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Organic Chemistry

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Separation, Purification and Structural Analysis of Organic Compounds

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A set of qualitative experiments were conducted in an organic chemistry lab.

Experiment 1

Chemist 1 treated cyclohexene with 1% aq. KMnO4. One of the products was a cis-glycol.

Experiment 2

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.

image\Ch 32 Experiment 2.png

Experiment 3

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.

Experiment 4

In Experiment 4, the chemists synthesized the following compound.

image\Ch 32 Expirement 4.png

How many sets of peaks (signals) are expected for the Compound B?

A 2
B 3
C 4
D 10
Ans. A

The compound B is tert-butyl alcohol.

image\Solutions ch 32, Q 7.png

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.

Separation, Purification and Structural Analysis of Organic Compounds Flashcard List

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