Consider the molecule shown below. There are at least 4 different locations that a nucleophile can react. Draw 4 different intermediates that could be formed for reaction of nucleophile at 4 different locations (use Nu for nucleophile). A B H;CO D Which intermediate do you think would be more stable? A B C or D Why would it be more stable?

10.

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2. The bromination of 2-butene is an exergonic reaction. H3C + HC. CH, Br. CH Br a. Draw the mechanism for the reaction (you may ignore the stereochemistry for this question). b. In the mechanism drawn above, identify any intermediates. Progress of the reaction Progress of the rea ction c. How many transition states are involved in the above mechanism?. Without drawing the transition state(s), indicate where they occur in the mechanism. Each step of the mechanism of reaction involves a transition state, therefore, Here there are two transition states, each with its own activation energy. d. Which of the following reaction co-ordinate diagrams best illustrates this reaction?.Explain briefly, On the diagram, draw the structures of the reactants, products and intermediates at the correct locations on the diagram and indicate which position(s) correspond to the transition Progress of the readion Progress of the reaction state(s).

27. Draw a circle around the compound that reacts most rapidly with NaN3 in DMSO and draw a rectangle around the molecule that reacts most slowly with NaN3 in DMSO. Br Br Br 28. Draw a circle around the compound that reacts most rapidly with NaOAc in HOAC and draw a rectangle around the molecule that reacts most slowly with NaOAc in HOAC. Br Br Br ***||

5. Consider the reaction below and answer the following questions + OH + H₂O a. Draw in ALL missing lone pair electrons as well as electron movement arrows on the reactant side Identify the nucleophile and electrophile on the reactant side b. c. Identify which side of the equilibrium will dominate. d. Draw resonance structures for the organic compound on the product side CHEM 241-Group05. Ormord d ****

Look at the atom in each molecule and classify as an electrophile or a nucleophile. How do you know if it is a electrophile or nucleophile? What makes it an electro or nucleophile? C in CH3Br  N in NH3 O in HO-

4. Show curved arrows that illustrate the resonance in each of the intermediates. Resonance (start with radical on C) Resonance (start with radical on F) O A Which carbon has the radical after resonance? O O O O O B C D E F Which carbon has the radical after resonance? O O O O O O B C D E F A

Which reagent can be used to convert ethanol (a poor nucleophile) into an alkoxide (a good nucleophile), which can then be used in an SN2 reaction to make a new O-C bond? Reagent Br Good HO, Nucleophile SN2 А. NaH В. HOC(CH3)3 · NaCl D.H20

How will the rate of each of the attach SN2 reactions change if it is carried out in a more polar solvent?