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Organic Chemistry Maxwell presented by Macmillan Learning 2-Methylcyclopentanone treated with lithium diisopropylamide (LDA) followed by addition of formaldehyde results in a crossed aldol reaction. Step 1: Add curved arrows. Select Draw Rings More /// || H C Complete the mechanism for the reaction by adding missing curved arrows, atoms, bonds, charges, and nonbonding electrons. Do not delete any pre-drawn bonds, charges, or lone pairs. If you accidentally delete a vital part of the structure, use the undo button in the lower-left corner of the panel to reset the structure. 1. LDA Atom Decorations 2 H₂O OH Erase Step 2: A second molecule of aldehyde is added. Complete the structure and add curved arrows. Select Draw Rings More ///// C H : 0: 0 Erase + NH(iPr);

14 of 23 button in the tower-left corner of the panet to reset the structure. Step 1: Add curved arrows. Select Draw Rings More ////// C H 0 Ⓒ N 3 Erase 0 Step 2: A second molecule of aldehyde is added. Complete the structure and add curved arrows. Select Draw Rings More ////// C H 0 Erase + NH(/Pr)₂

Step 3: water is added in the workup step. Complete the intermediate and add curved arrows to form the final product. Select Draw Rings More / || ||| 2 C H 0 Erase Q2 Q final product 16- OH