ORGANIC CHEMISTRY 1 Problem Set No.

1. Write structural formulas of your choice for all of the isomers with the molecular formula C4H8. 2. Write resonance structures for the azide ion, N3-. Explain how these resonance structures account for the fact that both bonds of the azide ion have the same length. 3. There are seven isomeric compounds with the formula C4H10O. Write their structures and classify each compound according to its functional group. 4. Identify all sweetener. functional groups in aspartame, an artificial

5. Write the expanded structure for aspartame and determine its molecular formula. 6. Write a. b. c. d. e. f. g. h. i. j. a structural formula for each of the following compounds 4-isopropylheptane trans-1,2-dimethylcyclopropane cyclopentylcyclopentane bicyclo[2.2.2]octane bicyclo[3.1.1]heptane 3-methylcyclobutene (Z)-1-cyclobutyl-1-pentene (E)-4-methyl-4-hexen-1-yne m-dinitrobenzene 3,5-dinitrophenol

7. Construct a qualitative potential-energy diagram for rotation around the C-C bond of 1,2-dibromoethane. Which conformation
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would you expect to be more stable? Label the anti and gauche conformations of 1,2,dibromoethane. 8. Give systematic names for each of the following compounds. No need to specify the stereochemistry.
Cl
Br

2
Br

6 5

8
O

Br

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