Chapter 21, Problem 21.15QAP

Consider the following nucleophilic substitution reaction. The compound listed above the arrow is the solvent for the reaction. If nothing is listed over the arrow, then the nucleophile is also the solvent for the reaction. Part 1 of 2 Br CH,CN + I¯ What is the correct mechanism for the reaction? Select the single best answer. @SN2 ○ SN 1 Part: 1/2 Part 2 of 2 Draw the products for the reaction. Include both the major organic product and the inorganic product. If more than one stereoisomer is possible, draw only one stereoisomer. Include stereochemistry where relevant. Click and drag to start drawing a structure. X હૈ

20.33 Think-Pair-Share (a) Rank the following dienes and dienophiles in order of increasing reactivity in the Diels-Alder reaction. (i) CO₂Et (ii) COEt || CO₂Et MeO MeO (b) Draw the product that results from the most reactive diene and most reactive dienophile shown in part (a). (c) Draw a depiction of the orbital overlap involved in the pericyclic reaction that oc- curs between the diene and dienophile in part (b). (d) Is the major product formed in part (b) the endo or exo configuration? Explain your reasoning.

20.40 The following compound undergoes an intramolecular Diels-Alder reaction to give a tricyclic product. Propose a structural formula for the product. CN heat An intramolecular Diels-Alder adduct