L1 title (These first six lines are dummy entries for info)
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Solubility Characteristics
Groups compounds into solubility classes.
Information about functional groups can be obtained particularly concerning the presence or absence of acidic or basic groups. Consult text for more details.


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Proton NMR Spectrum
Indicates types and numbers of protons.
Gives information on the types (from chemical shifts) and numbers (from integration ratios) of protons present. See a spectroscopy book for details.


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Mass Spectrum
Shows molecular and fragment ions.
Usually gives information about the molecular formula (molecular ion) and structure (fragment ions). Refer to a text for details.


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Ultraviolet-visible Spectrum
Mainly for compounds having multiple bonds.
Generally useful only for molecules with multiple bonds particularly if conjugated. Consult a book of spectroscopy for more information.


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Elemental Analysis
Reveals if N, S, P and halogens are present.
Detects elements other than C H & O, that is nitrogen, halogens, sulfur, phosphorus etc.


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Ignition Test
For compounds that burn or leave a residue.
Combustion with a smoky or sooty flame indicates a low H:C ratio (unsaturation). If a residue remains then the compound must be partly inorganic (eg a salt).


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Melting Point
For solids.
A characteristic of a compound. The range over which melting occurs can often be related to purity.


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Infrared Spectrum
Shows the types of bonds.
Gives details of the types of bonds present. For more details see a text book.


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Boiling Point
For liquids.
A characteristic of a compound. The range over which boiling occurs can often be related to purity.


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Specific Rotation
For chiral molecules.
Given only by optically active substances. These are usually of natural origin. Measurement is made with a polarimeter.


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Density
Useful measurement for liquids.
Density is the specific gravity referred to water at 4 degrees.


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Refractive Index
For liquids.
Measured using the D line of sodium light and a refractometer. Usually only determined in the laboratory for liquids.


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Neutralisation Equivalent
For acids.
A useful measurement to make for an acidic compound by titration with a base. Can be related to the molecular weight.
This test may only be performed on an acid. Test for this functional group first by doing a solubility determination.
This test may only be applied to an acid. Acids been shown to be absent by solubility and/or spectroscopic data.
01
Saponification Equivalent
Only for esters.
Esters are reacted with base to give the equivalent weight of the ester. Can be related to the molecular weight.
Only an ester can be saponified. Check for this group first by doing the hydroxamic acid test.
The ester functional group is absent as shown by a negative hydroxamic acid test or lack of a C=O signal in the ir or cmr spectrum.
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Carbon NMR Spectrum
Indicates the types of carbons present.
The chemical shift of a carbon can be related to its environment. Signal intensity (or integration) can NOT be relied upon. See a text for details.


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2,4-Dinitrophenylhydrazine Test
For aldehydes and ketones.
The reagent gives a yellow precipitate with aldehydes and ketones.

The absence of a C=O signal in the infrared and/or carbon nmr spectrum makes this test unnecessary.
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Reaction With Sodium Metal
Mainly for alcohols.
Alcohols react with sodium to evolve hydrogen. Aldehydes, ketones and esters may also react.

The lack of an O-H absorption in the infrared spectrum and/or the absence of exchangeable protons in the pmr spectrum makes this test redundant.
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Nitrous Acid Test
For amines.
Prim. amines- aliphatic give nitrogen; aromatic give diazonium salts at ice temp; these form azo dyes with 2-naphthol & nitrogen on heating. Sec. amines- form yellow N-nitroso compounds which give the Liebermann reaction. Tert. amines usually don't react.
This test is used to classify amines, so see if nitrogen is present first.
Since the compound does not contain nitrogen don't do this amine test.
05
Schiff's Reagent
Also known as fuchsin aldehyde reagent. A test for aldehydes.
Most aliphatic and some aromatic aldehydes give deep red to purple colours.
Do the more general 2,4-dinitrophenylhydrazine test.
The negative 2,4-dinitrophenylhydazine test, the lack of a C=O signal in the infrared or cmr spectrum, or the absence of a low field signal in the pmr spectrum has shown aldehydes to be absent.
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Barfoed's Reagent
A general test for monosaccharides (uses copper acetate solution).
Monosaccharides react to give a red precipitate of cuprous oxide within two minutes. Disaccharides also react on prolonged heating due to hydrolysis.
Since this test is used to distinguish between various classes of carbohydrates confirm their presence first with a Molisch test.
This is a classification test for carbohydrates. These have been shown to be absent by the negative Molisch test and/or spectral data.
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Hydroxamic Test (In Water)
A test for esters.
Esters react with hydroxylamine to yield hydroxamic acids which give deep colours with ferric chloride.

The absence of a C=O signal in the infrared and/or carbon nmr spectrum makes this test unnecessary.
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Reduction then Tollen's Reagent
For nitro compounds and their reduction products.
Tertiary nitro compounds (as well as nitroso, azoxy and azo compounds) are reduced with zinc and ammonium chloride to hydroxylamines which react with Tollen's reagent to give a silver mirror.
before testing for a nitro group, see if nitrogen is present.
Since the compound does not contain nitrogen don't do this test which is for a nitro group.
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Reaction With NaI In Acetone
A classification test for halogen compounds.
A precipitate is formed with halogen compounds. Aliphatic bromides react faster than chlorides and prim.>sec.>tert. Aromatic compounds usually do not react.
Test for the presence of halogen before performing this classification test which is for halogen compounds.
This is a classification test for halogens. Elemental analysis has shown these to be absent. Alternatively the absence of Br or Cl is precluded by mass spectral data.
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Iodoform Test
For methyl ketones.
A yellow precipitate of iodoform is formed from methyl ketones or compounds which can be oxidised to these compounds when they are reacted iodine and a base.
A test for methyl ketones. Do the more general 2,4,-dinitrophenylhydrazine test first.
This test for methyl ketones is precluded by a negative 2,4-dinitrophenylhydrazine test or by spectral (ir or cmr) information.
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Benedict's Test
For aldehydes (and reducing sugars).
A red precipitate of cuprous oxide is formed with aldehydes and reducing sugars.
A test for aldehydes or reducing sugars. Do a 2,4-ninitrophenylhydrazine test or a Molisch test first.
This aldehyde or reducing sugar test is precluded by a negative 2,4-dinitrophenylhydrazine or Molisch test or by spectral information.
1934
Tollen's Reagent
A test for aldehydes (also known as ammoniacal silver nitrate).
Aldehydes react and a silver mirror is formed.
This is a test for an aldehyde. Do the more general 2,4-dinitrophenylhydrazine test first.
The negative 2,4-dinitrophenylhydazine test, the lack of a C=O signal in the ir or cmr spectrum, or the absence of a low field signal in the pmr spectrum has shown aldehydes to be absent.
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Reaction With Acetyl Chloride
For alcohols and amines.
A reaction occurs with alcohols (giving esters) and with primary and secondary amines (forming amides).

The absence of an O-H or N-H vibration in the infrared spectrum and/or the lack of exchangeable protons in the pmr spectrum preclude this test.
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Hydroxamic Acid Test (Propanediol)
A test for amides and nitriles.
Nitriles, unsubstituted amides and many substituted amides react to form deep red to purple colours.
Confirm the presence of nitrogen before doing this amide or nitrile test.
Since nitrogen is absent and/or there is no C=O or CN stretch in the ir spectrum there is no point doing this test which is for an amide or nitrile.
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Potassium Permanganate Reaction
Also known as the Baeyer's Test. For unsaturated compounds.
Rapid decolourisation of the purple coloured reagent occurs with unsaturated hydrocarbons. Note: many other compounds such as alcohols, aldehydes, amines and phenols also react.


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Chromic Acid Test
Distinguishes between alcohols.
 Primary alcohols are oxidised to aldehydes and secondary alcohols to ketones. Tertiary alcohols usually don't react.
Before doing this alcohol classification test confirm the presence of the hydroxy group by testing the compound's reactivity with sodium or an acyl halide.
This is an alcohol classification test. The hydroxy group is absent as shown by spectral information and/or the compound's non-reaction with sodium and/or acyl halide.
203054
Molisch Test
A general test for carbohydrates.
Formation of a purple to violet colour occurs when a carbohydrate is reacted with 1-naphthol and sulfuric acid.

The lack of an -OH absorption in the infrared spectrum and/or the absence of exchangeable protons in the pmr spectrum makes this test redundant.
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Ferrous Hydroxide Test
For nitro groups.
Compounds with nitro groups give a brown precipitate of ferrous hydroxide.
Before testing for a nitro group, see if nitrogen is present.
Since the compound does not contain nitrogen do not do this test which is for a nitro group.
05
Bromine In Chlorobenzene Reaction
A test for unsaturation and phenols.
The red colour of bromine is discharged by unsaturated compounds (addition) and by phenols (substitution with HBr gas being evolved).


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Reaction With Hydriodic Acid
Used to cleave ethers.
Ethers react and iodo compounds are formed.


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Ferric Chloride Test
A test for phenols (and enols).
Intense colours (eg. red or green) are formed from phenols or enols.

Phenols or enols have been excluded by spectral data (lack of O-H or C=O in the ir and/or no exchangeable protons in the pmr).
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Rimini's Test
For primary amines.
A red-violet colour is given when primary amines are reacted with sodium nitroprusside.
This test is used to classify amines, so see if nitrogen is present first.
Either nitrogen has been shown to be absent or there is no N-H stretch in the infrared spectrum or there is no exchangeable signal in the pmr spectrum.
05
Ethanolic Silver Nitrate Reaction
Used to classify halogen compounds.
A precipitate is formed with aliphatic halogen compounds. The order of reaction is:- I > Cl > Br and tert. > sec. > prim. Aromatic compounds usually do not react.
Test for the presence of halogen before performing this classification test which is for halogen compounds.
This is a classification test for halogens; elemental analysis has shown these to be absent. Alternatively the absence of Br or Cl is precluded by mass spectral data.
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Benzenesulfonyl Chloride Reaction
A test for amines.
Primary amines give a product which is soluble in alkali while the product from secondary amines is insoluble. Tertiary amines don't react. Some hydroxy compounds also react.
This test is used to classify amines, so see if nitrogen is present first.
Either nitrogen has been shown to be absent or there is no N-H stretch in the infrared spectrum or there is no exchangeable signal in the pmr spectrum.
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Reaction With Ninhydrin
For amino acids.
A blue colour is formed with this reagent and amino acids.
Determine if nitrogen is present before performing this amino acid test.
This test is for amino acids which have been shown to be not present by the absence of nitrogen and/or spectral data (ir or cmr).
05
Carbylamine Test
For amines.
Primary amines give a nauseating odour of the corresponding carbylamine when reacted with base and chloroform.
This test is used to classify amines, so see if nitrogen is present first.
Either nitrogen has been shown to be absent or there is no N-H stretch in the infrared spectrum or there is no exchangeable signal in the pmr spectrum.
05
Reaction With Boric Acid
For polyhydric alcohols.
Polyhydric alcohols cause the initial pink colour of the reagent (boric acid and phenolphthalein) to disappear. The colour reforms on warming.
Before doing this alcohol classification test, confirm the presence of the hydroxy group by testing the compound's reactivity with sodium or an acyl halide.
The lack of an O-H absorption in the infrared spectrum and/or the absence of exchangeable protons in the pmr spectrum makes this test redundant.
203054
Periodic Acid Test
A test for diols.
A white precipitate of silver iodate is formed with 1,2-glycols (and with à-hydroxy aldehydes and ketones).
Before doing this alcohol classification test, confirm the presence of the hydroxy group by testing the compound's reactivity with sodium or an acyl halide.
The lack of an O-H absorption in the infrared spectrum and/or the absence of exchangeable protons in the pmr spectrum makes this test redundant.
203054
Reaction With Chromic Anhydride
A classification test for alcohols.
Primary and secondary alcohols are oxidised to  give a precipitate and a green colour within two seconds. Tertiary alcohols don't react.
Before doing this alcohol classification test, confirm the presence of the hydroxy group by testing the compound's reactivity with sodium or an acyl halide.
this is an alcohol classification test. The hydroxy group is absent as shown by spectral information and/or the compound's non-reaction with sodium and/or acyl halide.
203054
Reaction With Fuming Sulfuric Acid
Differentiates between hydrocarbons.
Only aromatic hydrocarbons dissolve; usually heat is evolved.


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Fusion With Sodium Hydroxide
For sulfonic acids.
Sulfonic acids and their salts are converted into the corresponding phenols.
Do elemental analysis and/or solubility classification first. For sulfonic acids or their salts.
For sulfonic acids or their salts. These have been shown to be absent by elemental analysis, solubility data and/or spectroscopic data.
0105
Carbon Disulfide Reagent
A test for amines.
A precipitate of nickel dithiocarbamate is given with secondary amines (reaction with nickel chloride and carbon disulfide).
This test is used to classify amines, so see if nitrogen is present first.
Either nitrogen has been shown to be absent or there is no N-H stretch in the infrared spectrum or there is no exchangeable signal in the pmr spectrum.
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Fehling's Reagent
For aldehydes or reducing sugars.
 A red precipitate of cuprous oxide is formed by aldehydes or reducing sugars.
A test for aldehydes or reducing sugars. Do a 2,4-dinitrophenylhydrazine test or a Molisch test first.
This aldehyde or reducing sugar test is precluded by a negative 2,4-dinitrophenylhydrazine or Molisch test or by spectral information.
1934
Lucas Test
Distinguishes between alcohols.
Prim. alcohols lower than hexyl dissolve; prim. alcohols, hexyl and above do not dissolve. Sec. alcohols give initially a clear solution which becomes cloudy and then a second phase forms. Tert. alcohols react immediately with formation of a second phase.
Before doing this alcohol classification test, confirm the presence of the hydroxy group by testing the compound's reactivity with sodium or an acyl halide.
This is an alcohol classification test. The hydroxy group is absent as shown by spectral information and/or the compound's non-reaction with sodium and/or acyl halide.
203054
Bromine Water Test
For unsaturated compounds and phenols.
Unsaturated compounds and phenols react with discharge of the reagent's colour (by addition and substitution respectively).


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Hydrolysis Reaction
Reaction with water.
Esters, amides, anhydrides and nitriles may all be hydrolysed.

The infrared spectrum has shown that hydrolysable groups are absent.
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Reaction With Benzoyl Chloride
For alcohols, amines and amino acids.
A reaction occurs with alcohols, amines and amino acids to give benzamides.

The absence of an O-H or N-H vibration in the infrared spectrum and/or the lack of exchangeable protons in the pmr spectrum preclude this test.
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Acid Formed By Oxidation
For alcohols, aldehydes and substituted aromatic hydrocarbons.
Oxidation of aliphatic alcohols and aldehydes usually give liquid carboxylic acids which are not suitable as derivatives. Most aromatic aldehydes and alkyl substituted aromatic hydrocarbons give useful derivatives on oxidation.


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S-Alkylthiuronium Picrate Salt
For aliphatic halogen compounds.
This derivative is best formed from aliphatic bromo or iodo compounds. Tertiary halides can give anomalous results.


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Sulfonamide
For some inert aromatic compounds and sulfonic acids.
Aromatic compounds (such as hydrocarbons, halogenated hydrocarbons and ethers) are reacted first with chlorosulfonic acid and then ammonia. Sulfonic acids are derivatised by reaction with a phosphorus chloride followed by ammonia.


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Methiodide
For tertiary amines only.
Iodomethane reacts with tertiary amines to form the quaternary ammonium iodide (methiodide). These salts are usually highly crystalline.


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Bromine Addition/Substitution Product
For unsaturated hydrocarbons, phenols and some other aromatic compounds.
Unsaturated compounds react with bromine by addition. Aromatic compounds susceptible to electrophilic substitution also react (eg phenols, ethers, polyalkyl substituted aromatic hydrocarbons).


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Aryloxyacetic Acid
For phenols.
A very good derivative for phenols. It is made by reacting the phenol with chloroacetic acid in the presence of aqueous base.


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Acetamide
For primary and secondary amines as well as amino acids.
A recommended derivative for primary and secondary amines which is best made by reacting the amine with acetic anhydride. Amino acids also react in a similar way.


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Benzoate (Benzoyl)
For phenols, alcohols, amines, amino acids and carbohydrates.
Phenols, alcohols and carbohydrates are esterified with benzoyl chloride to form benzoates while primary and secondary amines react to give benzoyl (or benzamide) derivatives.


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p-( or 4-)Nitobenzoate (Nitrobenzoyl)
For phenols, alcohols and amines.
Reaction of 4-nitobenzoyl chloride with phenols or alcohols forms esters (4-nitobenzoates) while reaction with primary and secondary amines yields the substituted amide (4-nitrobenzoyl).


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Phenylthiourea
For amines (primary and secondary), alcohols and phenols.
Phenylisothiocyanate reacts with primary or secondary amines or with alcohols or phenols to give phenylthioureas.


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p-( Or 4- )Toluidide
For carboxylic acids and esters.
These substituted amides are useful derivatives of acids and esters.


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Pyrazolone
For enols.
This derivative is made by reacting phenylhydrazine with a á-ketoester.


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Osazone (Phenylosazone)
For carbohydrates.
This derivative is made by reacting a carbohydrate with phenylhydrazine. Osazones are usually yellow crystalline solids with characteristic crystalline forms and times of formation.


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1-Naphthylurethane
For alcohols and phenols.
Preparation is by reaction of the alcohol or phenol with 1-naphthylisocyanate.


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Hydrogen 3-Nitrophthalate
For alcohols.
Prepared by reaction of the alcohol with 3-nitrophthalic anhydride.


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3,5-Dinitrobenzoate (Dinitrobenzoyl)
For alcohols, phenols, esters, ethers and amino acids.
Alcohols, phenols and ethers form 3,5-dinitrobenzoate esters with 3,5-dinitrobenzoyl chloride while amino acids form amides (3,5-dinitrobenzoyl derivatives). Esters react directly with 3,5-dinitrobenzoic acid by transesterification.


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S-Benzylthiuronium Salt
For carboxylic and sulfonic acids.
When alkali metal salts of carboxylic or sulfonic acids are reacted with S-benzylthiuronium chloride the product is a crystalline S-benzylthiuronium salt.


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Benzamide
For primary and secondary amines.
This solid derivative is formed when a primary or secondary amine is reacted with benzoyl chloride.


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Amide
For carboxylic acids and esters.
To make an amide from a carboxylic acid, the acid is first converted into the acyl chloride which is then reacted with ammonia. Esters may be reacted directly with ammonia to yield the amide.


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Acetate (Acetyl)
For phenols, alcohols and carbohydrates.
Phenols, alcohols and carbohydrates form acetates on reaction with acetic anhydride or acetyl chloride. The acetates of many alcohols are liquid and not suitable as derivatives.


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Acid Formed By Hydrolysis
For acyl halides, amides, anhydrides, esters and nitriles.
A wide variety of carboxylic acid derivatives may be hydrolysed thereby allowing the parent acid to be isolated. If this is a solid it usually makes a good derivative.


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Metho-p-(or 4-)Toluenesulfonate
For tertiary amines. Also called Methyl p-(or 4-)Toluenesulfonate
This is a quaternary ammonium salt made by reaction of the tertiary amine with methyl 4-toluenesulfonate.


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p-( Or 4-)Nitrophenylhydrazone
For aldehydes and ketones as well as carbohydrates.
A recommended derivative for aldehydes, ketones and carbohydrates. It is make by reacting them with 4-nitrophenylhydrazine.


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Phenylurethane
For alcohols and phenols.
Reaction of alcohols or phenols with phenylisocyanate gives the phenylurethane derivative.


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Semicarbazone
For aldehydes, ketones, enols and quinones.
A strongly recommended derivative which is made by reaction of these carbonyl compounds with semicarbazide hydrochloride and sodium acetate.


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p-( Or 4- )Toluenesulfonate
For phenols and amino acids.
Reaction of phenols or amino acids with 4-toluenesulfonyl chloride affords the corresponding 4-toluenesulfonates.


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Reduction Product
For nitriles and nitro compounds.
Reduction of nitriles and nitro compounds gives the corresponding amine which can be further derivatised if required, for example if it is a liquid.


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Alkylmercuric Halide
For aliphatic halogen compounds.
Primary and secondary amines are first converted into Grignard compounds which are then reacted with a mercuric halide.


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Benzenesulfonamide
For primary and secondary amines.
A good derivative for primary and secondary amines made by reacting them with benzenesulfonyl chloride.


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p-( Or 4- )Toluenesulfonamide
For primary and secondary amines.
A good derivative for primary and secondary amines made by reacting them with toluenesulfonyl chloride.


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Xanthylamide
For amides.
One of the few derivatives which can be made directly from an amide. This recommended derivative is prepared by reaction of the amide with xanthydrol.


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Picrate
For aromatic hydrocarbons and ethers as well as amines.
A solid, molecular complex (usually 1:1) can often be formed between picric acid and one of these compounds.


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Phenylhydrazone
For aldehydes and ketones.
Aldehydes and ketones react with phenylhydrazine to form this recommended derivative.


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p-( Or 4- )Bromophenacyl Ester
For carboxylic acids.
Carboxylic acids, as their salts, react with 4-bromophenacyl bromide to form crystalline 4-bromophenacyl esters.


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Nitration Product
For aromatic hydrocarbons and ethers as well as halogen compounds.
Aromatic compounds which are inert and susceptible to electrophilic attack can be nitrated. The reaction sometimes does not proceed cleanly.


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2,4-Dinitrophenylhydrazone
For aldehydes and ketones.
A highly recommended derivative for aldehydes and ketones. It is made by reaction with 2,4-dinitrophenylhydrazine.


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Oxime
For aldehydes, ketones and quinones.
These carbonyl containing compounds may be reacted with hydroxylamine hydrochloride and sodium acetate to form the corresponding oxime.


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Aroylbenzoic Acid
For aromatic hydrocarbons.
Aromatic hydrocarbons react with phthalic anhydride and aluminium chloride by an electrophilic substitution reaction to form an aroylbenzoic acid.


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Anilide
For carboxylic acids and aliphatic halogen compounds.
Carboxylic acids are first converted into acyl chlorides and then reacted with aniline to form this recommended derivative. Aliphatic halogen compounds, via a Grignard reagent, react with phenylisocyanate and then water to form an anilide. 


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