V Draw the possible products of this epoxide ring-opening reaction. Use a dash or wedge bond to indicate stereochemistry of substituents on asymmetric centers, Ignore any inorganic byproducts. 400 1) NaOH/H₂O 2) dilute HCI Your Aktiv Learning trial expires Select to Draw Q Problem 33

Rxn 1: prop-1-yne reacts with H2 and palladium on carbon  Rxn 2: Butan-2-one reacts with sodim borohydride/H+  Rxn 3: Butan-2-one reacts with methylmagnesium bromide in a Grignard reaction.

K Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. H Select to Add Arrows SU ㄱ :CI:O H Select to Add Arrows Problem 6

bo Secondary alcohols can also undergo elimination using the E1 mechanism. Since tertiary carbocations are more stable tha secondary carbocations, you will need to watch out for the possibility of carbocation rearrangements. If a more stable carbocation can be formed by a hydride or alkyl shift, this will occur before the beta hydrogen abstraction to give the alke O Macmillan Learning + Draw the carbocation rearrangement product of the secondary carbocation shown. O Macmillan Learning A hydride shift will occur. A tertiary carbocation should be formed.