Chapter 1.12, Problem 36P

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Q2: Resonance Forms a) Draw all resonance forms of the molecules. Include curved arrow notation. Label major resonance contributor. SO2 NO3 Page 3 of 4 Chem 0310 Organic Chemistry 1 HW Problem Sets CH3NSO (Thionitromethane, skeleton on the right) H N H3C S

A 10.00-mL pipet was filled to the mark with distilled water at the lab temperature of 22 oC. The water, delivered to a tared weighing bottle was found to weigh 9.973 g. The density of water at 22 oC is 0.99780 g/mL. Calculate the volume of the pipet in mL. (disregard air displacement for this calculation and record your answer to the proper number of significant digits.)

Resonance Formsa) Draw all resonance forms of the molecules. Include curved arrow notation. Label majorresonance contributor.

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f) The unusual molecule [2.2.2] propellane is pictured. 1) Given the bond length and bond angles in the image, what hybridization scheme best describes the carbons marked by the askerisks? 2) What types of orbitals are used in the bond between the two carbons marked by the askerisks? 3) How does this bond compare to an ordinary carbon-carbon bond (which is usually 1.54 Å long)? CH2 1.60Å H2C た C CH2 H2C H₂C * 120° C H2

Denote the dipole for the indicated bonds in the following molecules. H3C CH3 B F-CCl3 Br-Cl | H3C Si(CH3)3 OH НО. HO H O HO OH vitamin C CH3

Q2: Draw all applicable resonance forms for the acetate ion CH3COO. Clearly show all lone pairs, charges, and arrow formalism.