Lesson 4 Review Answers

Carboxylic acids, Esters & Ethers

1.     Name the following molecules.

a.     isopropyl methyl ether

b.     pentyl propanoate

c.     sodium butanoate

d.     2,2-dimethylpropanoic acid

e.     dimethyl ether

2.     Draw the following molecules.

3.     The below names are incorrect.  State what is wrong and give the correct name.

a.     Methyl 2-secbutylbutanoate     The longest branch is not named on the ester.  It should be methyl 2-ethyl-3-methylpentanoate. 

b.     1-hydoxy-1-nonanone    The compound is actually a carboxylic acid, as should be named such. The correct name would be nonanoic acid.

4.     The compound is an aldehyde.  The flame test proves it is not a alkyl halide.  The Br₂ test show it is not an alkene, alkyne or aromatic.  Since KMnO₄ is an oxidizing agent, the compound can be oxidized, which leave the option of an alcohol or aldehyde. When the product was collected and dissolved into a sodium bicarbonate solution, an acid-base reaction was seen by the presence of bubbling (CO₂), which is the trademark of a carboxylic acid.  Since both an alcohol and an aldehyde can be oxidized to a carboxylic acid, the IR was used to determine the unknown was an aldehyde, by the presence of the C=O around 1700cm^-1 and the aldehyde proton at about 2700cm^-1.

5.     Complete the following reactions