5. Which of the following molecules would you expect to have the most similar R₁ values? Explain why. H H of of f OH H C A B D

4. If any sugar shown below is a "reducing sugar," circle its corresponding letter. H OH HO НО НО, H OH НО H Н HO с Н H HO Н ОН 0 A OH -HH OH НО H H OH HO H OH OH H НО HO Н Н НО D HO B OH H OH Н- н OH HO Н Н OH О Н НО НО Н H OH Н OH

In each row, select the molecule with the highlighted H atom that is more acidic. H H O-H H H HH HH H 'S- HH HH H 'N' H Х

CI CI Select the compound that is one of the starting materials required for the Diels-Alder reaction that produces chlordane, and identify whether this compound is the diene or the dienophile. (select two choices) This is the dienophile. ㅁ CI CI CI CI CI CI ठ CI CI CI CI CI This is the diene. CI CI CI Cl 0 CI CI CI CI J P Cl CI

Draw the least stable resonance form the intermediate in the following electophilic substitution reaction.

Rank the labeled protons on the following molecule in order of increasing pK. Ha •O 0. Hb He

What is the systematic name of the product P of this chemical reaction? 0 || CH3-CH₂-CH₂-CH₂-CH₂-C-OH + NaOH X 5 P + H₂O

SNI or SN2? Draw the substitution product for each of the following (if there is one). Br Br H NaOCH3 OTS Br CH3OH NaCN H₂O G

Draw a structural formula for the substitution product of the reaction shown below. H/ ● (CH3)3C |YY Br ΔΟ H Na • 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. • Products that are initially formed as ions should be drawn in their neutral forms. SH acetone [F

complete the following reaction