Chemistry, Julia Burdge, 2st Ed McGraw Hill Chapter 20 Organic Chemistry Mr Truong Minh Chien ; losedtales@yahoo.com http://tailieu.vn/losedtales http://mba-programming.blogspot.com 2011, NKMB Co., Ltd Overview Structure Determines Properties • Organic compounds all contain carbon CO, CO2 , carbonates and carbides are inorganic other common elements are H, O, N, (P, S) • Carbon has versatile bonding patterns chains, rings, multiple bonds chain length nearly limitless • Carbon compounds generally covalent molecular; gases, liquids, or low melting solids; varying solubilities; nonconductive in liquid • C - C bonds unreactive (very stable) Chemistry, Julia Burdge, 2nd e., McGraw Hill Overview • Carbon uses sp3, sp2, and sp • • hybridization in forming the four bonds per carbon atom common to almost all carbon compounds With sp hybridization, there are two (2) π bonds and σ bonds With sp2 hybridization there is one (1) π bond and σ bonds Chemistry, Julia Burdge, 2nd e., McGraw Hill Why Carbon sp3, sp2, and sp hybridization Chemistry, Julia Burdge, 2nd e., McGraw Hill FUNCTIONAL GROUPS Alkane Organic chemistry is the study of Alkene compounds containing carbon Alkyne The goal of studying Organic Alkyl halide chemistry is the making of Aromatic carbon-carbon bonds, C-X, C-O, C-N, and C-S bonds to make new molecules Alcohol Aldehyde Ketone Carboxylic Acid Inorganic molecules like CO, and 10 Ester CO3-2 are not considered organic 11 Amine 12 Amide molecules Chemistry, Julia Burdge, 2nd e., McGraw Hill Bond Energies and Reactivities C-C S-S Si-Si N-N O-O 347 kJ H3C-CH3 NONREACTIVE IN AIR 214 kJ 213 kJ 159 kJ 138 kJ EXTREMELY REACTIVE Chemistry, Julia Burdge, 2nd e., McGraw Hill HS-SH H3Si-SiH SPONTANEOUS BURNS IN AIR H2N-NH2 EXTREMELY REACTIVE HO-OH REACTIVE Allotropes of Carbon - Diamond Chemistry, Julia Burdge, 2nd e., McGraw Hill Allotropes of Carbon - Graphite Chemistry, Julia Burdge, 2nd e., McGraw Hill Carbon Bonding • mainly forms covalent bonds • C is most stable when it has single covalent bonds, but does form double and triple bonds  C=C and C≡C are more reactive than C−C  C with single bonds is tetrahedral,  singles and double is trigonal planar  doubles or triple and single is linear Chemistry, Julia Burdge, 2nd e., McGraw Hill 10 Addition Polymerization • monomers add to the growing chain in such a manner that all the atoms in the original monomer wind up in the chain no other side products formed, no atoms eliminated • first monomer must “open” to start reaction done with heat or addition of an initiator • chain reaction each added unit ready to add another Tro, Chemistry: A Molecular Approach 139 Addition Polymerization initiator H H C Cl H H etc C C H H H C• + C H • H C Cl H H H H H H H C C C C• + Cl H Cl H C Cl H C H H C C C H Cl H • H H H H Cl C H C H H Cl H H C Cl initiator H H H H H H C C C C C C Cl H Cl H Cl H • 141 PETE (polyethylene terephthalate), HDPE (highdensity polyethylene), LDPE (low-density polyethylene), PP (polypropylene), CLPE (cross-linked polyethylene, V (vinyl) or PVC, also RLDPE (resin mix, already recycled The # is another way of identifying that polymer 142 Polyethylene CH2 CH2 CH2 CH2 n Polypropylene CH3 CH CH3 CH2 CH CH2 n 143 Figure 11.14 (a) 144 Polyethylene 144 Teflon CF2 CF2 CF2 CF2 n What would the following addition polymers look like O Cl C CH for PVC 145 O CH2 CH2 CH3 CH methyl methacrylate for Lucite, Plexiglass CH CH2 stryene for styrofoam What would the following addition polymers look like HC CH2 cat C H styrof oam CH2 styrene C H CH2 x 146 styrene monomer C H CH2 C H CH2 Condensation Polymerization • monomer units are joined by removing small molecules from the combining units polyesters, polyamides lose water • no initiator needed • chain reaction • each monomer has two reactive ends, so chain can grow in two directions Tro, Chemistry: A Molecular Approach 147 Condensation Polymerization + + O C HO O C O HO C CH2 CH2 OH O C OH + HO Tro, Chemistry: A Molecular Approach O CH2 CH2 OH + H2O 148 Nylon • polyamides • good physical properties  affected by moisture • • • • very good heat resistance excellent chemical resistance excellent wear resistance nylon 6,6 made by condensing 1,6–hexandiamine, H2N–(CH2)6–NH2, with hexandioic acid, HOOC–(CH2)4–COOH Tro, Chemistry: A Molecular Approach 149 Making Nylon 6,6 NH2 + 2HN O HO C C OH O O H N C N H C O + X H 2O x Tro, Chemistry: A Molecular Approach 151 Polyamide Chains can H-Bond 152 152 153 153 ... and σ bonds Chemistry, Julia Burdge, 2nd e., McGraw Hill Why Carbon sp3, sp2, and sp hybridization Chemistry, Julia Burdge, 2nd e., McGraw Hill FUNCTIONAL GROUPS Alkane Organic chemistry is... of studying Organic Alkyl halide chemistry is the making of Aromatic carbon-carbon bonds, C-X, C-O, C-N, and C-S bonds to make new molecules Alcohol Aldehyde Ketone Carboxylic Acid Inorganic molecules... isomerism Tro, Chemistry: A Molecular Approach 27 Possible Structural Isomers Carbon Molecular Possible Content Formula Isomers C4H10 C5H12 C6H14 C7H16 C8H18 18 C9H20 35 10 C10H22 75 Tro, Chemistry: