2. Draw the 4 bromonium intermediates formed in the following reaction. On each, indicate which carbon(s) will be attacked by the nucleophilic methanol. + Br2 MeOH show the four bromonium intermediates and place a star (*) near the electrophilic Cs 3. Predict the products of the following reaction, including stereoisomers.

Show how you would synthesize the target compound ne right from the starting compound on the left. Show reagents and conditions, and the structures of important intermediate compounds. Do not show any (arrow pushing) mechanism. Ignore stereochemistry in this question.

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The mechanism proceeds through a first cationic intermediate, intermediate 1. Nucleophilic attack leads to intermediate 2, which goes on to form the final product. In cases that involve negatively charged nucleophile, the attack of the nucleophile leads directly to the product. H. Br + CH3OH Br Intermediate 2 (product) Intermediate 1 In a similar fashion, draw intermediate 1 and intermediate 2 (final product) for the following reaction. OCH3 Cl2 MEOH ĆI racemic mixture Pay attention to the reactants, they may differ from the examples. In some reactions, one part of the molecule acts as the nucleophile. • You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate intermediate 1 and intermediate 2 using the the dropdown menu. → symbol from

Draw the organic product you would expect to isolate from the nucleophilic substitution reaction between the molecules shown. Note: You do not need to draw any of the side products of the reaction, only the substitution product. OH- 0 + I X Click and drag to start drawing a structure.

Draw the structure of the major organic product of the reaction below. CH₂ + CHCI 3 KOH Use the wedge/hash bond tools to indicate stereochemistry where it exists. Show stereochemistry in a meso compound. If the reaction produces a racemic mixture, just draw one stereoisomer. O. #[ ] در ? ChemDoodleⓇ

Answer the questions below with reference to the reaction shown here: Meo. `OH 2 Meo AICI3 (a) The reaction involves the initial formation of an "acylium ion" from 2: draw the mechanism for the formation of this ion. (b) Draw the structure of the intermediate formed when the acylium ion reacts with compound 1, and then show by means of curved arrows how this intermediate is transformed to the final product 3. (You do not need to show all the resonance forms of the intermediate.) Explain why the substitution takes place ortho to the OMe (c) substituent and not ortho to the methyl substituent.

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5a) Draw the product(s) of the reaction shown below. Additionally, identify the nucleophile, electrophile and leaving group.

Using curved-arrow notation, draw out the mechanism for the following reaction. Be sure to include stereochemistry and show all intermediates as well as the final product and include all lone pair electrons. Br Br2, H2O OH