The following alkene has stereoisomers. Draw the molecule in the box below which is the other stereoisomer of this alkene (You have two chances until the answer will be given; you have already tried 0 times) H-C O F HC-F FC H H Draw only one molecule in each drawing box. Compound #1

The following alkene has a stereoisomer which is referred to as a cis/trans diastereomer H₂C-C² H₂C C=C CI C-CI H₂ Draw this molecule's stereoisomer Draw only one molecule in each drawing box. Compound #1

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N,N-diethyl-m-toluamide (DEET) is the active ingredient in many insect repellent preparations. Following is one of the steps in its synthesis. In the box below draw the structure of the product of this reaction. H3C MgBr 1. CO2 2. H3O+ product • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Draw the Grignard reagent as a covalent magnesium bromide. 90-87 0 + 11 ? n [

Draw a structural formula for the substitution product of the reaction shown below. ● H3C HH Br + O • 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. ▼ In [F OCH 3 -85 ? Na CN CH3CH₂OH ChemDoodleⓇ >

Draw a resonance structure, complete with all formal charges and lone (unshared) electron pairs, that shows the resonance interaction of the acetoxy with the para position in phenyl acetate. phenyl acetate ● CH3 • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. In cases where there is more than one answer, just draw one. Sn [F ?

Write the complete common (not IUPAC) name of each molecule below. Note: if a molecule is one of a pair of enantiomers, be sure you start its name with D- or L- so we know which enantiomer it is. molecule H₂N O HO C=0 HN N+ H- CH₂ H common name (not the IUPAC name) NH3 0 5

Draw a structural formula for the substitution product of the reaction shown below. H/ ● (CH3)3C |YY Br ΔΟ H Na • 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. SH acetone [F

Does the molecule below exist as a pair of enantiomers? If so, change the bonds to wedges and dashes to reflect R stereochemistry. If the molecule does not exist as a pair of enantiomers, check the box below. H HO Does not exist as enantiomers X 3 J Ć ola Ar A: