What is Acetanilide? Rules for Estimating Stability of Resonance Structures 1. The amide shown here, and in Figure 2, is the primary amide from ethanoic acid (acetic acid); the amide is called ethanamide (acetamide). This work documents the properties of a number of isomers of molecular formula C2H5NO from the most stable, acetamide, through 1,2-oxazetidine and including even higher energy species largely of a dipolar nature. It is also known as N-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name Antifebrin . 3) Draw three resonance contributors of methyl acetate (an ester with the structure CH3COOCH3), and order them according to their relative importance to the bonding picture of the molecule. In terms of formal charge, a structure generally contributes more when (1) the formal charges on the atoms are minimized and (2) any negative formal charges are on more electronegative atoms and any positive charges are on more electropositive atoms. Dairy Sci., 90, 2007, 523-531. class: Standard polar; Column diameter: 0.25 mm; Column length: 60 m; Column type: Capillary; Description: 60 0C (3 min) ^ 2 0C/min -> 150 0C ^ 4 0C/min -> 200 0C; CAS no: 60355; Active phase: DB-Wax; Carrier gas: Helium; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Kim. After completing this section, you should be able to. 2. In the example below structure A has a carbon atom with a positive charge and therefore an incomplete octet. At this point, the NH2 is not yet attached to the carbon (and thus cannot donate electron density), but does so in the subsequent step because of the above reason. It is widely used as a plasticizer. A double bonded structure, or a structure with a substantial contribution of double bonding, would be expected to be planar, without free rotation about the C-N bond. And then for the nitrogen, we have one, two, three, four, five, six, seven. It is a member of the class of acetamides which results from the formal condensation of acetic acid (CH3COOH) with ammonia (NH3). In the drawing of resonance contributors, however, this electron movement occurs only in our minds, as we try to visualize delocalized pi bonds. Acetanilide's structure can be represented by either of two structures, which are related to each other by resonance. In what kind of orbitals are the two lone pairs on the oxygen? resonance structure here. ; Jones, P.R.H. Required fields are marked *. I feel like its a lifeline. Each atom should have a complete valence shell and be shown with correct formal charges. having four hanging out, which is typical of carbon and neutral carbon's valence electrons, so no formal charge there, and then the nitrogen has one, two, three, four, five outer electrons hanging out, which is equivalent to a neutral nitrogen's valence electrons, and so five minus five, you have no formal charge. - Properties & Explanation, Acetonitrile: Production, Hazards & Waste Disposal, What is Acetonitrile? The two alternative drawings, however, when considered together, give a much more accurate picture than either one on its own. Acetanilide is an organic chemical compound that's classified as an amide in terms of its functional group, and additionally contains an aromatic ring. Acetamide is also called Acetic acid amide, or Ethanamide or Acetimidic acid. To unlock this lesson you must be a Study.com Member. A resonance structure having less charge separation helps it contribute more because charge separation creates instability. This is easily explained by the resonance system shown in Figure 2, which suggests that the actual bond between C and N is about a 1 1/2 bond. one formal charge here. Molecules and ions with more than one resonance form: Some structural resonance conformations are the major contributor or the dominant forms that the molecule exists. When you have a headache or muscle soreness what do you typically use to help make you feel better? Food Chem., 46, 1998, 3207-3209. ass: Standard polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 10 K/min; Start T: 40 C; End T: 220 C; End time: 10 min; Start time: 5 min; CAS no: 60355; Active phase: RTX-Wax; Carrier gas: He; Phase thickness: 0.5 um; Data type: Normal alkane RI; Authors: Prososki, R.A.; Etzel, M.R. The charge is spread out amongst these atoms and therefore more stabilized. Varnishes like cellulose ester have acetanilide as an additive. Acetanilide only contains four types of atoms, which include carbon, hydrogen, nitrogen, and oxygen. It covers general chemistry topics required in Colleges and Universities. However, as will learn in chapter 19, the positively charged carbon created by structure B will explain how the C=O bond will react with electron rich species. Using a pKa table. Explain why your contributor is the major one. Benzene is an extremely stable molecule due to its geometry and molecular orbital interactions, but most importantly, due to its resonance structures. In the example below, structure B is much less important in terms of its contribution to the hybrid because it contains the violated octet of a carbocation. This is a very nice example of how resonance works. Acetamide is used in the manufacture of polymeric products, such as polyvinyl acetamide, a polymeric commodity used as an absorbent, as a co-monomer. The first resonance structure of acetamide, CH, CONH,, is shown. - Preparation & Uses, Acetylacetone: Structure, NMR & IR Spectra, Acetanilide: Formula, Resonance & Derivatives, Why is Acetone a Good Solvent? Only two of the isomers have been detected in emissions from the interstellar medium (ISM); possible further candidates are identified, and the likelihood of their being detectable is . It's chemical formula is usually written as C6 H5 NHCOCH3. Structure C would be next in stability because all of the non-hydrogen atoms have full octets, though now the negative charge is on carbon rather than oxygen. ; Rhee, M.S. And we can see from this table that nitrogen is more ; Yang, Z.C. This chemistry blog is aimed mainly at senior high school students or first year university students. Chemists depict compounds with Lewis structures. That's what gives us this And then we say, well, how many outer electrons are hanging out around the sulfur in - Uses & Overview, Anthracene: Lewis Structure, Formula & Resonance, Fluorenone: Structure, Solubility & Polarity, Fluorene: Polarity, Structure & Solubility, What are Hydrogenated Fats? Stable. - Structure, Properties & Formula, Butadiene: Uses, Polymerization & Production, Butanol: Structure, Boiling Point & Density, Butene: Structural Formula, Boiling Point & Isomers, Cyclohexane: Structure, Formula & Conformations, Cyclohexene: Hazards, Synthesis & Structure, What is Pentanol? But they aren't entirely second order, they are different because of the contributions of the other resonance structures. There certainly are a lot of choices out there for over-the-counter pain management and most likely you have a particular option that works best for you and your needs. Definition. What does each line represent in the diagram = ? 2) The resonance hybrid is more stable than any individual resonance structures. In chemical laboratories, it can be produced by dehydration of ammonium acetate. Acetanilide itself isn't used any longer as a pain reliever due to its toxic side effects. Structrure II would be the least stable because it has the violated octet of a carbocation. Acetanilide has been in use for treating fever and pain since the late 19th century, but it causes negative side effects; it interferes with the oxygen-carrying capacity of hemoglobin in the body. A carboximidic acid that is acetic acid in which the carbonyl oxygen is replaced by an imino group. So there you have it. When looking at the picture above the resonance contributors represent the negative charge as being on one oxygen or the other. Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2. Acetamide (systematic name: ethanamide) is an organic compound with the formula CH 3 CONH 2. Remember that the molecule does not actually switch between these structures. Get the detailed answer: Draw the Lewis structure for the acetamide (CH3CONH2), an organic compound, and determine the geometry about each interior atom. Acetanilide is an organic chemical compound (meaning it's composed of carbon and hydrogen mostly) that is classified as an amide in terms of its functional group. The delocalized electrons in the benzene ring make the molecule very stable and with its characteristics of a nucleophile, it will react with a strong electrophile only and after the first reactivity, the substituted benzene will depend on its resonance to direct the next position for the reaction to add a second substituent. This means the two structures are equivalent in stability and would make equal structural contributions to the resonance hybrid. ; Yook, H.S. She has a bachelor's degree in chemistry and master's degree in English from Madurai University. extra electron hanging out, which gives us a negative Acetamide, N-phenyl-Formula: C 8 H 9 NO; Molecular weight: 135.1632; . As a member, you'll also get unlimited access to over 88,000 4) Below is a minor resonance contributor of a species known as an enamine, which we will study more in Section 19.8 (formation of enamines) Section 23.12 (reactions of enamines). We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. Use formal charge to determine which of the resonance structures is most important to the structure of nitric acid. This website collects cookies to deliver a better user experience. The carbon is still For example, if we look at the above rules for estimating the stability of a molecule, we see that for the third molecule the first and second forms are the major contributors for the overall stability of the molecule. These molecules are considered structural isomers because their difference involves the breaking of a sigma bond and moving a hydrogen atom. As examples: Structure of Amides is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts. Related terms . Acetamide 60-35-5 544-44-5 53318-35-7. Get unlimited access to over 88,000 lessons. Major resonance contributors of the formate ion, Representations of the formate resonance hybrid. Electronegative. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. The nitrogen present forms a single bond with a benzene ring in the place of one of the two hydrogen atoms it has bonded with. - Structure, Uses & Hazards, Naphthol: Structure, Polarity & Solubility, Pentene: Structural Formula, Isomers & Uses, Propanoic Acid: Structure, Formula & Uses, What is a Biomaterial? The difference between the two resonance structures is the placement of a negative charge. Resonance in Acetanilide The first structure is the common representation of the acetanilide structure. It turns out that acetanilide's structure can be represented by either of two structures, which are related to each other by resonance. ; Ratcliffe, N.M.; Spencer-Phillips, P.T.N., Gas chromatography-mass spectrometry analyses of volatile organic compounds from potato tubers inoculated with Phytophthora infestans or Fusarium coeruleum, Plant Pathol., 50, 2001, 489-496. ass: Standard polar; Column length: 3.05 m; Column type: Packed; Heat rate: 8 K/min; Start T: 40 C; End T: 200 C; End time: 60 min; Start time: 4 min; CAS no: 60355; Active phase: Carbowax 20M; Substrate: Supelcoport; Data type: Linear RI; Authors: Peng, C.T. It finds some use as a plasticizer and as an industrial solvent. Six minus this seven, we have one extra electron. A carbocation (carbon with only 6 valence electrons) is the only allowed exception to the valence shell rules. You can never shift the location of electrons in sigma bonds if you show a sigma bond forming or breaking, you are showing a chemical reaction taking place. The resonance system shown in Figure 2 is based on measurements of the properties of amides. electrons are hanging out, the same as you would expect for a neutral carbon atom. Ka and pKa review. Para red is considered a derivative of acetanilide, simply because it's 'derived' from the compound as a building block. 3. for each of these elements, if you had just a free atom The compounds of the invention are useful in both therapeutic and diagno Exposure to Acetic acid amide may cause irritation to the mucous membranes, skin and eyes. Indicate which would be the major contributor to the resonance hybrid. All right, now let's work Stars. Resonance structures for an amide. Acetanilide only contains four types of atoms, which include carbon, hydrogen, nitrogen, and oxygen. It acts as a negative catalyst in the decomposition of hydrogen peroxide. Well they all are to an extent. If you're seeing this message, it means we're having trouble loading external resources on our website. outer electrons hanging out than we would typically ; Rankin, S.A., Solvent type affects the number, distribution, and relative quantities of volatile compounds found in sweet whey powder, J. talking about the charge of the entire ion. Enrolling in a course lets you earn progress by passing quizzes and exams. An example is in the upper left expression in the next figure. There are two simple answers to this question: 'both' and 'neither one'. { "2.01:_Polar_Covalent_Bonds_-_Electronegativity" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "2.02:_Polar_Covalent_Bonds_-_Dipole_Moments" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "2.03:_Formal_Charges" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "2.04:_Resonance" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "2.05:_Rules_for_Resonance_Forms" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "2.06:_Drawing_Resonance_Forms" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "2.07:_Acids_and_Bases_-_The_Brnsted-Lowry_Definition" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "2.08:_Acid_and_Base_Strength" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "2.09:_Predicting_Acid-Base_Reactions_from_pKa_Values" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "2.10:_Organic_Acids_and_Organic_Bases" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "2.11:_Acids_and_Bases_-_The_Lewis_Definition" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "2.12:_Noncovalent_Interactions_Between_Molecules" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "2.MM:_Molecular_Models" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "2.S:_Polar_Covalent_Bonds_Acids_and_Bases_(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]()" }, [ "article:topic", "showtoc:no", "license:ccbysa", "resonance contributors", "licenseversion:40", "author@Steven Farmer", "author@Dietmar Kennepohl", "author@Krista Cunningham", "author@Tim Soderberg", "author@William Reusch", "resonance hybride" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FOrganic_Chemistry_(Morsch_et_al.