All electrophilic aromatic substitution reactions occur via a two-step mechanism: addition of the electrophile to form a resonance-stabilized carbocation, followed by deprotonation by a base. In the step shown below, loss of a proton to form the substitution product was drawn using the resonance structure with the + 1 formal charge at the ortho position to the carbon bonded to the electrophile. Redraw the step shown with the other two resonance structures and use curved arrows to show how these other two resonance structures can be converted to the substitution product by removal of a proton with the base shown. Part: 0 / 2 Part 1 of 2 C H CAICI, Draw the mechanism that generates the final substitution product with the + 1 formal charge at the para position. Cl HCl AICI3

Complete the equation for the following proton-transfer reaction by using curved arrows to show the flow of electron pairs and drawing the products of the reaction. • Draw all atoms, including hydrogen atoms. Apply formal charges where appropriate. Assign lone pairs and radical electrons where appropriate. • Use the "starting points" menu to revert to the original molecule(s) shown. • Draw the appropriate electron-flow arrows. • Omit + signs between structures. ● ● H-O: == starting points == ↑ TAYY H T H-C-H H-N-H T H در ? ChemDoodle

The compound below is treated with chlorine in the presence of light. H₂C CH3 H₂C CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. Undo

Draw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 1-methylcyclohexanol as the major product. You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. ● If more than one structure fits the description, draw them all. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. ● ● ✓ ? ChemDoodleⓇ n [ ]#