Cumulative Outline

Cumulative Outline - CHEM 241 Organic Chemistry Course...

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CHEM 241 Organic Chemistry Course Outline Chapter 1 Resonance Induction “octet” rule Covalent / Ionic bonds Electronegativity Hybridization (sp, sp 2 , sp 3 ) Consequences of double and triple bonds Stability of alkanes vs. alkenes Carbocation / carboanion stability Chapter 2 n, iso, neo, sec, tert alkanes properties of alkanes (bonds, bond angles, reactivity) properties of alkenes properties of alkynes induced dipole forces C 1-4 : gases; C 5-19 : liquids; C 20+ : solids Branched alkenes and boiling points Chapter 3 Isomers Conformers and their restraints Constitutional Isomers: Positional and Functional Stereoisomers: Geometric (cis/trans) and Optical (Chiral) Newman Projections (stability o Hexane: staggered; pentane: some staggered, some eclipsed; butane: eclipsed; propane: even more eclipsed Strain: Torsional, van der Waals (steric), angular Ring-flipping: axial  equatorial (stability) Cis/trans 1,2-1,3-1,4 dimethyl cyclohexane o Trans-1,2 more stable than cis due to methyl crowding o Cis-1,3 more stable than trans because of equatorial o Trans-1,4 more stable than cis because of equatorial Ringo compounds Spiro compounds Polycyclic ring systems (bridgehead C) Chapter 4 Stability of alcohols Formation of alkyl halides Free radical halogenation (chain reaction)
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Stability, energy required, and time of rxn with 3 o , 2 o , 1 o , and Me C+ Reaction progress (energy diagram) Chapter 5: Alkenes Alkane properties: terminal/internal, mono-/di-/tri-/tetra- substation, cis/trans, E/Z Zaitsev’s Rule Dehydration of alcohols to form alkenes Regioselectivity and Stereoselectivity o Zaitsev: More highly substituted alkene is formed as major product o Van der Waals (steric) forces: large groups want to be trans Usefulness of H 2 SO 4 : not nucleophilic; HCl would proceed as substitution not as sulfuric acid would with elimination SN 2 : pentacoordinate at rate-determining step E 2 : water helps to pull off H from a C 1-2 hydride shift: C + moves hydride (H with 2e - ) to become secondary 1-2 methyl shift: C+ moves CH 3 to make more stable C+ and thus more substituted product Dehydrohalogenation to form alkenes One-step mechanism of dehydrohalogenation: H and Br must be anti
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This note was uploaded on 04/09/2008 for the course CHEM 241 taught by Professor Burnett during the Fall '07 term at UVA.

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Cumulative Outline - CHEM 241 Organic Chemistry Course...

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