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Strong nucleophiles

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  3. Strong Nucleophiles - • Usually anions with a full negative charge (easily recognizable by the presence of sodium, lithium or potassium counterions) • Participate in SN2-type substitutions Examples: NaOCH3 (any NaOR), LiCH3 (any RLi), NaOH or KOH, NaCN or KCN, NaCCR (acetylide anion), NaNH2, NaNHR, NaNR2, NaI, LiBr, KI, NaN
  4. g a dative covalent bond
  5. In chemistry, a nucleophile is a chemical species that forms bonds with electrophiles by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are Lewis bases. Nucleophilic describes the affinity of a nucleophile to bond with positively charged atomic nuclei. Nucleophilicity, sometimes referred to as nucleophile strength, refers to a substance's nucleophilic.
  6. With a few exceptions, a strong nucleophile is also a strong base. All nucleophiles are Brønsted bases — they donate a pair of electrons to form a bond to another atom. If they bond to a hydrogen atom, we call them bases. If they bond to any other atom (especially carbon), we call them nucleophiles. Strong Bases/Strong Nucleophiles A good base is usually a good nucleophile. So, strong bases — substances with negatively charged O, N, and C atoms — are strong nucleophiles.

That is, the relative strength of the nucleophile. Nucleophilicity depends on many factors, including charge, basicity, solvent, polarizability, and the nature of the substituents. Increasing the Negative Charge Increases Nucleophilicity Nucleophiles can be neutral or negatively charged Nucleophile are electron-rich species that form bonds with electron-poor species. When thinking in terms of acids and bases, bases tend to form bonds with protons making them strong nucleophiles while, acids usually donate protons making them weak nucleophiles

Die Stärke von Nucleophilen (Nu) wird als Nucleophilie bezeichnet. Es ist eine kinetische Größe, die ausdrückt, wie schnell ein Nucleophil mit einem Substrat reagiert. Die Nucleophilie eines Reagenzes beinhaltet zwei Größen. Die erste ist die Energiefreisetzung infolge der C-Nu-Bindungsbildung Die Nukleophilie (griechisch nukleos = Kern, philos = Freund) ist in der Chemie ein Maß für die Fähigkeit eines Atoms mit einem freien Elektronenpaar, ein (partiell) positiv geladenes Atom unter Ausbildung einer kovalenten Bindung anzugreifen (i) Strong/strong. In general, good bases are also good nucleophiles. Therefore, strong bases such as negatively charged oxygens and nitrogens will also be strong nucleophiles. Note, not all negatively charged oxygen and nitrogen nuc/bases fall into the strong/strong category. These exceptions populate the weak/strong and strong/weak categories

Some nucleophiles have lone pair of electrons on more than one atom and can attack through more than one site. Such nucleophiles are called ambident nucleophiles. In such cases, different products are possible due to attack through different sites. Attack by a specific site can be promoted under special conditions. Two well-known examples are discussed in detai Nucleophilicity (Nucleophile Strength)More free lessons at: http://www.khanacademy.org/video?v=Z9Jh-Q59xs The actual reaction with a variety of strong, sterically hindered bases/nucleophiles is shown (Equations 79-81). The mesityllithium products proved that a carbene intermediate is not possible. Unlike t -butyl alcohol and hexamethyldisilazane, trimethylbenzene, the conjugate acid of mesityllithium, is not prone to carbene insertion reactions In general, good bases are also good nucleophiles. Therefore, strong bases such as negatively charged oxygens and nitrogens will also be strong nucleophiles. Note, not all negatively charged oxygen and nitrogen nuc/bases fall into the strong/strong category. These exceptions populate the weak/strong and strong/weak categories Nucleophiles - Literally ʻnucleus-lovingʼ, nucleophiles are atoms that are electron rich and are going to react to decrease their electron density. Nucleophiles have extra electrons and want to give them away. Nucleophiles can be neutral or charged, but tend to have partial or full negative charges, or if neutral will have a lone pair

Simple mechanism with strong nucleophiles. Transesterification. Transesterification is the conversion of a carboxylic acid ester into a different carboxylic acid ester. Introduction. When in ester is placed in a large excess of an alcohol along with presence of either an acid or a base there can be an exchange of alkoxy groups. The large excess of alcohol is used to drive the reaction forward. For example, trinitromethane (HC(NO 2) 3), tricyanomethane (HC(CN) 3), pentacyanocyclopentadiene (HC 5 (CN) 5), and fulminic acid (HCNO) are all strong acids with aqueous pK a values that indicate complete or nearly complete proton transfer to water To summarize the regiochemistry of epoxide ring-opening reactions is regioselective for with either a strong nucleophile or an acid. This selectivity of unsymmetrical epoxides, however, is exactly the opposite as; Strong nucleophiles react at the less substituted position, while Weak nucleophiles react at the more substituted position (3o carbons Protic solvent molecules form very strong ion-dipole interactions with the negatively-charged nucleophile, essentially creating a 'solvent cage' around the nucleophile: In order for the nucleophile to attack the electrophile, it must break free, at least in part, from its solvent cage. The lone pair electrons on the larger, less basic iodide ion interact less tightly with the protons on the protic solvent molecules - thus the iodide nucleophile is better able to break free from.

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more. In an SN2 reaction with a strong nucleophile, the nucleophile always attacks from the side opposite to the leaving group. Since the leaving group (O-) is on the top, a nucleophile such as H- must attack from below. Comment on Ernest Zinck's post In an SN2 reaction with a strong nucleophile, the This video explains what factors to consider in determining whether something is a strong nucleophile or a weak nucleophile. It will also help explain what t... It will also help explain what t.. Weak nucleophiles are neutral and don't bear a charge. Some examples are CH3OH, H2O, and CH3SH. In this category I'd also put acids such as H2SO4 and HCl. Example 1 uses NaCN (a strong nucleophile). Likewise, what is Electrophile and Nucleophile with example The iodide ion has a negative charge, so it is attracted to the partial positive charge on the methyl carbon. It is a strong nucleophile because of its polarizability. HI is a strong acid, so iodide ion is a very weak base. It has no tendency to attack a proton on an OH grou Some good nucleophiles are also strong bases, e.g. $\ce{HO-}$. However, a species can be a good nucleophile and a weak base, e.g. $\ce{I-}$; or a species can be a weak nucleophile and a strong base, e.g. $\ce{t-BuO-}$. How can we separate this behavior? Nucleophilicity is a kinetic phenomenon. Nucleophilicity is most often defined based on the relative rate of the reactions of nucleophiles.

What Makes A Good Nucleophile? (1) - YouTube

Nucleophilic are electron rich species.All compounds containg lone pair of electrons are nucleophile. It donates a lone pair of electrons to any electron deficient species except hydrogen. As oxygen has lone lone pair of electrons but due to its h.. A strong Arrhenius base is a strong nucleophile. 4. Nucleophiles tend to give electrons for the formation of a bond. 5. None of these. Solution: None of these. Explanation: Nucleophiles are rich in electron species that can form bonding electrophiles (electron-deficient species). Strong bases are strong nucleophiles on the other hand acids are generally weak nucleophiles. Q9. The incorrect. The carbon-oxygen double bond is directly attacked by strong nucleophiles to give rise to the alkoxide. However, when weak nucleophiles are used, the carbonyl group must be activated with the help of an acid catalyst for the nucleophilic addition reaction to proceed. The carbonyl group has a coplanar structure and its carbon is sp 2 hybridized. However, the attack of the nucleophile on the C=O. The strong nucleophiles (Nu: -) that we have learned in this course are either hydride anion (H-) or alkyl anion (R-). As well, remember that attack by strong nucleophiles is not reversible. Hydride anion comes from hydride donor such as LiAlH 4 or NaBH 4 (however, NaBH 4 is not strong enough reaction on carboxylic acid derivatives except for acid chlorides). Alkyl anion comes from RM, where R. A scale of nucleophilicity (N‴ ) for relatively strong nucleophiles (e.g. carbanions and amines), spanning over 5 orders of magnitude was constructed directly from experimental rate constants for reactions of 34 nucleophiles with a benzhydrylium cation, (lil) 2 CH + (log k = N‴ in dimethyl sulfoxide at 2

In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons.. Electrophiles mainly interact with nucleophiles through. A scale of nucleophilicity (N‴) for relatively strong nucleophiles (e.g. carbanions and amines), spanning over 5 orders of magnitude was constructed directly from experimental rate constants for reactions of 34 nucleophiles with a benzhydrylium cation, (lil) 2 CH + (log k = N‴ in dimethyl sulfoxide at 20 °

strong base, hindered nucleophile methoxide anion smaller, attacks more easily What Makes a Good Nucleophile? solvent hinders nucleophile from approaching electrophile. 4.Not obscured by too polar a solvent. So, SN2 reactions are usually run in medium polarity solvents; polar enough to dissolve ionic species, not so polar to cage the nucleophile. Some Common Nucleophiles Comparing Nucleophile. Strong nucleophiles are generally those species with the following features: 1-They bear a negative charge-->This should be obvious, because anything bearing a negative charge is strongly attracted to a positively charge C atom. Therefore, it has a greater tendency for attacking it. Hence, it becomes a stronger nucleophile. 2-Large in size-->Larger species are more polarizable. Think about it. Nucleophiles. Nucleophile means nucleus loving which describes the tendency of an electron rich species to be attracted to the positive nuclear charge of an electron poor species, the electrophile. The nucleophilicity expresses the ability of the nucleophile to react in this fashion.. In general terms this can be appreciated by considering the availability of the electrons in the nucleophile

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  1. Start studying Common Strong/Weak Nucleophiles. Learn vocabulary, terms, and more with flashcards, games, and other study tools
  2. ute and 56 seconds to solve.
  3. es act as nucleophiles? A nucleophile is something which is attracted to, and then attacks, a positive or slightly positive part of another molecule or ion. All a
  4. Thus, for nucleophiles of different size (moving up or down in the periodic table) the _____ the size, the _____ the nucleophile (opposite to base strength). larger better Modified from Paula Y. Bruice Organic Chemistry 4th Ed. Pearson . Nucleophilicity of Nucleophiles in Different Rows Increasing Nucleophilicity solvent Polar aprotic Polar protic basicity < < < < < < Title: Lesson18.ppt.

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Know Your Strong Nucleophiles - Organic chemistry hel

Alkyl halide

A strong nucleophile is also a strong base. All nucleophiles are Bronsted bases — they donate a pair of electrons to form a bond to another atom. If they bond to a hydrogen atom, it is said to be bases. If they bond to any other atom (especially carbon) then it is called to be nucleophiles. A good base is usually a good nucleophile. So. <h2><span style=font-family:Times New Roman,Times,serif><span style=font-size:14pt><span style=color:#0070c0>Nucleophiles </span></span></span. The use of alkyl nucleophiles in transition-metal-catalysed cross-coupling reactions is particularly challenging owing to slow alkyl transmetallation to Pd aryl intermediates (1, Fig. 1a), as well.

What is a strong nucleophile? - Quor

  1. es), spanning over 5 orders of magnitude was constructed directly from experimental rate constants for reactions of 34 nucleophiles with a benzhydrylium cation, (lil)2CH+ (log k = N‴ in dimethyl sulfoxide at 20 °C). The equation log k = (E‴ + sEN‴ +c), where E‴ is an electrophilicity.
  2. Strong nucleophiles or strong base such as OH or OCH 3 S N 2 or E2 Weakly basic. Strong nucleophiles or strong base such as oh or och. School Universiti Teknologi Mara; Course Title MAT 238; Uploaded By syahshai. Pages 83 This preview shows page 67 - 78 out of 83 pages. •.
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  4. Nucleophiles are involved in speed of reaction while bases are involved in strong bond formations. 5. Nucleophiles are kinetic in nature while bases are thermodynamic. 6. Nucleophiles are fast and immediate chemical mediators needed during irreversible conditions while bases are slow chemical mediators that maintain an acid-based balance during reversible conditions. 7. Nucleophiles attack.

Nucleophile - Wikipedi

What are some examples of nucleophiles and strong bases

Nucleophile - Chemistry LibreText

How nucleophilic attack can open the highly strained ring of an epoxide. Created by Jay.Watch the next lesson: https://www.khanacademy.org/science/organic-ch.. Read ChemInform Abstract: DBU and DBN as Strong Nucleophiles: X‐Ray Crystal Structures of Onioand Dionio‐Substituted Phosphines., ChemInform on DeepDyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips

How to figure out substitution reactions- SN2 versus SN1

Strong nucleophiles such as amines react readily with the O-acylisourea and therefore need no additives: A common explanation of the DMAP acceleration suggests that DMAP, as a stronger nucleophile than the alcohol, reacts with the O-acylisourea leading to a reactive amide (active ester). This intermediate cannot form intramolecular side products but reacts rapidly with alcohols. DMAP acts as. Nucleophiles and Electrophiles — Organic Chemistry Tutor organicchemistrytutor.com. Nucleophiles, Electrophiles, and Leaving Groups schoolbag.info. PPT - Chapter 19. Aldehydes and Ketones: Nucleophilic slideserve.com. 8.3: More about nucleophiles - Chemistry LibreTexts libretexts.org. Leaving Groups Are Nucleophiles Acting In Reverse - Master pcdn.co. Scope of bis-nucleophiles.

Identifying Nucleophiles - Organic Chemistr

Nucleophiles are either fully negative ions or have a strong -ve charge. Common nucleophiles are hydroxide ions, cyanide ions, water and ammonia. Notice that each of these contains at least one lone pair of electrons either on an atom carrying a full negative charge or on a very electronegative atom carrying a substantial-charge. Electrophile: A electrophile is a species (cation) which is. SN1 nucleophiles also give minor E1 products E2 bases (only with 3 and 2 alkyl halides) -OH, -OCH3, -OCH2CH3, -OC (CH3)3, CN- (only on 3 alkyl halide) Substrates Primary: SN2 reaction with good nucleophiles E2 with VERY strong bases NO E1 or SN1!! Secondary: With basic nucleophiles, get mixture of E2 (major) and SN2 (minor In general, nucleophiles donate a pair of electrons to create a . covalent bond. However, in order to determine the strength of a nucleophile, four factors must be . considered. These factors are. For the four nucleophiles examined here the nucleophilicity in methanol solution increases in the order: CH 3 CO 2 (-) < HO (-) < CN (-) < CH 3 S (-) Basicity on the other hand refers to the proton affinity of the nucleophile. This can be estimated from the pK a 's of the corresponding acids, remembering that strong acids have weak conjugate bases and vice versa. The four nucleophiles.

Nucleophile in Chemie Schülerlexikon Lernhelfe

Test bank Questions and Answers of Chapter 17: Nucleophilic Addition to Polar Π Bonds 1: Addition of Strong Nucleophiles The computational study provides strong evidence for the key intermediate common to these reactions being epoxide B. This intermediate can be attacked by different nucleophiles, and the probability of the corresponding reactions can be estimated by the height of the free-energy barriers Strong nucleophiles: This is VERY important throughout organic chemistry, but will be especially important when trying to determine the products of elimination and substitution (E1, E2, SN1, SN2)reactions. Oct 22, 2019 · Fluoroantimonic acid is the world's strongest acid, proudly standing on the pedestal slightly above carborane. In solution, hydrogen cyanide is a weak acid that is mostly. Nucleophile definition is - a nucleophilic substance (such as an electron-donating reagent)

Nukleophilie - Wikipedi

(unstable anions, strong bases) OH- , RO- , NH2- SN2 Mechanism - Nucleophiles. Nucleophilicity: a kinetic property measured by the rate at which a Nu attacks a reference compound under a standard set of experimental conditions Basicity: a equilibrium property measured by the position of equilibrium in an acid-base reactio Substitution reactions for the complex [Au(dien)Cl] 2+ (dien=3-azapentane-1,5-diamine) have been explored. Second-order rate constants, k 2 , were predicted for chloride exchange and ring-opening processes using water and the stronger nucleophiles N3 − and SCN −.Under neutral and basic conditions, the deprotonated form of the complex [Au(dien-H)Cl] + dominates and reacts promptly with all. q We shall see that enols can be formed either by acid or base catalysis and that, once formed, they are highly reactive toward electrophiles (i.e., they are pretty strong nucleophiles). We shall also see that not all carbonyl compounds can form enols, but only those which have hydrogens of the alpha type. The carbon of an aldehyde or the two carbons of a ketone which are directly attached to. My understanding: Strong nucleophiles are able to provide/donate electrons. What's wrong with my logic/understanding? 1.)H2S is neutral so it doesn't seem like it would have any extra electrons to donate. 2.) S is fairly electronegative, so it will hold onto its electrons making it less likely to donate any of its electrons. Thanks in advance! Strong nucleophiles will also open the strained ether, as shown by reaction 3b. Cleavage reactions of β-lactones may take place either by acid-catalyzed acyl exchange, as in 4a, or by alkyl-O rupture by nucleophiles, as in 4b. Example 5 is an interesting case of intramolecular rearrangement to an ortho-ester. Finally, the β-lactam cleavage of penicillin G (reaction 6) testifies to the.

Strength of nucleophiles - sites

Chapter 17: Enols and Enolate Anions as Nucleophiles Enols: under acidic conditions 1. H-X, H 3O+ acids, (H 3C) 3Si-X: with enolates react at O Enolates: under basic conditions 2. Halogens (Cl 2; Br 2; I 2) 3. OH O enol enolate I. Nucleophiles Electrophiles Rx on O Rx on C R R' O aldehydes/ketones 4.R Z O Z = Cl, OR' 5.RXalkyl, allyl, & benzyl halides with enolates react at cabanion C Rx on C. Electrophile, in chemistry, an atom or a molecule that in chemical reaction seeks an atom or molecule containing an electron pair available for bonding. Electrophilic substances are Lewis acids (compounds that accept electron pairs), and many of them are Brønsted acids (compounds that donat

Nucleophile Order of Nucleophile - Entrance

Therefore nucleophiles can attack the electrophilic carbon of the nitrile group. Grignard (or organolithium) reagents attack the nitrile to generate the magnesium (or lithium) salt of an imine. Acid hydrolysis generates the imine, and under these acidic conditions, the imine is hydrolyzed to a ketone. Ch18 Ketones and Aldehydes (landscape) Page 12 The mechanism of this hydrolysis is discussed. A difunctionalization of alkenes through sequential addition of a radical and a nucleophile has been developed, which is suggested to proceed by a radical chain mechanism not requiring a catalyst. An electron transfer step to the oxidant benzoyl peroxide is facilitated by protonation with a strong acid o Needs strong nucleophile At this point in the course the strong nucleophiles given will all be negatively-charged, though ammonia and amines are also strong nucleophiles which can undergo S. N. 2 reactions. o Polar, aprotic solvents can help this along Aprotic means that the solvent is not a good source of protons. • No hydrogen bonding. Mr. Baker requires you to know four of these polar.

Reactions of alcohols with hydrohalic acids (HXMedia Portfolio

Nucleophilicity (Nucleophile Strength) - YouTub

Which of the following is NOT true about nucleophiles? answer choices . donates an electron pair to an electrophile to form a chemical bond. all molecules or ions with a free pair of electrons or at least one pi bond can act as nucleophiles. nucleophile are Lewis acids by definition. a nucleophile becomes attracted to a full or partial positive charge . Tags: Question 2 . SURVEY . 30 seconds. This aluminium anion also exhibits also a very strong basicity, which enables the fast deprotonation of benzene, and a significant nucleophilicity, which allows S N 2 and S N Ar reactions

Nucleophile - an overview ScienceDirect Topic

The nucleophiles synthesized and tested here were primarily oximes, which are known to be strong nucleophiles, and are of a similar series to the novel oximes synthesized earlier as reactivators (Chambers et al., 2013). Computational modeling was conducted to provide better insights into the binding of the substrates and proposed enhancers into the PON1 active site and to provide a model of an. The Role and Nucleophilicity of Chloride and Bromide Nucleophiles in Both Sn1 and Sn2 Substitution Reactions with Tert-Butanol and 1-Butanol By: Rachel Wolfson*, Louis Kuo, Lisa Holmes, Luciano Santino, Cooper Jamieson. ABSTRACT The purpose of this experiment is to determine the relative nucleophilicities of chloride and bromide in both an Sn1 and Sn2 reaction

HOW TO: Classification of nucleophiles and Bases as

D) when nucleophiles are used which are strong bases and the substrate is a 20 alkyl halide. E) in all of these cases. 48. What would you expect to be the chief organic product(s) when ten-butyl bromide reacts with sodium acetylide, i.e., C) E) None of these Page 1 because such nucleophiles are strong enough to react with iminium ions but weak enough not to react with their precursor alde-hydes. With the N parameters of enamines derived from phenylacetaldehyde and MacMillan's imidazolidinones one can rationalize why only strong electrophiles, such as stabilized carbenium ions (-8 < E < -2) or hexachlorocyclohexadienone (E = -6.75), are suitable. For example, cyanide ions are relatively strong nucleophiles, as well as good leaving groups. Likewise, when a cyanide ion bonds to the carbonyl group of the aldehyde, the intermediate formed is stabilized by resonance between the molecule and the cyanide ion. The following mechanism illustrates these points. The benzoin condensation reaction proceeds via a nucleophilic substitution followed. Strong nucleophiles (anionic) add directly to the C=O to form the intermediate alkoxide. The alkoxideis then protonated on work-up with dilute acid. Examples of such nucleophilic systems are : RMgX, RLi, RC≡CM, LiAlH 4, NaBH 4 . Weaker nucleophiles (neutral) require that the C=O be activated prior to attack of the Nu. This can be done using a acid catalyst which protonates on the Lewis basic. The strong bulky Bronsted bases favor E2 and strong nucleophiles favor SN2 process. For instance, bulky tert-butoxide anion (Me3CO- ) can abstract a proton from the periphery of the molecule but is hindered as a nucleophile. However, some anions such as thiol anion (RS- ) are less basic and more strongly nucleophilic. The E2 : SN2 ratio increases with increased substitution by alkyl groups.

All about Solvents: Non-Polar, Polar Aprotic, and Polar

There is another type of reactions initiated by nucleophiles, called nucleophilic elimination reactions. Nucleophilicity tells about the reaction mechanisms; thus, it is an indication of the reaction rates. For example, if the nucleophilicity is high, then a certain reaction can be fast, and if the nucleophilicity is low, reaction rate is slow. Since nucleophiles donate electrons, according to. Strong Nucleophiles - Usually anions with a full negative charge (easily recognizable by the presence of sodium, lithium or potassium counterions) Participate in SN2-type substitutions Examples: NaOCH 3 (any NaOR), LiCH 3 (any RLi), NaOH or KOH, NaCN or KCN, NaCCR (acetylide anion), NaNH 2 , NaNHR, NaNR 2 , NaI, LiBr, KI, NaN 3. Weak Nucleophiles - Typically neutral molecules; Participate. Thiols (Mercapto Groups) and Sulfides Are Strong Nucleophiles. Thiols are also known as nucleophiles. Thiols have a mercapto group (-SH). The presence of mercapto groups is known to give off a foul odor. Thiols show similar properties to alcohol (-OH), but are known to be very strong nucleophiles. It is also more acidic than alcohol. Therefore, unlike amines, thiols are weakly acidic in. react with strong nucleophiles such as organometallic compounds. •The electon-withdrawing effect of the isocyano group enhances the acidity of the a-C-H bond gorup in aliphatic isocyanides, as well as the ortho-methyl group in aromatic isocyanides. 1.3.4 Reactions with Nucleophiles •React with organometallic compounds Ito, Y. Chem. Commun., 1990, 403-405. Ito, Y. Pure Appl. Chem., 62(4. nucleophiles and strong bases. This means that great care must be taken to exclude even relatively weak acids (such as water or alcohols) from the reaction mixture in order to avoid the formation of by-products arising from proton transfer. Br Br Mg0 Et2O Mg Mg + Br electron transfer a radical anion a radical phenylmagnesium. Strong bases are typically good nucleophiles in substitution reactions. In an acid-base reaction, a proton is transferred from the conjugate acid of a weak base to a strong base. In a similar fashion, nucleophilic substitution reactions often involve the transfer of a carbon group from a weak base, the leaving group, to a stronger base, the nucleophile. Nucleophilic substitution reactions may.

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