understanding chemical reactions using electronegativity and resonance — master organic chemistry

7/28/2019 Understanding chemical reactions using electronegativity and resonance Master Organic Chemistry

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How to apply electronegativity and resonance to

understand reactivity

in Drawing Reaction Mechanisms, Organic Chemistry 1, Understanding Electron Flow, Where Electrons Are

One thing has been missing from the discussion of resonance. Whats the point?

Who cares if we can write out resonance structures? What does it matter if we can figure out the two or three

most stable resonance structures? So what?

Heres the point: we can apply resonance (and electronegativity) to figure out the electron densities of

molecules from first principles, and we can apply these electron densities toward understanding how a

molecule will react.

Put it another way: if you learn this skill, you will rely less on memorization for understanding reactions,

because youll be able to figure out the chemical behavior of molecules youve never seen before.

For instance: if youre a non-chemistry major I can pretty much guarantee youve never seen this reaction

before. But if you apply some of the principles in this post, you should be able to make some headway on it.

Lets look at these two aspects really quickly.

1. Applying electronegativities. When you have a bond between two atoms with different

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electronegativities, there will be a dipole (two opposite charges separated in space). That dipole will

give you a clue about the electron densities of those two atoms. For example in the molecule below,

the oxygen is more electronegative than carbon which means that the CO bond will be polarized

towards oxygen (it will have a higher electron density). This is different than formal charge, which

is where we have to assign a charge to an atom for accounting purposes.

2. Applying resonance: when you know the most stable two (or three) resonance forms, youll have a

good idea of what the resonance hybridlooks like. The resonance hybrid also tells you electron

densities, sometimes in a way that isnt immediately apparent from electronegativity (see below).

Heres some examples of resonance hybrids, along with the electron densities we get from applying both

electronegativity and resonance. In the picture, the partial charges () represent electron densities on the

hybrid.
http://www.chem.ucla.edu/harding/tutorials/resonance/draw_res_str.htmlhttp://en.wikipedia.org/wiki/Formal_chargehttp://en.wikipedia.org/wiki/Dipole


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Now for the punch line.

Once you know the partial charges on a molecule, you can then use it to figure out potential chemical

reactivity. How so?

Remember the one sentence summary of chemistry: opposite charges attract, like charges repel.

So any region ofnegative charge on a molecule will have some degree of attraction to a region of

positive charge on another molecule. In reactions electrons flow from areas ofhigh electron density to

low electron density. Another way of putting it: the partial negative charge (i.e. high electron density) will go

to a region of partial positive charge (i.e. low electron density).

So in the diagram below Ive put down some of the resonance hybrids (along with other molecules), and

drawn a selection of the interactions between the opposite charges. Although these arrows do not necessarilyrepresent actual reactions (although many do!) they at least represent potentially feasible reactions.
http://masterorganicchemistry.com/2011/08/24/how-and-why-electrons-flow/


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The key take-home skill from these examples is to be able so see how the resonance hybrid will determineelectron density, and how this can end up leading to hypotheses for feasible reactions.

Lets go back to the original question:

By applying electronegativity, we can judge that the CZn bond will be polarized towards carbon, which

makes it electron rich; it should be attracted to the carbon of the second molecule, which bothelectronegativity and resonance tell us should bear a partial positive charge. In fact this is a real reaction,

although we cant fully determine how well a reaction will work from first principles. Experimental

evidence is the one and only arbiter as to whether a reaction works or not.

Is this technique perfect, without exceptions? No. Its not perfect. Its not completely without

exceptions.* But its a good mental model for the underlying principles of chemical reactivity. The point

here is to give you a glimpse of how to apply the concepts of electronegativity and resonance

towards new and unfamiliar situations.

*Two prominent exceptions: electronegativity isnt the best for figuring out the reactivity of nitrile ion (CN()

and oxymercuration of alkenes. It doesnt predict reactivity of Cl-Cl and Br-Br, etc. which are not polarized.

**Note that this model doesnt tell you how reactive different species will be. That will require another set of


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mental models.

PS a long enough post as it is, but here are some unproductive interactions from the diagram above.

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Tagged as: charges, electronegativity, formal charge, opposite charges attract, resonance

{ 9 comments read them below oradd one }

azmanamJanuary 17, 2012 at 1:22 pm

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Did you mean to have Hs on the enol and protonated(?) ketone in the middle row of your examples?

The methyl group looks odd. :)

Reply

james January 17, 2012 at 2:07 pm

Thanks! fixed.

Reply

dr klbajaj January 19, 2012 at 1:22 am

FROM THE REACTION BETWEEN DIETHYLZINC AND ENAMINE THERE IS BOND

FORMATIONBETWEEN C-C RESULTING INTO AN INTERMEDIATE CONTAING

ZINC.IT WOULD HAVE BEEN MUCH BETTER TO SHOW HOW THE BREAKING OF

BOND BETWEEN C AND ZINCTAKES PLACE.THANKS FOR NICE EXPLANATION FOR

USE OF RESONANCE AND ELECTRNEGTIVITY IN REACTION MECHANISM

Reply


True, I didnt include the specific details of the arrows because they hadnt been introduced inthis series yet and the exact details werent important ; just wanted to show that this was a

*plausible* reaction. Sorry if this wasnt clear.

Reply

dr klbajaj January 24, 2012 at 4:42 pm

Iagree woth you.thanks

Reply

vu quoc January 19, 2012 at 4:15 pm

thanks for this topic. It is good.

Reply

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7/16

Thanks!

Reply

Joseph McClaren January 21, 2012 at 7:25 pm

The formal charge of + 1 on oxygen does not represent electron density

Thank You! I think this is something that confuses a lot of students.

Great article, very nice summary.

Id love to see more examples of working through the logic of where the electron density is. This is

essential for understanding how and when reactions will take place.

Reply

james January 22, 2012 at 2:52 am

Talked about it a bit here, but it didnt involve resonance.

http://masterorganicchemistry.com/2011/11/15/how_to_use_electronegativity/

Ive been meaning to write a post called Formal Charge has its plusses and minuses

Reply

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Addition of HCl to alkynes twice to give geminal dichlorides

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Addition of HI twice to alkynes to give geminal diiodides

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Addition of LiAlH4 to aldehydes to give primary alcohols

Addition of LiAlH4 to ketones to give secondary alcohols

Addition of NaBH4 to aldehydes to give primary alcohols

Addition of NaBH4 to ketones to give secondary alcoholsAddition of organocuprates (Gilman reagents) to acid chlorides to give ketones

Addition to alkenes accompanied by 1,2-alkyl shift

Additions to alkenes accompanied by 1,2-hydride shifts

Aldol addition reaction of aldehydes and ketones

Aldol Condensation

Alkylation of enamines with alkyl halides

Alkylation of enolates

Allylic bromination of alkanes using NBS

Baeyer-Villiger ReactionBase-promoted formation of enolates from ketones

Basic hydrolysis of esters (saponification)

Bromination of alkenes with Br2 to give dibromides

Bromination of aromatic alkanes to give alkyl bromides

Bromination of Aromatics to give Bromoarenes

Chlorination of alkenes with Cl2 to give vicinal dichlorides

Chlorination of Arenes to give Chloroarenes

Claisen Condensation of esters

Cleavage of ethers using acid (SN1 reaction)

Clemmensen Reduction of Ketones/Aldehydes to Alkanes

Conversion of acid chlorides to aldehydes using LiAlH(O-tBu)3

Conversion of acid chlorides to esters through addition of an alcohol

Conversion of alcohols to alkyl bromides using PBr3

Conversion of alcohols to alkyl chlorides using SOCl2

Conversion of alcohols to alkyl halides using HCl

Conversion of Alkyl halides to ethers (SN1)

Conversion of carboxylic acids into acid chlorides with SOCl2

Conversion of carboxylic acids to carboxylates using base

Conversion of carboxylic acids to esters using acid and alcohols (Fischer Esterification)Conversion of tertiary alcohols to alkyl bromides using HBr

Conversion of tertiary alcohols to alkyl iodides with HI

Conversion of thioacetals to alkanes using Raney Nickel

Curtius Rearrangement of Acyl Azides to Isocyanates

Decarboxylation of beta-keto carboxylic acids

Dehydration of amides to give nitriles

Deprotonation of alcohols to give alkoxides

Deprotonation of alkynes with base to give acetylide ions

Diels 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 diols

Elimination (E1) of alkyl halides to form alkenes

Elimination (E1) with 1,2-alkyl shift
http://www.masterorganicchemistry.com/reaction-guide/elimination-with-12-alkyl-shift/http://www.masterorganicchemistry.com/reaction-guide/elimination-e1-of-alkyl-halides-to-form-alkenes/http://www.masterorganicchemistry.com/reaction-guide/dihydroxylation-of-alkenes-with-cold-dilute-kmno4-to-give-vicinal-diols/http://www.masterorganicchemistry.com/reaction-guide/dihydroxylation-of-alkenes-to-give-12-diols-vicinal-diols/http://www.masterorganicchemistry.com/reaction-guide/diels-alder-reaction-of-dienes-and-dienophiles/http://www.masterorganicchemistry.com/reaction-guide/deprotonation-of-alkynes-with-base-to-give-acetylide-ions/http://www.masterorganicchemistry.com/reaction-guide/deprotonation-of-alcohols-to-give-alcohols/http://www.masterorganicchemistry.com/reaction-guide/dehydration-of-amides-to-give-nitriles/http://www.masterorganicchemistry.com/reaction-guide/decarboxylation-of-beta-keto-carboxylic-acids/http://www.masterorganicchemistry.com/reaction-guide/curtius-rearrangement-of-acyl-azides-to-isocyanates/http://www.masterorganicchemistry.com/reaction-guide/conversion-of-thioacetals-to-alkanes-using-raney-nickel/http://www.masterorganicchemistry.com/reaction-guide/conversion-of-tertiary-alcohols-to-alkyl-iodides-with-hi/http://www.masterorganicchemistry.com/reaction-guide/conversion-of-tertiary-alcohols-to-alkyl-bromides-using-hbr/http://www.masterorganicchemistry.com/reaction-guide/conversion-of-carboxylic-acids-to-esters-using-acid-and-alcohols-fischer-esterification/http://www.masterorganicchemistry.com/reaction-guide/conversion-of-carboxylic-acids-to-carboxylates-using-base/http://www.masterorganicchemistry.com/reaction-guide/conversion-of-carboxylic-acids-into-acid-chlorides-with-socl2/http://www.masterorganicchemistry.com/reaction-guide/conversion-of-alkyl-halides-to-ethers-sn1/http://www.masterorganicchemistry.com/reaction-guide/conversion-of-alcohols-to-alkyl-halides-using-hcl/http://www.masterorganicchemistry.com/reaction-guide/conversion-of-alcohols-to-alkyl-chlorides-using-socl2/http://www.masterorganicchemistry.com/reaction-guide/conversion-of-alcohols-to-alkyl-bromides-using-pbr3/http://www.masterorganicchemistry.com/reaction-guide/conversion-of-acid-chlorides-to-esters-through-addition-of-an-alcohol/http://www.masterorganicchemistry.com/reaction-guide/conversion-of-acid-chlorides-to-aldehydes-using-lialho-tbu3/http://www.masterorganicchemistry.com/reaction-guide/clemmensen-reduction-of-ketonesaldehydes-to-alkanes/http://www.masterorganicchemistry.com/reaction-guide/cleavage-of-ethers-using-acid-sn1-reaction/http://www.masterorganicchemistry.com/reaction-guide/claisen-condensation-of-esters/http://www.masterorganicchemistry.com/reaction-guide/chlorination-of-arenes-to-give-chloroarenes/http://www.masterorganicchemistry.com/reaction-guide/chlorination-of-alkenes-with-cl2-to-give-vicinal-dichlorides/http://www.masterorganicchemistry.com/reaction-guide/bromination-of-aromatics-to-give-bromoarenes/http://www.masterorganicchemistry.com/reaction-guide/bromination-of-aromatic-alkanes-to-give-alkyl-bromides/http://www.masterorganicchemistry.com/reaction-guide/bromination-of-alkenes-with-br2-to-give-dibromides/http://www.masterorganicchemistry.com/reaction-guide/basic-hydrolysis-of-esters-saponification/http://www.masterorganicchemistry.com/reaction-guide/base-promoted-formation-of-enolates-from-ketones/http://www.masterorganicchemistry.com/reaction-guide/baeyer-villiger-reaction/http://www.masterorganicchemistry.com/reaction-guide/allylic-bromination-of-alkanes-using-nbs/http://www.masterorganicchemistry.com/reaction-guide/alkylation-of-enolates/http://www.masterorganicchemistry.com/reaction-guide/alkylation-of-enamines-with-alkyl-halides/http://www.masterorganicchemistry.com/reaction-guide/aldol-condensation/http://www.masterorganicchemistry.com/reaction-guide/aldol-addition-reaction-of-aldehydes-and-ketones/http://www.masterorganicchemistry.com/reaction-guide/additions-to-alkenes-accompanied-by-12-hydride-shifts/http://www.masterorganicchemistry.com/reaction-guide/addition-to-alkenes-accompanied-by-12-alkyl-shift/http://www.masterorganicchemistry.com/reaction-guide/addition-of-organocuprates-gilman-reagents-to-acid-chlorides-to-give-ketones/http://www.masterorganicchemistry.com/reaction-guide/addition-of-nabh4-to-ketones-to-give-secondary-alcohols/http://www.masterorganicchemistry.com/reaction-guide/addition-of-nabh4-to-aldehydes-to-give-primary-alcohols/http://www.masterorganicchemistry.com/reaction-guide/addition-of-lialh4-to-ketones-to-give-secondary-alcohols/http://www.masterorganicchemistry.com/reaction-guide/addition-of-lialh4-to-aldehydes-to-give-primary-alcohols/http://www.masterorganicchemistry.com/reaction-guide/addition-of-hydroiodic-acid-to-alkenes-to-give-alkyl-iodides/http://www.masterorganicchemistry.com/reaction-guide/addition-of-hi-twice-to-alkynes-to-give-geminal-diiodides/http://www.masterorganicchemistry.com/reaction-guide/addition-of-hi-once-to-alkynes-to-give-alkenyl-iodides/http://www.masterorganicchemistry.com/reaction-guide/addition-of-hcl-to-alkynes-twice-to-give-geminal-dichlorides/


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Elimination (E1) with hydride shift

Elimination (E2) of alkyl halides to give alkenes

Elimination of alcohols to give alkenes using POCl3

Elimination of water from alcohols to form alkenes using acid

Formation of Acetals from Aldehydes and Ketones

Formation of alkynes through double elimination of vicinal dibromides

Formation of amides from acid chlorides and amines

Formation of Amides Using DCCFormation of anhydrides from acid halides and carboxylates

Formation of Bromohydrins from alkenes using water and Br2

Formation of bromohydrins from alkenes using water and NBS

Formation of Carboxylic Acids from Acyl Chlorides

Formation of carboxylic acids from Grignard reagents and CO2

Formation of chlorohydrins from alkenes using water and Cl2

Formation of Cyanohydrins from ketones and aldehydes

Formation of cyclopropanes from alkenes using methylene carbene (:CH2)

Formation of Diazonium Salts from Aromatic AminesFormation of enamines from ketones/aldehydes and secondary amines

Formation of epoxides from alkenes using m-CPBA

Formation of epoxides from bromohydrins

Formation of Gilman reagents (organocuprates) from alkyl halides

Formation of Grignard Reagents from Alkenyl Halides

Formation of Grignard Reagents from Alkyl Halides

Formation of hydrates from aldehydes/ketones and H2O

Formation of imines from primary amines and ketones

Formation of organolithium reagents from alkyl halides

Formation of thioacetals from aldehydes and ketones

Formation of tosylates from alcohols

Free Radical Bromination of Alkanes

Free Radical Chlorination of Alkanes

Friedel Crafts alkylation of arenes

Friedel-Crafts acylation of aromatic groups to give ketones

Hell-Vollhard-Zelinsky Reaction

Hofmann elimination of alkylammonium salts to give alkenes

Hofmann Rearrangement of Amides to Amines

Hydroboration of AlkenesHydroboration of alkynes using BH3 to give aldehydes

Hydrogenation of Alkenes to give Alkanes

Hydrogenation of Alkynes to Alkanes using Pd/C

Hydrolysis of acetals to give aldehydes and ketones

Hydrolysis of esters to carboxylic acids with aqueous acid

Hydrolysis of imines to give ketones (or aldehydes)

Hydrolysis of nitriles with aqueous acid to give carboxylic acids

Iodination of alkenes to give vicinal diiodides (1,2-diiodides)

Iodination of Aromatics with I2Keto-enol tautomerism

Nitration of aromatic groups

Opening of epoxides with acid and water to give trans diols

Opening of epoxides with nucleophiles under acidic conditions
http://www.masterorganicchemistry.com/reaction-guide/opening-of-epoxides-with-nucleophiles-under-acidic-conditions/http://www.masterorganicchemistry.com/reaction-guide/opening-of-epoxides-with-acid-and-water-to-give-trans-diols/http://www.masterorganicchemistry.com/reaction-guide/nitration-of-aromatic-groups/http://www.masterorganicchemistry.com/reaction-guide/keto-enol-tautomerism/http://www.masterorganicchemistry.com/reaction-guide/iodination-of-aromatics-with-i2/http://www.masterorganicchemistry.com/reaction-guide/iodination-of-alkenes-to-give-vicinal-diiodides-12-diiodides/http://www.masterorganicchemistry.com/reaction-guide/hydrolysis-of-nitriles-with-aqueous-acid-to-give-carboxylic-acids/http://www.masterorganicchemistry.com/reaction-guide/imine-hydrolysis/http://www.masterorganicchemistry.com/reaction-guide/hydrolysis-of-esters-to-carboxylic-acids-with-aqueous-acid/http://www.masterorganicchemistry.com/reaction-guide/hydrolysis-of-acetals-to-give-aldehydes-and-ketones/http://www.masterorganicchemistry.com/reaction-guide/hydrogenation-of-alkynes-to-alkanes-using-pdc/http://www.masterorganicchemistry.com/reaction-guide/hydrogenation-of-alkenes-to-give-alkanes/http://www.masterorganicchemistry.com/reaction-guide/hydroboration-of-alkynes-using-bh3-to-give-aldehydes/http://www.masterorganicchemistry.com/reaction-guide/hydroboration-of-alkenes/http://www.masterorganicchemistry.com/reaction-guide/hofmann-rearrangement-of-amides-to-amines/http://www.masterorganicchemistry.com/reaction-guide/hoffmann-elimination-of-alkylammonium-salts-to-give-alkenes/http://www.masterorganicchemistry.com/reaction-guide/hell-vollhard-zelinsky-reaction/http://www.masterorganicchemistry.com/reaction-guide/friedel-crafts-acylation-of-aromatic-groups-to-give-ketones/http://www.masterorganicchemistry.com/reaction-guide/friedel-crafts-alkylation-of-arenes/http://www.masterorganicchemistry.com/reaction-guide/free-radical-alkane-chlorination/http://www.masterorganicchemistry.com/reaction-guide/free-radical-bromination-of-alkanes/http://www.masterorganicchemistry.com/reaction-guide/formation-of-tosylates-from-alcohols/http://www.masterorganicchemistry.com/reaction-guide/formation-of-thioacetals-from-aldehydes-and-ketones/http://www.masterorganicchemistry.com/reaction-guide/formation-of-organolithium-reagents-from-alkyl-halides/http://www.masterorganicchemistry.com/reaction-guide/formation-of-imines-from-primary-amines-and-ketones/http://www.masterorganicchemistry.com/reaction-guide/formation-of-hydrates-from-aldehydesketones-and-h2o/http://www.masterorganicchemistry.com/reaction-guide/formation-of-grignard-reagents-from-alkyl-halides/http://www.masterorganicchemistry.com/reaction-guide/formation-of-grignard-reagents-from-alkenyl-halides/http://www.masterorganicchemistry.com/reaction-guide/formation-of-gilman-reagents-organocuprates-from-alkyl-halides/http://www.masterorganicchemistry.com/reaction-guide/formation-of-epoxides-from-bromohydrins/http://www.masterorganicchemistry.com/reaction-guide/formation-of-epoxides-from-alkenes-using-m-cpba/http://www.masterorganicchemistry.com/reaction-guide/formation-of-enamines-from-ketonesaldehydes-and-secondary-amines/http://www.masterorganicchemistry.com/reaction-guide/formation-of-diazonium-salts/http://www.masterorganicchemistry.com/reaction-guide/formation-of-cyclopropanes-from-alkenes-using-methylene-carbene-ch2/http://www.masterorganicchemistry.com/reaction-guide/formation-of-cyanohydrins-from-ketones-and-aldehydes/http://www.masterorganicchemistry.com/reaction-guide/formation-of-chlorohydrins-from-alkenes-using-water-and-cl2/http://www.masterorganicchemistry.com/reaction-guide/formation-of-carboxylic-acids-from-grignard-reagents-and-co2/http://www.masterorganicchemistry.com/reaction-guide/formation-of-carboxylic-acids-from-acyl-chlorides/http://www.masterorganicchemistry.com/reaction-guide/formation-of-bromohydrins-from-alkenes-using-water-and-nbs/http://www.masterorganicchemistry.com/reaction-guide/formation-of-bromohydrins-from-alkenes-using-water-and-br2/http://www.masterorganicchemistry.com/reaction-guide/formation-of-anhydrides-from-acid-halides-and-carboxylates/http://www.masterorganicchemistry.com/reaction-guide/formation-of-amides-using-dcc/http://www.masterorganicchemistry.com/reaction-guide/formation-of-amides-from-acid-chlorides-and-amines/http://www.masterorganicchemistry.com/reaction-guide/formation-of-alkynes-through-double-elimination-of-vicinal-dibromides/http://www.masterorganicchemistry.com/reaction-guide/formation-of-acetals-from-aldehydes-and-ketones/http://www.masterorganicchemistry.com/reaction-guide/elimination-of-water-from-alcohols-to-form-alkenes/http://www.masterorganicchemistry.com/reaction-guide/elimination-of-alcohols-to-give-alkenes-using-pocl3/http://www.masterorganicchemistry.com/reaction-guide/elimination-e2-of-alkyl-halides-to-give-alkenes/http://www.masterorganicchemistry.com/reaction-guide/elimination-e1-with-hydride-shift/


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Oxidation of aldehydes to carboxylic acids using Cr(VI)

Oxidation of aldehydes to carboxylic acids with Ag2O

Oxidation of aromatic alkanes with KMnO4 to give carboxylic acids

Oxidation of primary alcohols to aldehydes

Oxidation of Primary Alcohols to Aldehydes using PCC

Oxidation of primary alcohols to carboxylic acids

Oxidation of secondary alcohols to ketones using PCC

Oxidation of thiols to disulfidesOxidative cleavage of 1,2-diols to give aldehydes/ketones

Oxidative cleavage of alkenes to give ketones/carboxylic acids using ozone (O3) (oxidative

workup)

Oxidative cleavage of alkenes to ketones/carboxylic acids using KMnO4

Oxidative Cleavage of Alkynes with KMnO4

Oxidative Cleavage of Alkynes with Ozone (O3)

Oxymercuration of Alkenes to form Ethers using Hg(OAc)2

Oxymercuration of Alkynes

Oxymercuration: 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 ammonia

Partial reduction of alkynes with Lindlars catalyst to give cis alkenes

Pinacol Rearrangement

Polymerization of dienes with acid

Protection of alcohols as silyl ethers

Protonation of alcohols to give oxonium ions

Protonation of Grignard reagents to give alkanes

Reaction of alkyl halides with water to form alcohols (SN1)

Reaction of epoxides with nucleophiles under basic conditions

Reactions of Diazonium Salts

Reduction of aromatic ketones to alkanes with Pd/C and hydrogen

Reduction of aromatic nitro groups to amino groups

Reduction of carboxylic acids to primary alcohols using LiAlH4

Reduction of esters to aldehydes using DIBAL

Reduction of esters to primary alcohols using LiAlH4

Reduction of nitriles to primary amines with LiAlH4

Reductive Amination

SN2 of Cyanide with Alkyl Halides to give NitrilesSN2 reaction between azide ion and alkyl halides to give alkyl azides

SN2 Reaction of Acetylide Ions with Alkyl Halides

SN2 reaction of alkoxide ions with alkyl halides to give ethers (Williamson synthesis)

SN2 reaction of alkyl halides with hydroxide ions to give alcohols

SN2 reaction of amines with alkyl chlorides to give ammonium salts

SN2 reaction of carboxylate ions with alkyl halides to give esters

SN2 reaction of hydrosulfide ion with alkyl halides to give thiols

SN2 reaction of organocuprates (Gilman reagents) with alkyl halides to give alkanes

SN2 reaction of thiolates with alkyl halides to give thioethers (sulfides)SN2 reaction of water with alkyl halides to give alcohols

Substitution (SN1) with hydride shift

Substitution with accompanying alkyl shift

Sulfonylation of Arenes to give sulfonic acids
http://www.masterorganicchemistry.com/reaction-guide/sulfonation-of-aromatics-with-so3-and-acid/http://www.masterorganicchemistry.com/reaction-guide/substitution-with-alky-shift/http://www.masterorganicchemistry.com/reaction-guide/substitution-sn1-with-hydride-shift/http://www.masterorganicchemistry.com/reaction-guide/sn2-reaction-of-water-with-alkyl-halides-to-give-alcohols/http://www.masterorganicchemistry.com/reaction-guide/sn2-reaction-of-thiolates-with-alkyl-halides-to-give-thioethers-sulfides/http://www.masterorganicchemistry.com/reaction-guide/sn2-reaction-of-organocuprates-gilman-reagents-with-alkyl-halides-to-give-alkanes/http://www.masterorganicchemistry.com/reaction-guide/sn2-reaction-of-hydrosulfide-ion-with-alkyl-halides-to-give-thiols/http://www.masterorganicchemistry.com/reaction-guide/sn2-reaction-of-carboxylate-ions-with-alkyl-halides-to-give-esters/http://www.masterorganicchemistry.com/reaction-guide/sn2-reaction-of-amines-with-alkyl-chlorides-to-give-ammonium-salts/http://www.masterorganicchemistry.com/reaction-guide/sn2-reaction-of-alkyl-halides-with-hydroxide-ions-to-give-alcohols/http://www.masterorganicchemistry.com/reaction-guide/sn2-reaction-of-alkoxide-ions-with-alkyl-halides-to-give-ethers-williamson-synthesis/http://www.masterorganicchemistry.com/reaction-guide/sn2-reaction-of-acetylide-ions-with-alkyl-halides/http://www.masterorganicchemistry.com/reaction-guide/sn2-reaction-between-azide-ion-and-alkyl-halides-to-give-alkyl-azides/http://www.masterorganicchemistry.com/reaction-guide/sn2-of-cyanide-with-alkyl-halides-to-give-nitriles/http://www.masterorganicchemistry.com/reaction-guide/reductive-amination/http://www.masterorganicchemistry.com/reaction-guide/reduction-of-nitriles-to-primary-amines-with-lialh4/http://www.masterorganicchemistry.com/reaction-guide/reduction-of-esters-to-primary-alcohols-using-lialh4/http://www.masterorganicchemistry.com/reaction-guide/reduction-of-esters-to-aldehydes-using-dibal/http://www.masterorganicchemistry.com/reaction-guide/reduction-of-carboxylic-acids-to-primary-alcohols-using-lialh4/http://www.masterorganicchemistry.com/reaction-guide/reduction-of-aromatic-nitro-groups-to-amino-groups/http://www.masterorganicchemistry.com/reaction-guide/reduction-of-aromatic-ketones-to-alkanes-with-pdc-and-hydrogen/http://www.masterorganicchemistry.com/reaction-guide/reactions-of-diazonium-salts/http://www.masterorganicchemistry.com/reaction-guide/reaction-of-epoxides-with-nucleophiles-under-basic-conditions/http://www.masterorganicchemistry.com/reaction-guide/reaction-of-alkyl-halides-with-water-to-form-alcohols-sn1/http://www.masterorganicchemistry.com/reaction-guide/protonation-of-grignard-reagents-to-give-alkanes/http://www.masterorganicchemistry.com/reaction-guide/protonation-of-alcohols-to-give-oxonium-ions/http://www.masterorganicchemistry.com/reaction-guide/protection-of-alcohols-as-silyl-ethers/http://www.masterorganicchemistry.com/reaction-guide/polymerization-of-dienes/http://www.masterorganicchemistry.com/reaction-guide/pinacol-rearrangement/http://www.masterorganicchemistry.com/reaction-guide/partial-reduction-of-alkynes-with-lindlars-catalyst-to-give-cis-alkenes/http://www.masterorganicchemistry.com/reaction-guide/partial-reduction-of-alkynes-to-trans-alkenes-using-sodium-and-ammonia/http://www.masterorganicchemistry.com/reaction-guide/oxidative-cleavage-of-alkenes-using-ozone-o3-to-ketones-and-aldehydes-reductive-workup/http://www.masterorganicchemistry.com/reaction-guide/formation-of-alcohols-from-alkenes-using-hgoac2-and-water/http://www.masterorganicchemistry.com/reaction-guide/oxymercuration-of-alkynes/http://www.masterorganicchemistry.com/reaction-guide/oxymercuration-to-form-ethers-from-alkenes/http://www.masterorganicchemistry.com/reaction-guide/oxidative-cleavage-of-alkynes-with-ozone-o3/http://www.masterorganicchemistry.com/reaction-guide/oxidative-cleavage-of-alkynes-with-kmno4/http://www.masterorganicchemistry.com/reaction-guide/oxidative-cleavage-of-alkenes-to-ketonescarboxylic-acids-using-kmno4/http://www.masterorganicchemistry.com/reaction-guide/oxidative-cleavage-of-alkenes-to-give-ketonescarboxylic-acids-using-ozone-o3-oxidative-workup/http://www.masterorganicchemistry.com/reaction-guide/oxidative-cleavage-of-12-diols-to-give-aldehydesketones/http://www.masterorganicchemistry.com/reaction-guide/oxidation-of-thiols-to-disulfides/http://www.masterorganicchemistry.com/reaction-guide/oxidation-of-secondary-alcohols-to-ketones-using-pcc/http://www.masterorganicchemistry.com/reaction-guide/oxidation-of-primary-alcohols-to-carboxylic-acids/http://www.masterorganicchemistry.com/reaction-guide/oxidation-of-primary-alcohols-to-aldehydes-using-pcc/http://www.masterorganicchemistry.com/reaction-guide/oxidation-of-primary-alcohols-to-aldehydes/http://www.masterorganicchemistry.com/reaction-guide/oxidation-of-aromatic-alkanes-with-kmno4-to-give-carboxylic-acids/http://www.masterorganicchemistry.com/reaction-guide/oxidation-of-aldehydes-to-carboxylic-acids-with-ag2o/http://www.masterorganicchemistry.com/reaction-guide/oxidation-of-aldehydes-to-carboxylic-acids-using-crvi/


14/16

The Gabriel synthesis of amines

The haloform reaction: conversion of methyl ketones to carboxylic acids

The Malonic Ester Synthesis

The Robinson Annulation

Transesterification promoted by alkoxides

Wittig Reaction conversion of ketones/aldehydes to alkenes

Wolff Kishner Reaction conversion of ketones/aldehydes to alkanes

Wolff RearrangementResource Guide

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Thoughts On O-ChemVideos

A Simple Trick For Determining R/S

Applying E2 Reactions with Newman Projections

Bond Rotations: Exercise 1





Bond Rotations: The Steering Wheel Analogy

Bronsted and Lewis Acidity

Bulky Bases in Elimination Reactions

Carbocation Stability

Comparing E1 and E2 Mechanisms

Comparing E1 and E2 Stereochemistry

Comparing the E1 and SN1

Comparing the SN1 and SN2

Converting a Line Diagram to a Fischer Projection

Converting a Line Diagram to a Fischer Projection

Converting a Newman Projection to a Line DiagramCurved Arrows

Determining R/S on a Fischer Projection

E1 with Rearrangement

E1 With Rearrangement (2)

Elimination Exercise: Zaitsevs Rule

Elimination Reactions in Cyclohexanes

Elimination Reactions in Cyclohexanes (2)

Evaluating Resonance Forms (1) Charges

Evaluating Resonance Forms (2) OctetsEvaluating Resonance Forms (3) Negative Charge

Evaluating Resonance Forms (4) Positive Charge

Evaluating Resonance Forms (5) Aromaticity

Exercise: Condensed Formula (1)
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Exercise: Condensed Formula (2)

Factors That Affect Acidity (1) Charge Density

Factors That Affect Acidity (2) Electronegativity

Factors That Affect Acidity (3) Polarizability

Factors That Affect Acidity (4) Electron Withdrawing Groups

Factors That Affect Acidity (4) Resonance

Factors That Affect Acidity (6) Orbitals

Factors that affect acidity AromaticityFormal Charge (1) Atomic Charge

Formal Charge (2) Introduction to Formal Charge

Formal Charge Exercise: Allyl Carbocation

Formal Charge Exercise: CH2N2

Formal Charge Exercise: CH3NO2

Formal Charge Exercise: CN

Formal Charge Exercise: CO3

Formal Charge Exercise: Hidden Hydrogens

Formal Charge Exercise: Hidden Lone PairsFormal Charge Exercise: N3

Formal Charge Exercise: NH4

Formal Charge Exercise: O3

Formal Charge Exercise: Radicals and Carbenes

Hidden Hydrogens

How Formal Charge Can Mislead

How Heat Affects Elimination Reactions

How to draw an enantiomer

How To Use A pKa Table

In Summary: Resonance

Introduction to Elimination

Introduction to pKa

Introduction to Rearrangements

Introduction to Resonance

Introduction to the E2 Reaction

Introduction to the SN1: Experiments

Introduction to the SN2: Experiments

Key Patterns in Formal Charge

Line DrawingsMaking OH Into A Good Leaving Group

Rearrangement Reactions: Alkyl Shifts

Rearrangement: Hydride Shift

Rearrangements: Carbocation Stability

Resonance Common Mistakes (1)

Resonance Common mistakes (2)

SN1 Exercise: The Substrate

SN1 Reaction Energy Diagram

SN1 vs. SN2 OverviewSN1 With Alkyl Shift (1)

SN1 With Alkyl Shift (2)

SN1 With Hydride Shift

SN1/SN2/E1/E2 Substrate
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SN1/SN2/E1/E2 Decision Overview

SN1/SN2/E1/E2 Decision Solvent

SN1/SN2/E1/E2 Decision Temperature

SN1/SN2/E1/E2 Decision The Nucleophile/Base

SN1: Applying the SN1 Reaction

SN2 Exercise: Apply the SN2

SN2 Exercise: Leaving Groups

SN2 Exercise: The SubstrateSolvents in SN1 and SN2 Reactions

Stereochemistry Exercise 1





Strong and Weak Acids

Substitution: What is Substitution?

The 4 Components of Every Acid Base ReactionThe E1 Reaction

The Golden Rule of Acid Base Reactions

The Single Swap Rule

The SN1 Mechanism

The SN2 Mechanism

The SN2 Reaction Energy Diagram

Understanding R/S Relationships

Unequal Resonance Forms

Using Electronegativity to Find Reactive Sites on a Molecule

What Makes A Good Leaving Group?

What Makes A Good Nucleophile? (1)



Whats A Nucleophile?

Zaitsevs Rule

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understanding chemical reactions using electronegativity and resonance — master organic chemistry

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