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Lecture 2 Outline

Lecture 2 Outline. Naming & Functional Groups 3D Structure Conformers Rotamers Thermodynamics Kinetics Acids & Bases Introduction to Reactivity. memorize. Alkanes. The simplest organic molecules are alkanes. All alkanes have the formula C n H 2n+2. memorize. Alkanes.

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Lecture 2 Outline

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  1. Lecture 2 Outline • Naming & Functional Groups • 3D Structure • Conformers • Rotamers • Thermodynamics • Kinetics • Acids & Bases • Introduction to Reactivity

  2. memorize Alkanes The simplest organic molecules are alkanes All alkanes have the formula CnH2n+2

  3. memorize Alkanes

  4. IUPAC Rules for Alkane Nomenclature Find the parent hydrocarbon. This is based on the longest continuous carbon chain. If there are chains of equivalent length, then select the one with the most branch points as the parent. Number the atoms in the parent chain, beginning at the end nearer the first branch point. If there is branching an equal distance from both ends, then consider the next branch point (repeat as required). Identify and number the substituents. Remember there must be as many numbers as there as substitutents. Write out the name as a single word, using hyphens to separate the different prefixes and commas to separate the numbers. If two or more different substitutents are present, cite them in alphabetical order. With identical substituents, use the prefix di-, tri-, tetra- etc. as required. If a substituent has subranching (ie. its complex) then reapply the first 4 steps as if it were a compound. Numbering must begin at the point of attachment. Now set this substituent in parentheses. The prefixes di, tri, tetra etc., and tert- and sec- are not considered when alphabetizing, but cyclo, spiro, iso & neo are considered. Nomenclature

  5. Nomenclature Also table 2-3 Benzene

  6. Team-Work • Draw structure 2-20, re-draw & name the compounds below: Identify each carbon in this molecule as primary (1°), secondary (2°), or tertiary (3°) re-draw, circle, & name the functional groups in the following molecule: (note that you do not need to name this molecule, such complex molecules usually have common names, this molecule is a steroid)

  7. IUPAC Rules for Alkane Nomenclature Find the parent hydrocarbon. This is based on the longest continuous carbon chain. If there are chains of equivalent length, then select the one with the most branch points as the parent. Number the atoms in the parent chain, beginning at the end nearer the first branch point. If there is branching an equal distance from both ends, then consider the next branch point (repeat as required). Identify and number the substituents. Remember there must be as many numbers as there as substitutents. Write out the name as a single word, using hyphens to separate the different prefixes and commas to separate the numbers. If two or more different substitutents are present, cite them in alphabetical order. With identical substituents, use the prefix di-, tri-, tetra- etc. as required. If a substituent has subranching (ie. its complex) then reapply the first 4 steps as if it were a compound. Numbering must begin at the point of attachment. Now set this substituent in parentheses. The prefixes di, tri, tetra etc., and tert- and sec- are not considered when alphabetizing, but cyclo, spiro, iso & neo are considered. Nomenclature

  8. Lecture 2 Outline • Naming & Functional Groups • 3D Structure • Conformers • Rotamers • Thermodynamics • Kinetics • Acids & Bases • Introduction to Reactivity

  9. Molcules in 3D

  10. Team-Work • Problems 2-22,23 • For 23 you can approximate the energy of the y-axis, you do not have to provide a specific value

  11. Lecture 2 Outline • Naming & Functional Groups • 3D Structure • Conformers • Rotamers • Thermodynamics • Kinetics • Acids & Bases • Introduction to Reactivity

  12. Most Reactions Have: • Electron Rich Substrates (Base/Nucleophile) •  reacts with  • Electron Poor Substrates (Acid/Electrophile) • Every Reaction Has: • Reactant • Product • New Bond Formed • Bond (or lone pair) Broken • Transition State • Reaction Coordinate Diagram • Mechanism • Rate • Sometimes Reactions Have: • Intermediates • Leaving Groups • Stereospecific Outcomes • Hydride (or Alkyl) Shifts • Resonance Stabilization of • Reactant/Product/Intermediate Reactions • Reactions Can Be Analyzed By: • Nuclear Magnetic Resonance • Chromatography • Infrared Spectroscopy • Mass Spectrometry • Optical Rotation • Melting/Boiling Point • UV-Vis • Elemental Analysis • X-Ray Crystallography DG = 1.4 log K @ room temp. If the reaction equilibrium differs by 1.4 kcal/mol a 10:1 ratio of the two species is obtained, if 2.8 kcal/mol then 100:1, and so on

  13. pKa Table Knowing pKa values not only allows prediction of acid-base reactions, but also helps to determine leaving group ability and nucleophilicity

  14. Team-Work • Question 1: On the board • Problems: 2-1,2,3,4,6,8,9,10,11,15 • Remember that you are responsible for all vocabulary words even if we did not talk about them in class because you learned them in Gen. Chem.

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