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

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