Let's solve the problem step by step: --- ## 1. **Draw the Lewis Molecular Structures** ### **First Structure (left):** - This is a line-angle structure with an oxygen atom bonded to two tert-butyl groups. - Each "Y" shape represents a tert-butyl group (C(CH₃)₃). - The central atom is oxygen. #### **Lewis Structure:** ``` CH3 | CH3-C-O-C-CH3 | | CH3 CH3 ``` - Full structure: **Di-tert-butyl ether** --- ### **Second Structure (right):** - This structure shows an oxygen with one hydrogen (alcohol), and a tert-butyl group. - This is a tert-butyl alcohol. #### **Lewis Structure:** ``` CH3 | CH3-C-OH | CH3 ``` - Full structure: **tert-Butyl alcohol** --- ## 2. **Name the Compounds** - **First:** Di-tert-butyl ether (systematic: 2-tert-Butoxy-2-methylpropane) - **Second:** tert-Butyl alcohol (systematic: 2-methyl-2-propanol) --- ## 3. **Volatility** - **Volatility** is how easily a substance vaporizes. - **tert-Butyl alcohol** can form hydrogen bonds (has an -OH group). - **Di-tert-butyl ether** cannot form hydrogen bonds as strongly (only weak dipole interactions). **Answer:** **Di-tert-butyl ether** is **more volatile** (evaporates more easily) because it has weaker intermolecular forces. --- ## 4. **Boiling Point (BP)** - **tert-Butyl alcohol** has hydrogen bonding (strong intermolecular force). - **Di-tert-butyl ether** only has dipole-dipole/London forces. **Answer:** **tert-Butyl alcohol** has the **highest boiling point** due to hydrogen bonding. --- ## 5. **Water Solubility** - **tert-Butyl alcohol** is more water-soluble because it forms hydrogen bonds with water. - **Di-tert-butyl ether** is less soluble due to its bulky, non-polar groups. **Answer:** **tert-Butyl alcohol** is **more water-soluble**. --- ## **Summary Table** | Property | Di-tert-butyl ether | tert-Butyl alcohol | |---------------------|---------------------------|-------------------------| | Lewis Structure |  |  | | Name | Di-tert-butyl ether | tert-Butyl alcohol | | More Volatile? | **Yes** | No | | Higher Boiling Point?| No | **Yes** | | Water Solubility | Low | **High** | --- ## **Final Answers** - **Names:** Di-tert-butyl ether, tert-Butyl alcohol - **More volatile:** Di-tert-butyl ether - **Higher boiling point:** tert-Butyl alcohol - **More water soluble:** tert-Butyl alcohol Let me know if you need the Lewis dot structures drawn out in detail!