Homework 1

1. Draw the constitutional isomers for the following compounds:

a. C6H14
b. C2H4Cl2
c. C4H8 with only single bonds
d. C4H8 with one double bond

2. In the compounds below, classify each bond as covalent, polar covalent or ionic. Also, if
polar covalent, indicate the dipole moment using symbols 𝛿 + and 𝛿 −:
a. HBr
b. CO2
c. NaOH
d. NaOCH3
e. CH2O

3. Below is the structure of caffeine, but its lone pairs are not shown. Identify those lone
pairs:

4. The formation of a variety of compounds called oxazolidinones is important for the

synthesis of many different natural products and other compounds for potential use as
medicine. One method to prepare oxazolidinones involves the conversion of a
hydroximoyl chloride (1) into nitrile oxide (2)

Identify the formal charges that are missing from structure (1) and (2)