[Review Topics] [References] Draw two constitutional isomers that share the molecular formula C₂H6O. Your structures will have the same molecular formula but will have different connectivities. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. 9985 Hon ChemDoodle 4 O- SIF

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Consider the triple alcohol drawn below. It contains all three types (1º, 2º, and 3º) of alcohols (not counting methanol CH3OH). Note that all three O atoms must have two lone pairs of electrons, but these are not shown due to the limitations of my graphics program. OH LOH OH 1a. Directly on the image above, label each chiral center with a “star” (*). 1b. The triple alcohol above is treated with excess HCl. Because there is more HCl than needed, all three alcohols will be converted to chloralkanes. That is, all three alcohol groups will be undergo nucleophilic substitution to form three chloroalkanes. Draw the structures of ALL resulting products (there will obviously be more than one structure). 3° alcohols react exclusively via the SNl mechanism, while 1° alcohols go exclusively via SN2. The textbook is a bit wishy-washy about 2° alcohols, so for the purpose of this HW, assume an SN1 mechanism. There is no need to indicate the absolute configurations on any of your structures, but…