Chem 14C Discussion Problems (Updated 1-16) (1)

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Chem 14C Discussion Problems Winter 2020 1) Draw Lewis structures for the following species. Draw all lone pairs and indicate any non-zero formal charges on atoms. State the geometry about the central atom. a) N 3 - b) POBr 3 c) CH 2 Cl 2 2) b -pinene is a naturally occurring organic compound responsible for the odor from pine trees. In the box provided below, give the molecular formula of b -pinene. molecular formula = 3) Convert the following condensed formulas to their corresponding skeletal (line-angle) structures. CH 3 (CH 2 ) 4 CH 3 (CH 3 ) 2 CH(CH 2 ) 2 CH 2 OCH 3 4) Complete the following Lewis structure by adding p -bonds and lone pairs to give a structure where all atoms have a neutral formal charge. Do not add atoms, only p -bonds and lone pairs. Once you complete the Lewis structure on the left, convert your answer to a line-angle formula. H C S N C C N H

5) Using line-angle formulas, draw a saturated hydrocarbon that has exactly 6 carbons and contains a 3 ° amine, a 3 ° alkyl halide, and a 1 ° alcohol. 6) For the compound below, complete the following. a. Fill in the missing lone pairs of electrons. b. Indicate the hybridization of the labeled atoms (1 to 5). 1 (carbon): _____________ 3 (carbon): _____________ 5 (carbon): _____________ 2 (oxygen): _____________ 4 (carbon): _____________ c. Draw 3 additional resonance structures and use arrow-pushing to show the movement of electrons from one structure to the next. 7) Cations A and B are structurally similar, but they have very difference stabilities. Draw all resonance structures for the two cations and use the resonance structures you drew to explain which cation is more stable. O O 1 2 3 4 5 OH OH Cation A Cation B

8) Draw all additional resonance structures for each of the following compounds and indicate which structure(s) is the most significant resonance contributor. Draw arrow-pushing to get from one resonance structure to the next. Also, for each of the given structures, state the hybridization of the atom with the charge. 9) Determine the hybridization of all non-hydrogen atoms in the structure below. Be sure to consider resonance when determining hybridization. 10) Using Newman projections, draw the following conformations of the following molecule down the bolded bond: i. the highest energy staggered conformation O O O O H 2 N O OH

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ii. the lowest energy staggered conformation iii. the lowest energy eclipsed conformation 11) Draw both chair conformers of the following compound and circle the one that is favored at equilibrium. 12) Draw both chair conformers of the following compound and circle the one that is favored at equilibrium.

13) Draw both chair conformers of the compound shown below on the left. Circle the conformer that will be favored at equilibrium. 14) Using Newman projections, draw the following conformations of the molecule below down the bolded bond: i. highest energy staggered conformation(s) ii. lowest energy staggered conformation(s) iii. lowest energy eclipsed conformation(s) 15) Draw the corresponding line-angle formula for the compound represented by the Newman projection shown below. N CH 3 H H

Do NOT attempt these problems until after we cover stereochemistry in lecture. 16) State the relationship between the following pairs of molecules selecting from the following options: enantiomers, diastereomers, constitutional isomers, identical, unrelated . 17) Assign R/S stereochemistry for each chiral center in the compound shown below. OH HO O O OH OH R/S R/S

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