3. Draw a resonance structure for each of the following. You must use the correct notation for drawing resonance structures (double sided arrow and correct arrow pushing) and include formal charges. b 4. Of all 14 functional groups we discussed in class (and are in the tables in the PowerPoints), which 4 categories would you expect to, generally, have the highest boiling points? Are there specific circumstances in which any of these groups will have significantly lower boiling points? TABLE 2.4 Physical Properties of Representative Compounds \begin{tabular}{l|l|l|l} Compound & Structure & mp(C) & bp(C)(1 atm ) \\ \hline Methane & CH4 & 182.6 & 162 \\ \hline Ethane & CH3CH3 & 172 & 88.2 \\ \hline Ethene & CH=2CH2 & 169 & 102 \\ \hline Ethyne & HCCH & 82 & 84 sublimes \\ \hline Chloromethane & CH3Cl & 97 & 23.7 \\ \hline Chloroethane & CH3CH2Cl & 138.7 & 13.1 \\ \hline Ethyl alcohol & CH3CH2OH & 114 & 78.5 \\ \hline Acetaldehyde & CH3CHOCH & 121 & 20 \\ \hline Acetic acid & CH3CO2H & 16.6 & 118 \\ \hline Sodium acetate & CH3CO2Na2 & 324 & decomposes \\ \hline Ethylamine & CH3CH2NH2 & 80 & 17 \\ \hline Diethyl ether & (CH3CH2)2O & 116 & 34.6 \\ \hline Ethyl acetate & CH3CO2CH2CH3 & 84 & 77 \\ \hline \end{tabular}