Chapter 7 - Secondary Halides? Mixtures of products are...

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1 Secondary Halides? Mixtures of products are common. =>
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2 Secondary Halides CH 3 Cl CH 3 H + CH 3 CH 2 O CH 3 CH 2 OH CH 3 OCH 2 CH 3 CH 3 H CH 3 CH 25% CH 2 + 75% CH 3 Cl CH 3 H + CH 3 C CH 3 CH CH 2 100% CH 3 CH 3 O CH 3 C CH 3 OH Bulky base - Favors elimination CH 3 CH 3 Cl CH 3 H + CH 3 C CH 3 O CH 3 H O O CH 3 C O OH O CH 3 Weak nucleophile Favors substitution 100%
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3 I - - Weak Brønsted Base Reactive Nucleophile CH 3 CH CH 2 CH 3 Cl CH 3 H + 100% I H O H CH 3 I CH 3 H
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4 Alkenes - Functional Group Pi bond is the functional group. More reactive than sigma bond. Bond dissociation energies: C=C BDE 146 kcal/mol C-C BDE -83 kcal/mol Pi bond 63 kcal/mol =>
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6 Orbital Description Sigma bonds around C are sp 2 hybridized. Angles are approximately 120 degrees. No nonbonding electrons. Molecule is planar around the double bond. Pi bond is formed by the sideways overlap of parallel p orbitals perpendicular to the plane of the molecule. =>
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7 Bond Lengths and Angles Hybrid orbitals have more s character. Pi overlap brings carbon atoms closer. Bond angle with pi orbitals increases. Angle C=C-H is 121.7 ° Angle H-C-H is 116. 6 ° =>
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8 Pi Bond Sideways overlap of parallel p orbitals. No rotation is possible without breaking the pi bond (63 kcal/mole). Cis isomer cannot become trans without a chemical reaction occurring. =>
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IUPAC Nomenclature Parent is longest chain containing the double bond. -ane changes to -ene. (or -diene, -triene) Number the chain so that the double bond has the lowest possible number. In a ring, the double bond is assumed to
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Chapter 7 - Secondary Halides? Mixtures of products are...

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