Answer the following questions related to the separation of a mixture containing the following molecules: Compound 1 Structure OH 2 3 4 OH OH (a) What is the DOMINANT intermolecular force that will attract each compound to bind to silica gel? Compound 1 Intermolecular Force 2 3 4 H-Bonding H-Bonding Dipole-Dipole H-Bonding (b) The following compounds were separated by silica gel chromatography. Each compound was collected and placed in flasks labeled A, B, C and D respectively, in order of their elution from the column (i.e., the compound in flask A eluted first, B eluted second, C eluted third, and D eluted last). Indicate which compound 1-4 you would expect in each flask. Flask A Compound 3 B 2 C 1 D 4

Chemistry Provide the missing information for each letter in the following synthesis scheme.

O Reagents Available a. CH₂=CHCH₂CI, AICI 3 CH3 b. CH₂Br₂, OH™ C. CH3CH₂COCI, AICI 3 d. H₂, Pt e. NBS, CCI4 f. K* tBuO™ g. CO, HCI, CUCI/AICI3 h. CH3CH₂CH₂COCI, AICI 3 i. BrCH₂CH₂Br, OH- j. CH3CH₂CI, AICI 3 k. RCO3H I. H3O+ Using conditions from the table, show how you would synthesize this compound from catechol (1,2-benzenediol). Select reagents from the table in the order that you wish to use them, i.e. aced; do not include punctuation or spaces. If more than one route exists, choose the shorter one; in no case will a synthesis require more than 5 steps.

f. g. OCH 3 CO₂H OCH 3 pyruvic acid 1. SOCI22 2.? NaBH4 CH3OH methicillin (narrow-spectrum, B-lactam antibiotic)? H₂SO4 (cat) C6H8O4 (show structure)