Hydrocarbon Derivatives-Graphic Organizer MFRM

hYDROCARBON DERIVATIVES

Compounds that, in addition to carbon and hydrogen, contain in their molecular structure other atoms (heteroatoms).

Alcohols

Amines

families

Oxygenated derivatives

Nitrogen derivatives

Ethers

According to the element that is present:

Amides

Aldehydes and Ketones

Halogenatedderivatives

Carboxylic acids

Physical properties

Uses

Examples

Esters

Examples and Uses

Physical properties

Amines

1. Dimethylamine

• The unpleasant odors associated with the decomposition of organic matter, are caused by the presence of two amines (waste products of nitrogenous bio compounds): putrescine and cadaverine.
• The first is gaseous and even the 11-carbon is liquid; then they are solid.
• The melting and boiling points increase with the number of carbon atoms.
• Solubility decreases with increasing carbon atoms.

• Chemical formula: (CH3)2NH
• IUPAC name: N-methylmethanamine
• Common name: Dimethylamine

Is used in the manufacture of pharmaceuticals such as Stovaine and alpine, which are used as local anesthesics.

2. Ethylamine

• Chemical formula: C2H5NH2
• IUPAC name: Ethanamine
• Common name: Ethylamine

It is used as a raw material in the production of rubbers and resins.

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Ethers

In this family, oxygen is in between, separating two hydrocarbon radicals.

Classification

• Symmetrical ethers: When the two radicals are equal.
• Mixed or asymmetric ethers: When the radicals are different.

They are functional isomers of alcohols, so they have the same general formula:CnH2n+2O

Carboxilic acids

The functional group of this family is a combination of carbonyl and hydroxyl, and is called the carboxyl group.

The general formula for this family of derivatives is:CnH2nO2

• The carboxyl group is always at the end of the chain.
• The carbon of the fuction group is always considered the number one of the chain.
• This group gives an acidic character to these compounds.
• They act as weak acids.

Characteristics of Alcohols

Are formed when one or more hydrogens from a hydrocarbon are replaced by one or more hydroxyl groups (---OH).

Monoalcohols

• Only contain an ---OH group.
• Represented as: R---OH, where R--- is the hydrocarbon part of the molecule.
• General formula: CnH2n+2O.

According to the type of carbon to which the functional group is attached, are classified into:

• Primary alcohols: the functional group is attached to a primary carbon (bonded to one carbon and two hydrogens).
• Secondary alcohols: the functional group is attached to a secondary carbon (bonded to two carbons and one hydrogen).
• Tertiary alcohols: the functional group is attached to a tertiary carbon (three-carbon bonded and hydrogen-free).

Examples and Uses

Physical properties

• Chemical formula: C2H5NO or CH3CONH2
• IUPAC name: Ethanamide
• Common name: Acetamide/(Acetic acid amide

Amides

1. Acetamide

• Solutions of amides in water usually are neutral neither acidic nor basic.
• The amides generally have high boiling points and melting points.
• Low molar mass amides are soluble in water.
• These characteristics and their solubility in water result from the polar nature of the amide group and hydrogen bonding .
• They are colorless/olorless solids at room temperature except formamide.

Acetamide is used as a solvent for many inorganic and organic compounds, in explosives,as a plasticizer, hygroscopic agent, to manufacture methylamine, as a stabilizer. as a penetrating agent, but also as a fire suppressant.

2. Acrylamide

• Chemical formula: C3H5NO
• IUPAC name: prop-2-enamide
• Common name: Acrylamide

General applications

• They are used in the pharmaceutical industry for the preparation of alkaloids (sedatives) and other drugs, in the textile dye industries and in the synthesis of polymers for the manufacture of synthetic fibers. They are also part of cosmetic and antiperspirant formulations.

Has wide application in the indutrial field: in the extraction of metals, in the textile industry, in the production of dyes and as a binder in the manufacture of paper.

Examples and Uses

Aldehydes

Ketones

1. Methanal

1. Propanone

• Chemical formula: CH2O
• IUPAC name: Methanal

• Common name: Formaldehyde

• Chemical formula: C₃H₆O
• IUPAC name: propan-2-one

• Common name: Acetone

Its main applications are these: in solution 40 %, called formalin, it is used as a preservative of anatomical and biological pieces, and in liquid it serves to embalm corpses, stain textiles, preparation of explosives, food preservation, tanning of skins, elaboration of disinfectant and photographic products, and in the metallurgical industry.

It is used as a common solvent for organic materials, such as greases, rubbers, plastics and varnishes. It is the main ingredient in certain nail varnish removers.

2. Ethyl methyl ketone

• Chemical formula: C4H8O
• IUPAC name: Butan-2-one

• Common name: Methyl Ethyl Ketone (MEK)

2. Ethanal

• Chemical formula: CH3CHO
• IUPAC name: Ethanal

• Common name: Acetaldehyde

Is used as a plastic welding agent because it has the ability to dissolve polystyrene and various other plastics, in the production of varnishes, and paraffin wax, acts as a precursor in polymerization reactions. It is used as a cleaning agent, in glues, but also is used in the production of petroleum.

It is used in obtaining acetic acid. It has other important applications in the manufacture of polymers, dyes, mirrors, resins, disinfectants and photographic articles, among other products.

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Uses

• Halogenated derivatives are of synthetic origin and their uses and applications are very extensive, especially at the industrial level.
• They are good solvents for lipids, oils and fats and are therefore used intensively in the dry-cleaning industry.

Physical properties

• Aldehydes with up to 12 carbon atoms are liquids, except methane, which is a gas at room temperature.
• Ketones of 3-12 carbons are liquid, and from 13, both are solids.

Solubility

• Up to 4 carbon atoms are both soluble in water.
• Solubility decreases with increasing carbon numbers.

Density

• Increases with increasing molecular mass, but they are less dense than water.

Boiling points

• Are higher than those of ethers, but lower than those of alcohols.

Physical properties

• Are insoluble in water and soluble in organic solvents.
• Its boiling point increases with molecular mass.
• For the same hydrocarbon chain, the boiling point increases with increasing atomic mass of the halogen.
• Fluorinated and chlorinated are less dense than water.
• Brominated and iodinated are denser than water.

• The naturally ocurring halogenated compounds are found as products of the metabolism of fungi, lichens, bacterias and plants.
• They have also been found in volcanoes, meteorites, and mineral sediments.

Examples and Uses

Physical properties

1. Methyl tertiary butyl ether (MTBE)

• At room temperature, methyl ether and ethyl methyl ether are gases.
• They are liquids from the diethyl ether.
• Their boiling points are lower than those of alcohols of similar molecular mass.
• Its solubility in water is very similar to that of the corresponding alcohols.
• Are functional isomers of alcohols because, when they have the same number of carbon atoms, they have the same molecular formula.

• Chemical formula: C5H12O
• IUPAC name: 2-Methoxy-2-methylpropane

• Common name: MTBE

Is used as an additive in unleaded gasoline to promote combustion and increase octane rating and performance; in addition, it reduces the emission of greenhouse gases.

2. Ethylene oxide

• Chemical formula: C2H4O
• IUPAC name: Oxirane

• Common name: Ethylene oxide

Is used in the manufacture of ethylene glycol, used as antifreeze; it is also used to sterilize medical instruments and as an intermediate in the synthesis of nonionic surfactants (liquid detergents).

Physical properties

Examples and Uses

1. Formic acid

• At room temperature, carboxylic acids of up to 9 carbon atoms are liquids, and of more than 9 are solids.
• The first 4 are soluble in water, but their solubility decreases with the increase of the hydrocarbon chain.
• They are polar molecules and can form hydrogen bonds with each other and with other types of polarized molecules.
• The lower carboxylic acids (methanoic-butanoic) are colorless liquids totally soluble in water.
• Its boiling point is higher than that of alcohol.
• As the number of carbons increases the power of smell decreases.

• Chemical formula: (HCOOH)
• IUPAC name: Methanoic acid

• Common name: Formic acid

This acid, which produces blisters on the skin, is used for the preparation of ethers, salts, plastics and oxalic acid.

2. Stearic acid

• Chemical formula: (CH3(CH2)16COOH)
• IUPAC name: Octadecanoic acid

• Common name: Stearic acid

Is obtained from some animal fats, mainly from beef tallow. Is used in the manufacture of candles, soaps, cosmetics, lubricants and inks, among other products.

Aldehydes and Ketones

These two families of derivatives share the same functional group called carbonyl:

• Aldehydes: The carbonyl group is at the end of the hydrocarbon chain.
• Ketones: The position of the carbonyl group is intermediate.
• They are position isomers and have the same molecular formula:

CnH2nO

Physical properties

Examples and Uses

• Chemical formula: CH₃OH
• IUPAC name: Methanol

• Common name: Methyl alcohol/ Wood alcohol

SOLUBILITY

• At room temperature, the first four alcohols (1-4 carbon atoms) are liquid and insoluble in water.
• 5-12 carbon atoms are oily liquids inmiscible in water.
• Those greater than 12 are water-insoluble solids.

Is obtained by heating wood in the absence of air. It is used as an industrial solvent and, converted by oxidation to methane, as a raw material for the manufacture of polymers.

• Chemical formula:C₂H₆O
• IUPAC name: Ethanol

• Common name: Ethyl alcohol

DENSITY AND BOILING POINT

• Increase with greater molecular mass, and in isomers they decrease with increasing branching.

Is produced by fermentation of fruit sugar and starches from various grains. It is used as a solvent for some organic substances and is an ingredient in many pharmaceuticals, perfumes and flavorings.

Examples and Uses

Physical properties

• Are colourless in nature; however, the most significant physical property of Ester is its odour. They have a pleasant smell.
• Esters with higher acids are colourless solid compounds.

• Are soluble in water in normal conditions.

• Esters are highly volatile and are highly flammable.

• With the increase in the mass of Ester, the solubility in water decreases.

• The methyl and ethyl ester compounds have lower boiling points at room temperature than the parent acids.

• In comparison with acyl chlorides, anhydrides, and various acids, the Esters are less chemically reactive compounds.

1. Octyl acetate

• Chemical formula: C10H20O2
• IUPAC name:

• Common name:

Food processing use it either to impart a citrus flavor or in combination with other compounds to make artificial apple, peach, pear, and strawberry flavors.

2. Methyl butyrate

• Chemical formula: C5H10O2
• IUPAC name:

• Common name:

It is widely used in perfumes and as a food flavoring. Methyl butyrate has been used in combustion studies as a surrogate fuel for the larger fatty acid methyl esters found in biodiesel.

Examples and Uses

1. Chloroform

• Chemical formula: (CHCI3)
• IUPAC name: trichloromethane (TCM)
• Common name: Chloroform

Is used in the manufacture of plastic resins, fire extinguishers and refrigerants.

2. Dichlorodiphenyltrichloroethane

• Chemical formula: C14H9Cl5
• IUPAC name: 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane
• Common name: DDT

They are used as insecticides, specifically in the so-called pesticides or pesticides.

Amines

• Nitrogenous compounds derived from ammonia (NH3), where one or more hydrogens have been replaced by hydrocarbon radicals.
• According to the number of hydrogens substituted in ammonia, they are classified as primary, secondary, and tertiary amines.

Amides

These compounds can be considered derivatives of carboxylic acids, since an amino group (-NH2) replaces the hydroxyl group (-OH) in these compounds.

Esters

Compounds formed by the combination of two functional groups: the carboxyl group of acids and the hydroxyl group of alcohols, with the consequent formation of water.

• Esters are synthesized in the laboratory from a carboxylic acid with an alcohol.
• These syntheses are widely applied in the fragrance and flavoring industry to produce perfumes, sweets, cakes and chewing gum, among other commercial products.