The tosylate of (25,35)-3-phenylbutan-2-ol undergoes an E2 elimination on treatment with sodium ethoxide. Draw the structure of the alkene that is produced. Use the wedge hash bond tools to indicate stereochemistry where it exists. You do not have to explicitly draw H atoms. If a group is achiral, do not use wedged or hashed bonds oa it.

OH CO2 H3C CH3CHCH2CO, crotonate 3-hydroxybutyrate The hydration of crotonate to form 3-hydroxybutyrate occurs by the addition of -OH to the Re face of C. followed by protonation at the Si face of C2. Draw the product of the reaction, showing the stereochemistry. • Use the wedge/hash bond tools to indicate stercochemistry where it exists. • You do not have to explicitly draw H atoms. • If a group is achiral, do not use wedged or hashed bonds on it.

Predict the product or products of treating the given alkyne with the reagents shown. Show all atoms on chirality (sterec centers, using wedge-and-dash bonds to indicate stereochemistry. 1.2 Na, NH, 2. D₂, Pd Select Draw ////// H Templates *** More 7 C D H D mill 10 Era Q2 Q

CH3 H3C, CH3 с. ZH CH3 CH3 `CH3 `CH3 % Ortho 63 45 30 16 In Section 23.2, we learned that all alkyl groups are ortho/para directors. However, the relative amounts of ortho and para products depend on the specific identity of the alkyl group, as shown here for the nitration of various alkylbenzenes. What trend do you % Meta 3 8 11 % Para 34 49 62 73 observe? What factor accounts for that trend? fo

APPLY STEREOCHEMISTRY WHEN APPLICABLE: Does each reaction occur from SN1 or 2? What are the organic products?

Templates The lowest priority groups need to be on the vertical or the hash marks. lowest numbered C by IUPAC highest numbered C by IUPAC

NHCH3 NaOH, H₂O a. Draw the structure of the tetrahedral intermediate INITIALLY-FORMED in the reaction shown. You do not have to consider stereochemistry. • Do not include counter-ions, e.g., Na+, I, in your answer. • In cases where there is more than one answer, just draw one. **ELL ChemDoodleⓇ b. Draw the structures of the organic products of the acyl transfer reaction. You do not have to consider stereochemistry. • Draw the neutral form of the products; no charges. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple products using the + sign from the drop-down menu.

Draw the structure of the product formed in the reaction of an epoxide with ethoxide ion. If more than one stereochemical product is possible, draw only one isomer. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond and two in-plane bonds per chiral carbon. Select Draw Rings More Erase 0 1. CH3CH₂O- Na* 2. H+, CH3CH₂OH Q2Q The product(s) of the reaction are characterized as being racemic. R,S. S,S. R,R. S. achiral. R. **** C H

V. Show a synthesis of the following mostly (Z)-alkene molecule starting from benzene (C6H6), any other alkynes (R-C C-R) or alcohols (R-OH) of four (4) carbons or fewer, and any other necessary reagents and solvents that do not become part of the product. (20 pts) [reaction mechanisms are NOT required] H CH3 C=C OH -C-CH₂CH₂CH2CH2CH2CH3 H₂CH₂CH₂CH₂ CH₂O