question

H+,H20

answer

reduces an alkene to an alocohol will do hydride shifts

question

1.Hg(Oac)2,THF/H2O 2. NaBh4

answer

reduces an alkene to an alcohol, with no hydride shifts

question

1. BH3 2. NaOH H2O2

answer

reduces an alkene to an alcohol at the very end of the molecule

question

H2,, Pd/C, BaSO4

answer

reduces an alkyne to a cis alkene

question

Na, NH3

answer

reduces an alkyne to a trans alkene

question

-NH2

answer

takes a proton off of an alkyne

question

Mg/THF

answer

takes an alkane and forms a grignard reagent (Mg)

question

tBuli/THF

answer

takes an alkane and forms a grignard reagent (Li)

question

H2NNH2, KOH

answer

reduces carbonyls into alkanes (Basic Conditions)

question

Zn/Hg, HCl

answer

reduces carbonyls into alkanes (Acidic conditions)

question

Na2Cr2O7, HCl, ∆

answer

substitutes a carboxylic acid for a methly group on a aromatic compound

question

NaNO2, HCl

answer

turns a primary amine into a diazonium group

question

AIBN

answer

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

question

AlBr3

answer

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

question

AlCl3

answer

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

question

BF3

answer

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

question

BH3

answer

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

question

Br2

answer

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

question

CH2N2 (Diazomethane)

answer

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

question

Cl2

answer

Chlorine is a very good electrophile. It will react with double and triple bonds, as well as aromatics, enols, and enolates to give 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).

question

CN (cyanide)

answer

Cyanide ion, commonly written as KCN or NaCN, is a good nucleophile for substitution reactions (such as the SN2). It is also used to form cyanohydrins. Cyanide ion will also catalyze the benzoin condensation.

question

CrO3

answer

Chromium trioxide is an oxidizing agent for alcohols. Its strength depends on the additives present. When in the presence of pyridine, 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.

question

CuBr

answer

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

question

CuCl

answer

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

question

CuI

answer

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

question

DCC (dicyclohexyl carbodiimide)

answer

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

question

Dess-martin periodinane

answer

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

question

DIBAL (diisobutylaluminum hydride)

answer

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

question

FCl3

answer

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

question

Fe

answer

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

question

FeBr3

answer

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

question

Gilman reagents

answer

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

question

Grignard reagents

answer

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.

question

H2

answer

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

question

H2CrO4

answer

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

question

H2O2

answer

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.

question

H2SO4

answer

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

question

HBr

answer

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

question

HCl

answer

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

question

Hg(OAc)2

answer

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

question

HgSO4

answer

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

question

HI

answer

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

question

HIO4

answer

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

question

HNO2

answer

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

question

HNO3

answer

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

question

I2

answer

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

question

KMnO4

answer

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

question

KOC(CH3)3

answer

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.

question

LDA (lithium diisopropylamide)

answer

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

question

Li

answer

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

question

LiAlH[OC(CH3)3]3

answer

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

question

LiAlH4

answer

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

question

Lindlar Catalyst

answer

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

question

mCPBA (m-chloroperoxybenzoic acid)

answer

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

question

Me2S

answer

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

question

Mg

answer

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

question

MsCl

answer

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

question

Na

answer

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

question

NaBH(OAc)3

answer

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

question

NaBH4

answer

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

question

NaCNBH3

answer

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

question

NaH

answer

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

question

NaIO4

answer

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

question

NaN3

answer

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

question

NaNH2

answer

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

question

NBS (n-bromosuccinimide)

answer

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

question

NCS (n-chlorosuccinimide)

answer

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

question

NH2NH2

answer

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

question

NH2OH

answer

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

question

NH3

answer

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.

question

Ni-B

answer

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

question

NIS (n-iodosuccinimide)

answer

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

question

O3 (ozone)

answer

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

question

OH-

answer

Hydroxide ion is a strong base and good nucleophile.

question

Organolithium reagents

answer

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.

question

OsO4

answer

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

question

P2O5

answer

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

question

Pb(OAc)4

answer

Lead tetraacetate will cleave 1,2-diols (vicinal diols) into aldehydes/ketones, similar to NaIO4 and HIO4.

question

PBr3

answer

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

question

PCC (pyridinium chlorochromate)

answer

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

question

PCl3

answer

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

question

PCl5

answer

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

question

Pd-C

answer

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

question

POCl3

answer

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

question

Potassium phthalimide

answer

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

question

PPh3

answer

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

question

Pt

answer

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

question

Pyridine

answer

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

question

Ra-Ni (Rayney nickle)

answer

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

question

RO-OR (peroxides)

answer

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

question

AgNO3 (silver nitrate)

answer

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

question

Ag2O (silver oxide)

answer

Silver oxide is used in the Tollens reaction to oxidize aldehydes to carboxylic acids. This is the basis of a test for the presence of 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.

question

Sn

answer

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

question

SO3

answer

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

question

SOBr2

answer

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

question

SOCl2

answer

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

question

TBAF (tetra-n-butylammonium fluoride)

answer

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

question

TMSCI

answer

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

question

TsCl (toluenesulfonyl chloride)

answer

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

question

TsOH (p-toluenesulfonic acid)

answer

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

question

Zn

answer

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

question

Zn-Cu

answer

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

question

Zn-Hg

answer

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

question

Magnesium monoperoxypthalate hexahydrate (MMPP)

answer

MMPP forms epoxides

Main Organic Chemistry Reagents – Flashcards

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