Question

1. Rank in order of most polar to least polar. Acetanilide, acetylsalicylic acid, adipic acid, and salicylic acid

2. The melting points of pure benzoic acid and pure 2-naphthol are 122.5 and 123 degrees Celsius. Given a pure sample that is known to be one of these compounds, describe a procedure that would allow you to make a determination

Answer 1

1)

Acetanilide > salicylic acid > acetylsalicylic acid > adipic acid

2)

Prepare 2 new samples (A and B), A with a mix of your pure sample and sample of benzoic acid, and B with a mix of your pure sample and a sample of 2-naphtol. Measure both melting points. If the melting point of the sample is broad and depressed, then that sample (A or B) is likely a mixture. If the melting point of the sample is sharp and the same temperature, then that sample (A or B) is likely a pure sample (i.e. the 2 compounds in the mixture are identical).