Organic Chemistry - Midterm 1b

Which has the highest boiling point n first structure

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Which has the highest boiling point? N First structure can hydrogen bond with water, and can participate fully (has hydrogen and lone pair) Second structure capable of hydrogen bonding with water, but only using lone pairs. The hydrogen bonding will be weaker for this compound. The firstcompound is capable of stronger hydrogen bonds with water, and so will be more soluble in water. Both structures are capable of van der Waals interactions only. First structure is an open-chain compound, second structure is a ring. Rings pack together better making boiling more difficult. Both structures are capable of van der Waals interactions Second structure has a dipole and is capable of dipole-dipole interactions. These are stronger than VdW and so the second structure will have stronger intermolecular forces and a higher boiling point 1 2 1 1 2 2 OH O and Which is least soluble in water? 6) Draw the important resonance forms for the following. Identify the major and minor forms and show the resonance hybrid structure. ( 12 points ) N N N N N N N N N N δ + δ + 2 2 2 2 1 1 major major minor 1 1 7) For the following: a) Draw both chair conformations of the following compound. Indicate which form is the most stable and justify your choice ( 6 points ) O H 3 C CH 3 O O most stable, both Me's equitorial 2 2 2 b) Draw the “flat” line structure of the following (be sure to indicate stereochemistry). (
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