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home blog online tutoring reaction guide study guides contact mission feedback members login reaction guide moc elite master organic chemistry looking for the blog? click here. new? start here study and exam tips organic 1 index organic 2 index free “cheat sheets” feedback organic chemistry exam coming up? get immediate access to our awesome organic chemistry “cheat sheets”, available in minutes via download, and get caught up in a hurry! get started! looking for something specific? copyright © 2018 masterorganicchemistry.com. all rights reserved organic chemistry is awesome about james account advanced substitution topics – sun nov 10 alkene mini course – thanks! alkene mini-course alkenes: common exam problems (with solutions) alkyne webinar sun dec 15 at 9pm est alkynes are a blank canvas blog cancel subscription carbon carbon bonds common mistakes in organic chemistry: pentavalent carbon confirming your email address… crash course on alkenes crash course on alkenes – checkout dashboard don’t be futyl, learn the butyls feedback form styling sandbox page from gen chem to organic chem getting started home home-2 how to draw a cyclohexane chair how to succeed in organic chemistry how to succeed in organic chemistry initiation, propagation, termination introduction to substitution webinar tuesday nov 5 leah nomenclature guest post manage subscription members login mission moc elite moc private facebook group my organic chemistry story – what’s yours? new acid-base webinar new! reagents app october 22 acid-base webinar online organic chemistry tutoring org 2 post index organic 1 organic 2 organic chemistry for the mcat organic chemistry study advice post index post index 2 post index draft post index draft 2 privacy policy products organic chemistry reagent guide reaction guide 1,4-addition of enolates to enones (“the michael reaction”) 1,4-addition of nucleophiles to enones 1,4-addition of organocuprates (gilman reagents) to enones acidic cleavage of ethers (sn2) addition of alcohols to alkenes with acid addition of aqueous acid to alkenes to give alcohols addition of dichlorocarbene to alkenes to give dichlorocyclopropanes addition of dichloromethylene carbene to alkenes addition of grignard reagents to aldehydes to give secondary alcohols addition of grignard reagents to esters to give tertiary alcohols addition of grignard reagents to formaldehyde to give primary alcohols addition of grignard reagents to ketones to give tertiary alcohols addition of grignard reagents to nitriles to give ketones (after hydrolysis) addition of hbr once to alkynes to give alkenyl bromides addition of hbr to alkenes addition of hbr twice to alkynes to give geminal dibromides addition of hcl once to alkynes to give alkenyl chlorides addition of hcl to alkenes to give alkyl chlorides addition of hcl to alkynes twice to give geminal dichlorides addition of hi once to alkynes to give alkenyl iodides addition of hi twice to alkynes to give geminal diiodides addition of hydroiodic acid to alkenes to give alkyl iodides 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 alcohols addition 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 reaction base-promoted formation of enolates from ketones basic hydrolysis of esters (saponification) beckmann rearrangement bromination of alkenes with br2 to give dibromides bromination of aromatic alkanes to give alkyl bromides bromination of aromatics to give bromoarenes cannizarro reaction 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 dienophiles dihydroxylation 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 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 enamine hydrolysis 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 dcc formation 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 amines formation 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 addition of hbr to alkenes free radical bromination of alkanes free radical chlorination of alkanes friedel crafts alkylation of arenes friedel-crafts acylation of aromatic groups to give ketones halogenation of alkynes hell-vollhard-zelinsky reaction hofmann elimination of alkylammonium salts to give alkenes hofmann rearrangement of amides to amines hydroboration of alkenes hydroboration 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 i2 keto-enol tautomerism kiliani-fischer synthesis nitration of aromatic groups nucleophilic aromatic substitution (snar) nucleophilic aromatic substitution via arynes opening of epoxides with acid and water to give trans diols opening of epoxides with nucleophiles under acidic conditions 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 disulfides oxidative 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 water ozonolysis of alkenes to ketones and aldehydes (reductive workup) partial reduction of alkynes to trans alkenes using sodium and ammonia partial reduction of alkynes with lindlar’s 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 sharpless epoxidation sn2 of cyanide with alkyl halides to give nitriles sn2 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 stille reaction substitution (sn1) with hydride shift substitution with accompanying alkyl shift sulfonylation of arenes to give sulfonic acids suzuki reaction the gabriel synthesis of amines the haloform reaction: conversion of methyl ketones to carboxylic acids the heck reaction the malonic ester synthesis the mannich reaction 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 rearrangement resource guide resources share your organic chemistry story sign up for the reaction guide sign up to be a flashcards beta tester! signup for the reaction guide something has gone wrong spectroscopy video – thanks! spectroscopy video checkout stereochemistry webinar sunday nov 3 store action study and exam tips summary sheets test page testtypg thanks for joining! thanks! you’re signed up for the newsletter. thanks! you’re signed up for the reaction guide the cat line diagram the web of reactions thoughts on o-chem tips #9109 (no title) conjugation “initial tails” and “final heads” 3 ways to make oh a better leaving group a simple formula for 7 important aldehyde/ketone reactions acetoacetic acids (again!) activating and deactivating actors in every acid base reaction addition – elimination addition pattern 1 – carbocations addition pattern 2 – 3 membered rings addition reactions alcohol personality adjustment aldehydes and ketones – addition alkene pattern #3 – the “concerted” pathway alkyl rearrangements alkynes – 3 patterns alkynes: deprotonation and sn2 amines aromaticity: lone pairs avoid these resonance mistakes best way to form amines bulky bases carbocation stability carbocation stability revisited carboxylic acids are acids chair flips cis and trans conformations conjugate addition curved arrow refresher curved arrows decarboxylation determining aromaticity diels alder reaction – 1 dipoles: polar vs. covalent bonding e2 reactions electronegativity is greed for electrons electrophilic aromatic substitution electrophilic aromatic substitution – directing groups elimination reactions enantiocats and diastereocats enolates epoxides – basic and acidic evaluating resonance forms figuring out the fischer find that which is hidden formal charge frost circles gabriel synthesis grignards hofmann elimination how acidity and basicity are related how are these molecules related? how stereochemistry matters how to stabilize negative charge how to tell enantiomers from diastereomers hybridization hybridization shortcut hydroboration imines and enamines importance of stereochemistry intermolecular forces intro to resonance ketones on acid kinetic thermodynamic making alcohols into good leaving groups markovnikov’s rule mechanisms like chords mish mashamine more on the e2 newman projections nucleophiles & electrophiles nucleophilic aromatic substitution nucleophilic aromatic substitution 2 order of operations! oxidation and reduction oxidative cleavage paped pi donation pointers on free radical reactions protecting groups protecting groups proton transfer putting it together (1) putting it together (2) putting it together (3) putting the newman into action reaction maps rearrangements recognizing endo and exo redraw / modify return of the sn2 robinson annulation robinson annulation mech second most important reactions of alkynes: lindlar – na/nh3 sigma and pi bonding sn1 vs sn2 sn1/sn2 – putting it together sn1/sn2/e1/e2 – exceptions sn1/sn2/e1/e2 – nucleophile sn1/sn2/e1/e2 – solvent sn1/sn2/e1/e2 – substrate sn1/sn2/e1/e2 – temperature stereochemistry strong acid strong base strong and weak oxidants strong and weak reductants stronger donor wins substitution sugars (2) synthesis (1) – “what’s different?” synthesis (2) – what reactions? synthesis (3) – figuring out the order synthesis part 1 synthesis study buddy synthesis: walkthrough of a sample problem synthesis: working backwards t-butyl tautomerism the awesomeness of the sn2 the claisen condensation the e1 reaction the inflection point the meso trap the michael reaction the nucleophile adds twice (to the ester) the one-sentence summary of chemistry the second most important carbonyl mechanism the single swap rule the sn1 reaction the sn2 reaction the wittig reaction three exam tips tips on building molecular orbitals top 10 skills try the acid-base reaction first two key reactions of enolates welcome what makes a good leaving group? what makes a good nucleophile? what to expect in org 2 work backwards zaitsev’s rule tuesday oct 22 acid base webinar at 9pm est videos a simple trick for determining r/s applying e2 reactions with newman projections bond rotations: exercise 1 bond rotations: exercise 2 bond rotations: exercise 3 bond rotations: exercise 4 bond rotations: exercise 5 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 fischer projection to a line diagram converting a line diagram to a fischer projection converting a newman projection to a line diagram curved arrows determining r/s on a fischer projection e1 with rearrangement e1 with rearrangement (2) elimination exercise: zaitsev’s rule elimination reactions in cyclohexanes elimination reactions in cyclohexanes (2) evaluating resonance forms (1) charges evaluating resonance forms (2) octets evaluating resonance forms (3) negative charge evaluating resonance forms (4) positive charge evaluating resonance forms (5) aromaticity exercise: condensed formula (1) exercise: condensed formula (2) factors that affect acidity – aromaticity 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 formal 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 pairs formal 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 drawings making 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 overview sn1 with alkyl shift (1) sn1 with alkyl shift (2) sn1 with hydride shift sn1: applying the sn1 reaction sn1/sn2/e1/e2 – substrate 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 sn2 exercise: apply the sn2 sn2 exercise: leaving groups sn2 exercise: the substrate solvents in sn1 and sn2 reactions stereochemistry exercise 1 stereochemistry exercise 2 stereochemistry exercise 3 stereochemistry exercise 4 stereochemistry exercise 5 strong and weak acids substitution: what is substitution? the 4 components of every acid base reaction the 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) what makes a good nucleophile? (2) what makes a good nucleophile? (3) what’s a nucleophile? zaitsev’s rule you’re almost subscribed to the reaction guide!

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