Properties

Physical properties of organic compounds typically of interest include both quantitative and qualitative features. Quantitative information includes melting point, boiling point, and index of refraction. Qualitative properties include odor, consistency, solubility, and color. Diamond is one well known allotrope of carbon. The hardness and high dispersion of light of diamond make it useful for both industrial applications and jewellery. Diamond is the hardest known natural mineral. This makes it an excellent abrasive and makes it hold polish and luster extremely well. No known naturally occurring substance can cut (or even scratch) a diamond, except another diamond. Graphite (named by Abraham Gottlob Werner in 1789, from the Greek (graphein, "to draw/write", for its use in pencils) is one of the most common allotropes of carbon. Unlike diamond, graphite is an electrical conductor. Thus, it can be used in, for instance, electrical arc lamp electrodes. Likewise, under standard conditions, graphite is the most stable form of carbon. Therefore, it is used in thermochemistry as the standard state for defining the heat of formation of carbon compounds. Graphite conducts electricity, due to delocalization of the pi bond electrons above and below the planes of the carbon atoms. These electrons are free to move, so are able to conduct electricity. However, the electricity is only conducted along the plane of the layers. In diamond, all four outer electrons of each carbon atom are 'localised' between the atoms in covalent bonding. The movement of electrons is restricted and diamond does not conduct an electric current. In graphite, each carbon atom uses only 3 of its 4 outer energy level electrons in covalently bonding to three other carbon atoms in a plane. Each carbon atom contributes one electron to a delocalised system of electrons that is also a part of the chemical bonding. The delocalised electrons are free to move throughout the plane. For this reason, graphite conducts electricity along the planes of carbon atoms, but does not conduct in a direction at right angles to the plane. Lonsdaleite (named in honour of Kathleen Lonsdale), also called hexagonal diamond in reference to the crystal structure, is an allotrope of carbon with a hexagonal lattice. In nature, it forms when meteorites containing graphite strike the Earth. The great heat and stress of the impact transforms the graphite into diamond, but retains graphite's hexagonal crystal lattice. Lonsdaleite was first identified in 1967 from the Canyon Diablo meteorite, where it occurs as microscopic crystals associated with [4][5] diamond.

Melting and boiling properties

In contrast to many inorganic materials, organic compounds typically melt and many boil. In earlier times, the melting point (m.p.) and boiling point (b.p.) provided crucial information on the purity and identity of organic compounds. The melting and boiling points correlate with the polarity of the molecules and their molecular weight. Some organic compounds, especially symmetrical ones, sublime, that is they evaporate without melting. A well known example of a sublimable organic compound is para-dichlorobenzene, the odiferous constituent of modern mothballs. Organic compounds are usually not very stable at temperatures above 300 C, although some exceptions exist.

Solubility
Neutral organic compounds tend to be hydrophobic, that is they are less soluble in water than in organic solvents. Exceptions include organic compounds that contain ionizable groups as well as low molecular weight alcohols, amines, and carboxylic acids where hydrogen bonding occurs. Organic compounds tend to dissolve in organic solvents. Solvents can be either pure substances likeether or ethyl alcohol, or mixtures, such as the paraffinic solvents such as the various petroleum ethers and white spirits, or the range of pure or mixed aromatic solvents obtained from petroleum or tar fractions by physical separation or by chemical conversion. Solubility in the different solvents depends upon the solvent type and on the functional groups if present.

Solid state properties

Various specialized properties of molecular crystals and organic polymers with conjugated systems are of interest depending on applications, e.g. thermo-mechanical and electro-mechanical such as piezoelectricity, electrical conductivity (see conductive polymers and organic semiconductors), and electrooptical (e.g. non-linear optics) properties. For historical reasons, such properties are mainly the subjects of the areas of polymer science and materials science.

Hexagonal diamond has also been synthesized in the laboratory (1966 or earlier; [6] published in 1967) by compressing and heating graphite either in a static press [7] or using explosives. It has also been produced by chemical vapor [8][9][10] deposition, and also by the thermal decomposition of a polymer, poly(hydridocarbyne), at atmospheric pressure, under argon atmosphere, at temperature 110 C (230 F)

It was first produced by Bernard Redfern in the mid 1950s at the laboratories of The Carborundum Company, Manchester, UK. He had set out to develop a polymer matrix to mirror a diamond structure and discovered a resole (phenolic) resin that would, with special preparation, set without a catalyst. Using this resin the first glassy carbon was produced.

Carbon nanofoam
Carbon nanofoam is the fifth known allotrope of carbon discovered in 1997 by Andrei V. Rode and co-workers at the Australian National University in Canberra. It consists of a low-density cluster-assembly of carbon atoms strung together in a loose three-dimensional web. Each cluster is about 6 nanometers wide and consists of about 4000 carbon atoms linked in graphite-like sheets that are given negative curvature by the inclusion of heptagons among the regularhexagonal pattern. This is the opposite of what happens in the case of buckminsterfullerenes, in which carbon sheets are given positive curvature by the inclusion of pentagons. Amorphous carbon or free, reactive carbon, that does not have any crystalline structure (also called diamond-like carbon). As with all glassy materials, some short-range order can be observed. Amorphous carbon is often abbreviated to aC for general amorphous carbon, aC:H or HAC for hydrogenated amorphous carbon, or to taC for tetrahedral amorphous carbon In mineralogy, amorphous carbon is the name used for coal, soot and other impure forms of the element, carbon that are neither graphite nor diamond. In a crystallographic sense, however, these materials are not truly amorphous, but are polycrystalline or nanocrystalline materials of graphite or diamond within an amorphous carbon matrix. Carbon nanotubes (CNTs) are allotropes of carbon with a cylindrical nanostructure. Nanotubes have been constructed with length-to[1] diameter ratio of up to 132,000,000:1, significantly larger than for any other material. These cylindrical carbon molecules have unusual properties, which are valuable fornanotechnology, electronics, optics and other fields of materials science and technology. In particular, owing to their extraordinary thermal conductivity and mechanical and electrical properties, carbon nanotubes find

Buckminsterfullerenes
The buckminsterfullerenes, or usually just fullerenes or buckyballs for short, were discovered in 1985 by a team of scientists from Rice University and the University of Sussex, three of whom were awarded the 1996 Nobel Prize in Chemistry. They are named for the resemblance of their allotropic structure to the geodesic structures devised by the scientist and architect Richard Buckminster "Bucky" Fuller. Fullerenes are molecules of varying sizes composed entirely of carbon, which take the form of a hollow sphere, ellipsoid, or tube. As of the early twenty-first century, the chemical and physical properties of fullerenes are still under heavy study, in both pure and applied research labs. In April 2003, fullerenes were under study for potential medicinal use binding specific antibiotics to the structure to target resistant bacteria and even target certain cancer cells such as melanoma. C70 fullerene is the fullerene molecule consisting of 70 carbon atoms. It is a cagelike fused-ring structure which resembles a rugby ball, made of 25hexagons and 12 pentagons, with a carbon atom at the vertices of each polygon and a bond along each polygon edge. It was first intentionally prepared in 1985 by Harold Kroto, James R. Heath, Sean O'Brien, Robert Curl and Richard Smalley at Rice University. Kroto, Curl and Smalley were awarded the 1996 Nobel Prize in Chemistry for their roles in the discovery of cage-like fullerenes. The name is a homage toBuckminster Fuller, [2] whose geodesic domes these molecules resemble. Glassy carbon or vitreous carbon is a class of non-graphitizing carbon widely used as an electrode material in electrochemistry, as well as for high temperature crucibles and as a component of some prosthetic devices.

applications as additives to various structural materials. For instance, nanotubes form a tiny portion of the material(s) in some (primarily carbon fiber) baseball bats, [2] golf clubs, or car parts. Nanotubes are members of the fullerene structural family. Their name is derived from their long, hollow structure with the walls formed by one-atom-thick sheets of carbon, called graphene. These sheets are rolled at specific and discrete ("chiral") angles, and the combination of the rolling angle and radius decides the nanotube properties; for example, whether the individual nanotube shell is a metal or semiconductor. Nanotubes are categorized as single-walled nanotubes(SWNTs) and multi-walled nanotubes (MWNTs). Individual nanotubes naturally align themselves into "ropes" held together by van der Waals forces, more specifically, pi-stacking.

Carbon Family (14) - includes a nonmetal (carbon), two metalloids (silicon and germanium) and two metals (tin and lead) - vary greatly in both physical and chemical properties - occur in nature in both combined and elemental forms - have four valence electrons - are relatively unreactive - tend to form covalent compounds (tin and lead also form ionic compounds) organic compounds are mainly composed of ten elements. These are C, H, O, N, S, P, F, Cl, Br and I. compounds obtained from plants such as starch, sugar, cellulose, oils, fats, etc., contain mainly carbon, hydrogen and oxygen while those obtained from animals such as urea, uric acid, proteins, etc., contain nitrogen besides carbon, hydrogen and oxygen. Certain organic compounds are very complex and possess very high molecular masses. For instance, molecular masses for proteins range from several thousands to over a million. ii) Quadri-covalency of carbon:- the carbon present in organic compounds is always quadric-covalent in nature. It combines with other atoms by covalent bonds. This gives rise to the identical behavior of all organic compounds. A carbon atom can link with other carbon atom by

single, double or triple bonds. The property of catenation is very strong in organic compounds. Organic compounds are essentially covalent compounds. They show characteristics of covalent compounds. a) They are volatile in nature. b) They have low melting and boiling points. c) They are generally insoluble in water but soluble in organic solvents. d) They are bad conductors of electricity. e) They do not furnish ions. They show molecular reactions. In general, the reactions of organic compounds are slow. They never proceed to completion and their yields are generally of low order. iii) Colour and odour:- Organic compounds possess distinct colour and odour. iv) Action of heat:- Organic compounds are not stable towards heat. They decompose on heating at high temperature. Some of them decompose on heating leaving a black residue. v) Combustion:- Organic compounds readily burn in air. They burn with smoky or non-smoky flame. One of the products of combustion is always carbon dioxide. vi) Homologous series:- Organic compounds have been classified into many classes each having the same functional group. The classes are known as homologous series. The compounds belonging to the same class show similar chemical properties. vii) Polymerism: - Quite a number of organic compounds exhibit polymerism (when a molecular formula of an organic compound is a simple multiple of the other). For example, benzene (C 6H6) is a polymer of acetylene (C2H2). viii) Isomerism:- Organic compounds show the phenomenon of isomerism

Classification: Color: Atomic weight: State: Melting point:

Carbon is a nonmetal black (graphite), transparent (diamond) 12.011 solid 3550 oC, 3823 K

1st ionization energy 2 ionization energy 3 ionization energy Electron affinity Minimum oxidation number Min. common oxidation no. Maximum oxidation number Max. common oxidation no. Electronegativity (Pauling Scale) Polarizability volume Reaction with air Reaction with 15 M HNO3
rd nd

1086.5 kJ mol-1 2352.6 kJ mol-1 4620.5 kJ mol-1 121.55 kJ mol-1 -4 -4 4 4 2.55 1.8 3 vigorous, CO2 mild, w/ht C6(CO2H)6(mellitic/graphitic acid) none none CO , CO2 CH4 and many CxHy CCl4 70 pm 25-470 W m-1 K-1 (graphite), 470 W m-1 K-1 (diamond) 0.07 x 106 S m-1 3550 oC, 3823 K

Note: At normal atmospheric pressure, carbon does not melt when heated, it sublimes. i.e. when heated, carbon undergoes a phase change directly from solid to gas. If the pressure is increased to 10 atmospheres carbon (graphite) is observed to melt at 3550 C. Boiling point: 3825 C, 4098 K
o

The boiling point quoted is recorded when the graphite vapor pressure above subliming graphite reaches 1 atmosphere. Electrons: Protons: Neutrons in most abundant isotope: Electron shells: Electron configuration: Density @ 20oC: 6 6 6 2,4 1s 2s 2p
2 2 2 3

Reaction with 6 M HCl Reaction with 6 M NaOH Oxide(s) Hydride(s) Chloride(s) Atomic radius
3

2.267 g/cm (gr), 3.513 g/cm (di)

3

Atomic volume:

5.31 cm /mol (gr), 3.42 cm /mol (di)

Ionic radius (1+ ion) Ionic radius (2+ ion) Ionic radius (3+ ion) Ionic radius (1- ion) Ionic radius (2- ion) Ionic radius (3- ion) Thermal conductivity Electrical conductivity Freezing/Melting point:

Structure:

hexagonal layers (graphite), tetrahedral (diamond)

Hardness: Specific heat capacity Heat of fusion Heat of atomization Heat of vaporization

0.5 mohs (graphite), 10.0 mohs (diamond) 0.71 J g-1 K-1 (graphite), 0.5091 J g-1 K-1 (diamond) 117 kJ mol-1 (graphite) 717 kJ mol-1 710.9 kJ mol-1

Functional Groups and Their Properties

Group Alkanes CnH2n+2 Polarity Non-polar Volatility/M.P./B.P. Very volatile, smaller molecules are gases B.P. increases with size due to increased dispersion forces and larger mass Soluble in Water No Acid-base Behavior None Common Compounds Methane, propane, butane, octane (gasoline) Wax

Alkenes/Alkynes CnH2n /CnH2n-2 Haloalkanes RX

Non-polar Slightly Polar non-polar

Alcohols R- OH

Polar bond capable of H-bonds

Ethers R-O-R Amines R-NH2 or R2NH or R3N Aldehydes R-CHO O

Polar bonds, no Hbonds Polar bonds, capable of H-bonds Polar carbonyl group (C=O) H-bond can form between carbonyl and water Polar carbonyl group (C=O) H-bond can form between carbonyl and water

Have similar b.p to alkanes w/ same # of carbons but a few degrees lower since they have fewer electrons = less dispersion forces Most haloalkanes are liquids at room temp Only CH3Cl, CH3Br and CH3CH2Cl are gasses Dispersion forces are more important than dipole-dipole forces B.P decreases with # of substituents since temporary dipole is stronger for long chains and attractions are more effective when molecules can pack closely Volatile when pure but often mixed w/ H2O Higher boiling points than alkanes b/c of hydrogen bonding Volatility and B.P increase as length of chain increases Volatile Lower boiling points than alcohols b/c no hydrogen bonding Low volatility High boiling points b/c of H-bonding B.P. is higher than that of similarly sized alkanes b/c of dipole-dipole forces. B.P. is lower than alcohols since dipole-dipole forces are weaker than H-bonds. B.P. increase with size of carbon chain See aldehydes

No

None

Slightly

None

PVC CFCs Teflon

Yes, decreases w/ length of carbon chain

Weakly acidic and basic (amphoteric) like water b/c of OH

Ethanol, isopropyl alcohol, menthol

First anesthetic diethyl ether Yes Basic b/c of lone pair, R-NH2 even more basic than NH3 Carbonyl can act as a base Amino acids Ammonia Formaldehyde

Yes, decreases w/ length of carbon chain

R Ketones R-CO-R O

H
Yes, decreases w/ length of carbon chain Carbonyl can act as a base Acetone (nail polish remover)

Carboxylic Acids R-COOH O

Polar, capable of hydrogen bonds

Low volatility Higher boiling points b/c of hydrogen bonding

Yes decreases w/ length of carbon chain

Acid Methanoic is stronger than ethanoic b/c of R group.

Acetic acid - vinegar

R Esters COOR O

OH
Polar, no H-bonds H-bond can form between carbonyl and water More volatility than carboxylic acids and lower boiling points b/c cant H-bond Liquids at room temp for smaller molecules Small esters: yes, solubility decreases w/ size of chain Yes Amine part of amide is basic Polyester Fatty acids

R Amides O

R
Polar, amine can hydrogen bond High m.p. b/c of hydrogen bonding Amides are liquids or solids at room temp Proteins (polypeptide) Nylon

NH R