Draw both resonance structures of the anion formed by the reaction of the most acidic C-H bond of the compound below with base. • Include all valence lone pairs in your answer. • For structures having different hydrogens of comparable acidity, assume that the reaction occurs at the less-substituted carbon. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate resonance structures using the symbol from the drop-down menu. ● 0- SCH₂CH3 *.. ? ChemDoodle ( S ✪O-Sn [F Previous Next> Save and Exit

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Examine the molecule below, and select the statements that apply. If it can lose H, draw its conjugate base. If it can gain H, draw its conjugate acid. Show all lone pairs and non-zero formal charges. OH This molecule will not lose an H This molecule could lose an H™. Its conjugate base is: This molecule will not gain an H™ This molecule could gain an H". Its conjugate acid is: do

Which arrow (x, y, or z) points toward the most acidic proton in the molecule to the right? (Arrows pointing toward C can be assumed to point at the H attached to that C.) Which structural feature plays the most significant role in influencing the relative acidities of the indicated protons? a. inductive effect b. size c. resonance d. hybridization

a. If methane were to behave as an acid (if possible), draw the Lewis structure of its resulting conjugate base. b. Reflecting on your answer for Part A and using the three acid-base models above, would you predict the conjugate base would form? (Does this situtation make sense)? C. If methane were to behave as a base (if possible), draw the Lewis structure of its resulting conjugate acid. d. Reflecting on your answer for Part A and using the three acid-base models above, would you predict the conjugate acid would form? (Does this situtation make sense)? e. Considering your responses to Parts B and D, would you predict methane would behave as an acid, a base, either, or neither? Explain your reasoning.

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Practue Consider the two hydrogens shown in the following reaction. HO. NaH NH a. Draw the two possible conjugate bases b. Circle the conjugate base in part a that is weaker c. Briefly justify your answer in part b. Structures may be helpful in your explanation. d. Using the data from part b, predict the outcome of the reaction and briefly explain your choice.

In the boxes below each structure, provide the appropriate labels: acid, conjugate acid (CA),base, conjugate base (CB). Using pKa values (table given) determine which side the equilibrium willfavor, or if it will not favor either side write “neither”