OCHEM_UNIT_10 - OCHEM UNIT 10: NUCLEOPHILIC SUBSTITUTION...

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Unformatted text preview: OCHEM UNIT 10: NUCLEOPHILIC SUBSTITUTION REACTIONS A. INTRODUCTION 1. ALKYL HALIDES REVISITED R X or R = alkyl group X = F, Cl, Br, I, and others. Electrophile = electron poor = electron loving An electrophile reacts with a nucleophile in a polar reaction . 2. TYPES OF POLAR REACTIONS a. Reactions of Nucleophiles Nucleophiles undergo two types of polar reactions :-Substitution reactions-Elimination reactions. b. Substitution Reactions 1 Nu :- + C X C Nu + :X- Ex: c. Elimination Reactions H B :- + C C C C + : X- + B H X Ex: Read pages 237 - 238. Do Problems on page 238. Note: This Unit is about substitution reactions. 3. TYPES OF SUBSTITUTION REACTIONS 2 There are two types of substitution reactions:-SN1-SN2 B. SN2 REACTIONS 1. INTRODUCTION Nu :- + R X R Nu + :X- Ex: 2. THE KINETICS OF SN2 Recall: Nu :- + R X R Nu + :X- Rate = k[nucleophile][substrate] 3 Note: The reaction is bimolecular (a second-order reaction). In other words, the rate of the reaction depends on both nucleophile and substrate. S = substitution N = Nucleophilic 2 = bimolecular Ex: OH :- + CH 3 I CH 3 OH + :I- Rate = k[CH 3 I][OH- ] Note: If we double [CH 3 I], the rate doubles. If we double [OH- ], the rate also doubles. 3. REACTION MECHANISM Rate = k[Nu][R-X] 4 The SN2 reaction occurs in one single step . Have concerted bond breaking and bond forming . In other words, bond breaking and bond forming occur at the same time. Have a nucleophilic backside attack ....
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OCHEM_UNIT_10 - OCHEM UNIT 10: NUCLEOPHILIC SUBSTITUTION...

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