This structure has a lower pKa than usual because the conjugate base of the structure has unusual stability. Using the provided resonance structures, draw the curved electron- pushing arrows to show the deprotonation step. Then, draw the curved electron-pushing arrows to show the interconversion between resonance hybrid contributors. Be sure to account for all bond-breaking and bond-making steps. 56°F Mostly sunny H:O H HH H H Na O Select to Add Arrows NaH > Q Search Problem 24 of 25 hp Please select a drawing or

Phenols generally have lower pk, values than aliphatic alcohols owing to phenoxide ion stabilization by resonance that delocalizes charge into the aromatic ring. a Draw all the resonance contributors for the phenoxide ion below. Draw only one of the two equivalent “Kekule benzene" structures. NEC Include all valence lone pairs in your answer. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.

3. Circle the most acidic proton(s) in the molecule given below and draw the corresponding conjugate base. Then, draw three additional major resonance contributors of the conjugate base. O= H conjugate base

Be sure to answer all parts. One step in the synthesis of occidentalol, a natural product isolated from the eastern white cedar tree, involved the following reaction. + 8.0 CH3O Part 1 out of 2 2 attempts left A Check my work CH3O H draw structure ... B O several steps $ H Draw the structure of A (use hashed wedged onds to denote endo bonds and wedged bonds to denote exo bonds). "Кон OH Next part (-)-occidentalol G

Curved arrows are used to illustrate the flow of electrons. Using the provided resonance structures, draw the curved electron-pushing arrows to show the interconversion between resonance hybrid contributors. Be sure to account for all bond-breaking and bond-making steps. :O: Select to Add Arrows :0:

(Review Topica) Referencen) Classify the following substituents according to whether they are electron donors or electron acceptors relative to hydrogen by the resonance and the inductive mechanisms, -CH,CH, ethyl 1. Inductive effect donor Resonance effect no effect 2. -CH,CH,CH2-ÖCH, Inductive effect Resonance effect : 3. Inductive effect acceptor v Resonance effect acceptor c-NHCH,CH,NH2 Submit Answer Retry Entire Group No more group attempts remain

Draw all the resonance contributors for the phenoxide in below. draw only one of the two equivalent "Kekule benzene" structures. include all valence lone pairs in answer.

draw the major organic product of the Bronsted acid-base reaction. Include all lone pairs and charges as appropriate. Ignore any counterions.

For each molecule or ion circle the appropriate letter to indicate if the structure is Aromatic (A), Anti-Aromatic (AA) OR Neither (N) aromatic or anti-aromatic.

6. Circle the most acidic and put an X over the least acidic in each set of three. (Please help with subparts a-c)