Chapter 22 - Organic and Biological Molecules
22.1 - Alkanes: Saturated Hydrocarbons
- They are compounds composed of mostly carbon and hydrogen atoms that typically contain chains or rings of carbon atoms
- Alkanes:
* It contains compounds with only C¬C single bonds
* They are said to be saturated because each carbon present is bonded to the maximum number of atoms (4)
* The carbon atoms are described as being sp3 hybridized
* Their structural isomerism involves the formation of branched chains
* They react with O2 to form CO2 and H2O (called a combustion reaction)
* They undergo substitution reactions - Alkenes:
* It contains one or more C“C double bond
* The simplest alkene is C2H4 (ethylene) which is described as containing sp2 hybridized carbon atoms
* Restricted rotation about the C“C bonds in alkenes can lead to cis-trans Isomerism
* They undergo additional reactions - Alkynes:
* It contains one or more C‚C triple bonds
* The simplest example is C2H2 (acetylene), described as containing sp-hybridized carbon atoms
* They also undergo additional reactions - Aromatic hydrocarbons
* It contains rings of carbon atoms with delocalized p electrons
* It undergoes substitution reactions rather than addition reactions
22.2 - Alkenes and Alkynes
- Multiple carbon-carbon bonds result when hydrogen atoms are removed from alkanes
- The root hydrocarbon name ends in -one rather than -ane
- In alkenes containing more than three carbon atoms, the location of the double bond is indicated by the lowest numbered carbon atom involved in the bond
* Alkynes are unsaturated hydrocarbons containing at least one triple carbon-carbon bond
* The simplest alkyne is C2H2
* For cyclic alkenes, number through the double bond toward the substituent - Since alkenes and alkynes are unsaturated, their most important reactions are addition reaction
- Halogenation of unsaturated hydrocarbons involves the addition of halogen atoms
- Another important reaction involving certain unsaturated hydrocarbons is polymerization, a process in which many small molecules are joined together to form a large molecule
22.3 - Aromatic Hydrocarbons
- They contain carbon, hydrogen, and oxygen
- It serves as a food source for most organisms
- Monosaccharides are most commonly five-carbon and six-carbon polyhydroxy ketones and aldehydesMonosaccharides combine to form more complex carbohydrates, such as sucrose, starch, and cellulose
- Benzene is the simplest aromatic molecule. More complex aromatic systems can be viewed as consisting of a number of “fused” benzene rings
- When benzene is used as a substituent, it is called the phenyl group
22.4 - Hydrocarbon Derivatives
- They are molecules that are fundamentally hydrocarbons but that have additional atoms or groups of atoms
- Alcohols are characterized by the presence of the hydroxyl group
* Alcohols are classified according to the number of hydrocarbon fragments bonded to the carbon where the OOH group is attached
* They usually have much higher boiling points than might be expected from their molar masses.
* Although there are many important alcohols, the simplest ones, methanol, and ethanol, have the greatest commercial value. - Methanol is prepared industrially (approximately 4 million tons annually in the United States) by the hydrogenation of carbon monoxide:
- Methanol is used as a starting material for the synthesis of acetic acid and for many types of adhesives, fibers, and plastics
- Ethanol is the alcohol found in beverages such as beer, wine, and whiskey;
- It is produced by the fermentation of glucose in corn, barley, grapes, etc
- Many carboxylic acids are synthesized by oxidizing primary alcohols with a strong oxidizing agent
22.5 - Polymers
- Polymers form the basis for synthetic fibers, rubbers, and plastics and have played a leading role in the revolution that has been brought about in daily life by chemistry
- The first synthetic polymers were produced as by-products of various organic reactions and were regarded as unwanted contaminants
- Polyethylene is a tough, flexible plastic used for piping, bottles, electrical insulation, packaging films, garbage bags, and many other purposes.
* Its properties can be varied by using substituted ethylene monomers. - Other polyethylene-type polymers are made from monomers containing chloro, methyl, cyano, and phenyl substituents,
- Large molecules formed from many small molecules (called monomers)
- Addition polymerization: Monomers add together by a free radical mechanism
- Condensation polymerization: Monomers connect by splitting out a small molecule, such as water
- Molecular weight (not molar mass) is the common terminology in the polymer industry
22.6 - Natural Polymers
- A class of natural polymers with molar masses ranging from 600 to 1,000,000
- Fibrous proteins form the structural basis of muscle, hair, and cartilage
- Globular proteins perform many biologic functions, including transport and storage of oxygen, catalysis of biologic reactions, and regulation of biological systems
- The protein is built in several steps. First, a tRNA molecule brings an amino acid to the mRNA
* Once this amino acid is in place, another tRNA moves to the second codon site of the mRNA with its specific amino acid
* The process is repeated down the chain, always matching the tRNA anticodon with the mRNA codon - Building blocks of proteins (monomers) are amino acids, which connect by a condensation reaction to form a peptide linkage
- Hydrogen bonding can also occur between different protein chains, joining them together in an arrangement called a pleated sheet
- The overall shape of the protein is called its tertiary structure and is maintained by several different types of interactions: hydrogen bonding, dipole-dipole interactions, ionic bonds, covalent bonds, and London dispersion force
- Protein structure:
* Primary: The order of amino acids in the chain
* Secondary: The arrangement of the protein chain
* Tertiary structure: The overall shape of the protein - Carbohydrates from another class of biologically important molecule