AL CHEM ORGANIC

Question

Describe the tests that can be carried out rapidly in a test tube to distinguish the following compounds from one another.

A: CH3CH=CHCl

B: CH2=CHCH2Cl

C: CH3CH2CH2Cl

Answer 1

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First step:

Mixing all of the 3 chemicals with bromine water in the dark. Owing to the unsaturated C=C bond, addition reaction readily occurs for A and B even in the dark while substitution for C cannot proceed.

So C is distinguished.

Second step:

Mixing A and B with aqueous NaOH and alcohol is formed for B but no reaction for A.

This is because A, vinyl halide (i.e. the halogen group is bonded to either C of C=C bond) has the C atom being less e- deficient, thus NOT susceptible to be attacked by the nucleophile OH- ions.

But for B, The C atom bonded to the Cl atom is more e- deficient and hence it is more readily be attacked by nucleophile since there is no overlapping of p-orbitals as a result of Cl and C of C=C are NOT neighbouring atoms.

Source(s): My chemical knowledge