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CHEM301 F10 CA9A

CHEM301 F10 CA9A - CHEM301 Fall 2010 Dr Ruder 1 Class...

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CHEM301, Fall 2010 Dr. Ruder 1 Class Activity 9A Substitution Nucleophilic Bimolecular, SN2 One-step nucleophilic substitution. Model 1 : Nucleophilic Substitution Reactions In a substitution reaction, an incoming group replaces another group referred to as the leaving group. Two examples of substitution reactions are shown below. Br H H H I + I H H H + Br H O O H H H S O O CH 3 HO H H H O S O O CH 3 + + Questions 1. For each reaction in Model 1: (a). Identify the incoming group (on the reactants side) by drawing a box around it. (b). Circle the leaving group (on the reactants side). (c). Can incoming groups and leaving groups contain more than one atom? (d). Provide an explanation for why these reactions are called substitution reactions. 2. Add a δ + and δ - on the compounds that contain the leaving group to indicate which way the C- leaving group bond is polarized. 3. Use curved arrows to illustrate the mechanism that will accomplish each substitution reaction shown in Model 1. (Remember that curved arrows show electron movement.) 4. For the following questions remember that “phile ” means “lover of”: (a). What is the charge of a nucleus, (circle one) + or - ? (b). A nucleophile is attracted to another atom with what charge, (circle one) + or –? (c). A nucleophile has electrons to (circle one) donate / accept . Based on this answer, would a nucleophile be considered a Lewis Acid or a Lewis Base? (d). For the two reactions in Model 1, identify the nucleophile in each reaction. (e). An electrophile is an atom that is attracted to another atom with (circle one) + or – charge? (f). An electrophile has electrons to (circle one) donate / accept . Based on this answer, would an electrophile be considered a Lewis Acid or a Lewis Base? (g). For the two reactions in Model 1, identify the atom that is acting as the electrophile.
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CHEM301, Fall 2010 Dr. Ruder 2 Model 2: One-Step Nucleophilic Substitution (SN2) The mechanism for an SN2 reaction is shown below. The transition state is the highest potential energy species between the reactant and the product.
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