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Drawing Organic Structures Functional Groups Constitutional Isomers

Drawing Organic Structures Functional Groups Constitutional Isomers. Dr. Clower CHEM 2411 Spring 2014 McMurry (8 th ed.) sections 1.12, 3.1, 3.2. Draw these structures…. C 2 H 6 CH 4 O C 3 H 6 (contains C=C) C 4 H 10 (multiple possible answers). More Lewis structures…. CH 5 N CHN

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Drawing Organic Structures Functional Groups Constitutional Isomers

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  1. Drawing Organic StructuresFunctional GroupsConstitutional Isomers Dr. Clower CHEM 2411 Spring 2014 McMurry (8th ed.) sections 1.12, 3.1, 3.2

  2. Draw these structures… • C2H6 • CH4O • C3H6(contains C=C) • C4H10(multiple possible answers)

  3. More Lewis structures… • CH5N • CHN • HNO3 • Remember… • Keep in mind total available valence electrons • Try to minimize formal charges • Patterns for formal charge

  4. Drawing Organic Structures • Example: isopropyl alcohol (C3H80) • Lewis structure • Show all bonds, atoms, lone pairs • Condensed structure • Omit some bonds (C─C, C─H, O─H, N─H) • Often omit lone pairs • Skeletal structure/line-angle drawing • Show bond framework as lines • C atoms at intersections of lines (bonds) and end of each line • H atoms bonded to C are not shown • Heteroatoms (atoms other than C and H) are shown

  5. Drawing line-angle structures

  6. Interpreting line-angle structures • What is the molecular formula for adrenaline? • What is the molecular formula for thalidomide?

  7. Drawing Organic Structures • Draw Lewis and line-angle structures for this condensed structure: (CH3)3CCH2COCHCH2

  8. Functional Groups • Collection of atoms at a site within a molecule with a common bonding pattern • Reacts in a typical way, generally independent of the rest of the molecule • Four broad classes • Hydrocarbons • Compounds containing O • Compounds containing N • Compounds containing S or P

  9. 1. Hydrocarbons • Alkane: single bonds, sp3carbons • Cycloalkane: carbons form a ring • Alkene: double bond, sp2 carbons • Cycloalkene: double bond in ring • Alkyne: triple bond, sp carbons • Aromatic (arene): contains a benzene ring • Not a hydrocarbon, but related… • Alkyl halide: R─X • R = any carbon group • X = halogen

  10. 2. Compounds containing oxygen • Alcohol: R─OH • Ether: R─O─R' • Carbonyl group: C=O • Aldehyde: RCHO • Ketone: RCOR'

  11. Carboxylic acids and their derivatives • Carboxylic Acid: RCOOH • Acid Chloride: RCOCl • Ester: RCOOR' (RCO2R’) • Amide: RCONH2 • Acid Anhydride: RCO2COR

  12. 3. Compounds containing nitrogen • Amines: RNH2, RNHR', or R3N • Amides: RCONH2, RCONHR, RCONR2 • Nitrile: RCN

  13. 4. Compounds containing S or P • Phosphates (PO42-) • Thiol(R─SH) • Sulfides (R─S─R) • Sulfoxides (S=O) • Thioester (RCOSR)

  14. Isomers • Isomers have the same molecular formula, but different arrangements of atoms • Constitutional isomers • differ in their connectivity • Stereoisomers • differ in the spatial arrangement/orientation of their atoms

  15. Constitutional Isomers • Molecules with the same molecular formula, but different connectivity • Same number and kinds of atoms • Differ in which atoms are bonded • Example: C4H10 • Straight-chain (“normal”) alkane vs. branched-chain alkane

  16. Constitutional Isomers

  17. Constitutional Isomers • Are the following pairs of molecules constitutional isomers, the same molecule, or neither? (a) (b) (c) (d)

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