1. BH3 2. NaOH H2O2 reduces an alkene to an alcohol at the veryend of the molecule

1.Hg(Oac)2,THF/H2O 2. NaBh4 reduces an alkene to an alcohol, with nohydride shifts

Ag2O (silver oxide)

Silver oxide is used in the Tollens reaction to oxidize aldehydes to carboxylic acids. This is the basis of a test for the presenceof aldehydes, since a mirror of metallic silver will be deposited on the flask. It is also commonly used as a base for the

Hofmann elimination.

AgNO3 (silver nitrate)

Silver nitrate will react with alkyl halides to form silver halides and the correspondingcarbocation.

AIBN

AIBN is a free radical initiator. Upon heating, it decomposes to give nitrogen gas and 2 freeradicals

AlBr3

AlBr3 is a Lewis acid. It is useful for promoting electrophilic aromatic substitution, both inbromination of aromatics and also in the Friedel-Crafts reaction.

AlCl3

Aluminum chloride is a strong Lewis acid. It is used to promote reactions such as chlorination of aromatic compounds, aswell as Friedel-Crafts reactions. It can also be used in the Meerwein-Ponndorf-Verley reduction.

BF3

Boron trifluoride is a strong Lewis acid and is commonly used for the formation of thioacetalsfrom ketones (or aldehydes) with thiols. The product is a thioacetal.

BH3

Borane (BH3) is a reagent for the hydroboration of alkenes and alkynes. It is sometimes writtenas B2H6.

Br2

Bromine will react with alkenes, alkynes, aromatics, enols, and enolates, producing brominated compounds. In the presenceof light, bromine will also replace hydrogen atoms in alkanes. Finally, bromine is used to promote the Hoffmann

rearrangement of amides to amines.

CH2N2 (Diazomethane)

Diazomethane is used for two main purposes. First, it converts carboxylic acids into methyl esters, andsecond it is used in the Wolff rearrangement as a means of extending carboxylic acids by one carbon.

Cl2

Chlorine is a very good electrophile. It will react with double and triple bonds, as well as aromatics, enols, and enolates togive chlorinated products. In addition it will substitute Cl for halogens when treated with light (free radical conditions).

Finally, it assists with the rearrangement of amines to amines (the Hoffmann rearrangement).

CN (cyanide)

Cyanide ion, commonly written as KCN or NaCN, is a good nucleophile for substitution reactions (such as theSN2). It is also used to form cyanohydrins. Cyanide ion will also catalyze the benzoin condensation.

CrO3

Chromium trioxide is an oxidizing agent for alcohols. Its strength depends on the additives present. When in the presence ofpyridine, it will oxidize primary alcohols to aldehydes, as well as secondary alcohols to ketones. When acid is present,

primary alcohols and aldehydes are oxidized to carboxylic acids.

CuBr

Copper (I) bromide is used in the Sandmeyer reaction, where an aryl diazoniuim salt is converted toan aryl bromide. Occasionally, it is also used for the preparation of organocuprates.

CuCl

Copper (I) chloride is used for the conversion of aryl diazonium salts to aryl chlorides (theSandmeyer reaction). It is also occasionally used for the formation of organocuprates.

CuI

Copper (I) Iodide is used to form organocuprates (Gilman reagents) when two equivalents oforganolithium reagents are added.

DCC (dicyclohexyl carbodiimide)

Dicyclohexyl carbodiimide (DCC) is a reagent used for the synthesis of amides from amines andcarboxylic acids. It is essentially a reagent for dehydration (removes water).

Dess-martin periodinane

Dess-martin periodinane is an oxidizing agent. It will oxidize primary alcohols to aldehydes without going tothe carboxylic acid (similar to PSS). It will oxidize secondary alcohols to ketones.

DIBAL (diisobutylaluminum hydride)

Di-isobutyl aluminum hydride (DIBAL) is a strong, bulky reducing agent. It is most useful for the partial reduction of estersto aldehydes. It will also reduce other carbonyl compounds such as amides, aldehydes, ketones, and nitriles.

FCl3

Iron (III) chloride (ferric chloride) is a Lewis acid. It is useful in promoting the chlorination ofaromatic compounds with Cl2, as well as in the Friedel-Crafts reaction.

Fe

Iron metal will reduce nitro groups to amines in the presence of an acid such as HCl.

FeBr3

Iron (III) bromide (ferric bromide) is a Lewis acid. It is useful for promoting the bromination ofaromatic compounds, as well as in the Friedel-Crafts reaction.

Gilman reagents

Organocuprate reagents (Gilman reagents) are carbon nucleophiles. They will do [1,4] additions to alpha-beta unsaturatedketones, as well as SN2 reactions with certain types of alkyl halides. They can also add to acyl halides to give ketones.

Grignard reagents

Grignard reagents are extremely good nucleophiles and strong bases. They react with many electrophiles containing a C=O(carbonyl) group such as aldehydes, ketones, esters, and carbon dioxide, as well as epoxides.

H+,H20 reduces an alkene to an alocohol will dohydride shifts

H2

Hydrogen gas is used for the reduction of alkenes, alkynes, and many other species with multiplebonds, in concert with catalysts such as Pd/C and Pt.

H2CrO4

Chromic acid is a strong acid and an oxidant. It will oxidize secondary alcohols to ketones and primaryalcohols to carboxylic acids. It is sometimes generated by using K2Cr2O7 in the presence of a strong acid.

H2NNH2, KOH reduces carbonyls into alkanes (BasicConditions)

H2O2

Hydrogen peroxide (H2O2) is the preferred oxidant in the hydroboration reaction, resulting in the formation of alcohols.Furthermore, it will oxidize aldehydes to carboxylic acids. This is seen in its use for the oxidative workup in ozonolysis.

H2,, Pd/C, BaSO4 reduces an alkyne to a cis alkene

H2SO4

Sulfuric acid is a strong acid. It is particularly useful as an acid for elimination reactions, since the conjugatebase is a very poor nucleophile. It is used in many other reactions simply as a strong acid.

HBr

Hydrobromic acid is a strong acid. It can add to compounds with multiple bonds such as alkenes andalkynes. It can also react with primary, secondary, and tertiary alcohols fo form alkyl bromides.

HCl

Hydrochloric acid is a strong acid. As a reagent, it can react with multiple bonds in alkenes andalkynes, forming chlorinated compounds. It can also concert alcohols to alkyl chlorides.

Hg(OAc)2

Mercuric acetate is a useful reagent for the oxymercuration of alkenes and alkynes. It makes double bonds more reactivetowards nucleophilic attack by nucleophiles such as water and alcohols. The mercury is removed using NaBH4 or H2SO4 in

the case of addition to alkynes.

HgSO4

Mercuric sulfate is a Lewis acid. In the presence of aqueous acid (H3O+) it will perform theoxymercuration of alkynes to ketones.

HI

Hydroiodic acid is a strong acid. As a reagent, it can add iodine to compounds with multiplebonds such as alkenes and alkynes. It can also convert alcohols to alkyl halides, and cleave ethers.

HIO4

Periodic acid is an oxidant that is useful for the cleavage of 1,2 diols (vicinal diols) into aldehydesor ketones.

HNO2

Nitrous acid is primarily used to convert aromatic amines to diazonium salts, which can be converted into many differentcompounds via the Sandmeyer reaction. It can also be made from NaNO2 if a strong acid such as H2SO4 or HCl is added.

HNO3

Nitric acid is a strong acid. It will add NO2 to aromatic compounds (usually in the presence of another acidsuch as H2SO4) and will also oxidize primary alcohols and aldehydes to carboxylic acids.

I2

Iodine is a good electrophile. It will react with carbon-carbon multiple bonds such as alkenesand alkynes, along with other nucleophiles. It is also used in the iodoform reaction.

KMnO4

Potassium permanganate is a very strong oxidizing agent. It will oxidize primary alcohols and aldehydes to carboxylicacids, secondary alcohols to ketones, form diols from alkenes, and oxidatively cleave carbon-carbon multiple bonds.

KOC(CH3)3

Potassium tert-butoxide is a strong, sterically hindered base. It is the prototypical "bulky base",useful for forming less substituted (Hoffmann) alkenes in elimination reactions.

LDA (lithium diisopropylamide)

Lithium di-isopropylamide (LDA) is a strong, bulky, non-nucleophilic base. It is the reagent of choice for selectivelyremoving a proton from the least hindered carbon next to a ketone. It can also be used to form the Hofmann product in E2

reactions.

Li

Lithium is a metal reducing agent similar to sodium and potassium, although weaker. It will convert alkyl halides to alkyllithium compounds. It will also form alkoxides from alcohols and reduce aromatic groups (The Birch reduction).

LiAlH4

Lithium aluminum hydride is a very strong reducing agent. It will reduce aldehydes, ketones, esters, andcarboxylic acids to alcohols, and amides and nitriles to amines. It will also open epoxides.

LiAlH[OC(CH3)3]3

LiAlH[OC(CH3)3]3 is a strong but bulky reducing agent. Less reactive than LiAlH4, it will convertacyl halides to aldehydes.

Lindlar Catalyst

Lindlar's catalyst is a poisoned palladium metal catalyst that performs partial hydrogenation of alkynes in thepresence of hydrogen gas. It always gives the cis-alkene, in contrast to Na/NH3, which gives the trans.

Magnesium monoperoxypthalatehexahydrate (MMPP)

MMPP forms epoxides

mCPBA (m-chloroperoxybenzoic acid)

meta-chloroperoxybenzoic acid (m-CPBA) is an oxidizing agent. One of its main uses is in the formation of epoxides fromalkenes. It will also oxidize ketones to form esters, a reaction known as the Baeyer-Villiger reaction.

Me2S

Dimethyl sulfide is used in the "reductive workup" for ozonolysis, especially when one wants to obtain aldehydes fromalkenes. It reduces the ozonide that is formed, leading to formation of dimethyl silfoxide (DMSO)

Mg

Magnesium metal is used for the formation of Grignard reagents from alkyl and alkenyl halides.

Mg/THF takes an alkane and forms a grignardreagent (Mg)

MsCl

Methanesulfonyl chloride (mesyl chloride or MsCl) is used to turn alcohols into good leavinggroups. It behaves essentially identically to TsCl for this purpose.

Na

Sodium is a strong reducing agent. It will reduce alkynes to trans-alkenes, and form hydrogen gas whenadded to alcohols, forming alkoxides. It is also used in the Birch reduction of aromatic groups.

Na2Cr2O7, HCl, ∆ substitutes a carboxylic acid for a methlygroup on a aromatic compound

NaBH4

Sodium borohydride is a reagent for the reduction of ketones and aldehydes, it will also reduceacid halides. It is also used in the oxymercuration reaction to replace mercury with H.

NaBH(OAc)3

NaBH(OAc)3 (sodium triacetoxy borohydride) is a reducing agent for the reductive amination of ketones andaldehydes to amines. In this respect, it is identical to sodium cyanoborohydride, NaCNBH3

NaCNBH3

Sodium cyanoborohydride is a reducing agent. It is generally used for reductive amination - the reduction ofimines to amines. Its common to perform this reaction under slightly acidic conditions.

NaH

Sodium hydride is a very strong base and a poor nucleophile. It is useful for deprotonatingalcohols and alkynes, among others. One advantage is that the byproduct is H2, which is a gas.

NaIO4

Sodium periodate is a strong oxidant. It will cleave 1,2 diols (vicinal diols) to give aldehydes andketones.

NaN3

Sodium azide is a good nucleophile that will participate in SN2 reactions.

NaNH2

Sodium amide is a very strong base, useful for the deprotonation of alkynes and in elimination reactions toward theformation of alkynes from dihalides. It can also be used to generate arynes, which can undergo nucleophilic attack.

Na, NH3 reduces an alkyne to a trans alkene

NaNO2, HCl turns a primary amine into a diazoniumgroup

NBS (n-bromosuccinimide)

NBS is a source of reactive bromine. It is most often used for allylic bromination and in theformation of halohydrines from alkenes.

NCS (n-chlorosuccinimide)

N-chlorosuccinimide is a source of reactive, electrophilic, chlorine. It is used for the formation ofchlorohydrins from alkenes.

-NH2 takes a proton off of an alkyne

NH2NH2

Hydrazine is a good reductant and nucleophile. It is used in the Wolff-Kishner reaction, a way of convertingketones to alkanes. It is also used in the final step of the Gabriel amine synthesis to liberate the free amine.

NH2OH

Hydroxylamine is used to the formation of oximes from aldehydes or ketones. The resultingoximes can be converted into amides using the Beckman rearrangement.

NH3

Ammonia is a base and a nucleophile. It is often used as a solvent in reactions involving Li, Na,and K. It has a fairly low boiling point of -33 celcius.

Ni-B

Nickle boride is a reagent that acts similarly to the Lindlar catalyst, reacting with alkynes to givecis-alkenes.

NIS (n-iodosuccinimide)

N-iodosuccinimide is a source of electrophilic iodine, similar to NBS and NCS. When added to analkene in the presence of water, it will form iodohydrins.

O3 (ozone)

Ozone will cleave alkenes and alkynes to give carbonyl compounds. This is called oxidative cleavage. The products formedcan be dependent on the type of workup used. Reductive workup preserves aldehydes, whereas oxidative workup will oxidize

any aldehydes to carboxylic acids.

OH-

Hydroxide ion is a strong base and good nucleophile.

Organolithium reagents

Organolithium reagents are extremely strong bases and good nucleophiles. They react with carbonyl compounds (aldehydes,ketones, esters, etc) and epoxides. Being strong bases, they will also react with groups containing acidic hydrogens.

OsO4

Osmium tetroxide is a reagent for the formation of 1,2-diols (vicinal diols) from alkenes. Theselectivity for this reaction is always syn.

P2O5

P2O5 is a dehydration reagent. It is used for conversion of carboxylic acids to anhydrides, andalso the formation of nitriles from amides.

Pb(OAc)4

Lead tetraacetate will cleave 1,2-diols (vicinal diols) into aldehydes/ketones, similar to NaIO4and HIO4.

PBr3

Phosphorus tribromide is a reagent for converting alcohols to alkyl bromides. It will also convertcarboxylic acids to acid bromides (acyl bromides)

PCC (pyridinium chlorochromate)

Pyridinium chlorochromate (PCC) is reagent for the oxidation of primary alcohols to aldehydes and secondary alcohols toketones. It is much milder than reactants such as H2CrO4 and KmnO4, which will oxidize primary alcohols to carboxylic

acids.

PCl3

Phosphorus trichloride is a reagents for the conversion of alcohols to alkyl chlorides. It will alsoconvert carboxylic acids to acid chlorides (acyl chlorides)

PCl5

Phosphorus pentachloride will convert alcohols to alkyl chlorides, and carboxylic acids to acidchlorides (acyl chlorides)

Pd-C

Palladium adsorbed on charcoal (carbon) is a heterogeneous catalyst. In the presence of hydrogengas H2, it will convert alkenes and alkynes to alkanes. The hydrogens are delivered syn.

POCl3

Phosphorus oxychloride (POCl3) is used for the dehydration of alcohols to alkenes. Essentially it converts alcohols to a goodleaving group, which is then removed by an added base (often pyridine). It can also be used to convert amides to nitriles.

Potassium phthalimide

Sodium (or potassium) pthalimide is a nitrogen-containing nucleophile used in the Gabriel synthesis. Potassium pthalimidereacts with alkyl halides to form a C-N bond, which is then hydrolyzed by treatment with hydrazine (NH2NH2) to give a

primary amine.

PPh3

PPh3 is used for the formation of ylides in the Wittig reaction. It can also be used for reductiveworkup in the ozonolysis of alkenes.

Pt

Platinum is a "noble metal," is used as a catalyst for the reduction of carbon-carbon multiplebonds in the presence of hydrogen gas.

Pyridine

Pyridine is a mild base. Since it bears no charges it is especially soluble in organic solvents. It is often used inreactions that generate HCl and other strong acids - think of it like a sponge for strong acid.

Ra-Ni (Rayney nickle)

Rayney nickle is a reagent for the reduction (hydrogenation) of double bonds. It sees the most useas a reagent for the replacement of sulfur by hydrogen.

RO-OR (peroxides)

Peroxides are used to initiate free-radical reactions. The oxygen-oxygen is very weak, and willfragment homolytically to generate radicals.

Sn

In the presence of acid, tin will reduce nitro groups to form amines.

SO3

Sulfur trioxide is a reagent for the sulfonylation of aromatic groups. In the presence of acid, itwill lead to the formation of sulfonic acids.

SOBr2

Thionyl bromide is a useful reagent for the formation of alkyl bromides from alcohols, as well asacid bromides (acyl bromides) from carboxylic acids.

SOCl2

Thionyl chloride is used for the formation of alkyl chlorides from alcohols and acid chlorides(acyl chlorides) from carboxylic acids.

TBAF (tetra-n-butylammonium fluoride)

Tetrabutylammonium fluoride (TBAF) is a source of fluoride ion. It is used to cleave silyl ethers,which are common protecting groups for alcohols.

tBuli/THF takes an alkane and forms a grignardreagent (Li)

TMSCI

TMSCl is a protecting group for alcohols. When added to alcohols, it forms a silyl ether, which is inert to most reagentsexcept for fluoride ion and acid. Note that the reagent can be written two ways (CH3)3SiCl and TMSCl.

TsCl (toluenesulfonyl chloride)

Tosyl chloride TsCl will convert alcohols to sulfonates, which are excellent leaving groups inelimination and substitution reactions.

TsOH (p-toluenesulfonic acid)

Tosic acid (p-toluenesulfonic acid) is a very strong acid. The conjugate base is a very poornucleophile, which makes it a good acid for elimination reactions. It is similar to H2SO4

Zn

Zinc is a metal reducing agent. It is useful for the reduction of ozonides, and also in the reductionof nitro groups to amines (in the presence of acid).

Zn-Cu

Zinc-copper couple is reducing agent, used to form carbenes (actually carbenoids) from alkyldihalides. When these are added to alkenes, they form cyclopropanes.

Zn-Hg

In the presence of acid, zinc amalgam will reduce ketones alkanes, in a process called theClemmensen reaction.

Zn/Hg, HCl reduces carbonyls into alkanes (Acidicconditions)