Chapter_10_-_Organohalides

Chapter_10_-_Organohalides - OH H Cl PBr 3 H OH H Br 11 C C...

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CHM 138 H The Chemistry of the Alkyl Halides Chapter 10 1
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Alkyl Halides N COOH OH OH N H O F Lipitor O N H F 3 C Prozac >$6,000,000,000/yr Cl H Cl Cl Chloroform 2
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Nomenclature Br 1 2 3 4 5 6 7 8 9 10 2-Bromo-5-ethyl-8-methyldecane 3
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Common names - the name of the hydrocarbon group is followed by the name of the halide chloro ethane chloro ethene 3-chloro propene ethyl chloride vinyl chloride allyl chloride H 2 C CHCH 2 Cl H 2 C CH Cl CH 3 CH 2 Cl Cl Cl Cl 4
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PROPERTIES OF ALKYL HALIDES C X X=F, Cl, Br, I δ+ δ− Halomethane Bond strength kJ/mol Electronegativity of X CH 3 F 452 4.0 CH 3 Cl 351 3.0 CH 3 Br 293 2.8 CH 3 I 234 2.5 5
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6
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C F C Cl C Br C I Bond length Bond Strength 7
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Preparation of alkyl halides 1) HALOGENATION OF ALKANES (review) 2) REACTION OF ALKENES WITH HX OR X 2 (review) 3) FROM ALCOHOLS 8
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(1) Halogenation of alkanes (Chapter 5 review) 9
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(2) Reaction of alkenes with HX or X 2 Br Br Br 2 Br H HBr 10
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(3) Alkyl halides from alcohols HBr OH Br SOCl 2 H
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Unformatted text preview: OH H Cl PBr 3 H OH H Br 11 C C C OH C C C Br C C C OH H + H Br Br _ C C C OH H + Br _ 3 o > 2 o > 1 o fast 12 C H C OH C H C Br C H C OH H + H Br Br _ C H C OH H + Br _ 3 o > 2 o > 1 o slow 13 H H C OH H H C Br H H C OH H + H Br Br _ H H C OH H + Br _ 3 o > 2 o > 1 o slower 14 3 o > 2 o > 1 o Recall Markovnikov H Br Br 15 Oxidation Level H C H H H H C OH H H HO C OH H H H C OH OH OH HO C OH OH OH C O H H C O OH H C O OH HO C O O 16 Oxidation Level H C OH H H H C H H H H C Cl H H H C NH 2 H H 17 Hydrogenation/Reduction C C H 2 C C H H N C H 2 N C H H O C H 2 O C H H 18 Oxidation Level Cl Cl Cl OH O 19 Grignard Reagent R Br Mg o R Mg Br _ _ 2+ R Mg Br _ _ 2+ H O H RH R Mg Br _ _ 2+ H C O H R CH 2 OH H + 20...
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Chapter_10_-_Organohalides - OH H Cl PBr 3 H OH H Br 11 C C...

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