Solubility of Organic Compounds

● ”polar solutions dissolve in polar solvents and vice versa with non polars”
● Organic compounds are usually nonpolar

Polar HC derivatives are:

1. Alcohol
2. Aldehyde
3. Ketone
4. Carboxylic Acid
5. Ester
6. Amines
7. Amides
8. Phenols (?)

Preparation of Acetylene
● Acetylene is colorless, odorless, flammable, and has reaction with lime water
● CaC2 + H2O HC≡CH

Reaction with Baeyer’s Test (KMnO4)

● Tests for unsaturation carbon bonds (Alkene or alkyne)
● If +, decolorizes from purple to brown

● HC≡CH + MnO2 (Carboxylate salt)

Reaction with cuprous chloride (CuCl)

● Product is Cuprous acetylide (Cu≡CCu)
● HC≡CH + CuCl Cu≡CCu
● Reddish brown precipitate and flammable
● Cu≡CCu + HCl HC≡CH + CuCl (white precipitate)

Equations with Acetylene

1. Combustion of Acetylene (HC≡CH + O2 CO2 + H2O + soot)
2. Reaction with Lime Water (HC≡CH + Ca(OH)2 CaCO3 + H2O)
Properties of Hydrocarbons
Naphthalene Gasolene Kerosene Vaseline Paraffin

Color White Red Colorless White White

Odor Pungent Pungent Pungent Odorless Odorless

Density Denser Less dense Less dense Less dense Less dense

Litmus Paper - - - - -

Solvent H2O - - - - -

Ether + + + + +

EthylOH - - - - -

CHCl3 + + + + +

H2SO4 - + + - -

Beyer’s Test - + + - -

Flammability Flammable Flammable Flammable Flammable Flammable

Aliphatics

Physical Properties Chemical Properties

Non-polar Unsaturated = Addition reaction

Insoluble in water Saturated = Substitution reaction

Less dense in water But reacts mainly like a substitution reaction

Primary alcohol Secondary alcohol Tertiary alcohol

 Ethyl Alcohol Isopropyl Alcohol Tert. Butyl Alcohol

Chromic acid test

(H2CrO4)
● It is able to
identify
aldehydes,
primary
alcohol,
secondary
alcohol, but Blue-green color Blue green color No reaction
not tertiary CH3CH2OH + H2CrO4
alcohol. R-COH oxidizes
into R-COOH
(carboxylic acid)

Lucas test (ZnCl2 in No reaction 10 min 5 min

HCl) White insoluble layer White insoluble layer
● Categorizes (Alkyl halide) (Alkyl halide)
alcohols using C4H9OH + HCl +
a solution of ZnCl2 C4H9Cl +
anhydrous H2O
zinc chloride
in
concentrated
hydrochloric
acid

Esterification
● A chemical reaction in which an alcohol and an acid react to form an ester, as the
reaction product, and water
● Alcohol + Carboxylic acid = Ester + Water

Test for Phenols

● Ar-OH + NaOH 5% soluble Phenoxide salt
(Ar-OH + NaOH Ar-O-Na+ + H2O)
● Ar-OH + FeCl Violet color solution
(Ar-OH + FeCl Ar-O-Fe-CL2 + HCl)
● β-naphthol (C10H7OH) + FeCl Yellow-green solution
Properties of Aldehydes (R-COH) and Ketones (R-COR’)
Formalin (CH2O) Acetone ((CH₃)₂CO) Benzaldehyde
(C6H5CHO)

Color Colorless Colorless Colorless

Blue Litmus paper - - -

Red Litmus paper - - -

Polymerization White substrate (Can - -

be polymerized by
simple heating)

DNP Test or Brady's + + +

reagent Orange precipitate Orange precipitate Orange precipitate
(2,4-dinitrophenyl
hydrazine)

Tollens' test or + - +
silver-mirror test

Benedict’s test + - -

Iodoform’s test - Yellow precipitate -

(Methyl ketone)

Sodium nitroprusside - Wine-red mix -

test
● to detect the
presence of
thiol groups of
cysteine in
proteins
DNP Test
● reacts with carbonyl compounds (aldehydes and ketone) to give a coloured precipitate.

Tollen’s Test
● used to distinguish between an aldehyde and a ketone

Benedict’s Test or Fehling’s test (product is red brick precipitate)

● Solely for aliphatic aldehydes

Iodoform’s Test (product is yellow precipitate)

● To check the presence of carbonyl compounds
HC Derivatives Formula Group Sources Uses

Alkyl Halides R-X -X Halogenation of Propellants, paint

(Chloromethane) hydrocarbons, removers, fire
substitution of extinguishers
alcohols

Alcohols R-OH -OH Oils, animal Fermentation,

(Ethanol) tissues, Medicinal, and
hydration of industrial
alkenes purposes

Phenols Ar-OH -OH Decomposing Disinfectants,

(Salicylic acid) organic preservatives,
material, antioxidants
conversion of
coal

Ethers R-O-R’ -O- Byproducts of Anesthesia,

(Diethyl ether) esters or antiseptics,
alcohols additives to start
diesel or petrol
engines

Aldehyde R-COH C=O Industrial Preservation of

(Formaldehyde) manufacturing, organisms,
Food sources disinfectant

Ketone R-COR’ C=O Metabolism, Solvent in

(Acetone) fermentation, industries,
plants, insects medications

Carboxylic Acid R-COOH Ascorbic acid, Disinfectants for

(Acetic acid) C=OOH vinegar, Fatty textiles, Cellulose
acids for plastic and
esters

Ester R-COOR’ C=O Fruits, flowers, Solvents,

(Ethyl acetate) fermentation, essential oils,
esterification personal and
care products

Amine R-NH2 NH Alkaloids, Analgesics, dyes,

(Methylamine) putrefaction, disinfections,
foods, living emulsifiers
organisms

Amide R-CONHRR’ NH Alkaloids, Papers, crayons,

(Acetamide) proteins and rubber
peptides
HC Derivatives Physical State Density Solubility in H2O Melting
compared to Point/Boiling
water Point

Alkyl Halides Colorless, Generally less Insoluble Low MP/BP,

(Chloromethane) odorless solids, dense than increase with
liquids, or gases water chain length

Alcohols Colorless liquids Less dense than Soluble Moderate MP/BP,

(Ethanol) at room water increase with
temperature chain length.

Phenols Colorless to Slightly denser Moderately Higher MP/BP

(Salicylic acid) white solids than water soluble than alcohols
when pure

Ethers Colorless, Less dense than Soluble on small Low MP/BP,

(Diethyl ether) pleasant water ethers increases with
smelling liquids chain length
that are volatile
in room
temperature

Aldehyde Heavy molecular Slightly denser Soluble on small Low MP/BP,

(Formaldehyde) weight than water aldehydes increases with
aldehydes are chain length
solids and
liquids in room
temperature

Ketone Colorless liquids Slightly denser Soluble on small Low MP/BP

(Acetone) at room than water ketones
temperature,
volatile

Carboxylic Acid Colorless liquids Denser than Soluble on small High MP/BP
(Acetic acid) with pungent water carboxylic acids
odors

Ester Solids, liquids, Less dense than Insoluble Moderate MP/BP,

(Ethyl acetate) or gases at room water less than
temperature carboxylic acids

Amine Liquids at room Aliphatic = less Soluble on small Low MP/BP,

(Methylamine) temperature, dense amines increases with
some are gases Aromatic = chain length
denser

Amide Solids at room Similar to water Soluble on small Moderate to high

(Acetamide) temperature amides MP/BP
 Aliphatic Alkanes Alkenes Alkynes
(Butane) (Butene) (Butyne)

Formula CnH2n+2 CnH2n CnH2n-2

Group C-C C=C C≡C

Sources Petroleum, natural Dehydration of Industrial preparation

gas alcohols of acetylene and
other natural sources

Uses Production of Anti-freezing for Torches to weld

plastics, fibers, motor car radiations, metals, syntheses to
cooking and heating making buckets, make polymers
purposes, LPG, bags,etc.
Diesel, Kerosene etc.

Physical States Odorless and Heavy molecular Odorless and

colorless liquids and weight alkenes are colorless liquids,
gases; least reactive solids and liquids in solids, and gases
than alkenes and room temperature with the exception of
alkynes ethylene which has a
distinct odor; Most
reactive than alkanes
and alkenes

Density compared to Less dense than Less dense than Less dense than
water water water water

Solubility in H2O Insoluble Insoluble Insoluble

Melting Point/Boiling Low MP/BP Moderate MP/BP; High MP/BP; higher

Point lower than Alkynes than the rest of the
Hydrocarbons