CHEM 221 Assignment 1

L1-Electrons, Bonds and Molecular Properties

L2-Molecular Representations
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1) The formal charge on the nitrogen on the structure shown below is:

2) Draw a correct Lewis structure for acetonitrile, CH3CN, including all non-bonding lone pairs.

3) Draw 2 possible Lewis structures for the compound with molecular formula C3H6.

4) Write a Lewis structure for a compound with the molecular formula H2N2.

5) Assign the correct formal charge to each nitrogen atom in the following Lewis structure. (All non-
bonding electrons are included.)

6) Draw additional resonance contributors for:

7) Draw the important resonance forms for the structure shown below.

8) Draw a line-angle formula for (CH3)2CHCH2CH2NH2.

9) Draw the line-angle formula for three compounds with molecular formula C3H8O.

10) What is the approximate value of any HCC bond angle in H2C=CHCCl3?

11) Complete the structure of methyl azide by adding any necessary formal charges.

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12) The structure of uracil is shown below. What is the molecular shape of the nitrogens?

13) Are the two compounds shown below best described as cis-trans isomers, constitutional isomers,
or not isomeric?

14) Are the two compounds shown below best described as cis-trans isomers, constitutional isomers,
or not isomeric?

15) Are the two compounds shown below best described as cis-trans isomers, constitutional isomers,
or not isomeric?

16) Provide the skeletal structures of the five constitutional isomers with molecular formula C6H14.

17) Are the two compounds shown below best described as cis-trans isomers, constitutional isomers,
or not isomeric?

18) Provide the condensed formulas of three structural isomers with molecular formula C5H12 and
arrange them in order of increasing boiling point.

19) The structure of Tamiflu, an antiinfluenza drug, is shown below. Circle and identify each functional
group in Tamiflu.