Chapter 16.8, Problem 19CC

Draw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 2-methyl-2-butanol 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.

- For the dehydration shown, use curved arrows to show the formation of the carbocation intermediate in the presence of sulfuric acid H2SO4H2SO4, then draw the structures of the minor and major products of the elimination. Picture: Cyclohexane (no double or triple bonds) with a methyl group and an alcohol group (HO 4e- on O) on C1 (bottom) reacting with H2SO4 -> "Major and Minor Products"  -The H2SO4H2SO4 is abbreviated as H+H+ in the drawing module. Do not delete any pre‑drawn bonds, charges, or lone pairs. If you accidentally make a mistake, remove the last change by using the undo button on the lower left or revert the drawing palette to the original state by selecting the More menu, then select Reset Drawing. Step 1: Use curved arrows to complete the protonation mechanism of the alcohol. Step 2: Use a curved arrow to show the formation of the carbocation intermediate for the elimination. (Picture 1)   -Step 3: This tertiary carbocation intermediate readily undergoes…

Shown below is a carbocation intermediate in an electrophilic addition reaction of HCl with an alkene. For the conformation shown, select each hydrogen whose bond to carbon is aligned for effective hyperconjugation with the vacant p orbital on the positively charged carbon. Each adjacent carbon will have only one C-H bond so aligned. • Gray = C; white = H; red = 0; blue = N; dark green = Cl; brown =Br; light green =F; purple = I; yellow = S; orange = P. • Double click to select atoms. • You can zoom in and out using the mouse scroll wheel (or pinch to zoom on touch screens).