Introductory Organic Chemistry: Formulas and Naming

1. Write structural formulas for the following compounds:

a. 2,4-dimethylpentane

b. 3-bromo-1-chlorohexane

c. 1,2-dimethylcyclobutane

d. 2-chloro-1-methylcyclohexane

2. Write expanded formulas for the following compounds, and name them, using the IUPAC system:

a. CH3CH2C(CH3)2CH3

b. CH3CH2Cl

c. CHCl2CHBrCl

d. (CH3)3CF

3. What is the molecular formula for the alkane with 39 carbon atoms? What is the molecular formula for the cycloalkane with 38 carbon atoms?

4. Write the structural formula for all the possible isomers (the number is indicated in parentheses) for each of the following compounds, and name each isomer by the IUPAC system.

a. C4H9Cl (4)

b. C4H8Br2 (9)

5. Draw all possible staggered and eclipsed conformations of 1-bromopropane (looking end-on at the bond between carbon-1 and carbon-2). Underneath each, draw the corresponding "dash-wedge" and "sawhorse" structures. Rank the structures in order of decreasing stability.

6. Draw the formula for the preferred chair conformation of:

a. cis-1,3-dibromocyclohexane

b. trans-1-methyl-2-ethylcyclohexane

c. trans-1-chloro-4-iodocyclohexane

7. Which of the following two isomers in each case will be more stable? Explain your answer by drawing conformational structures for each compound.

a. cis-1,3-dichlorocyclohexane or trans-1,3-dichlorocyclohexane

b. cis-1,2-dibromocyclohexane or trans-1,2-dibromocyclohexane

8. Explain the difference between structural isomerism and conformational isomerism. Give examples.

9. Draw structural formulas for all possible products of the dichlorination of cyclohexane. Include cis-trans isomers.