2. Predicting SN2 vs E2 Selectivity, and Stereochemistry For each set of conditions, circle the favored reaction and draw the major product. Assume the reactions are irreversible. Include stereochemistry when products contain stereocenter(s). (a) Favored reaction (circle one): SN2 or E2 HạC CH, H.C Br NaOCH3 Y 80 °C CH3 (b) Favored reaction (circle one): SN2 or E2 H3C. CH3 CH3 Nal Br 23 °C (c) Favored reaction (circle one): SN2 or E2 Br H3C was NaOCH3 0°C

Q1: Determine the major product(s) of the following reaction with correct stereochemistry where applicable. H2SO4 (cat.) H) XH OH heat Br 1) MeOH SN1 Q2. Ranke the following in the order of increasing reactivity towards SN1 reaction. CH3 CH3 CH3 H2C CH2 CH3 CH3 H₂C CH2 CH3 CH3 H2C CH2 H3C Br H3C Br H3C CI Br I ။ III IV Least reactive Most reactive

For the following dehydrohalogenation (E2) reaction, draw the major organic product(s), including stereochemistry CI (Cн Сок СH, HII (Cн, СОн

Please show the major products with appropriate stereochemistry where needed.

1a. Provide the products/reactants of the SN1 reactions below. Be very careful of the stereochemistry if applicable. (Recall that in SN1 reaction, the reactant’s chirality (aka configuration of the halo-carbon) is converted to both enantiomer – so you might need show both structures with dashed and wedge bonds 1b. Draw the mechanism (use curved arrow) of of EITHER c or d above

3. Complete the following reaction scheme. Give all product(s) and indicate major or minor and any relevant stereochemistry. OH Br heat -8 IBr heat (c) Br NaCN DMF

3. For the following reactions A-C, please draw the products including stereochemistry where appropriate. | a) H3C. сно b) A H3C H3C COOH c) COOH

Please show the major products with stereochemistry where needed.

The following are several isomers of C10H14 with two fused six-membered rings. A B D E G H (a) Identify which will react with ethene in a Diels-Alder reaction and which will not. (b) Draw one more isomer with two fused six-membered rings that will react with ethene in a Diels-Alder reaction.

Provide the structure of the product(s) with stereochemisty if appropriate. If multiple products indicate major product or if products are formed in equal amounts. If there is no reaction expected explain why. 1. H3180* 2. K2CO3 Mel CH3 1. CrO3, H30* H3C HO, 2. DCC, HN A, [-H2O] HO