Separation, Purification and Structural Analysis of Organic Compounds
A set of qualitative experiments were conducted in an organic chemistry lab.
Chemist 1 treated cyclohexene with 1% aq. KMnO4. One of the products was a cis-glycol.
Chemist 2 conducted qualitative tests for some carbonyl compounds. Aldehydes and ketones gave a positive test for the reagent 2, 4-dinitro- phenyl hydrazine. The compound tested for the confirmation was propanone. The product formed as a result of this test involving propanone is shown below.
In Experiment 3, three compounds were tested. These three compounds were treated with concentrated hydrochloric acid in the presence of zinc chloride (ZnCl2). Compound A was ethyl alcohol, Compound B was tert-butyl alcohol, and Compound C was 2-propanol. The reactions were based on unimolecular substitution mechanism.
In Experiment 4, the chemists synthesized the following compound.
How many sets of peaks (signals) are expected for the Compound B?
The compound B is tert-butyl alcohol.
Even though there are three methyl groups, all the methyl groups are equivalent and so are their protons. So the methyl protons give rise to one peak. The hydroxylic proton will give rise to another peak, totaling two sets of NMR peaks.