2015. 7. 30. How to Use a pKa Table — Master Organic Chemistry

http://www.masterorganicchemistry.com/2010/09/29/how­to­use­a­pka­table/ 1/16

HomeBlogOnline TutoringReaction GuideStudy GuidesContact »Members Login

Master Organic Chemistry

Enter an organic chemistry search term

New? Start HereStudy And Exam TipsOrganic 1 IndexOrganic 2 IndexSummary SheetsFeedback

How to Use a pKa Tableby James

in Alcohols, General Chemistry, Organic Chemistry 1, Where Electrons Are

Today we’ll talk about an incredibly important skill that might take some time to graspbut pays tremendous dividends. We’ll go through the exact details of how to use a pKatable. [Background for pKa – read this post ]   Understanding the proper use of a pKatable will give you the ability to recognize which acid-base reactions will happen andwhich will not. This will come up a lot as you progress through Org 1 and Org 2. It mightbe helpful to go back and review some of the factors that affect acidity that were talkedabout earlier.

Let’s say you’re given the following question:

Exam coming up? Get an instant set ofawesome "cheat sheets" for Org 1 and

Org 2

2015. 7. 30. How to Use a pKa Table — Master Organic Chemistry

http://www.masterorganicchemistry.com/2010/09/29/how­to­use­a­pka­table/ 2/16

By acidity, we’re talking about Bronsted acidity here – in other words, the ability todonate a proton.

Let’s say we’re given a pKa table with the following values.

Where do we start with this problem?

2015. 7. 30. How to Use a pKa Table — Master Organic Chemistry

http://www.masterorganicchemistry.com/2010/09/29/how­to­use­a­pka­table/ 3/16

1. Remember that a pKa table ranks molecules in order of their acidity, fromstrongly acidic (e.g. HCl with pKa of –8) to weakly acidic (e.g. methane, pKa of ~50).

2. What determines whether or not an acid-base reaction will happen in the firstplace? We apply the following principle to acid-base reactions: A stronger acid willtend to react with a stronger base to produce a weaker acid and a weaker base.

3. It’s easy enough to use a pKa table to determine acid strength – we can see at aglance that H2O (pKa of 15) is a stronger acid than NH3 (pKa of 38). The questionis, how do we determine base strength?

Here’s how we do it. Draw out the conjugate bases of the acids on your pka table byremoving a proton.

E.g. NH3 –> NH2(-) or   CH4 –> CH3 (-).

Here’s the key principle: The order of base strength is the inverse of acid strength. Theweaker the acid, the stronger the conjugate base. Using this principle, you can alsouse the pKa table to give you the strengths of bases. I call this the inverse pKa table.

Here’s a pKa table with the conjugate bases included:

4. Here’s how we apply this knowledge to the problem.

Find the acid on the pKa table. Find the base on the inverse pKa table. Do the acid basereaction – that is, add a proton to the base and remove a proton from the acid.

5. Evaluate: Is the new acid stronger or weaker? Is the new base stronger or weaker?

6. Examples.

2015. 7. 30. How to Use a pKa Table — Master Organic Chemistry

http://www.masterorganicchemistry.com/2010/09/29/how­to­use­a­pka­table/ 4/16

Example A : We have CH4 and HO(-) We can find CH4 on the pKa table – it has a pKaof 50. Hydroxide ion, HO(-) is not on the left side of the pKa table, but it is on the“inverse” pKa table – it is the conjugate base of water, H2O. So CH4 is the acid and HO(-) is the base in this reaction.

Doing the proposed acid base reaction, we transfer a proton from CH4 to HO (-). Theproducts of this reaction would therefore be CH3(-) and water.

Now we ask the question – how do these compare in strength to our starting acids andbases? Water has a pKa of ~15, and CH4 has a pKa of 50. Our product is a stronger acid.From the inverse pKa table, we also note that CH3(-) is a stronger base than HO(–). Ourproduct is a stronger base.

Verdict – the reaction won’t happen. We need to go to a weaker acid-base pair (see#2, above). So we write “NR”.

Here’s another example.

Example B – Take HCΞCH and NH2(–). HCΞCH has a pKa of 25; on the other hand,NH2(–) is on the conjugate base table. Drawing out the products of the acid basereaction will give us NH3 (weaker acid than HCΞCH) and HCΞC(–) (weaker base thanNH2(–). This reaction will go.

Example C : Take NH3 and HCl. This time, we can find both HCl and NH3 on the pKatable. But HCl has a pKa of (–8) and NH3 has a pKa of 38. HCl will clearly act as an acidhere, and NH3 will act as a base.

We can write out our acid base reaction: HCl + NH3 → NH4(+) Cl(–)

Our acidic product, NH4, has a pKa of 9. Our product is a weaker acid than HCl. Ourbasic product, Cl(-) ranks below NH3 on our inverse pKa scale. Our product is a weakerbase than NH3. Conclusion: this reaction is also a go. And, indeed, if you find yourselfin a freezing hut with only a bottle of concentrated HCl and aqueous ammonia to keepyou company, adding them together will definitely warm up your day. This is about theonly situation in which I would recommend this.

Q. How do you deal with a compound that is similar but not on the table? Takehexane, for instance. Even though it is not technically on the list, its behavior is similarenough to methane – they’re both alkanes, after all – that we make the assumption thatthe pKa’s are roughly the same. Similarly, an amine like trimethylamine (NMe3) will havesimilar behavior to NH3 in the reaction with HCl.

One final point on the big-picture type view. Note the pattern. The conjugate base ofmethane (H3C(–) ) is strong enough to deprotonate anything below it on the pKa table(that is, pretty much everything). Methyllithium, CH3Li, is an incredibly strong base.Conversely, acetylide ion, HCC(–) is strong enough to effectively deprotonate any acidwith a pKa under ~25, and acetate ion (CH3COO(–)) is weaker still, only able todeprotonate any acid with a pKa lower than 5.

2015. 7. 30. How to Use a pKa Table — Master Organic Chemistry

http://www.masterorganicchemistry.com/2010/09/29/how­to­use­a­pka­table/ 5/16

That’s why I compare a strong base like methyl lithium to a royal flush in poker – it willessentially defeat  any hand (acid) it encounters.

Next Post:A Handy Rule of Thumb for Acid Base Reactions

1

0

4

Tweet

Related Posts:

Walkthrough of Acid-Base Reactions (3) – Acidity TrendsWalkthrough of Acid Base Reactions (2): BasicityWalkthrough of Acid Base Reactions (1)Five Key Factors That Influence Acidity

Tagged as: acidity, acids, bases, basicity, conjugate acid, conjugate base, equilibrium, pkatables, skills, stability

{ 4 comments… read them below or add one }

26

Share

2015. 7. 30. How to Use a pKa Table — Master Organic Chemistry

http://www.masterorganicchemistry.com/2010/09/29/how­to­use­a­pka­table/ 6/16

Chemistry user May 28, 2011 at 11:23 pm

Thank you very much! This is a helpful trick for my Organic I exam!

Reply

Arpan May 31, 2013 at 3:13 pm

THANK YOU VERY MUCHthis article has provided a concrete way of judging an acid base reaction for which Iwas helplessly strugglinggreat sitekeep maintaining and improving it

Reply

Dayakar September 6, 2013 at 9:27 am

thanks for providing the information about Pka ,it is very useful in the acid basereactions.

Reply

Robert January 18, 2014 at 5:55 pm

Hi, could I use pka tables to see what pka a Base e.g. must have to deprotonate anAlkohol. In principle it should be higher than 16.

Reply

Leave a Comment

Name *

E-mail *

Website

2015. 7. 30. How to Use a pKa Table — Master Organic Chemistry

http://www.masterorganicchemistry.com/2010/09/29/how­to­use­a­pka­table/ 7/16

Submit

Sign Up To Get WeeklyOrganic Chemistry Tips

And get the free "How To Succeed In Organic Chemistry" E-book

Please enter your first name *

Please enter your email *

Sign me up! 

About Master Organic Chemistry

Imagine having a comprehensive online guide to help you solveyour own problems in organic chemistry. That's my mission withthis site. After earning a Ph.D. at McGill and doing a postdoc atMIT, I applied to be a professor. That didn't work out. So I decidedto teach organic chemistry anyway. Master Organic Chemistry is thesite I wish I had when I was learning the subject.

Organic Chemistry Guides

Get The Latest Updates

facebooktwitterrssemailRecent PostsPopular PostsRecent Comments

Synthesis (6) - Reactions of AlcoholsPosted on: Jul 27, 2015

Thiols And ThioethersPosted on: Jul 05, 2015

Protecting Groups For AlcoholsPosted on: Jun 17, 2015

Intramolecular Reactions of Alcohols and EthersPosted on: Jun 12, 2015

2015. 7. 30. How to Use a pKa Table — Master Organic Chemistry

http://www.masterorganicchemistry.com/2010/09/29/how­to­use­a­pka­table/ 8/16

Demystifying Alcohol OxidationsPosted on: May 21, 2015

Copyright © 2015 MasterOrganicChemistry.com. All rights reservedOrganic Chemistry Is Awesome

About JamesAccountAdvanced Substitution Topics – Sun Nov 10Alkene Crash Course – Thanks!Alkene Mini Course – Thanks!Alkene Mini-CourseAlkene WebinarAlkenes: Common Exam Problems (With Solutions)Alkyne Webinar Sun Dec 15 at 9pm ESTAlkynes Are A Blank CanvasBlogCommon Mistakes In Organic Chemistry: Pentavalent CarbonConfirming your email address…Crash Course On AlkenesCrash Course On Alkenes – CheckoutDashboardDon’t Be Futyl, Learn The ButylsElimination Webinar – Sunday Nov 24 at 9pm ESTFeedbackForm Styling Sandbox PageFrom Gen Chem To Organic ChemGetting StartedHomeHome-2How To Draw A Cyclohexane ChairHow To Succeed In Organic ChemistryHow To Succeed In Organic ChemistryInitiation, Propagation, TerminationInterviewIntroduction To Spectroscopy SeminarIntroduction To Substitution Webinar Tuesday Nov 5Leah Nomenclature Guest PostMembers LoginMissionMy Organic Chemistry Story – What’s Yours?New Acid-Base WebinarNEW! Reagents AppNMR Video CheckoutOctober 22 Acid-Base WebinarOnline Organic Chemistry TutoringOrg 2 Post IndexOrganic 1

2015. 7. 30. How to Use a pKa Table — Master Organic Chemistry

http://www.masterorganicchemistry.com/2010/09/29/how­to­use­a­pka­table/ 9/16

Organic 2Organic Chemistry Study AdvicePost IndexPost Index 2Post Index Draftpost index draft 2PremiumProducts

Organic Chemistry Reagent GuideReaction Guide

1,4-addition of enolates to enones (“The Michael Reaction”)1,4-addition of nucleophiles to enones1,4-addition of organocuprates (Gilman reagents) to enonesAcidic cleavage of ethers (SN2)Addition Of Alcohols To Alkenes With AcidAddition of aqueous acid to alkenes to give alcoholsAddition of Dichlorocarbene to alkenes to give dichlorocyclopropanesAddition of dichloromethylene carbene to alkenesAddition of Grignard reagents to aldehydes to give secondary alcoholsAddition of Grignard reagents to esters to give tertiary alcoholsAddition of Grignard reagents to formaldehyde to give primary alcoholsAddition of Grignard reagents to ketones to give tertiary alcoholsAddition of Grignard reagents to nitriles to give ketones (after hydrolysis)Addition of HBr once to alkynes to give alkenyl bromidesAddition of HBr to AlkenesAddition of HBr twice to alkynes to give geminal dibromidesAddition of HCl once to alkynes to give alkenyl chloridesAddition of HCl to Alkenes to Give Alkyl ChloridesAddition of HCl to alkynes twice to give geminal dichloridesAddition of HI once to alkynes to give alkenyl iodidesAddition of HI twice to alkynes to give geminal diiodidesAddition of Hydroiodic Acid to Alkenes to Give Alkyl IodidesAddition of LiAlH4 to aldehydes to give primary alcoholsAddition of LiAlH4 to ketones to give secondary alcoholsAddition of NaBH4 to aldehydes to give primary alcoholsAddition of NaBH4 to ketones to give secondary alcoholsAddition of organocuprates (Gilman reagents) to acid chlorides to giveketonesAddition to alkenes accompanied by 1,2-alkyl shiftAdditions to alkenes accompanied by 1,2-hydride shiftsAldol addition reaction of aldehydes and ketonesAldol CondensationAlkylation of enamines with alkyl halidesAlkylation of enolatesAllylic bromination of alkanes using NBSBaeyer-Villiger Reaction

2015. 7. 30. How to Use a pKa Table — Master Organic Chemistry

http://www.masterorganicchemistry.com/2010/09/29/how­to­use­a­pka­table/ 10/16

Base-promoted formation of enolates from ketonesBasic hydrolysis of esters (saponification)Beckmann RearrangementBromination of alkenes with Br2 to give dibromidesBromination of aromatic alkanes to give alkyl bromidesBromination of Aromatics to give BromoarenesCannizarro ReactionChlorination of alkenes with Cl2 to give vicinal dichloridesChlorination of Arenes to give ChloroarenesClaisen Condensation of estersCleavage of ethers using acid (SN1 reaction)Clemmensen Reduction of Ketones/Aldehydes to AlkanesConversion of acid chlorides to aldehydes using LiAlH(O-tBu)3Conversion of acid chlorides to esters through addition of an alcoholConversion of alcohols to alkyl bromides using PBr3Conversion of alcohols to alkyl chlorides using SOCl2Conversion of alcohols to alkyl halides using HClConversion of Alkyl halides to ethers (SN1)Conversion of carboxylic acids into acid chlorides with SOCl2Conversion of carboxylic acids to carboxylates using baseConversion of carboxylic acids to esters using acid and alcohols (FischerEsterification)Conversion of tertiary alcohols to alkyl bromides using HBrConversion of tertiary alcohols to alkyl iodides with HIConversion of thioacetals to alkanes using Raney NickelCurtius Rearrangement of Acyl Azides to IsocyanatesDecarboxylation of beta-keto carboxylic acidsDehydration of amides to give nitrilesDeprotonation of alcohols to give alkoxidesDeprotonation of alkynes with base to give acetylide ionsDiels Alder Reaction of dienes and dienophilesDihydroxylation of Alkenes to give 1,2-diols (vicinal diols)Dihydroxylation of alkenes with cold, dilute KMnO4 to give vicinal diolsElimination (E1) of alkyl halides to form alkenesElimination (E1) with 1,2-alkyl shiftElimination (E1) with hydride shiftElimination (E2) of alkyl halides to give alkenesElimination of alcohols to give alkenes using POCl3Elimination of water from alcohols to form alkenes using acidEnamine HydrolysisFormation of Acetals from Aldehydes and KetonesFormation of alkynes through double elimination of vicinal dibromidesFormation of amides from acid chlorides and aminesFormation of Amides Using DCCFormation of anhydrides from acid halides and carboxylatesFormation of Bromohydrins from alkenes using water and Br2

2015. 7. 30. How to Use a pKa Table — Master Organic Chemistry

http://www.masterorganicchemistry.com/2010/09/29/how­to­use­a­pka­table/ 11/16

Formation of bromohydrins from alkenes using water and NBSFormation of Carboxylic Acids from Acyl ChloridesFormation of carboxylic acids from Grignard reagents and CO2Formation of chlorohydrins from alkenes using water and Cl2Formation of Cyanohydrins from ketones and aldehydesFormation of cyclopropanes from alkenes using methylene carbene (:CH2)Formation of Diazonium Salts from Aromatic AminesFormation of enamines from ketones/aldehydes and secondary aminesFormation of epoxides from alkenes using m-CPBAFormation 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 arenesFriedel-Crafts acylation of aromatic groups to give ketonesHalogenation of AlkynesHell-Vollhard-Zelinsky 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 (1,2-diiodides)Iodination of Aromatics with I2Keto-enol tautomerismKiliani-Fischer 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 Ag2O

2015. 7. 30. How to Use a pKa Table — Master Organic Chemistry

http://www.masterorganicchemistry.com/2010/09/29/how­to­use­a­pka­table/ 12/16

Oxidation 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 1,2-diols 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)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 (Williamsonsynthesis)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 givealkanesSN2 reaction of thiolates with alkyl halides to give thioethers (sulfides)

2015. 7. 30. How to Use a pKa Table — Master Organic Chemistry

http://www.masterorganicchemistry.com/2010/09/29/how­to­use­a­pka­table/ 13/16

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

Reaction Guide Checkout PageResonance Crash CourseResonance Crash Course – Thanks!Resonance Crash Course CheckoutResonance Practice Exam Questions With SolutionsResonance WebinarResource GuideResourcesShare Your Organic Chemistry StorySign Up For The Reaction GuideSign Up To Be A Flashcards Beta Tester!Signup 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 DiagramThe Web of ReactionsThoughts On O-Chem

2015. 7. 30. How to Use a pKa Table — Master Organic Chemistry

http://www.masterorganicchemistry.com/2010/09/29/how­to­use­a­pka­table/ 14/16

TipsA Simple Formula For 7 Important Aldehyde/Ketone ReactionsAldehydes And Ketones – AdditionDetermining AromaticityDiels Alder Reaction – 1Electrophilic Aromatic SubstitutionElectrophilic Aromatic Substitution – Directing GroupsEnolatesFiguring Out The FischerOrder of Operations!Protecting GroupsRecognizing Endo and ExoSynthesis (1) – “What’s Different?”Synthesis (2) – What Reactions?Synthesis (3) – Figuring Out The OrderSynthesis: Walkthrough of A Sample ProblemSynthesis: Working BackwardsThe Claisen CondensationThe Second Most Important Carbonyl MechanismThree Exam TipsTips On Building Molecular Orbitals

Tuesday 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)Elimination Exercise: Zaitsev’s Rule

2015. 7. 30. How to Use a pKa Table — Master Organic Chemistry

http://www.masterorganicchemistry.com/2010/09/29/how­to­use­a­pka­table/ 15/16

Elimination 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 – AromaticityFactors 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) – OrbitalsFormal 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 Shifts

2015. 7. 30. How to Use a pKa Table — Master Organic Chemistry

http://www.masterorganicchemistry.com/2010/09/29/how­to­use­a­pka­table/ 16/16

Rearrangement: Hydride ShiftRearrangements: Carbocation StabilityResonance – Common Mistakes (1)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: Applying the SN1 ReactionSN1/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/BaseSN2 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