You have 5 test tubes (shown below): Tube 1: 2 drops of unknown A and 5 drops of

Question

You have 5 test tubes (shown below):
Tube 1: 2 drops of unknown A and 5 drops of AgNO3 Tube 2: 2 drops of unknown B and 5 drops of AgNO3 Tube 3: 2 drops of unknown C and 5 drops of AgNO3 Tube 4: 2 drops t-butylchloride + 5 drops of AgNO3 (CONTROL) Tube 5: 5 drops of AgNO3 (BLANK) (Figure 6)
You perform the tests above and find that Tube 1 (Unknown A) and Tube 4 (control) form a white precipitate.
You perform another test with NaI/ 2-butanone, this time without Unknown A.
This is shown below as well. (Figure 7)
Tube 1: 1 drop unknown B+ 5 drops NaI/ 2-butanone Tube 2: 1 drop unknown C+ 5 drops NaI/ 2-butanone Tube 3: 1 drop 1-chlorobutane + 5 drops NaI/ 2-butanone (Control) Tube 4: 5 drops NaI/ 2-butanone (Blank)
Tube 2 (Unknown C) and Tube 3 (control) form a white precipitate.
From the list of compounds below (Figure 8), what is unknown A? And what is unknown C?


2 drops unknown A+ 5 drops AgNO3 2 drops unknown B+ 5 drops AgNO3 2 drops unknown C+ 5 drops AgNO3 2 drops t-butylchloride+ 5 drops AgNO3 CONTROL 5 drops AgNO3 BLANK

Explanation / Answer

The unknown A is t-butyl chloride because it formed a white precipitate with AgNO3 solution directly due to the formation of stable tertiary carbocation.

The unknown C is 1-chlorobutane because it formed a white precipitate in presence of NaI which catalyzes the reaction of alkyl halide with AgNO3 solution

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