Chap6chem12a

Chap6chem12a - Chap 6 Alkyl Halides 1. alkyl Halide-...

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1 Chap 6 Alkyl Halides 1. alkyl Halide- halogen bound to a sp 3 carbon atom. vinyl halide 1. Preparation of Alkyl Halides. A) Free radical halogenation + C l 2 H C l 50% C CH 3 H 3 C H CH 3 + Br 2 C CH 3 H 3 C Br CH 3 + HBr + HCl h ν h ν + Br 2 Br h ν or can use N O O Br generates Br . N-bromosuccinimide N B S *show mechanism
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2 Ex. 6-1 . Predict the product of the following reaction. 2. Substitution and Elimination reactions. A negative charged species can have two functions. Base or a nucleophile N O O Br + HBr N O O H + Br 2 helps keep the concentration of Br 2 low and constant so bromine dosen't add to the double bond. C H 2 C H 2 CH 2 CH 3 N B S h ν CHCH 2 CH 2 CH 3 Br + HBr Base X - Nucleophile X - C C C C H X + HX + Br -
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3 Ex. A. Evidence of Rxn. 1. rate = k[ - OCH 3 ][2-(R)-bromobutane] 2 nd order reaction, bimolecular. 2. Inversion of stereochemistry. B. Explanation. 1. Needs to have a transition state that involves both species. (CONCERTED) 2. LV group and Nuc must be on opposite sides. CH 3 O - + Br H nucleophile (R)-electrophile H O CH 3 (S) Leaving gbroup CH 3 O - + Br H H O C H 3 (S) C H 3 O C Br C H 3 H C H 2 C H 3 + Br -
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4 called Sn 2 rxn- substitution nucleophilic bimolecular C. Strength of Nucleophiles- ability to donate e', less steric hinderance. A) Nucleophilicity usually follows strength of basecity. strong base = strrong nucleophile but not the same property, basicity leads to elimination. B)
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This note was uploaded on 09/02/2011 for the course CHEM 12a taught by Professor Harrison during the Spring '11 term at West Valley.

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Chap6chem12a - Chap 6 Alkyl Halides 1. alkyl Halide-...

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