Organic Chemistry

Marcela Leal #08 , Roberta Prez #12

Alkanes
What is it?
Substances consisting entirely of singlebonded carbon and hydrogen atoms and lacking functional groups are called Alkanes. There are three basic types of structure that they are classified in: the linear straight-chain alkanes, branched alkanes, and also cycloalkanes. Alkanes that have a ring or cyclic structure are called cyclicalkanes, while those that are without are called acyclic. Properties of Alkanes Ring Strain and the Structure of Cycloalkanes Physical Properties of Alkanes. !

Shape

Uses
-heating! -electricity generation! -Cooking! -production of polymers! - serve as intermediate in the synthesis of drugs, pesticides and other chemicals! - components of gasoline (pentane and octane)! - paraffin wax!

!
IUPAC Naming Properties:
Cycloalkanes! " Nomenclature of Cycloalkanes! " Physical Properties of Cycloalkanes! " Ring Strain and the Structure of Cycloalkanes! " Rings: cis/trans and axial/equatorial relationships! Haloalkanes! Nomenclature of Alkanes! Physical Properties of Alkanes! Straight-Chain and Branched Alkanes!

The following table contains the systematic names for the first twenty straight chain alkanes. It will be important to familiarize yourself with these names, as they will be the basis for naming many other organic molecules throughout your course of study.!

Alkenes
What is it?
Alkenes area class of hydrocarbons that contain only carbon and hydrogens. Properties of Alkenes Nuclear Magnetic Resonance (NMR) of Alkenes Physical Properties of Alkenes Synthesis of Alkenes Alkenes by Dehydration of Alcohols Reactions of Alkenes Addition Reactions of Alkenes Catalytic Hydrogenation of Alkenes Catalytic Hydrogenation of Alkenes: Relative Stability of Double Bonds Electrophilic Addition of Halogens to Alkenes Addition of Radicals to Alkenes Hydrogenation of Alkenes.!

Shape

Uses

Alkenes find many diverse applications in industry. They are used as starting materials in the syntheses of alcohols, plastics, laquers, detergents, and fuels.
Properties:

IUPAC Naming

Alkenes contain carbon-carbon double bonds and are unsaturated hydrocarbons with the molecular formula is CnH2n. This is also the same molecular formula as cycloalkanes. Alkenes are named by dropping the -ane ending of the parent and adding -ene.!

Degree of Unsaturation! Dienes! " Addition Reactions of Dienes! " Diels-Alder Cycloaddition! Nomenclature of Alkenes! Nuclear Magnetic Resonance (NMR) of Alkenes! Physical Properties of Alkenes! Structure and Bonding in Ethene-The Pi Bond

Alkynes
What is it?
Alkynes are organic molecules made of the functional group carbon-carbon triple bonds. They are written in the empirical formula of C n H 2n-2 . They are unsaturated hydrocarbons. Properties of Alkynes Acidity of Terminal Alkynes Nomenclature of Alkynes Spectroscopy of the Alkynes Synthesis of Alkynes Preparation of Alkynes by Double Elimination Preparation of Alkynes from Alkynyl Anions Reactions of Alkynes Electrophilic Addition Reactions of Alkynes Hydration of Alkynes and Tautomerism. !

Shape

Uses The uses of alkynes occur most often in nature and medicine.!

IUPAC Naming

Properties

Alkynes are organic molecules made of the functional group carbon-carbon triple bonds. They are written in the empirical formula of CnH2n-2. They are unsaturated hydrocarbons. Like alkenes have the suffix ene, alkynes use the ending yne. This suffix is used when there is only one alkyne in the molecule.!

Acidity of Terminal Alkynes! Nomenclature of Alkynes! Properties and Bonding in the Alkynes! Spectroscopy of the Alkynes

Halocarbons
What is it?
The haloalkanes, also known as alkyl halides, are a group of chemical compounds comprised of an alkane, such as propane or butane, and one or more hydrogens that have been replaced by a halogen atom. The halogens we will be concerned with are fluorine, chlorine, bromine, and iodine.!

Shape

Uses They were used as refrigerants, propellants for aerosols, for generating foamed plastics like expanded polystyrene or polyurethane foam, and as solvents for dry cleaning and for general degreasing purposes.!

IUPAC Naming Properties Functional group suffix ="halide (i.e. fluoride, As we will see, there is a fairly large chloride, bromide, iodide)! distinction between the structural and ! physical properties of haloalkanes and the Substituent name =halo- (i.e. fluoro, chloro, structural and physical properties of alkanes. bromo, iodo)! As mentioned above, the structural ! differences are due to the replacement of Structural unit :haloalkanes contain R-X one or more hydrogens with a halogen atom. where X = F, Cl, Br, I etc.! The differences in physical properties are a result of factors such as electronegativity, bond length, bond strength, and molecular size.!

Alcohol
What is it? Shape

Any of a class of chemical compounds having the general formula ROH, where R represents an alkyl group and OH a hydroxyl group, as in methyl alcohol, CH 3 OH, or ethyl alcohol, C 2"H 5 OH.
IUPAC IUPAC Naming Naming
In the IUPAC system of nomenclature, functional groups are normally designated in one of two ways. The presence of the function may be indicated by a characteristic suffix and a location number. This is common for the carbon-carbon double and triple bonds which have the respective suffixes ene and yne. Halogens, on the other hand, do not have a suffix and are named as substituents, for example: (CH3)2C=CHCHClCH3 is 4chloro-2-methyl-2-pentene. If you are uncertain about the IUPAC rules for nomenclature you should review them now.

Uses Drinks, fuel, Industrial methylated spirits (meths), and solvent.

Properties Alcohols are one of the most important molecules in organic chemistry. They can be prepared from many different types of compounds and they can be converted into many different types of compounds. Alcohols are molecules containing the hydroxy functional group (-OH) that is bonded to a carbon atom of an alkyl or substituted alkyl group. The hydroxy functional group strongly contributes to the physical properties of alcohols.

Aldehyde
What is it? Shape Uses
Aldehydes are used for many things such as perfumes and flavorings. Other uses of Aldehydes include disinfectants and dying items. Aldehyde is also used in Bake Lite.

Any of a class of organic compounds containing the group #CHO, which"yields acids when oxidized and alcohols when reduced.
IUPAC Naming
The IUPAC system of nomenclature assigns a characteristic suffix -al to aldehydes. For example, H2C=O is methanal, more commonly called formaldehyde. Since an aldehyde carbonyl group must always lie at the end of a carbon chain, it is always is given the #1 location position in numbering and it is not necessary to include it in the name." There are several simple carbonyl containing compounds which have common names which are retained by IUPAC.

Properties
Aldehydes undergo a wide variety of chemical reactions, including polymerization. Their combination with other types of molecules produces the so-called aldehyde condensation polymers, which have been used in plastics such as Bakelite and in the laminate tabletop material Formica. Aldehydes are also useful as solvents and perfume ingredients and as intermediates in the production of dyes and pharmaceuticals. Certain aldehydes are involved in physiological processes. Examples are retinal (vitamin A aldehyde), Important in human vision, and pyridoxal phosphate, one of the forms of vitamin B6. Glucose and other so-called reducing sugars are aldehydes, as are several natural and synthetic hormones.

Ketone
What is it? Shape Uses Uses

Any of a class of organic compounds containing a carbonyl group, CO, attached to two alkyl groups, as CH 3 COCH 3"or CH 3"COC 2"H 5.
IUPAC Naming
The IUPAC system of nomenclature assigns a characteristic suffix of -one to ketones. A ketone carbonyl function may be located anywhere within a chain or ring, and its position is usually given by a location number. Chain numbering normally starts from the end nearest the carbonyl group. Very simple ketones, such as propanone and phenylethanone do not require a locator number, since there is only one possible site for a ketone carbonyl function. The common names for ketones are formed by naming both alkyl groups attached to the carbonyl then adding the suffix -ketone. The attached alkyl groups are arranged in the name alphabetically.

Ketones are produced on massive scales in industry as solvents, polymer precursors, and pharmaceuticals.

Properties
Ketone compounds have important physiological properties. They are found in several sugars and in compounds for medicinal use, including natural and synthetic steroid hormones. Molecules of the anti-inflammatory agent cortisone contain three ketone groups. Only a small number of ketones are manufactured on a large scale in industry. They can be synthesized by a wide variety of methods, and because of their ease of preparation, relative stability, and high reactivity, they are nearly ideal chemical intermediates. Many complex organic compounds are synthesized using ketones as building blocks. They are most widely used as solvents, especially in industries manufacturing explosives, lacquers, paints, and textiles. Ketones are also used in tanning, as preservatives, and in hydraulic fluids.

Carboxylic Acid
What is it? Shape Uses
1. Higher fatty acids are used in the manufacture of soaps.! 2. Organic acids are used in foods, cold drinks, preparation of many drugs such as aspirin, phenacetin etc.! 3. Acetic acid is used as coagulant in the manufacture of rubber.! 4. Acetic acid is also used in the manufacture of various dye stuffs, perfumes and rayon.

Any organic acid containing one or more carboxyl groups.

IUPAC Naming The IUPAC system of nomenclature assigns a characteristic suffix to these classes. The e ending is removed from the name of the parent chain and is replaced -anoic acid. Since a carboxylic acid group must always lie at the end of a carbon chain, it is always is given the #1 location position in numbering and it is not necessary to include it in the name."

Properties
Carboxylic acids occur widely in nature. The fatty acids are components of glycerides, which in turn are components of fat. Hydroxyl acids, such as lactic acid (found in sour-milk products) and citric acid (found in citrus fruits), and many keto acids are important metabolic products that exist in most living cells. Proteins are made up of amino acids, which also contain carboxyl groups. Compounds in which the #OH of the carboxyl group is replaced by certain other groups are called carboxylic acid derivatives, the most important of which are acyl halides, acid anhydrides, esters, and amides.

Ester
What is it? Shape Uses
1. Esters are used for making artificial flavors and essences. These are used in cold drinks, ice-creams, sweets and perfumes. 2. Esters are used as solvents for oils, fats, gums, resins, cellulose, paints, varnishes, etc. 3. Esters are used as plasticizers.

A compound produced by the reaction between an acid and an alcohol with the elimination of a molecule of water, as ethyl acetate, C 4 H 8"O 2, or dimethyl sulfate, C 2 H 6 SO 4.
IUPAC Naming Carboxylic acid esters, formula RCOOR$ (R and R$ are any organic combining groups), are commonly prepared by reaction of carboxylic acids and alcohols in the presence of hydrochloric acid or sulfuric acid, a process called esterification. In the reaction the hydroxyl group (OH) of the carboxylic acid is replaced by the alkoxy group (R$O) of the alcohol. Properties

The reverse of the esterification reaction is an example of hydrolysis. Esters may also be obtained by reaction of acid halides or acid anhydrides with alcohols or by reaction of salts of carboxylic acids with alkyl halides. One ester may be converted to another ester by reaction (transesterified) with an alcohol, a carboxylic acid, or a third ester in the presence of a catalyst.