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OCHEM_UNIT_10 - OCHEMUNIT10: REACTIONS A.INTRODUCTION 1. RX...

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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
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                                                                                                           Nu : -    + C X    C Nu  +  :X -                                                           Ex: c. Elimination Reactions                                       H                                                                                      B : -     + 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
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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
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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
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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 . Read pages 244 – 247. Do problems on page 247.
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