Map: Organic Chemistry (Vollhardt and Schore), { "21.01:_Naming__the_Amines" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "21.02:_Structural_and__Physical__Properties_of_Amines" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "21.03:_Spectroscopy_of__the_Amine__Group" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "21.04:_Acidity__and__Basicity__of_Amines" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "21.05:_Synthesis_of_Amines__by_Alkylation" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "21.06:_Synthesis_of_Amines__by_Reductive_Amination" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "21.07:_Synthesis_of_Amines__from__Carboxylic_Amides" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "21.08:_Quaternary_Ammonium_Salts:__Hofmann_Elimination" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "21.09:_Mannich___Reaction:_Alkylation_of_Enols__by__Iminium__Ions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "21.10:_Nitrosation_of_Amines" : "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_in_Organic_Molecules" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "02._Structure_and_Reactivity:_Acids_and_Bases_Polar_and_Nonpolar_Molecules" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "03._Reactions_of_Alkanes:_Bond-Dissociation_Energies_Radical_Halogenation_and_Relative_Reactivity" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "04._Cycloalkanes" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "05._Stereoisomers" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "06._Properties_and_Reactions_of_Haloalkanes:_Bimolecular_Nucleophilic_Substitution" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "07._Further_Reactions_of_Haloalkanes:_Unimolecular_Substitution_and_Pathways_of_Elimination" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "08._Hydroxy_of_Functional_Group:_Alcohols:_Properties_Preparation_and_Strategy_of_Synthesis" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "09._Further_Reactions_of_Alcohols_and_the_Chemistry_of_Ethers" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "10:_Using_Nuclear_Magnetic_Resonance_Spectroscopy_to_Deduce_Structure" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "11:_Alkenes:_Infrared_Spectroscopy_and_Mass_Spectrometry" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "12:_Reactions_to_Alkenes" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13:_Alkynes:_The_Carbon" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "14:_Delocalized_Pi_Systems:_Investigation_by_Ultraviolet_and_Visible_Spectroscopy" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "15:_Benzene_and_Aromaticity:_Electrophilic_Aromatic_Substitution" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "16:_Electrophilic_Attack_on_Derivatives_of_Benzene:_Substituents_Control_Regioselectivity" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "17:_Aldehydes_and_Ketones_-_The_Carbonyl_Group" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "18:_Enols_Enolates_and_the_Aldol_Condensation:_ab-Unsaturated_Aldehydes_and_Ketones" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "19:_Carboxylic_Acids" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "20:_Carboxylic_Acid_Derivatives" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "21:_Amines_and_Their_Derivatives" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22:_Chemistry_of_the_Benzene_Substituents:_Alkylbenzenes_Phenols_and_Benzenamines" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "23:_Ester_Enolates_and_the_Claisen_Condensation" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "24:_Carbohydrates:_Polyfunctional_Compounds_in_Nature" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "25:_Heterocycles:_Heteroatoms_in_Cyclic_Organic_Compounds" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "26:_Amino_Acids_Peptides_Proteins_and_Nucleic_Acids:_Nitrogen-Containing_Polymers_in_Nature" : "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:ccbyncsa", "licenseversion:40" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FMap%253A_Organic_Chemistry_(Vollhardt_and_Schore)%2F21%253A_Amines_and_Their_Derivatives%2F21.04%253A_Acidity__and__Basicity__of_Amines, \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\), Comparing the Basicity of Alkylamines to Amides, Organic Chemistry With a Biological Emphasis, status page at https://status.libretexts.org. << /Type /Page /Parent 8 0 R /Resources 3 0 R /Contents 2 0 R /MediaBox *;xUg!@9=XKf"aP>ax/L6ER{*UVV&r
r^(>GS;E!,uf:^8:wI/s5-q'GZ8TS3qgm}lE53_;)]Uq84?1S]~3Y!upVdSO*ZeN!K4Wb>tnSd[o*ojo PEG1334172-76-7 Biotin-PEG7-NH2 ,PEG1334172-76-7 Biotin-PEG7-NH2 Remember, in any case, there will be only ONE protonation at a time. Describe the general structure of a free amino acid. << /Length 4 0 R /Filter /FlateDecode >> The alcohol cyclohexanol is shown for reference at the top left. Aromatic herterocyclic amines (such as pyrimidine, pyridine, imidazole, pyrrole) are significantly weaker bases as a consequence of three factors. An amino acid has this ability because at a certain pH value all the amino acid molecules exist as zwitterions. a) the stronger acid or SH NH2 or b) the stronger base NH2 Cl c) the greater bond angle CH3 or CH3 trans-1,2-dimethylcyclohexane d) the more stable isomer or trans-1,3-dimethylcyclohexane e) the higher boiling point CH3 f) the tertiary amine CH3 or NH2 g) the greater solubility in water h) the more stable base i) the stronger acid or. The two immiscible liquids are then easily separated using a separatory funnel. and also C->N->O->F- C size is larger than N,O and F. The first of these is the hybridization of the nitrogen. Acid with values less than one are considered weak. When evaluating the basicity of a nitrogen-containing organic functional group, the central question we need to ask ourselves is: how reactive (and thus how basic and nucleophilic) is the lone pair on the nitrogen? Bases will not be good nucleophiles if they are really bulky or hindered. I guess hydrazine is better. endobj In $\ce{H3N+-NH2}$, although the lone pair cannot be accommodated, but the positive charge present on its sides , to an extent, should neutralize the intensity of the lone pair, making it somewhat stable. Amine are basic and easily react with the hydrogen of acids which are electron poor as seen below. Strong nucleophilesthis is why molecules react. Than iodide is able to replace OH group. This destabilizes the unprotonated form. The ONLY convenient method for identifying a functional group is to already know some. explain why amines are more basic than amides, and better nucleophiles. This reaction may be used to prepare pure nitrogen. The conversion of 1 and 2-alcohols to aldehydes and ketones is an important reaction which, in its simplest form, can be considered a dehydrogenation (loss of H2). For amines one can take advantage of their basicity by forming the protonated salt (RNH2+Cl), which is soluble in water. xKo@|9R{&CV{:%r;_PQ0flf7|;0E"$w] g(o6Mf=aVZ_v7b6QD9$0 5TFN>0d8K4[:KsW
`0p'a`b>lxvlU7a8\!E^-\:,U Most base reagents are alkoxide salts, amines or amide salts. What is the acid that reacts with this base when ammonia is dissolved in water? for (CH3)3C- > (CH3)2N->CH3O- Indeed, the S=O double bonds do not consist of the customary & -orbitals found in carbon double bonds. Site design / logo 2023 Stack Exchange Inc; user contributions licensed under CC BY-SA. Hi, Abel already answered that at one time only one $\ce{-NH_2}$ takes part when we determine basicity and the second $\ce{-NH_2}$ plays no role. Which is a better nucleophile: hydroxide anion or amide anion? Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. To learn more, see our tips on writing great answers. -ve charge easily, hence NH2 is more acidic than OH. Two additional points should be made concerning activating groups. If you know this, you can predict the products of organic chemistry reactions, even ones that you have not seen before. RCO2 is a better nucleophile than RCO2H). With reference to the discussion of base strength, the traditional explanation for the basestrengthening effect of electronreleasing (I) substituents is that such substituents help to stabilize the positive charge on an arylammonium ion more than they stabilize the unprotonated compound, thereby lowering G. 5 0 obj Thus if the Ka for an ammonium ion is know the Kb for the corresponding amine can be calculated using the equation Kb = Kw / Ka. the second loop? Nucleophilicity of Sulfur Compounds Thiolate conjugate bases are easily formed, and have proven to be excellent nucleophiles in SN2 reactions of alkyl halides and tosylates. NH4NO2(s)2H2O(g)+N2(g)NH_4NO_2(s) \longrightarrow 2H_2O(g) + N_2(g) What do you call molecules with this property? For more information on this and other topics of organic chemistry interest, please visit organic chemistry, Dr. Mike Pa got a bachelors degree in chemistry from Binghamton University, a masters degree in organic chemistry from the University of Arizona and a PhD in bio-organic chemistry from the University of Arizona. An energy diagram showing the effect of resonance on cyclohexanol and phenol acidities is shown on the right. inorganic chemistry - Which is more basic, hydrazine or ammonia In 2006, we started AceOrganicChem.com in order to make learning organic chemistry fast and easy. Scan a molecule for known acidic functional groups. 4_LD`yMtx}Y?mO=h QMtF]k1Ygx; MathJax reference. Michael David Wiley Ph.D. in Organic Chemistry, University of Washington (Graduated 1969) Author has 188 answers and 231.1K answer views 4 y Related Is NH2- a stronger base than OH-? Given that the K expression for a chemical equation formed from adding two or more other equations is the mathematical product of the input equations K constants. 6 0 R /F2.0 7 0 R >> >> It is noteworthy that the influence of a nitro substituent is over ten times stronger in the para-location than it is meta, despite the fact that the latter position is closer to the hydroxyl group. Is my statement correct? Charged vs. noncharged species a charged molecule is more acidic than a neutral molecule pK a = 15.5 pK a = 40 CH 3OH vs CH 3NH 2 pK a = 9.4 pK . If base is added, ion removal of the H^+ ion from the amino group of the zwitterion produces a negatively charged amino acid. Why is ammonia so much more basic than water? As explained earlier, although NH3 is a weak base and standard solution of ammonia has a pH 11 but still, it is amphoteric in nature which means it can act as both acid as well as a base under different conditions. Polar acidic amino acids - contain a carboxylate (-COO-) R group . Make certain that you can define, and use in context, the key term below. Fortunately, the Ka and Kb values for amines are directly related. What about the alpha effect? If the iodide ion is a stronger nucleophile than the hydroxide ion, why does the latter displace the former in a reaction involving aqueous Sodium hydroxide and alkyl iodide? In between, he did NOT compete at the 1996 Olympics, make the Atlanta Braves opening day roster, or become the head coach of the Indiana Pacers, as he had intended. If you do not recall pKa values for all of the acidic groups, a few general principles can guide you. The effect of delocalization can be seen when viewing the electrostatic potential maps of aniline an methyl amine. Stack Exchange network consists of 181 Q&A communities including Stack Overflow, the largest, most trusted online community for developers to learn, share their knowledge, and build their careers. This gives the nitrogen in the resulting ammonium salt four single bonds and a positive charge. 1) Using the knowledge of the electron donating or withdrawing effects of subsituents gained in Section 16.6, rank the following compound in order of decreasing basicity. endstream Calculating probabilities from d6 dice pool (Degenesis rules for botches and triggers). x[rSl3.74N9! This means basicity of ammonia is greater compared to that of hydrazine. (The use of DCC as an acylation reagent was described elsewhere.) The alcohol is oxidized; DMSO is reduced to dimethyl sulfide; and water is taken up by the electrophile. 2003-2023 Chegg Inc. All rights reserved. The acids shown here may be converted to their conjugate bases by reaction with bases derived from weaker acids (stronger bases). Furthermore additional nitro groups have an additive influence if they are positioned in ortho or para locations. If this spring is cut in half, does the resulting half spring have a force constant that is greater than, less than, or equal to kkk ? Asking for help, clarification, or responding to other answers. This is because it can react at more sites and will not be sterically hindered if it is smaller or linear. a) p-Chloroaniline, methyl p-aminobenzoate, p-nitroaniline You should compare either Ka1, or Ka2, with the corresponding values for Ammonia. The lone pair of electrons on the nitrogen atom of amines makes these compounds not only basic, but also good nucleophiles. In addition to acting as a base, 1o and 2o amines can act as very weak acids. Oxidation of 1 and 2-alcohols to aldehydes and ketones changes the oxidation state of carbon but not oxygen. Describe the categorization of these amino acids, and which amino acids that belong to each group. How much does it weigh? Amines react with water to establish an equilibrium where a proton is transferred to the amine to produce an ammonium salt and the hydroxide ion, as shown in the following general equation: \[RNH2_{(aq)}+H_2O_{(l)} \rightleftharpoons RNH3^+_{(aq)}+OH^_{(aq)} \label{16.5.4}\]. 706 Organic Chemistry made easy, Strong nucleophiles you need to know [with study guide & chart], Epoxidation of Alkenes [with free study guide], Solvent-Separated Ion Pair in SN1 reactions, How is Organic II Different from Organic I (and how to study Organic II), Steps of a Free Radical Reactions [simplified with a great diagram], What is a hydrogen bond? << /Length 5 0 R /Filter /FlateDecode >> This difference is basicity can be explained by the observation that, in aniline, the lone pair of electrons on the nitrogen are delocalized by the aromatic p system, making it less available for bonding to H+ and thus less basic. This has a lot to do with sterics. Thiols and Sulfides Compounds incorporating a C-S-H functional group are named thiols or mercaptans. { Nomenclature_of_Sulfur_Compounds : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Nucleophilicity_of_Sulfur_Compounds : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Thiols_and_Sulfides : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, { Acid_Halides : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Alcohols : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Aldehydes_and_Ketones : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Alkanes : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Alkenes : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Alkyl_Halides : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Alkynes : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Amides : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Amines : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Anhydrides : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Arenes : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Aryl_Halides : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Azides : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Carbohydrates : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Carboxylic_Acids : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Chirality : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Conjugation : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Esters : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Ethers : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Fundamentals : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Hydrocarbons : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Lipids : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Nitriles : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Organo-phosphorus_Compounds" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Phenols : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Phenylamine_and_Diazonium_Compounds : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Polymers : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Reactions : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Spectroscopy : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Thiols_and_Sulfides : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, [ "article:topic", "showtoc:no", "license:ccbyncnd", "licenseversion:30", "author@William Reusch" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FSupplemental_Modules_(Organic_Chemistry)%2FThiols_and_Sulfides%2FNucleophilicity_of_Sulfur_Compounds, \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\), conversion of 1 and 2-alcohols to aldehydes and ketones, status page at https://status.libretexts.org.
Buffalo High School Boys Basketball Roster, Articles I
Buffalo High School Boys Basketball Roster, Articles I