5 key factors that affect acidity in organic chemistry — master organic chemistry
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5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic ChemistryTRANSCRIPT
12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
http://www.masterorganicchemistry.com/2010/09/22/fivekeyfactorsthatinfluenceacidity/ 1/23
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Five Key Factors That Influence Acidityby James
in Alcohols, Alkanes, Alkenes, Alkynes, Carboxylic acids, Chemical Bonds, Esters, Functional Groups,Ketones, Organic Chemistry 1, Understanding Electron Flow, Where Electrons Are
I’ve written in schoolmarmish tones before about how pKa is one of the most important measures youcan learn in organic chemistry, and not knowing some basic pKa values before an exam is a lot likewalking up to a poker table without knowing the values of the hands: you’re going to lose your shirt.
Today we’ll talk about what’s behind the trends in acidity for different molecules and discuss the mostimportant factors that determine these values. Before we get started, however, let’s quickly review thebasics of acidity and basicity. Here’s the condensed version:
1. Bronsted acids are proton donors, Lewis acids are electron pair acceptors. Converse: Bronstedbase = proton acceptor, Lewis base = electron pair donor.
2. A conjugate base is what you obtain when you remove a proton (H+) from a compound. Forinstance, HO() is the conjugate base of water. O(2) is the conjugate base of HO(). Conversely,conjugate acids are what you obtain when you add a proton to a compound. The conjugate acid ofwater is H3O(+).
3. Quick quiz: is pH 1 acidic or basic? pKa is similar to pH in that low (and even negative values)denote strong acids. That’s because pKa is based on the equilibrium:
12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
http://www.masterorganicchemistry.com/2010/09/22/fivekeyfactorsthatinfluenceacidity/ 2/23
4. According to this, anything which stabilizes the conjugate base will increase the acidity.Therefore pKa is also a measure of how stable the conjugate base is. Put another way, strong acidshave weak conjugate bases, and vice versa.
With that out of the way, let’s get started.
Factor #1 – Charge.
Removal of a proton, H+ , decreases the formal charge on an atom or molecule by one unit. This is, ofcourse, easiest to do when an atom bears a charge of +1 in the first place, and becomes progressivelymore difficult as the overall charge becomes negative. The acidity trends reflect this:
Note that once a conjugate base (B) is negative, a second deprotonation will make the dianion (B 2).While far from impossible, forming the dianion can be difficult due to the buildup of negative charge andthe corresponding electronic repulsions that result.
Factor #2 – The Role of the Atom
This point causes a lot of confusion due to the presence of two seemingly conflicting trends.
Here’s the first point: acidity increases as we go across a row in the periodic table. This makes sense,right? It makes sense that HF is more electronegative than H2O, NH3, and CH4 due to the greaterelectronegativity of fluorine versus oxygen, nitrogen, and carbon. A fluorine bearing a negative charge isa happy fluorine.
But here’s the seemingly strange thing. HF itself is not a “strong” acid, at least not in the sense that itionizes completely in water. HF is a weaker acid than HCl, HBr, and HI. What’s going on here?
12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
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You could make two arguments for why this is. The first reason has to do with the shorter (and stronger)HF bond as compared to the larger hydrogen halides. The second has to do with the stability of theconjugate base. The fluoride anion, F(–) is a tiny and vicious little beast, with the smallest ionic radius ofany other ion bearing a single negative charge. Its charge is therefore spread over a smaller volume thanthose of the larger halides, which is energetically unfavorable: for one thing, F(–) begs for solvation,which will lead to a lower entropy term in the ΔG.
Note that this trend also holds for H2O and H2S, with H2S being about 10 million times more acidic.
Factor #3 – Resonance.
A huge stabilizing factor for a conjugate base is if the negative charge can be delocalized throughresonance. The classic examples are with phenol (C6H5OH) which is about a million times more acidicthan water, and with acetic acid (pKa of ~5).
12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
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Watch out though – it isn’t enough for a π system to simply be adjacent to a proton – the electrons of theconjugate base have to be in an orbital which allows for effective overlap (for a dastardly trick questionin this vein that routinely stymies Harvard premeds, look here.)
Factor #4 – Inductive effects. Electronegative atoms can draw negative charge toward themselves,which can lead to considerable stabilization of conjugate bases. Check out these examples:
Predictably, this effect is going to be related to two major factors: 1) the electronegativity of the element
12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
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(the more electronegative, the more acidic) and the distance between the electronegative element and thenegative charge.
Factor #5 – Orbitals. Again, the acidity relates nicely to the stability of the conjugate base. And thestability of the conjugate base depends on how well it can accomodate its newfound pair of electrons. Inan effect akin to electronegativity, the more s character in the orbital, the closer the electrons will be tothe nucleus, and the lower in energy (= stable! ) they will be.
Look at the difference between the pKa of acetylene and alkanes – 25! That’s 10 to the power of 25, asin, “100 times bigger than Avogadro’s number”. Just to give you an idea of scale. That’s the amazingthing about chemistry – the sheer range in the power of different phenomena is aweinspiring.
There’s actually a mnemonic I’ve found that can help you remember these effects. This is credited to Dr.Christine Pruis, Senior Lecturer at Arizona State University Tempe.
Charge
Atom
Resonance
Dipole Induction
Orbitals
= CARDIO.
Tread carefully with mnemonics, but there you go.
12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
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How to Use a pKa TableAlcohols (3) – Acidity and BasicityWalkthrough of AcidBase Reactions (3) – Acidity TrendsWalkthrough of Acid Base Reactions (2): Basicity
Tagged as: acidity, acids, bases, basicity, charge stability, conjugate acid, conjugate base, dipoles,electronegativity, hybridization, polarizability, resonance
45 comments… read them below or add one
Heero Fong January 12, 2011 at 12:54 pm
I just wanted to say you are doing an absolutely fantastic job of teaching organic chemistry andmaking it comprehensible. I’ve been reading your posts for the last few days, and material whichwas alien to me before as finally started to make sense.
Thanks!
Reply
James January 12, 2011 at 7:09 pm
Thanks!
Reply
howaida jouni March 12, 2011 at 4:19 pm
thanks for making org chemistry easier but i have a question about resonance, you didnt mention
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12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
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electron donation or withdrawal by resonance
Reply
James March 13, 2011 at 1:32 pm
That’s a thorny issue… it can be hard to separate the influence of inductive and resonanceeffects. Do you have a specific example that you’re thinking of?
Reply
Ali October 19, 2011 at 2:36 am
I was the most confused person who could not understand the concept. I read your note. I received100% on Acidity part on my Exam. Thank you!
Reply
james October 19, 2011 at 3:10 am
This is the kind of comment that makes my day. Thanks!
Reply
Pat November 5, 2011 at 12:03 am
I love this site… I hate reading organic chem txt books because most are boooooring but you makestudying for Ochem the highlight of my friday evening… You are funny, and your delivery styleis absolutely amazing!! I am in Ochem II, barely made it through the first but I am excelling in mysecond…. Thank you sir for doing this!! I appreciate it more than you know… Good day!
Reply
Lara February 14, 2012 at 1:24 am
Thank you so much for this summary sheet, I was having so much trouble trying to figure out whatmade a molecule more acidic – and here it all is! Fully explained and easily understandable.Fantastic stuff.
Reply
Laina March 12, 2012 at 7:06 pm
12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
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I just wanted to thank you for all the work you put into this site. I’m an undergraduate at Yale andfor the past semester, I’ve been afraid I’ll fail Orgo. Thanks to your site, I no longer feel as stressedbecause you’ve done such a good job of explaining things. So, yes, thank you!!
Wishing you the best!
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james March 13, 2012 at 8:56 am
Thanks Laina. Glad you find it useful. Let me know if theres anything I can do to make thesite more helpful for your needs.
Reply
Ala March 22, 2012 at 6:03 pm
I have a problem where I have to determine the most stable conjugate base, which indicates thestrongest acid. I just want to know, is it possible to have a strong acid according to its pKa value,but according to atom, resonance, etc. another acid is stronger?
Reply
james March 23, 2012 at 5:31 pm
pKa represents an experimental measurement. Experimental measurements are primary – theconcepts we pull out of them, such as the factors mentioned, are secondary. So what you’rementioning isn’t possible, assuming all other variables are the same.
Reply
Mariana April 24, 2012 at 7:27 pm
I just don’t seem to understand why does ionic radius increase acidity? I mean, Binding Energydecreases and it’s more easy to lose an electron, if acids are compounds that accept electrons howdoes acidity increase?
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james April 26, 2012 at 8:16 pm
Basicity is all about the stability of negative charge. With larger atoms, essentially thecharge is more spread out over a greater volume. Lower charge densities are more stable.See also here: http://masterorganicchemistry.com/2012/04/25/walkthroughofacidbase
12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
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reactions3aciditytrends/
Reply
Naomi Bowens June 2, 2012 at 3:44 am
I feel sooo much more confident about orgo bc of u =)
Reply
Guvanthi July 29, 2012 at 5:03 pm
All these stuff were very useful to me. Got to know more things that I didn’t know before. Thanksa lot..! Similar article on basicity will be appreciated a lot..!
Reply
Tom August 1, 2012 at 7:22 pm
On the figure describing inductive effects on pKa of carboxylic acids you have bromoacetic acidwith pKa of 2.86 on one line and 2.97 on the next. Why the difference?
Reply
james August 6, 2012 at 9:57 pm
Fixed. Thanks for the spot – Evans’ pKa table says 2.86. Not sure where I pulled the 2.97from.
Reply
Luis Sanchez September 7, 2012 at 12:05 am
This site is so helpful. It makes organic chemistry way easier. Thank you!
Reply
james September 8, 2012 at 7:11 pm
Glad you find it helpful Luis.
Reply
12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
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strea September 12, 2012 at 5:34 pm
Oh wow, this is amazing. I was starting to think there was no site/book that had exactly thisinformation, this compactly (and brilliantly, might I add) presented. Thank you so much! You’vegot no idea how much this helped (and how much it reduced my study time, god knows we can alldo with extra time on our hands :) ). Thanks again!
Reply
Yash February 20, 2013 at 10:25 pm
This is awesome :D ! I never quite got a hold of this topic since the past 23 months and now afterreading this page it’s all crystal clear to me ! And as for the mnemonic , when i told it to my chemteacher , he was impressed and asked me for the website :D ! Great job, keep it up :D
Reply
james February 22, 2013 at 3:59 pm
Great, glad you found it useful!
Reply
Annie March 1, 2013 at 7:41 pm
Can you please make these notes available as PDF?
Thanks.
Reply
Akash Sharma April 16, 2013 at 2:38 am
you can use web2pdf for that……google it…it also has browser plugin..
Reply
Akash Sharma April 16, 2013 at 2:34 am
Organic is my favourite part in chemistry. Your post and contents provided me a good quick
12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
http://www.masterorganicchemistry.com/2010/09/22/fivekeyfactorsthatinfluenceacidity/ 11/23
revision before my exams and I did extremely well…..Thanks to you….you have a good way of teaching organic chemistry..I would definitely recommend this site to my friends who think organic is boaring subject….Once again thanks…..
Reply
Chris June 12, 2013 at 10:42 am
I am curious how you came up with this CARDIO acronym? And when? I have heard it from oneother person a few years ago.
Reply
james June 19, 2013 at 9:04 pm
I shamelessly stole it from a comment thread on SDN.
Reply
Pegah Biparva June 12, 2013 at 6:53 pm
Did you get the CARDIO acronym from a Dr. Christine Pruis or Chad’s Reviews from ArizonaState University? Dr. Pruis is our Organic Chemistry professor and came up with this acronym 78years ago, so perhaps that is the ‘credit’ you speak of? If so, that is awesome!
Reply
Emily September 23, 2013 at 3:26 pm
This was really clear and helpful Thank you so much!!
Reply
James Ashenhurst September 24, 2013 at 10:30 pm
Awesome, glad to hear it.
Reply
vicky October 28, 2013 at 10:18 am
12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
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i didnt get 5 point orbital as s character increases then t should be sp3<sp2<sp
Reply
Hamza January 16, 2014 at 8:09 pm
When trying to choose a compounds with the highest acidity, according to CARDIO, how do youdetermine which factor you should prioritize first?For example:Suppose you’re trying to determine which compound is more acidic, CHCH or benzene ring?When you remove the proton the benzene ring is stabilized by resonance but the HCC has a lot ofs character in its orbital. How would you determine which compound is more acidic?
Reply
nichole March 6, 2014 at 9:42 am
Just wanted to sincerely thankyou for transforming an extremely difficult subject into somethingcomprehensible and futhermore enjoyable. There’s something to be said for that specific talent andit is greatly appreciated. Your use of acronyms and descriptive context have improved both mylabs and test marks.Thank you.
Reply
Mariah March 12, 2014 at 8:56 pm
do lone pairs count when figuring out the hybridization of an orbital?
Reply
Mariah March 12, 2014 at 9:08 pm
and for factor #5… do we look at the hybridization of the acid or the conjugate base?ex// ch3 has a hybridization orbital of sp3 but its CB ch2 has a hybridization of sp2
Reply
muhammad shahroz April 14, 2014 at 4:37 pm
Fantastic! What an explanation…. Truely helpful and admirable….
Reply
12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
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Em May 5, 2014 at 6:49 pm
Thank you so much! Love reading through everything! You make it so understandable andinteresting! I really appreciate the links to more topics too!
Reply
mydoubts2 May 31, 2014 at 4:01 am
why is OH more basic than SH. “” is minus sign
Reply
Kiki June 3, 2014 at 4:17 pm
Thank you so much!! You have made my MCAT studying more a light jog ;)
Reply
Laura August 3, 2014 at 10:10 pm
Why is it that HF is more acidic than HI (#2) , but when its connected to the carboxyl group it is Ithat is more acidic? Anyone?
Reply
Brandon September 26, 2014 at 4:51 pm
Hey! These pages have been great, where can we find the answers to the problems you usuallygive at the end?
Reply
Sidra November 5, 2014 at 3:33 pm
why staboilization of conjugate base enhance acidity ?
Reply
James November 6, 2014 at 11:46 am
12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
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Equilibrium tends to proceed toward the more stable product, yes? So what happens to theequilibrium HA –> H+ A as you make A more stable?
Reply
Hannah November 7, 2014 at 2:23 pm
this was so helpful thank you!
Reply
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Imagine having a comprehensive online guide to help you solve your ownproblems in organic chemistry. That's my mission with this site. After earning aPh.D. at McGill and doing a postdoc at MIT, I applied to be a professor. Thatdidn't work out. So I decided to teach organic chemistry anyway. Master OrganicChemistry is the site I wish I had when I was learning the subject.
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Formation of epoxides from alkenes using mCPBAFormation of epoxides from bromohydrinsFormation of Gilman reagents (organocuprates) from alkyl halidesFormation of Grignard Reagents from Alkenyl HalidesFormation of Grignard Reagents from Alkyl HalidesFormation of hydrates from aldehydes/ketones and H2OFormation of imines from primary amines and ketonesFormation of organolithium reagents from alkyl halidesFormation of thioacetals from aldehydes and ketonesFormation of tosylates from alcoholsFree Radical Addition of HBr To AlkenesFree Radical Bromination of AlkanesFree Radical Chlorination of AlkanesFriedel Crafts alkylation of arenesFriedelCrafts acylation of aromatic groups to give ketonesHalogenation of AlkynesHellVollhardZelinsky ReactionHofmann elimination of alkylammonium salts to give alkenesHofmann Rearrangement of Amides to AminesHydroboration of AlkenesHydroboration of alkynes using BH3 to give aldehydesHydrogenation of Alkenes to give AlkanesHydrogenation of Alkynes to Alkanes using Pd/CHydrolysis of acetals to give aldehydes and ketonesHydrolysis of esters to carboxylic acids with aqueous acidHydrolysis of imines to give ketones (or aldehydes)Hydrolysis of nitriles with aqueous acid to give carboxylic acidsIodination of alkenes to give vicinal diiodides (1,2diiodides)Iodination of Aromatics with I2Ketoenol tautomerismKilianiFischer SynthesisNitration of aromatic groupsNucleophilic Aromatic Substitution (SNAr)Nucleophilic Aromatic Substitution Via ArynesOpening of epoxides with acid and water to give trans diolsOpening of epoxides with nucleophiles under acidic conditionsOxidation of aldehydes to carboxylic acids using Cr(VI)Oxidation of aldehydes to carboxylic acids with Ag2OOxidation of aromatic alkanes with KMnO4 to give carboxylic acidsOxidation of primary alcohols to aldehydesOxidation of Primary Alcohols to Aldehydes using PCCOxidation of primary alcohols to carboxylic acidsOxidation of secondary alcohols to ketones using PCCOxidation of thiols to disulfidesOxidative cleavage of 1,2diols to give aldehydes/ketonesOxidative cleavage of alkenes to give ketones/carboxylic acids using ozone (O3) –(“oxidative workup”)Oxidative cleavage of alkenes to ketones/carboxylic acids using KMnO4Oxidative Cleavage of Alkynes with KMnO4Oxidative Cleavage of Alkynes with Ozone (O3)
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Oxymercuration of Alkenes to form Ethers using Hg(OAc)2Oxymercuration of AlkynesOxymercuration: Alcohols from alkenes using Hg(OAc)2 and WaterOzonolysis of alkenes to ketones and aldehydes (reductive workup)Partial reduction of alkynes to trans alkenes using sodium and ammoniaPartial reduction of alkynes with Lindlar’s catalyst to give cis alkenesPinacol RearrangementPolymerization of dienes with acidProtection of alcohols as silyl ethersProtonation of alcohols to give oxonium ionsProtonation of Grignard reagents to give alkanesReaction of alkyl halides with water to form alcohols (SN1)Reaction of epoxides with nucleophiles under basic conditionsReactions of Diazonium SaltsReduction of aromatic ketones to alkanes with Pd/C and hydrogenReduction of aromatic nitro groups to amino groupsReduction of carboxylic acids to primary alcohols using LiAlH4Reduction of esters to aldehydes using DIBALReduction of esters to primary alcohols using LiAlH4Reduction of nitriles to primary amines with LiAlH4Reductive AminationSharpless EpoxidationSN2 of Cyanide with Alkyl Halides to give NitrilesSN2 reaction between azide ion and alkyl halides to give alkyl azidesSN2 Reaction of Acetylide Ions with Alkyl HalidesSN2 reaction of alkoxide ions with alkyl halides to give ethers (Williamson synthesis)SN2 reaction of alkyl halides with hydroxide ions to give alcoholsSN2 reaction of amines with alkyl chlorides to give ammonium saltsSN2 reaction of carboxylate ions with alkyl halides to give estersSN2 reaction of hydrosulfide ion with alkyl halides to give thiolsSN2 reaction of organocuprates (Gilman reagents) with alkyl halides to give alkanesSN2 reaction of thiolates with alkyl halides to give thioethers (sulfides)SN2 reaction of water with alkyl halides to give alcoholsStille ReactionSubstitution (SN1) with hydride shiftSubstitution with accompanying alkyl shiftSulfonylation of Arenes to give sulfonic acidsSuzuki ReactionThe Gabriel synthesis of aminesThe haloform reaction: conversion of methyl ketones to carboxylic acidsThe Heck ReactionThe Malonic Ester SynthesisThe Mannich ReactionThe Robinson AnnulationTransesterification promoted by alkoxidesWittig Reaction – conversion of ketones/aldehydes to alkenesWolff Kishner Reaction – conversion of ketones/aldehydes to alkanesWolff Rearrangement
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12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
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Resonance Crash Course – Thanks!Resonance Crash Course CheckoutResonance Practice Exam Questions With SolutionsResonance WebinarResource GuideResourcesShare Your Organic Chemistry Success StorySign Up For The Reaction GuideSignup for the Reaction GuideSomething Has Gone WrongSpectroscopy Video – Thanks!Stereochemistry Crash CourseStereochemistry Crash CourseStereochemistry Practice Exam Questions With Solutions (Beginner/Intermediate)Stereochemistry WebinarStereochemistry Webinar Sunday Nov 3Store ActionStudy and Exam TipsSummary SheetsTest PagetesttypgThanks for Joining!Thanks! You’re signed up for the newsletter.Thanks! You’re Signed Up For The Reaction GuideThe Cat Line DiagramThoughts On OChemTuesday Oct 22 Acid Base Webinar at 9pm ESTVideos
A Simple Trick For Determining R/SApplying E2 Reactions with Newman ProjectionsBond Rotations: Exercise 1Bond Rotations: Exercise 2Bond Rotations: Exercise 3Bond Rotations: Exercise 4Bond Rotations: Exercise 5Bond Rotations: The “Steering Wheel” AnalogyBronsted and Lewis AcidityBulky Bases in Elimination ReactionsCarbocation StabilityComparing E1 and E2 MechanismsComparing E1 and E2 StereochemistryComparing the E1 and SN1Comparing the SN1 and SN2Converting a Fischer Projection To A Line DiagramConverting a Line Diagram to a Fischer ProjectionConverting a Newman Projection to a Line DiagramCurved ArrowsDetermining R/S on a Fischer ProjectionE1 with RearrangementE1 With Rearrangement (2)
12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
http://www.masterorganicchemistry.com/2010/09/22/fivekeyfactorsthatinfluenceacidity/ 22/23
Elimination Exercise: Zaitsev’s RuleElimination Reactions in CyclohexanesElimination Reactions in Cyclohexanes (2)Evaluating Resonance Forms (1) ChargesEvaluating Resonance Forms (2) OctetsEvaluating Resonance Forms (3) Negative ChargeEvaluating Resonance Forms (4) Positive ChargeEvaluating Resonance Forms (5) AromaticityExercise: Condensed Formula (1)Exercise: Condensed Formula (2)Factors That Affect Acidity (1) Charge DensityFactors That Affect Acidity (2) ElectronegativityFactors That Affect Acidity (3) PolarizabilityFactors That Affect Acidity (4) Electron Withdrawing GroupsFactors That Affect Acidity (4) ResonanceFactors That Affect Acidity (6) – OrbitalsFactors that affect acidity – AromaticityFormal Charge (1) – Atomic ChargeFormal Charge (2) – Introduction to Formal ChargeFormal Charge Exercise: Allyl CarbocationFormal Charge Exercise: CH2N2Formal Charge Exercise: CH3NO2Formal Charge Exercise: CNFormal Charge Exercise: CO3Formal Charge Exercise: Hidden HydrogensFormal Charge Exercise: Hidden Lone PairsFormal Charge Exercise: N3Formal Charge Exercise: NH4Formal Charge Exercise: O3Formal Charge Exercise: Radicals and CarbenesHidden HydrogensHow Formal Charge Can MisleadHow Heat Affects Elimination ReactionsHow to draw an enantiomerHow To Use A pKa TableIn Summary: ResonanceIntroduction to EliminationIntroduction to pKaIntroduction to RearrangementsIntroduction to ResonanceIntroduction to the E2 ReactionIntroduction to the SN1: ExperimentsIntroduction to the SN2: ExperimentsKey Patterns in Formal ChargeLine DrawingsMaking OH Into A Good Leaving GroupRearrangement Reactions: Alkyl ShiftsRearrangement: Hydride ShiftRearrangements: Carbocation StabilityResonance – Common Mistakes (1)
12/17/2014 5 Key Factors That Affect Acidity in Organic Chemistry — Master Organic Chemistry
http://www.masterorganicchemistry.com/2010/09/22/fivekeyfactorsthatinfluenceacidity/ 23/23
Resonance – Common mistakes (2)SN1 Exercise: The SubstrateSN1 Reaction Energy DiagramSN1 vs. SN2 OverviewSN1 With Alkyl Shift (1)SN1 With Alkyl Shift (2)SN1 With Hydride ShiftSN1/SN2/E1/E2 – SubstrateSN1/SN2/E1/E2 Decision – OverviewSN1/SN2/E1/E2 Decision – SolventSN1/SN2/E1/E2 Decision – TemperatureSN1/SN2/E1/E2 Decision – The Nucleophile/BaseSN1: Applying the SN1 ReactionSN2 Exercise: Apply the SN2SN2 Exercise: Leaving GroupsSN2 Exercise: The SubstrateSolvents in SN1 and SN2 ReactionsStereochemistry Exercise 1Stereochemistry Exercise 2Stereochemistry Exercise 3Stereochemistry Exercise 4Stereochemistry Exercise 5Strong and Weak AcidsSubstitution: What is Substitution?The 4 Components of Every Acid Base ReactionThe E1 ReactionThe Golden Rule of Acid Base ReactionsThe Single Swap RuleThe SN1 MechanismThe SN2 MechanismThe SN2 Reaction Energy DiagramUnderstanding R/S RelationshipsUnequal Resonance FormsUsing Electronegativity to Find Reactive Sites on a MoleculeWhat Makes A Good Leaving Group?What Makes A Good Nucleophile? (1)What Makes A Good Nucleophile? (2)What Makes A Good Nucleophile? (3)What’s A Nucleophile?Zaitsev’s Rule