The reaction below is a base-catalyzed aldol reaction. O || CH₂-C-H CH3-C-H Ethanal (Acetaldehyde) H I CH3-C-H Ethanal (Acetaldehyde) NaOH Draw curved arrows to show the movement of electrons in the step of the mechanism shown below. Arrow-pushing Instructions AC⇒x= :O: || :CH₂-C-H OH Bl CH3-CH—CH2-CH -CH₂-1-1 a 3-Hydroxybutanal (B-hydroxyaldehyde; formed as a racemic mixture) :0:* :0: || CH3—CH—CH2-C-H A tetrahedral carbonyl addition intermediate X

I-O0 I Complete the curved arrow mechanism for this reaction: H HO. HO. TOH CHO. Me H. Me MeOH + Me Me - H20 Me

Draw the structure of all products of the mechanism below. c* + H H H H H Click and drag to start drawing a structure. но H :0:

Draw the curved arrows for the following mechanisms. Describe what is hap step (mechanism patterns). (Take it one step at a time and note the differences). :0: R CI: H-O-H :Ö:0 :0: :CI: :CI: H2O OH OH2 Br Br H-Br O-H H-8-H :0: OH Br 1 Br H2O H₂O

Add curved arrow(s) to draw step 4 of the mechanism. Modify the given drawing of the product as needed to show the intermediate that is formed in this step. 70DCX HH²+1+1+1+15 H₂C HC CH₂ CH₂ H,C CH₂ CH, H C F CI Br 1 77

Which of the following will be oxidized by Tollens reagent to an acid? (image added)

NaOH H3C-C-o-cH3 H3C-C-o Na* HO-CH3 H20 Write a detailed mechanism for ester saponification (shown above) which proceeds in two steps followed by a proton transfer. Then draw curved arrows that o electron reorganization for the mechanism step below. Arrow-pushing Instructions : H- H3C-C-0-CH3 :ö-H H.

Draw the product of the reduction of the given aldehyde. Include all hydrogen atoms. H3C- ་་་་་་་ CH3 reduction Select Draw Templates More Erase / # C 0 H G P 2Q

Indicate what conditions would be required for each reaction shown below in order for the overall conversion to occur. Draw the intermediate product for each step.

aldol condensation