1. Carbocation rearrangements For each carbocation, circle if the carbocation rearranges or doesn't rearrange. If it rearranges, draw the arrow-pushing mechanism and the resulting carbocation. (a) (circle one): rearranges or doesn't rearrange H3C H y (b) (circle one): rearranges or doesn't rearrange F3C H ୪ H (c) (circle one): rearranges or doesn't rearrange H3C CH3 (d) (circle one): rearranges or doesn't rearrange zo H3CO CH3 CH3

a) Draw the mechanism, using good curved arrow notation, for the reaction of 2-methyl-2- butene with bromine in water, omitting any stereochemistry: b) (R)-3-butyn-2-ol is treated with 2 mol of HBr, yielding optically active Compound A (C4H8OBr2). Draw the structure of the reaction with the correct stereochemistry. c) Name Compound A above, including stereochemistry. d) Compound A is treated with HBr to yield Compound B (C4H7Br3). The resulting solution is optically inactive. Draw the product(s) obtained and explain why there is a loss in optical activity.

2. a) b) Ez Draw the products of each / elimination Фоснасня H |||| Br H3 C H Ф OCH₂CH3

Draw the conformed out of which an E2 elimination reaction can occur?