Draw the complete mechanism for this reaction. Include the stereochemistry at the two chirality centers marked with ", showing whether the ring substituents in the product are cis or trans. OH Br₂ H₂C Br HBr

The southern pine beetle utilizes a multi-component aggregation pheromone (one component shown below) to start mass colonization of healthy trees. The biosynthetic pathway involves the cyclization of this acetal from the straight chain structure. Draw the straight chain structure that could be used to form this acetal. Use wedges and dashes to correctly depict the stereochemistry. H3C- OH ✔

Draw the products of the following reactions, indicating both regiochemistry and stereochemistry when appropriate. Use wedge and hash bonds ONLY when needed to show reaction stereochemistry. In cases where there is more than one answer, just draw one.

Trans-1-bromo-2-methylcyclohexane will yield a non-Zaitsev elimination product (3-methylcyclohexene) upon reaction with KOH. Show this reaction by drawing the chair conformations of the reactant and product. Include the curved arrows and explain why the product is not a non-Zaitsev product.