Reaction Guide
The Reaction Guide gives individual descriptions, examples, and mechanisms of more than 170 of the most common reactions encountered in undergraduate organic chemistry. Only members can access all of the full pages. Reactions highlighted in red are open-access.
| Alkanes | ||
|---|---|---|
| Free radical chlorination [hν, Cl2] | Free radical bromination [hν, Br2] | Allylic bromination [NBS] |
| Alkenes | ||
| Addition of HCl | Addition of HBr | Addition of HI |
| Addition of H3O(+) | Chlorination [Cl2] | Bromination [Br2] |
| Iodination [I2] | Chlorohydrin formation [Cl2/H2O] | Bromohydrin formation [Br2/H2O] |
| Iodohydrin formation [I2/H2O] | Oxymercuration [Hg(OAc)2/H2O] | Oxymercuration [Hg(OAc)2/ROH] |
| Hydroboration | Epoxidation [RCO3H] | Dihydroxylation [OsO4] |
| Dihydroxylation [KMnO4] | Cyclopropanation | Dichlorocyclopropanation |
| Ozonolysis (Reductive workup) | Ozonolysis (Oxidative workup) | Oxidative Cleavage [KMnO4] |
| Hydrogenation | Rearrangements (H shift) | Rearrangements (Alkyl shift) |
| Alkynes | ||
|---|---|---|
| Deprotonation (acetylide formation) | SN2 with alkyl halides | Partial reduction (Lindlar) |
| Partial reduction [Na/NH3] | Hydroboration | Oxymercuration |
| Addition of HCl, HBr, or HI (once) | Addition of HCl, HBr, or HI (twice) | Hydrogenation |
| Ozonolysis | Oxidative cleavage [KMnO4] | Alkyne formation via elimination |
| Substitution Reactions (SN2) [nucleophile in brackets] | ||
| Alcohol formation [HO(–)] | Alcohol formation [H2O] | Nitrile formation [CN(-)] |
| Thiol formation [HS(–)] | Ether formation [RO(–)] Williamson | Thioether formation [RS( –)] |
| Azides [N3(–)] | Ester formation [RCO2(–)] | Acetylide addition [RC≡C(–)] |
| Alkanes [Gilman reagents] | Alcohol formation [thru ether cleavage] | Ammonium salt formation [RNH2] |
| Substitution Reactions (SN1) [nucleophile in brackets] | ||
|---|---|---|
| Alcohol formation [H2O] | Ether formation [ROH] | Alcohol formation [ether cleavage] |
| Alkyl chloride formation [HCl] | Alkyl bromide formation [HBr] | Alkyl iodide formation [HI] |
| SN1 w/ rearrangement [alkyl shift] | SN1 w/rearrangement [hydride shift] | |
| Elimination Reactions | ||
|---|---|---|
| E2: Alkenes from alkyl halides | Alkenes from alcohols [strong acid] | Alkenes from alcohols [POCl3] |
| E1: Alkenes from alkyl halides | E1 with rearrangement [alkyl shift] | Hoffmann Elimination |
| Alkyne formation via elimination | E1 with rearrangement [hydride shift] | |
| Reactions of Organometallics | ||
|---|---|---|
| Grignard formation [alkyl halides] | Grignard formation [alkenyl halides] | Reaction of Grignards with acid [H+] |
| Addition of Grignards to aldehydes | Addition of Grignards to ketones | Addition of Grignards to esters |
| Reaction of Grignards with CO2 | Addition of Grignards to nitriles | Formation of organolithium reagents |
| Formation of Gilman reagents | SN2 with Gilman reagents | Addition of Gilman reagents to enones |
| Addition of Gilman to acyl halides | ||
| Reactions of Epoxides | ||
| Epoxide opening [basic conditions] | Epoxide opening [acidic conditions] | Epoxide opening [diol formation] |
| Epoxide formation [from halohydrins] | Epoxide formation [from alkenes] | |
| Reactions of Alcohols and Thiols | ||
| Deprotonation [alkoxide formation] | Protonation [onium ion formation] | Conversion to ethers [Williamson reaction] |
| Conversion to tosylates/mesylates | Conversion to alkyl chlorides [SOCl2] | Conversion to alkyl bromides [PBr3] |
| Oxidation to aldehydes [PCC] | Oxidation to ketones [PCC + others] | Oxidation to carboxylic acids [H2CrO4 + others] |
| Protection as silyl ethers | Thiol formation [SN2] | Thiol oxidation to disulfides |
| Reactions of Dienes | ||
| Diels–Alder reaction | Polymerization of dienes | |
| Reactions of Aromatics (Arenes) | ||
| Nitration [HNO3/H2SO4] | Chlorination [Cl2 plus catalyst] | Bromination [Br2 plus catalyst] |
| Sulfonylation [SO3/H2SO4] | Friedel Crafts alkylation [R-X plus catalyst] | Friedel Crafts acylation [RCOX plus catalyst] |
| Iodination [I2/catalyst] | Side chain oxidation [KMnO4] | Reduction of nitro groups |
| Reduction of aromatic ketones | Side chain bromination | |
| Reactions of Aldehydes and Ketones | ||
| Hydrate formation [H2O] | Cyanohydrin formation [CN(–)] | Reduction of aldehydes [NaBH4] |
| Reduction of aldehydes [LiAlH4] | Reduction of ketones [NaBH4] | Reduction of ketones [LiAlH4] |
| Grignard addition to aldehydes | Grignard addition to ketones | Acetal formation [ROH/H+] |
| Acetal hydrolysis [H3O+] | Imine formation [RNH2] | Enamine formation [R2NH] |
| Wolff-Kishner: reduction to alkanes | Clemmensen reduction to alkanes | Oxidation to carboxylic acid [H2CrO4 or KMnO4] |
| Keto-Enol tautomerism | Enolate formation | Aldol addition reaction |
| Alkylation of enolates | Wittig reaction: alkene formation | Thioacetal formation |
| Imine hydrolysis | Oxidation to carboxylic acids [Tollens] | Haloform reaction |
| Baeyer-Villiger Reaction | Aldol Condensation | |
| Reactions of Carboxylic Acids | ||
| Deprotonation [carboxylate formation] | Formation via Grignard and CO2 | Conversion to acid chloride [SOCl2] |
| Reduction [LiAlH4] | Fischer esterification | Decarboxylation [of β-keto acids] |
| Reactions of Esters | ||
| Reduction to aldehydes [DIBAL-H] | Reduction to alcohols [LiAlH4] | Hydrolysis to carboxylic acid [acidic] |
| Hydrolysis to carboxylic acid [basic] | Addition of Grignard reagents to esters | Claisen condensation |
| Transesterification [basic conditions] | ||
| Reactions of Acyl Halides | ||
| Conversion to esters [ROH] | Conversion to carboxylic acids [H2O] | Conversion to anhydrides [RCO2(–)] |
| Conversion to amides [RNH2] | Conversion to ketones [Gilman reagents] | Conversion to aldehydes [LiAlH(OtBu)3] |
| Reactions of α,β-unsaturated ketones [enones] | ||
| Michael reaction [conjugate addition of enolates] | Conjugate addition of Gilman reagents | Conjugate addition of other nucleophiles |
| Reactions of Amines and Amides | ||
| Dehydration of amides to nitriles [P2O5] | Hofmann rearrangement | Gabriel Synthesis of amines |
| Reductive Amination | Formation of Diazonium Salts | Reactions of Diazonium Salts |
| Amide Formation Using DCC | Amide Formation from Acid Halides | Curtius Rearrangement |
| Reactions of Nitriles | ||
| Addition of Grignard reagents to nitriles | Reduction to amines [LiAlH4] | Hydrolysis to carboxylic acids |
| Miscellaneous | ||
| Robinson annulation | Alkylation of enamines | Oxidative cleavage of vicinal diols |
| Reduction of thioacetals to alkanes [Raney Ni] | Malonic Ester Synthesis | Pinacol Rearrangement |
| Hell-Vollhard-Zolinsky Reaction | Wolff Rearrangement | |
{ 17 comments… read them below or add one }
I’m a “printer”. I find wonderful resources (and this is website is one of the best – it’s incredible) and print them and carry them with me to study like flashcards. I wonder if there might be a “view/print” option that allows you to see the name of the reaction (like you have above) with just a tidy concise example/mechanism below it. That way someone could print off, say, reactions of alcohols. They would have a super fast review on their hands. With of course, the option of logging back on to click the reaction and get more detailed information (as you have it set up now). But mostly, I just need a memory jogger now and then, or confirmation that yes, the intermediate is a carbocation and not an oxacyclopentane, or no, I haven’t lost my marbles and gotten a set of electron pushing arrows in the wrong spot. They do go indeed from such and such to such and such.
Thank you!!!!!!!!!!!!!!!
Thanks Jennifer – that’s something I’d like to do, just working for the moment on just getting the reactions up!
This guide is great. One thing I was wondering though, would 1,2/1,4/1,6 addition to conjugated dienes go under reactions of alkenes and if so, do you think you’ll get around to posting that? Same for the Diels-Alder reaction. Thanks again, I greatly appreciate your efforts and passion for organic chemistry!
thanks! I need to reorganize this page soon. If you look near the bottom, you’ll see a section on a,B-unsaturated ketones.
WOW! this site helped me understand those reaction clearly thanks a lot! EXCELLENT SITE!
Thanks, glad you find it useful.
The working link to the first one is
http://masterorganicchemistry.com/reaction-guide/free-radical-alkane-chlorination/
Helpful and timely
. Thank you.
Glad you’re finding it useful Judith!
Without your site I probably would not have gotten a B+ in Organic. I tell everybody to use your site. Hopefully I do better in organic 2. Thanks a million.
check the page source code, hydrate formation on aldehydes and ketones are redirected to addition of LiAlH4 on ketones
I can’t seem to access conversion to esters in the acid chloride section
I mean in the acyl halide section
Never-mind it was a problem with my browser
Hi James,
Excellent contribution! But I wonder is there any pdf or somekind of print version which might help people use these reaction guide as flash cards or carry them?
JK
As a pdf it would be huge. Re: flashcards, we’re working on it, stay tuned!
The Staudinger reaction would be cool to have up here. Thanks!