13. a. Label the reactive features of the following reactants, select the most reactive feature, then write and highlight what it needs. Also, state if a carbocation, carbon radical, or carbanion will start to develop, and/or if aromatic character will be lost as a result of a reaction between these molecules. phenol + Cl, and FeCl, b. Use mechanism arrows to illustrate the reaction that occurs. If applicable, use stabilization resources to deal with the carbocation, carbon radical, or carbanion that starts to develop during the reaction, and draw the structure of any resonance- stabilized intermediate. Continue labelling and diagramming the reaction until you find the major stable product(s). Finally, state the stereochemistry of the major product(s) and use either Fisher projection or perspective formula representations to illustrate that stereochemistry.

4. For each of the following, determine if either a (a) hydride shift or (b) methyl shift has occurred, AND draw the curved arrows necessary to show the shift. If a hydride shift occurs, you will need to draw in the applicable hydrogen. You should also classify all of the carbocations as 1°, 2°, or 3°. a. H3C CH3 + b. + CH3 CH3 CH3 C. CH3 H3C H3C H3C + CH3 d. هه

14. a. Label the reactive features of the following reactants, select the most reactive feature, then write and highlight what it needs. Also, state if a carbocation, carbon radical, or carbanion will start to develop, and/or if aromatic character will be lost as a result of a reaction between these molecules. (R)-3-methylpent-1-ene + HBr b. Use mechanism arrows to illustrate the reaction that occurs. If applicable, use stabilization resources to deal with the carbocation, carbon radical, or carbanion that starts to develop during the reaction, and draw the structure of any resonance- stabilized intermediate. Continue labelling and diagramming the reaction until you find the major stable product(s). Finally, state the stereochemistry of the major product(s) and use either Fisher projection or perspective formula representations to illustrate that stereochemistry.

12. a. Label the reactive features, highlight the most reactive one, then highlight what it needs. Also, state if the reaction will start to create a carbocation, carbon radical, or carbanion, or will cause loss of aromatic character. If a carbocation, carbon radical, or carbanion starts to develop, label where that will occur. chlorobenzene + HNO, with tr. H,SO, b. Use mechanism arrows to illustrate the reaction that occurs. c. If applicable, use stabilization resources to deal with the carbocation, carbon radical, or carbanion that starts to develop during the reaction, and draw the structure of any resonance-stabilized intermediate. d. Continue labeling and diagramming the reaction until you find the major stable product(s). e. Finally, state the stereochemistry of the major product(s) and use either Fisher projection or perspective formula representations to illustrate that stereochemistry.

An organic chemistry Teaching Assistant (TA) suggested in your last discussion section that there is only one major organic product of the following reaction and that this reaction builds a ring. If the TA is right, draw the product in the drawing area below. If the TA is wrong, just check the box below the drawing area. CH3O O CH3O. 1. NaOMe ? 2. H3O+ Click and drag to start drawing a structure. The TA is wrong. G ☐: ☑ × 0

Part A Provide the structure of the major organic product(s) in the reaction below. CH,MgBr Draw the molecule(s) on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default.