Organic Chemistry 332 – Sapling Learning CH 19

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Draw and name the organic product of the following reaction:

Draw the major organic product(s) for the following Friedel-Crafts acylation reaction:

Draw the major organic product of the following Friedel-Crafts alkylation. (An excess of benzene is present.) Do not draw any aluminum byproducts.

Select the correct name(s) for the structure shown.

Complete the mechanism for the generation of the electrophile used for bromination in electrophilic aromatic substitution. Add curved arrows, bonds, electron pairs, and charges where indicated.

Shown on the left is a cationic intermediate for the electrophilic addition of chlorine to the para position of phenol. Draw the resonance stucture that is the major contributor. Include all nonbonding electrons.

Draw the major organic product(s) for the following reaction. Multiple products may be drawn in one box, in any order.

Draw the major organic product(s) for the following reaction. Multiple products may be drawn in one box, in any order. Charges and nonbonding electrons do not need to be included.

Benzene can be nitrated with a mixture of nitric and sulfuric acids.

Draw the 3-atom electrophile in the reaction. Include any formal charges.

Draw and name the organic product of the following reaction:

Complete the mechanism for the generation of the electrophile used for Friedel-Crafts acylation with the following acyl halide. Add curved arrows, bonds, electron pairs, and charges where indicated.

Complete the mechanism for the generation of the electrophile used for Friedel-Crafts alkylation with the following alkyl halide. Add curved arrows, bonds, nonbonding electron pairs, and charges where indicated.

Select the best reagents for each of the following five reactions.

Synthesis of disubstituted benzenes involves two steps, each introducing one of the functional groups. For the synthesis of p-chlorobenzenesulfonic acid, select the reagent for each step and draw the structure of the monosubstituted intermediate compound.

Draw the major organic product(s) for the following reaction. Multiple products may be drawn in one box, in any order. Include charges as needed.

Show how to carry out the following transformation in the highest yield possible. Select the appropriate reagents and draw the correct organic product at each step.

For each structure below, provide the common name (which happens to be the official IUPAC name). Spelling counts.

a) Complete the generic mechanism for an electrophilic aromatic substitution (EAS) reaction using El as the electrophile and show how the sigma complex is resonance stabilized. Use curved arrows to show the mechanism and the conversion between resonance structures. Make sure to add any missing charges. Note the use of a generic base in the last step. b) Label the reaction coordinate diagram for a typical EAS reaction shown below by correctly placing the letter for each structure on the diagram.

19. B. CONTINUED

19. c CONTINUED

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