Gilman reagents are versatile reagents for making new carbon-carbon bonds. Draw the product of the reaction of a phenyl Gilman reagent with this compound. CF3 • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Explicitly define the cis/trans stereochemistry of fused rings using wedge or hash bonds. If enantiomers are formed, draw both. Separate multiple products using the + sign from the drop-down menu.

Draw a structural formula for the substitution product of the reaction shown below. Na OČCH3 "Br H3C- DMF H3C DMF = dimethylformamide %3D • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If more than one stereoisomer of product is formed, draw both. Separate multiple products using the + sign from the drop-down menu. • Products that are initially formed as ions should be drawn in their neutral forms. C орy aste ChemDoodle

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Draw the structure of each isomer.

Draw a structural formula(s) for the major organic product(s) of the following reaction. acetone Nal Br S enantiomer • 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 on it. 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. C P opy aste C Previous Next

[References] The synthesis of carbohydrates can be particularly difficult because of the large number of chiral centers and OH functional groups present. Epoxides can be useful synthetic intermediates in carbohydrate synthesis. Draw the product of the reaction of a phenyl Gilman reagent with this epoxide. Å . • • Use the wedge/hash bond tools to indicate stereochemistry where it exists. Explicitly define the cis/trans stereochemistry of fused rings using wedge or hash bonds. If enantiomers are formed, draw both. Separate multiple products using the + sign from the drop-down menu. 0 Θ F ? ChemDoodle remove Previous Nex

Draw the structure of the organic product of the reaction between cyclohexene and Q3 then (CH3)2S. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. Separate multiple products using the + sign from the drop-down menu. • In cases where there is more than one answer, just draw one. ● TAYY ChemDoodleⓇ Sn [F

Draw one of the two enantiomers of the major product from this reaction. Use a dash or wedge bond to indicate stereochemistry of substituents on asymmetric centers. Ignore inorganic byproducts. 1. BH3-THF 2. H2O2, NaOH Q

Draw a structural formula for the substitution product of the reaction shown below. H3C CI CH3OH • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If more than one stereoisomer of product is formed, draw both. • Separate multiple products using the + sign from the drop-down menu.

Draw a structural formula for the substitution product of the reaction shown below. H CH3 O Br OCH₂CH3 **** • Use the wedge/hash bond tools to indicate stereochemistry where it exists. If more than one stereoisomer of product is formed, draw both. . Separate multiple products using the + sign from the drop-down menu. Products that are initially formed as ions should be drawn in their neutral forms. ? a ChemDoodleⓇ N-H n [F < тс