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Problem 3

Draw line structures corresponding to the following compounds. Show all lone pair electrons (and don't forget that non-zero formal charges are part of a correctly drawn structure!) a) 2,2,4 -trimethylpentane b) 3 -phenyl-2-propenal c) 6-methyl-2,5-cyclohexadienone d) 3 -methylbutanenitrile e) 2,6 -dimethyldecane f) 2,2,5,5 -tetramethyl- 3 -hexanol g) methyl butanoate h) \(N\) -ethylhexanamide

Problem 6

Draw correct Lewis structures for ozone \(\left(\mathrm{O}_{3}\right)\), azide ion, \(\left(\mathrm{N}_{3}^{-}\right),\) and bicarbonate ion, \(\mathrm{HCO}_{3}^{-}\). Include lone pair electrons and formal charges, and use your General Chemistry textbook to review VSEPR theory, which will enable you to draw correct bond geometries.

Problem 7

Draw one example each of compounds fitting the descriptions below, using line structures. Be sure to include all non-zero formal charges. All atoms should fit one of the common bonding patters discussed in this chapter. There are many possible correct answers - be sure to check your drawings with your instructor or tutor. a) an 8 -carbon molecule with secondary alcohol, primary amine, amide, and cis-alkene groups b) a 12 -carbon molecule with carboxylate, diphosphate, and lactone (cyclic ester) groups. c) a 9-carbon molecule with cyclopentane, alkene, ether, and aldehyde groups

Problem 9

a) Draw four constitutional isomers with the molecular formula \(\mathrm{C}_{4} \mathrm{H}_{8}\). b) Draw two open-chain (non-cyclic) constitutional isomers of cyclohexanol (there are more than two possible answers).

Problem 10

Draw structures of four different amides with molecular formula \(\mathrm{C}_{3} \mathrm{H}_{7} \mathrm{NO}\).

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