CHM 215 Chapter 1 PDF

CHAPTER ONE REPRESENTATIVE CARBON COMPOUNDS I Organic Chemistry is most broadly defined as the chemistry of the compounds of carbon. An organic compound is best defined as a compound containing carbon. Approximately 95% of known compounds are classified as organic compounds. The element...

CHAPTER ONE REPRESENTATIVE CARBON COMPOUNDS I Organic Chemistry is most broadly defined as the chemistry of the compounds of carbon. An organic compound is best defined as a compound containing carbon. Approximately 95% of known compounds are classified as organic compounds. The element whose atoms have a unique ability to bond to each other and to other kinds of atoms is carbon.  C C C C C C Single bond Double bond Triple bond       Bond Order (B.O.) 1 2 3 As the Bond Order (B.O.) As the Bond Length (B.L.) As the Bond Strength (B.S.) As the E to break the bond FORMAL CHARGES OF CARBON, NITROGEN AND OXYGEN ATOMS Formal Charge Carbon Nitrogen Oxygen -1 C N O N 0 C N O C N O C N C +1 C N O N O N O N Formal Charge Oxygen Sulfur -1 O S O O S S 0 +1 O O O S S S 0 S S S S  O a. H2C N N b. H C O N O c. H3C S CH3 3 Formal Charge (F.C.) = Group number - # of V e’s assigned to the atom (# of e’s on the atom) in the structure.  Alkanes CnH2n+2 n = 1, 2, 3....etc If n = 4 C4H10 H H H H 1 2 4 1 2 3 4 3 H C C C C H CH3CH2CH2CH3 H H H H 3 Condensed 1 Dash 2 4 Formula Formula Bond-Line Formula In ALKANES, all carbon atoms should have single bonds & sp3 Hybridization Alkenes CnH2n n = 2, 3....etc If n = 2 C2H4 H H C C H2CCH2 H H sp2  Alkynes CnH2n-2 n = 2, 3....etc If n = 2 C2H2 H C C H HCCH sp THE FIRST TEN CONTINUOUS CHAIN ALKANES Name Condesed Molecular Formula Methane CH4 Ethane CH3CH3 CnH2n+2 n = 1, 2, 3....etc Propane CH3CH2CH3 Butane CH3CH2CH2CH3 Pentane CH3CH2CH2CH2CH3 Hexane CH3CH2CH2CH2CH2CH3 Heptane CH3CH2CH2CH2CH2CH2CH3 Octane CH3CH2CH2CH2CH2CH2CH2CH3 Nonane CH3CH2CH2CH2CH2CH2CH2CH2CH3 Decane CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 FUNCTIONAL GROUPS IN ORGANIC CHEMISTRY Functional Group Name Functional Group Name Alkane R H Alcohol R OH Alkene C C H C C C C OH C C OH C C OH Alkyne C C H H C o o o 1 2 3 Alkyl Halide R X Ether R O R H C C C C X C C X C C X Nitrile R C N H H C o o o Nitro R NO2 1 2 3 Primary Secondary Tertiary  Functional Group Name Functional Group Name Alkane O R H Carboxylic Acid R C OH o H Amine 1 R N O H Ester R C OR o R 2 R N O H C Lactone O R o 3 R N R O Amide O R C NH2 Aldehyde R C H O O C H Lactam N Ketone R C R  Formula Molecular Condensed Dash Bond-Line H H C2H6O CH3CH2OH H H C C O H O H H H H CH3OCH3 C H O H C O H H INDEX OF HYDROGEN DEFICIENCY (IHD) DEGREE OF UNSATURATION  Ring  Group 5  Increase  Group 6  No Effect  Group 7  Decrease  3 1 C4H10 IHD = 0 4 2 CnH2n+2 3 1 C4H8 IHD = 1 4 2 CnH2n 4 1 C4H8 IHD = 1 3 2 CnH2n a. C4H4N2 C4H10 12 b. C9H7OCl C9H20 19 c. C2H6O2S C2H6  Group 5  Increase  Group 6  No Effect  Group 7  Decrease  APPROACH TO THE AN CLASSIFICATIONS OF ISOMERS We can classify isomers (different compounds that have the same molecular formula) by asking and answering a series of questions.  H H CH3CH2OH H C C O H H H C2H6O H H CH3OCH3 H C O C H H H  compounds have the Do the same molecular formula? Yes No Are they different? They are not isomers Yes No They are isomers They are identical Do they differ in connectivity? Yes No They are constitutional isomers They are stereoisomers  Constitutional Isomers  Have same formula  Have same IHD  Have different connectivity Stereo of Geometrical Isomers  Have same formula  Have same IHD  Have same connectivity  Have different arrangement of atoms in space  H H CH3CH2OH H C C O H H H C2H6O H H CH3OCH3 H C O C H H H CH3CH2OH & CH3OCH3 are Constitutional Isomers  Constitutional Isomers of C4H9Br IHD = 0 Br CH3CH2CH2CH2Br CH3CHCH2CH3 n-isomer sec-isomer CH3 CH3 CH3 CH CH2Br CH3 C Br CH3 iso-isomer tert- or t-isomer Constitutional Isomers of C4H9Br Br n-Butyl Bromide Br sec-Butyl Bromide Br iso-Butyl Bromide Br t-Butyl Bromide  CH3 CH3 CH CH2CH2Br iso-Pentyl Bromide CH3 t-Pentyl Bromide CH3 C CH2CH3 Br CH3 CH3 C CH2CH2Br neo-Hexyl Bromide CH3  Geometrical Isomers  Have same formula  Have same connectivity  Have same IHD  Have different arrangement of atoms in space  C2H2Cl2 H H Cl H C C C C Cl Cl IHD = 1 Cl H A B cis - isomer trans - isomer H Cl C C H Cl C A & C are Constitutional Isomers A & B are Geometrical Isomers B & C are Constitutional Isomers  C2H2ClBr IHD = 1 H H Cl H C C C C Cl Br Br H A B cis - isomer trans - isomer Z - isomer E - isomer A & B are Geometrical Isomers  C2HFClBr IHD = 1 H F Cl F C C C C Cl Br Br H X Y Z - isomer E - isomer X & Y are Geometrical Isomers RESONANCE STRUCTURE (R.S.)  Good Luck Dr. Imad A. Abu-Yousef