Draw the major product of this reaction. Use a dash or wedge bond to indicate the stereochemistry of substituents on asymmetric centers, where applicable. Ignore inorganic byproducts and CO2. > · ·||| 1.03 2. Zn, HOAc Q

Draw the structural formula for the product formed upon hydroboration/oxidation of the Alkene below.

[Review Topics] [References] An alkene having the molecular formula C6H10 is treated sequentially with ozone (03) and zinc/acetic acid to give the product/s shown. CH3CCH,CH,CH2CH Draw a structural formula for the alkene. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. P. aste Ado ChemDoodle Previous Next

a-pinene When a-pinene reacts with 1. BH3; 2. H₂O2, NaOH, H₂O 4 possible cis,trans isomers can be formed, but one of these is formed more readily than the others. Draw the structure of this preferred isomer. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • To aid you in your drawing, the structure of a-pinene is provided for you in the drawing palette.

1) RCO H 2) [H₂SOJ. ? Modify the given structure to draw the major product(s). Use the single bond tool to interconvert between double and single bonds. If a racemic mixture of enantiomers is expected, draw both enantiomers. Note: you can select a structure and use Copy and Paste to save drawing time. H₂C. OH th CH, CH₂ OH H₂C OH aff CH₂ CH₂ Edit Drawing

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.

Use the References to access important values if needed for this question. Draw the structure of the organic product of the following dehydration reaction. If more than one product is possible, draw the structure of the major product. tosH heat CH • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. P. opy aste [片 CH4 Previous Ne ChemDoodle" Sa

Draw the predominant product(s) of the following reactions including stereochemistry when it is appropriate. 2 HBr CH3-CEC-CH3 + • Consider E/Z stereochemistry of alkenes. • Do not show stereochemistry in other cases. If no reaction occurs, draw the organic starting material. • 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. WP ***** ? ChemDoodleⓇ n [F < 56

f) 5. Write the organic product(s) of the following substitution reactions. Indicate cis or trans, axial or equatorial, or R or S or racemic, where appropriate. If there is no reaction write NR. a) d) Br b) Ph (R) Br Hill (S) (S) (R) F Br (S) Br CI esbun to nois Br Br excess NaN, DMSO solvent NaN 3 DMSO solvent KCN DMSO solvent (S) NaO Ac DMSO solvent excess KCN DMSO solvent as ant olght way new soigh oblid yashhodsa s to nol SM2 du 5071 631 2031 203uborg sbiler yabancone lears a to nobosen Z KCN DMSO solvent ancifoser: the galwollet sit to (e)bubong sing bannot as stogbong to autxime adw erabatesh

CH3 CH₂CH₂C CHCH3 *%8 [.. You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • If there is more than one major product possible, draw all of them. • Separate multiple products using the + sign from the drop-down menu. H₂O ·OO ? Ⓡ ChemDoodle H₂SO4 ? [F <