1. (CH3)₂ CuLi 2. EtOH Draw the molecule(s) on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default. Show the appropriate stereochemistry by choosing the dashed or wedged buttons and then clicking a bond on the canvas. To change the bond type, select the Insert menu and change the Bond setting. 7 H 12D EXP. CONT

1-chloro-3-hexyne Draw the molecule on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default. H: 22 EXP" CONT 0 0 CI H2 Br CH3 [1] F P.

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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.

1. Consider the following acidic molecules. A OH D HO -OH O=C -OH Structure of dianion of C (HPO4²-) B HO O=A HO E POH OH P-O -P-OH OH OH с a. Draw the structure of dianions (i.e., after deprotonating the second most acidic proton) for molecules C and E. Make sure to indicate any formal charges on any atoms within each structure. Structure of dianion of E (H₂P₂O72²-)

O 8. Label the following pairs of compounds as exactly the same, completely different, isomers, or resonance structures. CH3CH(CH3)CHCHCOOCH₂CH3 H-Z x O C(CH3)2CHNHCH3 (CH₂)₂ CH₂ N/ N O :O:

8:23 PM Wed Feb 2 * 41% Question 10 of 30 O Done Draw the structural condensed form of 4-methyl-2-pentene. Atoms, Bonds and Rings Charges Draw or tap a new bond to see smart suggestions. Undo Remove Reset

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2. SN2 reactions to fight cancer Cyclophosphamide is a chemotherapy medication used to treat various types of cancers (i.e. lymphoma, leukemia, and breast cancer). It belongs to a group of cytotoxic alkylating agents known as Nitrogen mustards. The activity of these drugs is attributed to the chloroethylamine groups. CI R. 'N I R NH Cl + Cl R'-NH₂ Cyclophosphamide In this exercise, you will explore the mechanism responsible for the cytotoxic activity of Nitrogen mustards and how it is possible to tune their activity (therefore their toxicity) by modifying their chemical structure. R. 2.1 Identify and label all nucleophiles/electrophiles in the following reaction. `N I R chloroethylamine 2.2 Based on your above analysis, draw two possible SN2 reaction mechanisms Intermolecular reaction (reaction between reaction sites on different molecules) Intramolecular reaction (reaction between reaction sites within the same molecule) 2.3 Which of the above reaction will be faster? Why? 2.4 Copy…

ouro- 6)- Draw the structures for the least and most polar molecules (i.e.,isomers) of Bromo-chloro-fl iodoethene (C2BrCIFI). Briefly explain your choice. Structure of least polar: Structure of most polar: